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Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

Jens C. Frisvad, Lars L. H. Møller, Thomas O. Larsen and 2 more

Applied Microbiology and Biotechnology · 2018 · Review

doi:10.1007/s00253-018-9354-1

Abstract

This review presents an update on the current knowledge of the secondary metabolite potential of the major fungal species used in industrial biotechnology, i.e., Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei. These species have a long history of safe use for enzyme production. Like most microorganisms that exist in a challenging environment in nature, these fungi can produce a large variety and number of secondary metabolites. Many of these compounds present several properties that make them attractive for different industrial and medical applications. A description of all known secondary metabolites produced by these species is presented here. Mycotoxins are a very limited group of secondary metabolites that can be produced by fungi and that pose health hazards in humans and other vertebrates when ingested in small amounts. Some mycotoxins are species-specific. Here, we present scientific basis for (1) the definition of mycotoxins including an update on their toxicity and (2) the clarity on misclassification of species and their mycotoxin potential reported in literature, e.g., A. oryzae has been wrongly reported as an aflatoxin producer, due to misclassification of Aspergillus flavus strains. It is therefore of paramount importance to accurately describe the mycotoxins that can potentially be produced by a fungal species that is to be used as a production organism and to ensure that production strains are not capable of producing mycotoxins during enzyme production. This review is intended as a reference paper for authorities, companies, and researchers dealing with secondary metabolite assessment, risk evaluation for food or feed enzyme production, or considerations on the use of these species as production hosts.

Full text

From PubMed Central, U.S. National Library of Medicine, as current on Oct 18, 2026. Paragraph numbers are ours, so an answer can point at one.

Introduction

Earlier reviews on the safety of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei have been published (Schuster et al.; Tanaka et al.; Barbesgaard et al.; Jørgensen; Blumenthal ), but since these reviews were written, much progress has been made in the taxonomy, toxicology, natural product chemistry, genomics, genetics, and molecular biology of these fungi.

There is a clear distinction between mycotoxins and other secondary metabolites with attractive properties for diverse applications. Fungal species containing industrial strains have the potential to produce a rather limited number of compounds that are toxic to vertebrates (mycotoxins) and a large variety of other compounds that can display anticarcinogenic or antimicrobial activity, antioxidant activity, be pigments, etc. (Mushtaq et al. ). A clear definition of mycotoxin and secondary metabolite is presented here to provide a clear basis for the consideration of safety. The fungal strains that represent the workhorses of industrial biotechnology have a long and extensively documented history of safe use for food and feed applications. Strains belonging to the Aspergillus species A. niger and A. oryzae have been used for fermentation of food for more than 2 millennia and to manufacture food enzymes for over 50 years, while strains of Trichoderma reesei have been used safely for decades in enzyme production. Hundreds of enzymes produced in these species are considered as safe by regulatory authorities. Furthermore, mycotoxins and other secondary metabolites are not produced during the controlled, industrially relevant growth conditions where nutrients are not limited and where there is no growth challenge by any other microorganism.

This report includes a comprehensive update of the current knowledge about the mycotoxin and the promising secondary metabolite potential of these industry relevant fungal species. We have considered all published work and have critically evaluated the validity of the data and the accuracy of the taxonomic identification in each case. Consequently, not all publications have been included herein. The report is divided into three sections (taxonomy, mycotoxins, and secondary metabolite potential) for each species.

Taxonomy of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

Traditional identification of fungal species relied on microscopic and macroscopic morphological traits, e.g., sporulation structures and other phenotypic features like growth and colony features (see Fig. 1 for examples of A. niger, A. oryzae, and its close relative Aspergillus flavus, together with T. reesei). In the last decades, taxonomical classification aided by secondary metabolite profiles has also proven successful (Frisvad and Larsen; Samson et al. ). More recently, the use of diagnostic gene sequences like rRNA and, later, the availability of whole genome sequences, have enabled direct comparison of different species at the nucleotide level, throughout the genome. In fact, rDNA-derived ITS sequences are recommended as one of the main “barcodes” for species identification (Samson et al. ). However, at least in some Aspergillus clades, there is limited variation in, e.g., ITS sequences, requiring the use of additional barcodes like calmodulin or β-tubulin (Samson et al. ). The level of resolution of these molecular techniques provides new ways to investigate what defines the species boundaries (Vesth et al. ). Still, differences in DNA sequences alone cannot always provide a biological understanding. Also, the profiles of secondary metabolites are species-specific (Frisvad and Larsen ) and thereby consistent with phylogenetic relationships in fungi (Larsen et al.; Kocsubé et al. ). When taxonomical identification is required, it is therefore advantageous to combine the accumulated knowledge on morphological, physiological, and molecular characteristics. Taxonomical classification of A. niger, A. oryzae, and T. reesei together with relevant related species is described in the following texts.

Aspergillus niger

Aspergillus niger is placed within the Aspergillus niger clade in the Aspergillus section Nigri (Varga et al. ). The species is well-circumscribed, but it has a sibling species, with the same properties, called Aspergillus welwitschiae (Hong et al. ). The latter species shares all morphological, physiological, and chemical characters with A. niger (Fig. 1), and the two species can only be distinguished by sequencing preferably one of the secondary bar-coding genes (Hong et al. ). The DNA barcodes of Aspergillus welwitschiae are as follows: ITS (internally transcribed spacer regions and the 5.8 S of the ribosomal gene): FJ629340; BenA (β-tubulin): FJ629291; CaM (calmodulin): KC480196, while A. niger has the following barcodes: ITS: EF 661186; BenA (β-tubulin): EF661089; CaM (calmodulin): EF661154; RPB2 (RNA polymerase B2: EF661058). Different strains of Aspergillus niger have been genome-sequenced (see Baker; Pel et al.; Andersen et al. ).

Other species closely related to A. niger are Aspergillus neoniger, Aspergillus tubingensis, Aspergillus vadensis, Aspergillus luchuensis, Aspergillus eucalypticola, Aspergillus costaricaensis, and Aspergillus piperis, but it is mostly A. luchuensis (formerly Aspergillus acidus or Aspergillus foetidus var. acidus), A. vadensis, and A. tubingensis that are used in the industry. In some cases, the latter have been misidentified as A. niger, and A. niger is by far most commonly used species in the industry (Frisvad et al. ). A. luchuensis is found in fermented Puerh tea (Mogensen et al. ) and is used often for koji production (also under the names Aspergillus kawachii and Aspergillus awamori) (Fujimoto et al.; Hong et al.; Fujii et al. ). A. niger sensu stricto is the most commonly used species in biotechnology (Andersen et al.; Frisvad et al. ). An often examined typical strain of A. niger is ATCC 1015.

Unlike the situation in A. flavus, which has a taxonomically accepted domesticated form A. oryzae, the domesticated form of A. niger, A. awamori (Nakazawa, Sakaguchi et al.; Raper and Fennell; Murakami; Al-Musallam ), has not been accepted as a valid name, probably because of a mistaken neotypification. Perrone et al. used the name A. awamori for a taxon that was isolated from Welwitschia mirabilis, but since the ex-type isolate (CBS 557.65) was not from a koji environment, that species was renamed A. welwitschiae by Hong et al.. Other names such as Aspergillus usamii and A. kawachii have also been used for domesticated forms of A. niger or A. luchuensis (Hong et al. ). However, none of these names have been officially taken up for the domesticated form of A. niger. The names Aspergillus phoenicis and Aspergillus ficuum predate A. niger and have therefore been rejected, and the name A. niger officially conserved because of the economical importance of the latter species (Kozakiewicz et al. ).

Average nucleotide identity (ANI) has become the gold standard for taxonomic confirmation of prokaryotes. Two species having > 95% ANI are considered the same species (Rodriguez and Konstantinidis ). Although ANI is not widely used in eukaryotes and there are no studies done to layout an ANI-based species framework in fungi, ANI values can still be used to determine the relatedness of two strains or species and can give a better resolution of phylogenetic tree-based inferences (Goris et al. ). ANI can also discriminate between closely related populations, and it provides a higher resolution than other sequence analyses, at least in bacteria (Rodriguez and Konstantinidis ).

We performed comparative genomics within species of the Nigri clade for which the genome sequence is available using ANI that showed a relatively high identity (85% or higher) between different species in this clade, while a lower level (~ 76%) was obtained when comparing to species outside the clade like A. oryzae or Aspergillus nidulans (Table 1). Remarkably, a higher ANI was obtained when comparing A. tubingensis and A. luchuensis (~ 93%) and a slightly lower ANI when comparing A. tubingensis with A. vadensis or A. luchuensis with A. vadensis (~ 92%). These three species appear to be more closely related (Table 1), and they all produce asperazines (Nielsen et al. ). A phylogenetic tree based on the above-mentioned genome comparison displays the closer relationship between these three species and the clustering of A. niger and Aspergillus brasiliensis (Fig. 2).

Recently, wild-type A. niger has been considered as a class 2 microorganism by the German authorities (BAUA see previous texts) because of its potential mycotoxin production and pathogenicity to humans and animals. It is important to discriminate between (1) mycotoxin production as a health hazard during food manufacture and spoilage and corn silage and (2) the growing number of reports of opportunistic pathogens that have resulted in disease, normally in immunocompromised patients. In fact, the baker’s yeast (Saccharomyces cerevisiae) can also be considered as a pathogen since it has been associated with disease in severely immunocompromised patients. Perhaps the concept of what constitutes a “pathogen” needs a comprehensive revision and it is not solely related to the taxonomy of the microbe (Casadevall and Pirofski ).

Aspergillus oryzae

A. oryzae is regarded by most taxonomists as the domesticated form of A. flavus (Blochwitz; Wicklow; Klich and Pitt; Georgianna et al.; Rokas; Varga et al.; Gibbons et al.; Houbraken et al.; Frisvad et al. ). Wicklow claims that domestication (in rice fermentations) has resulted in the following phenotypic differences: conidia in A. oryzae are smoother and slightly larger (to adapt to the rice habitat), amylase production is higher, the conidiophore stipes are longer, the mycelium is more floccose, and the conidium color en masse is light brownish green rather than yellow grass green as compared to A. flavus (Fig. 1). While there are no genotypic differences between A. oryzae and A. flavus (Thom and Church; Raper and Fennell; Murakami; Christensen; Pitt et al.; Wicklow; Klich and Pitt,; Geiser et al.,; Gibbons et al.; Powell et al.; Varga et al. 2011; Gilbert et al.; Frisvad et al. ), there are several morphological and physiological differences between the two species as listed previously. Furthermore Aspergillus oryzae cannot produce aflatoxins, aspergillic acid, and flavimine, that are otherwise present in most strains of Aspergillus flavus (Thom and Church; Raper and Fennell; Murakami; Christensen; Wicklow; Klich and Pitt,; Pitt et al.; Varga et al. 2011; Frisvad et al. 2018; Fig. 1). Klich and Mullaney were able to distinguish between strains of A. oryzae and A. flavus by DNA restriction enzyme fragment polymorphisms. Nearly all strains of A. flavus produce a bright orange reverse on the medium AFPA (Aspergillus flavus parasiticus agar), while A. oryzae strains produce a cream-colored reverse (Bothast and Fennell; Hamsa and Ayres; Pitt et al. ).

In accordance with this, genome sequencing of A. flavus (Nierman et al.; Faustinelli et al. ) and strains of A. oryzae (Machida et al.; Galagan et al.; Umemura et al.,,; Zhao et al.,,,,) have shown that these two species are very similar. Interestingly, the first sequenced strain of A. oryzae may be an A. flavus “sensu stricto.” The isolate RIB40 produces large globose sclerotia (Rank et al.; Fig. 1) and was isolated from a broad bean, Kuriyamacho, Kyoto, Japan, in a field, not from a fermentation factory. Based on the first identification as A. oryzae var. brunneus, it has brownish conidia and, therefore, resemble A. oryzae. RIB40 does not produce aflatoxin as it contains disabling mutations in the gene cluster (Tominaga et al. ). It has been shown that A. flavus isolates gradually lose their ability to produce spores, sclerotia, and aflatoxin-producing capability after several serial transfers (Torres et al.; Horn and Dorner; Chang et al. ). The production of large globose sclerotia is characteristic for A. flavus sensu stricto (Geiser et al. ), and only few strains of A. flavus (for example NRRL 3251) produce small sclerotia (Hesseltine et al.; Saito and Tsuruta ), while other strains with small sclerotia belong to the species Aspergillus minisclerotigenes, Aspergillus aflatoxiformans, Aspergillus austwickii, and Aspergillus cerealis (Varga et al. 2011; Frisvad et al. 2018). Overall, none of the characterized true A. oryzae isolates produce aflatoxins. For A. flavus, the situation is more complex since some isolates, including the ex-type strain (NRRL1957), do not produce aflatoxin. However, aflatoxin production has been shown for a large number of A. flavus including NRRL3357.

Genome sequencing has allowed several comparative studies to be carried out (Abe et al.; Payne et al.; Kobayashi et al.; Rokas et al.; Machida et al. ). A. oryzae is used extensively in enzyme production at industrial scale (Barbesgaard et al.; Jørgensen ) and as a successful expression host for production of secondary metabolites (Sakai et al.; Liu et al.; Minami et al.; He et al. ). In practice, sequence barcodes for A. oryzae include the following: (1) ITS (accession no. EF661560); (2) BenA (β-tubulin, accession no. EF661483); (3) CaM (calmodulin accession no. EF661506); and (4) RPB2 (RNA polymerase B2, accession no. EF661438) and for A. flavus: (1) ITS: (AF027863); (2) BenA (EF661485); (3) CaM (EF661508); and RPB2 (EF661440). Remarkably, the barcodes are not sufficient to effectively separate A. flavus and A. oryzae. More elaborate molecular techniques are required to distinguish these species (Godet and Munaut ). ANI analysis showed a very high degree of sequence homology, well above 99%, between RIB40 and other A. oryzae strains used in industrial enzyme production like A1560 (synonym IFO 4177), while a slightly lower percentage is observed when comparing A. flavus and A. oryzae (Table 1). The use of the % identity between A. oryzae RIB40, A1560 or A. flavus NRRL3357 (99.9% versus 99.1%) does not allow a direct species discrimination based on ANI. Furthermore, ANI between A. oryzae and species from the Nigri section display an ANI value below 80%. Members of the Nigri section display an ANI of 85% or higher. Lower ANI (approx. 75%) is obtained when comparing either A. oryzae/A. flavus to A. nidulans or species from the Nigri section to A. nidulans. Overall, as in the case of A. niger, the above-mentioned data demonstrate that genome homology data alone cannot be used for taxonomical purposes and need to be complemented by phenotypic properties.

Trichoderma reesei

Trichoderma reesei (anamorph) has also been named Hypocrea jecorina (teleomorph and holomorph), but with the new nomenclatural system used after 2011, Trichoderma reesei is considered the correct name for this fungus (Samuels et al.; Samuels et al., Fig. 1). Most of the industrial strains have a single common ancestor, RUT-C30, which displays a blue-green color on solid medium (Fig. 1). The genome sequence has also been reported for this species (Martinez et al. ). The T. reesei type strain is QM6a.

Mycotoxins are a very limited group of fungal secondary metabolites

Fungal secondary metabolites can be defined as outward-directed, small differentiational molecules of restricted taxonomic distribution that are genetically encoded by clustered genes and accumulated and normally secreted. Secondary metabolites are a very heterogeneous chemical group of low molecular weight compounds that include antimicrobials, antioxidants, pigments, hormones, and metal chelators. A great number of these compounds have therefore a very significant potential application.

In general, any competition-selected fungal species has the potential to produce hundreds of individual secondary metabolites coded by up to 90 biosynthetic gene clusters (Clevenger et al.; Lind et al. ). The major biosynthetic classes of secondary metabolites are polyketides, non-ribosomal peptides, terpenes, and shikimic acid-derived compounds, but many compounds are hybrids of these classes. The genes coding for the enzymes involved in the biosynthesis of these compounds are associated in gene clusters. The genomes of A. niger, A. oryzae, and T. reesei include 78, 75, and 27 gene clusters for secondary metabolite biosynthesis, respectively (Lind et al.; Zeilinger et al.; Wasil et al. ), although these numbers may vary depending on the strain and the software package used. Furthermore, each biosynthetic gene cluster may be responsible for the production of a large number of precursors, shunt products, and final products. For example Aspergillus oryzae was reported to produce many members (26) of the cyclopiazonic acid biosynthetic family of compounds (Liu et al. ), including cyclopazonic acids, speradines, cyclopiamides, and asporydines. With the development of new genome mining approaches (Kjærbølling et al. ) and algorithms such as antiSMASH (Blin et al. ), the prediction of secondary metabolite encoding gene clusters has become easier. On the other hand, the chemical modifications based on important accessory tailoring genes on the core structure of secondary metabolites may be more difficult to predict from sequences (Bertrand et al. ) and often require full structure elucidation. In this context, it is important to note that majority of gene clusters are not expressed under standard cultivation and that no fungal species synthesizes all potential secondary metabolites at any given time. As mentioned previously, production of secondary metabolites does not normally occur under production-relevant growth conditions where no species competition or nutrient starvation threat is used.

Mycotoxins are a very limited group of fungal secondary metabolites. Regarding biotechnology, mycotoxins are important if they pose a safety concern in the industrial application of fungi for enzyme or bulk metabolite production as well as in other areas like food spoilage and in building environments. There have been numerous definitions of the word mycotoxin (Bennett and Inamdar; Taevernier et al. ), but a strict consensus definition that we endorse is the following: Mycotoxins are secondary metabolites genetically encoded by clustered genes and produced by fungi. These mycotoxins are acutely or chronically toxic and pose health hazards or death in humans and other vertebrates when acquired in small amounts via a natural route (orally, by inhalation, or via the skin). This definition is a combination of that of Jarvis and Miller, Frisvad, Bennett and Inamdar, and Taevernier et al.. Taevernier et al. suggested that a quantitative level of cell cytotoxicity on preferably human cell cultures with an IC50 (the concentration required for 50% of cell viability) of less than 1000 μM could be used to determine whether a fungal secondary metabolite was considered a mycotoxin or not. We cannot accept this definition as such molecules may be cytotoxic, while not necessarily being toxic when acquired via a natural route. Earlier claims of mycotoxicity were based on other toxicity data, such as toxicity including cancerogenicity after intraperitoneal or subcutaneous injection (Dickens and Jones; Cole and Cox; Lu et al. ), but this too is not a natural route of intake. For example, patulin and penicillic acid were originally claimed to be cancerogenic based on subcutaneous injection (Dickens and Jones ), but Enomoto and Saito rightly mention that experimental production of cancer should be confirmed in animals by oral administration of mycotoxin.

The safe use of fungal strains is recognized in official classifications of biological agents into risk groups; e.g., BAUA (German Federal Institute for Occupational Safety and Health) classifies A. niger and A. oryzae as risk group 2 biological agents. Importantly, BAUA recognizes that strains belonging to these species may still be classified as risk group 1 biological agents if documentation of safety and/or history of safe use is provided.

In the following sections, we describe the mycotoxins that are potentially produced by the three industrial organisms and relevant related species. Only mycotoxins with a documented effect are described. All other secondary metabolites are described in the section on secondary metabolite potential and are not considered mycotoxins according to the definition herein.

Mycotoxins potentially produced by Aspergillus niger

Aspergillus niger has been claimed to produce a very large number of mycotoxins and other secondary metabolites (Table 2; Nielsen et al. ). Apart from a large number of volatiles and small organic acids (Wani et al.; Priegnitz et al.; Costa et al. ), A. niger sensu stricto can produce very few mycotoxins but a large number of other secondary metabolites. In many cases, fungi identified as A. niger were indeed A. tubingensis or other closely related species (Table 2).

Fumonisins

Fumonisins are strongly reduced polyketides with two added tricaballyllic acid groups and an amino group added from a non-ribosomal peptide. They are mycotoxins associated with multiple human and animal diseases, as they are produced in large amounts in cereals by common Fusarium species (Braun and Wink; Cendoya et al. ). Fumonisins induce leukoencephalomalacia in horses, nephro- and hepato-toxicity in rodents, and pulmonary toxicity in pigs, and they have been classified as International Agency for Research on Cancer (IARC) type 2B carcinogens in humans (esophageal cancer) (Cendoya et al. ). However, Aspergillus niger and its sibling species A. welwitschiae (originally named A. awamori) also produce fumonisins of the B2, B4, and B6 types (Frisvad et al.; 2010) and may produce fumonisins in cereals and grapes (Logrieco et al.; Mogensen et al.; Munkvold et al. ). Several industrial strains have the capability to produce fumonisins (Frisvad et al. 2010; Han et al. ), so it is important to use strains that do not produce these mycotoxins. Current A. niger production strains have been developed that either have been selected due to the lack of fumonisin production or contain a deletion of the fumonisin gene cluster (unpublished results).

The impact of fumonisins on human health remains poorly understood (Voss and Riley ). It has been known for long that fumonisins are hepatotoxic, nephrotoxic, atherogenic (induces formation of plaque in arteries), immunosuppressive, and embryotoxic in experimental animal systems (Nair ). Structurally, fumonisin B1 shows similarity to the cellular sphingolipids, and this similarity has been shown to disturb the metabolism of sphingolipids leading to accumulation of sphinganine in cells and tissues. The cellular mechanisms behind fumonisin B1-induced toxicity include the induction of oxidative stress, apoptosis, and cytotoxicity, as well as alterations in cytokine expression (Stockmann-Juvala and Savolainen ). Mechanistically, the toxicity of fumonisin B2 and B3 is relatively poorly understood, but a comparison of the toxicities of fumonisin B1, B2, and B3 individually and in combination has shown that all three are toxic, but with fumonisin B1 being the most toxic of the three (Henry and Wyatt ).

Ochratoxin

Ochratoxin A (OTA) is a mycotoxin that is a common contaminant of a wide variety of food products. The molecular structure comprises a chlorinated polyketide dihydroisocoumarin ring linked to phenylalanine and, as shown in different producing fungal species, a polyketide synthase (PKS) is a major part of the biosynthetic pathway (Wang et al.; Massi et al.; Gallo et al.; Gill-Serna et al. ). OTA inhibits protein synthesis and energy production, induces oxidative stress, cell apoptosis and necrosis, and DNA adduct formation, and is mostly recognized as a nephrotoxin (Heussner and Bingle; Közégi and Poór ). It is classified as an IARC type B2 carcinogen in human beings.

Oxalic acid

Oxalic acid is a strong dicarboxylic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate, is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous. Oxalic acid is hepatotoxic, but it will only have a negative effect in quite high doses (Jahn ). Aspergillus niger infections are often accompanied with oxalosis (Kredics et al.; Oda et al. ), and in one case, calcium oxalate produced by A. niger in the lungs caused hyperoxaluria in the kidneys (Vaideeswar and Sakhdeo 2009), so both kidneys and the liver can be affected. However, such cases are rare and will only happen in severely immunocompromised patients. Otomycoses are often caused by Aspergillus tubingensis rather than A. niger (Kredics et al. ).

Improved safety of A. niger industrial strains

As mentioned previously, A. niger has the potential to produce ochratoxin, fumonisin, and oxalic acid. Industrial strains have been developed by classical mutagenesis and by deletion of the genes involved in the biosynthesis (Susca et al. ).

Mycotoxins from Aspergillus oryzae and A. flavus

A. oryzae and its closely related species A. flavus can produce a very limited number of mycotoxins (Table 3). Their macroscopic similarity has contributed to a disparity of reports on the potential production of mycotoxins from either species. Mycotoxins produced by these species are described in the following texts with attention to knowledge about the potential production of these compounds by either species and reports that describe production in wrongly assigned species.

A. oryzae is a domesticated species originating probably from Aspergillus flavus, and the two species can not be distinguished by DNA sequence differences. Since A. oryzae is domesticated, it can only be expected to be found in fermentation environments. Any A. oryzae recovered in nature can only be found there if it has escaped such a fermentation plant, and based on its adaptation to the fermentation environment, it must be expected to be a poor competitor in cereals, oilseeds, and nuts, where A. flavus is a very competitive species (Wicklow ).

Aflatoxins

The aflatoxins (B1 and B2 primarily) are polyketides that have been found in many strains of Aspergillus flavus, albeit not the culture ex type of A. flavus (Varga et al. ). Aflatoxin (AFL) has been reported from strains of Aspergillus oryzae, but these data are based on misidentified strains or misidentified mycotoxins or contaminated cultures (Varga et al. ). It has been shown that strains of Aspergillus oryzae sensu stricto cannot produce AFL, as a result of the lack of essential parts of the gene cluster, e.g., deletion of the aflR gene involved in induction of biosynthesis (Cary and Ehrlich; Chang et al.; Lee et al.,; Tominaga et al.; Takahashi et al.,; Kiyota et al.; Hong et al.; Lee et al.; Tao and Chung ). Therefore, AFL production can be excluded in A. oryzae sensu stricto. Furthermore, current industrial strains contain a deletion of the whole AFL gene cluster, providing additional safety in enzyme production. Type G aflatoxins (aflatoxin G1 and G2) have rarely been reported from Aspergillus flavus. In some cases, the G type aflatoxins were produced by A. parasiticus and other species from section Flavi (Varga et al. 2011), rather than isolates that confidently can be allocated to A. flavus sensu stricto. Saldan et al. reported on aflatoxin G1 production by A. flavus ATCC 9643, but this strain may not be an A. flavus sensu stricto. Five Korean strains of A. flavus sensu stricto were reported to produce the G-type aflatoxins (Frisvad et al. ).

Cyclopiazonic acids

Cyclopiazonic acid (= α-cyclopiazonic acid) (CPA) is an indol tetrameric acid, hybrid polyketide/non-ribosomal peptide/DMAT (dimethylallyl terpene unit) compound that was isolated from A. flavus originally by Luk et al. and Gallagher et al. but has since been found repeatedly in A. flavus (Varga et al. ). It was originally isolated from a fungus identified as Penicillium cyclopium, but the strains of Penicillium-producing cyclopiazonic acid were Penicillium griseofulvum and Penicillium commune (Frisvad; Frisvad et al. ). CPA has also been isolated repeatedly from Aspergillus oryzae (Orth; Ohmomo et al., erroneously reported as A. versicolor; see Domsch et al.; Frisvad; Tokuoda et al.; Shaaban et al. ). It is possible to remove the CPA gene cluster and thus avoid CPA production in biotechnological processes (Kato et al. ). A. oryzae and A. flavus can produce a large number of secondary metabolites related to CPA including iso-α-cyclopiazonic acid, β-cyclopiazonic acid (= bissecodehydrocyclopiazonic acid), α-cyclopiazonic acid imine, 2-oxocyclopiazonic acid, cyclopiamide (A), cyclopiamide E & H, speradine A, B, C, D, E, F, H, I, 3-hydroxy-speradine A, cAATrp, and asperorydine A-M (Ohmomo et al.; Holzapfel et al.; Hu et al.,; Ma et al.; Tokuoka et al.; Xu et al.; Uka et al.; Liu et al. ) from A. oryzae and A. flavus, but speradine A is also produced by Aspergillus tamarii (Tsuda et al. ). Some of the strains reported as A. oryzae producing these tetramic acids have been isolated from marine sources, so they may in fact be A. flavus. However, the speradines are related to CPA, produced by many strains of both A. flavus and A. oryzae, and so speradines are not unlikely secondary metabolites in A. oryzae. There have been some problems with the naming of speradine B that is a different speradine in Penicillium dipodomyicola (Wang et al. ) than that from A. flavus, so some of the speradines need to be renamed.

β-nitropropionic acid

β-nitropropionic acid (BNP) is one of the real mycotoxins reported from authentic Aspergillus oryzae strains, but also from A. flavus strains (Bush et al.; Nakamura and Shimoda; Iwasaki and Kosikowski; Orth ). It has caused sugarcane disease in children eating sugarcane infected with Nigrospora spp. that produce β-nitropropionic acid also (Liu et al.; Ming; Fu et al.; Johnson et al.; Fernagut et al.; He et al. ). The genetic basis for production of BNP is not completely understood. Therefore, BNP levels are monitored in industrial enzyme productions.

Mycotoxins from Trichoderma reesei

It seems that chemotaxonomy is working excellently at the species level in Trichoderma (Kang et al. ). In the latter paper, T. reesei was not included, and it is only few mycotoxins that are ascribed to T. reesei (Zeilinger et al. ) (Table 4). Reported mycotoxins from T. reesei (claimed to be a mutant of QM 9414 and called P-12) include trichodermin (Watts et al. ), but this ability to produce trichodermin by T. reesei has been rejected by Nielsen et al.. The latter authors claimed that only Trichoderma brevicompactum can produce trichodermin, and possibly also Trichoderma arundinaceum (Zeilinger et al. ). There are also some trichothecene genes in Trichoderma gamsii and Trichoderma asperellum, but such genes have not been observed in T. reesei (Zeilinger et al. ). Also, the mycotoxin gliotoxin has been mentioned as a potential secondary metabolite in Trichoderma, because a gene cluster seems to be present in the genome of this fungus (Zeilinger et al. ). However, gliotoxin has never been detected in any culture of T. reesei (Martinez et al.; Kubicek and Druzhinina ). T. reesei thus seems to be unable to produce mycotoxins.

Toxicity of fungal mycotoxins relevant for A. niger, A. oryzae, and T. reesei

Mycotoxins often affect different vertebrate species very differently. However, to enable a comparison of the relative toxicity of the mycotoxins potentially produced by A. niger, A. oryzae, and T. reesei, an overview of acute oral toxicity is provided (Table 5). In the enzyme industry, it is ensured that production strains based on A. niger, A. oryzae, and T. reesei do not produce mycotoxins when grown at large scale.

As shown previously, A. niger can produce the mycotoxins ochratoxin A, fumonisins B2, B4, and B6, and oxalic acid, and A. oryzae can produce the mycotoxins cyclopiazonic acid and β-nitropropionic acid, and T. reesei has not been convincingly shown to produce any mycotoxins.

Improved safety of A. oryzae industrial strains

As mentioned previously, A. oryzae strains are not able to produce aflatoxins due to the presence of disabling mutations in the gene cluster. Modern industrial strains have been developed that contain a large DNA deletion. This region includes the aflatoxin gene cluster and genes involved in the biosynthesis of cyclopiazonic acid (CPA, Christensen et al. ). Thus, during industrial enzyme production using strains derived from A1560 containing the chromosomal deletion, the presence of neither aflatoxin nor CPA is a concern.

Secondary metabolite potential

Fungal secondary metabolites are very diverse and include compounds with a wide range of applications (e.g., antibiotics, cancer treatment, immunosuppressing drugs, pigments, antioxidants).

Like many other fungi, Aspergillus species are capable of producing a very large number of drugs and drug-lead compounds. Among the best known for medical applications are the antibiotic penicillin to combat bacterial infections, the cholesterol-lowering mevinolin from Aspergillus terreus, the anticancer compound fumagillin from Aspergillus fumigatus, the antifungal echinocandin from Aspergillus pachycristatus and mulundocandin from Aspergillus mulundensis (Baltz et al.; Houbraken et al.; Zeiliger et al.; Bills et al.; Park et al. ).

Fungi produce a large number of other secondary metabolites. Among them, fungal pigments such as polyketide-derived azaphilones are used to add color and as antioxidants in food. Aspergillus species are used to produce yellow and brown pigments like fumigatin (Hanson ). Additionally, red pigments have been reported in, e.g., an A. flavus strain (Gurupavithra et al. ). Carotenes are important terpenoid pigments and antioxidants that are produced in many bacteria, fungi, algae, and plants. Interestingly, carotene is produced by few Aspergillus species and not by Trichoderma reesei (Avalos and Limon ).

Secondary metabolites described in A. niger

Aspergillus niger has been claimed to produce a very large number of secondary metabolites (Table 6; Nielsen et al. ) including isoflavones which are actually plant metabolites (Umezawa et al.; Nielsen et al. ). Apart from many volatiles and small organic acids (Wani et al.; Priegnitz et al.; Costa et al. ), A. niger sensu stricto can produce a variety of other secondary metabolites. In many cases, fungi identified as A. niger were indeed A. tubingensis or other closely related species (Table 2).

Asperazine and similar diketopiperazine heterodimers (Varoglu et al.; Li et al. ) are not produced by A. niger, but consistently by A. tubingensis, A. vadensis, and A. luchuensis (Nielsen et al.; Varga et al.; Hong et al. 2013). However, such re-identifications from A. niger to A. tubingensis mean that co-occurrring metabolites are not necessarily produced by A. niger. For example, an asperazine- and asperazine A-producing isolate of A. tubingensis also produced cyclo(D-Phe-L-Trp), cyclo(L-Trp-L-Trp), walterolactone A, campyrones A-C, and kojic acid. According to our data, campyrones A-C are only produced by strains of A. tubingensis, and not by A. niger (but see Talontsi et al. ). Varoglu and Crews reported on asperic acid, hexylitaconic acid, malformin C, and pyrophen production by an asperazine-producing fungus, which should also be identified as A. tubingensis. Several of these compounds have later been found in A. tubingensis including 2-methylene-3-(6-hydroxyhexyl)-butanedioic acid, 2-carboxymethyl-3-hexyl-maleic acid anhydride, 2-methylene-3-hexyl-butanedioic acid (Almassi et al. ), demethylkotanin, TMC-256A1, TMC-256-C1 with an asperazine derivative (Ovenden et al. ), ergosterimide, 5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone, asperamide A & B, aspergillusol, asperpyrone A & C, dianhydroauransperone C, fonsecinone A-D, isopyrophen, nigerasperone A–C, aurasperone A–B, pyrophen, cyclo(L-Trp-L-Ile), cyclo(L-Trp-L-Phe), cyclo(L-trp-L-Tyr) (Zhang et al.,,,, ) asperic acid, campyrone A & C, tubigenoid anhydride A, 2-carboxymethyl-3-hexylmaleic anhydride (Koch et al. ), 6-isovaleryl-4-methoxy-pyran-2-one, asperpyrone A, campyrone A and rubrofusarin B (Ma et al. ), nigerapyrone A-E and asnipyrone A & B, and nigerasterols (Liu et al., ), and malformin A1, cyclo(Gly-L-Pro) and cyclo(Ala-Leu) (Tan et al. ). Gibberellic acid reported from A. “niger” NRRL 2270 (Ates and Gökdere ) is rather produced by A. tubingensis (this strain has indeed been reidentified as such) (Frisvad et al. ). A strain of Pestalotiopsis theae was probably overgrown by a strain of A. tubingensis, and thus, further secondary metabolites from A. tubingensis include pastalazine A & B and pestalamide A–C together with asperazine, aspernigrin A, and carbonarone A (see Ding et al. ).

A strain identified as A. niger was reported to produce asperiamide B and C (Wu et al. ), but it also produces the aflatoxin precursors averufin and nidurufin, so this strain was probably an A. flavus.

Small acids of Aspergillus niger

Oxalic acid, gluconic acid, and citric acid are small chelating organic acids derived from the citric acid cycle, but since they are secreted and accumulated may be characterized as secondary metabolites (Poulsen et al.; Niu et al. ). These are by far the small organic acids produced in the highest amounts, but other acids can be produced by A. niger (Table 5).

Aflavinines

Aflavinines are indoloterpenes biosynthesized from tryptophan and dimethylallyl units. They are only produced in sclerotia of A. niger (Frisvad et al. ). Such sclerotia are not produced on ordinary laboratory media, except if they are induced by the presence of small dried fruits, such as raisins (Frisvad et al. ). Most aflavinines are antiinsectan, but are not known to be toxic towards vertebrates (Gloer et al. ).

Asperamides

Asperamides are sphingolipids and unusual cerebrosides (Zhang et al.,,,). Such sphingolipids appear to be pretty widespread in fungi, but their function in fungi is often unknown. The similar flavusides from A. flavus are antibacterial (Yang et al. ).

Asperenones

The terpenes asperenones, asperyellones, and asperrubrols are carotenoid-like secondary metabolites. Asperenone is a human platelet aggregation inhibitor, and a strain of A. niger has been optimized for higher production of this bioactive compound (Chidananda et al. ).

Aspergitides

Aspergitides are NRP-derived tetrapeptides which are potentially anti-inflammatory (Lee et al. ). These hydrophobic tetrapeptides have some similarity with fungisporins and nidulanins which appear to be generally present in Aspergillus and Penicillium species (Ali et al.; Klitgaard et al.; Hautbergue et al. ).

Aspergillin

Aspergillin is a green polyketide (Ray and Eakin ) that may be connected with the production of the black pigment in the spores of A. niger. Other (yellow) pigments, such as funalenone and naphtho-γ-pyrones, are also connected with black melanin (Jørgensen et al. ).

Aspernigrins

The aspernigrins, carbonarones, nygerones, pestalamides, pyrophen, and tensidols are all related 2-benzylpyridin-4-one-containing metabolites of non-ribosomal peptide (NRP) and polyketide origin. They have several effects such as inhibiting HIV virus, being antifungal, or having neuroprotective effects (Hiort et al.; Ye et al.; Ding et al., Bandara et al.; Zhou et al. ). They have been isolated from Aspergillus section Nigri isolates and from fungi claimed to be Cladosporium (Ye et al. ) and Pestalotiopsis theae (Ding et al. ). The latter two fungi appear to have been overgrown by Aspergillus niger and Aspergillus tubingensis, respectively, as all secondary metabolites from these fungi have only been found in Aspergillus section Nigri (Nielsen et al. ).

Azanigerones

The azanigerones A–F needed chromatin remodeling in order to be produced by Aspergillus niger (Zabala et al. ). These compounds are polyketides, and little is known of their activity. However, like other azaphilones, they can probably bind amino acids, but no nitrogen-containing derivatives have been found yet.

Cycloleucomelone

Cycloleucomelone, leucomelone, and atromentin are shikimic acid-derived secondary metabolites that have been found in basidiomycetes (Turner; Turner and Aldridge ) but also species in Aspergillus section Nigri (Hiort et al.; Nielsen et al. ). These types of compounds may have radiation-protective characteristics, and they are widespread in Aspergillus (Frisvad and Larsen ). The analogous (heteroisoextrolites) terphenyllins are for example produced by members of Aspergillus section Candidi and aspulvinones by Aspergillus section Terrei (Turner; Turner and Aldridge; Frisvad and Larsen ).

Funalenone and naphtho-γ-pyrones

These polyketides have some genes in common with the pksA gene for production of the black pigment in Aspergillus niger (Jørgensen et al. ). Some naphtho-γ-pyrones have been claimed to be toxic (Ghosal et al. ), but they are not mycotoxins according to the definition accepted here. In fact, they can be exploited industrially as they have anti-oxidant, anti-cancer, anti-microbial, anti-HIV, anti-hyperuricuric, and anti-tubercular effects (Choque et al. ).

Malformins

Malformins are NRP cyclic peptides that originally were cited as toxic (Anderegg et al.; Kobbe et al.; Cole and Cox ), but they are not within the definition of mycotoxins in a strict sense, as malformin A has an oral LD50 of more than 50 mg/kg body weight in male mice. The toxicity data of Anderegg et al. and Kobbe et al. were based on malformin injection, which is not a natural route of intake. Furthermore, malformins have never been detected after mycotoxicosis caused by A. niger. Malformins are very promising anti-cancer agents, however (Park et al. ).

Nafuredin

Nafuredin is a polyketide terpene-derived secondary metabolite and is an inhibitor of anaerobic electron transport in pig roundworm, but it has very low effect on mammalian enzymes (Ui et al. ). It is a promising antihelminthic drug lead candidate.

Nigerasterols

Nigerasterols are terpene-derived sterols that display potent activity against tumor cell lines (Liu et al. ). There are as yet no data on vertebrate toxicity. The fungus (MA-132) was identified only by using ITS sequences, so it may be another species in Aspergillus section Nigri than A. niger that produces nigerasterols.

Nigerazines, aspernigerin, and nigragillins

The nigerazines, nigragillins, and aspernigerin are all related NRP-derived secondary metabolites. They are weakly insecticidal, and nigerazine B inhibits the root growth of lettuce seedlings (Caesar et al.; Iwamoto et al. ). They have not been reported as mycotoxins.

Nigerloxin

Nigerloxin is derived from an inhibitor of soy bean lipoxygenase and rat lens aldose reductase (Rao et al.,). It is a polyketide NRP hybrid. It is a strong antioxidant and is anti-diabetic and of low toxicity (Rao et al.; Suresha and Srinivasan; Vasantha et al. ).

Pseurotins

Pseurotins are NRP polyketide hybrid secondary metabolites that have neuritogenic (Komagata et al. ), antibiotic (Mehedi et al.; Pinheiro et al. ), anti-inflammatory (Shi et al. ), chitin-synthase inhibitor (Wenke et al. ), and antileishmanial and anticancer (Martinez-Luis et al. ) characteristics. Pseurotin A & D was reported to be produced together with chlovalicin (Uchoa et al. ) probably coded by an intertwined gene clusters, as is the case for Aspergillus fumigatus, where pseurotin A and fumagillin, chemically closely related to chlovalicin, are coded by an intertwined gene cluster (Wiemann et al.; Kishimoto et al. ). However, psurotins have not been reported from any other isolate of A. niger (Nielsen et al. ), so the two metabolites may be produced by another species in Aspergillus section Nigri.

Pyranonigrins

The pyranonigrins A–K are NRP-PK derived antioxidant secondary metabolites from A. niger (Hiort et al.; Miyake et al.; Kishimoto et al. ). There are several pyranonigrins isolated from Aspergillus niger, including pyranonigrin A–K (Kishimoto et al. ).

TAN-1612

The polyketide tetracyclic compound TAN-1612=BMS-192548 has been isolates from Aspergillus tubingensis WB 2346 and A. niger ATCC 1015 (Li et al. ). It is a neuropeptide Y receptor and neurokinin-1 receptor inhibitor (Kodukula et al.; Shu et al. ).

Tensyuic acids

The tensyuic acids are itaconic acid-derived secondary metabolites with anti-protozoan and antibacterial activities (Hasegawa et al.; Matsumara et al. ).

Yanuthones

The yanuthones are meroterpenoids with a 6-methyl salicylic acid precursor and terpene units attached (Holm et al.; Petersen et al.; Nielsen et al. ). There are no toxicity data for yanuthones, but they have antifungal activity (Petersen et al. ).

Secondary metabolites described in A. oryzae and A. flavus

A. flavus and A. oryzae can produce many secondary metabolites (Table 7). These can be subdivided into biosynthetic families. It is very interesting to note that, e.g., ustiloxin B and ustilaginoidin C, have both been isolated from the rice false smut pathogen Villosiclava virens (= Ustilaginoidea virens) even though they are not biosynthetically related. However, these two types of secondary metabolites have also been found in Aspergillus flavus (Umemura et al.; Tsukui et al.; Yoshimi et al. ). This is remarkable as both unrelated fungi occur on rice. One speculation could be that the gene clusters for both ustiloxins and ustilaginoidins were horizontally transferred from one fungus to the other during evolution. Ustilaginoidins are bis-naphtho-γ-pyrones (even called “mycotoxins” in the paper of Meng et al. and ustiloxins for toxic cyclic peptides by Tsukui et al. ). Like the heteroisoextrolite (Frisvad and Larsen ) analogues in Aspergillus section Nigri (normally also called naphtho-γ-pyrones, Nielsen et al.; Lu et al.; Choque et al. ), the ustilaginoidins are probably also involved in the formation of the green conidium color of Aspergillus section Flavi as it is known for the involvement of naphtho-γ-pyrones in black pigmentation in Aspergillus section Nigri isolates (Chiang et al.; Jørgensen et al.; Frisvad et al.; Niu et al. ). Other important secondary metabolites are described subsequently. Additionally, secondary metabolites that have been erroneously assigned to A. flavus or A. oryzae are also listed (Table 8).

Aflatrems

Aflatrem and β-aflatrem and their precursors are indoloterpenes that have been found in sclerotia of Aspergillus flavus (Gallagher and Wilson; Gallagher et al.,; Valdes et al.; Tanaka et al.; TePaske et al.; Zhang et al.; Duran et al.; Nicholson et al.; Ehrlich and Mack; Tang et al.; Gilbert et al. ). Aspergillus oryzae RIB 40 was found to produce the 13-desoxypaxilline precursor to aflatrem (Rank et al. ), and aflatrem has been heterologously expressed in A. oryzae NSAR1 (Tagami et al. ). However, if RIB40 is indeed a real A. flavus, A. oryzae sensu stricto isolates are not be able to produce sclerotia and sclerotial metabolites such as aflatrem.

Aflavarins

Aflavarins are polyketides found in the sclerotia of Aspergillus flavus (TePaske et al. ). These polyketides have not yet been found in any A. oryzae strain. Leporins, also found in A. leporis (TePaske et al. ), have been found in A. flavus (Cary et al. ), but they are not expected to be produced by A. oryzae.

Aflavinins

The aflavinins are sclerotium-borne indoloterpenes first isolated from A. flavus (Gallagher et al.,; Cole et al.; Wicklow and Cole; Gloer et al. ). These indoloterpenes and aflavazol were also isolated from the sclerotia of A. oryzae RIB40 (TePaske et al.; Rank et al. ). The aflavinins isolated from A. flavus (possibly A. minisclerotigenes or A. aflatoxiformans) include aflavinine, dihydroxyaflavinine, monohydroxyaflavinine, and monohydroxyisoaflavinine (Nozawa et al.; Tang et al. ).

Asperfuran

Asperfuran is a dihydrobenzofuran compound that was isolated from Aspergillus oryzae “HA 302-84” (Pfefferle et al. ), but it has also been isolated under the name of arthrographol from Arthrographis pinicola (Ayer and Nozawa ) and as asperfuran from Penicillium species (Yamaji et al.; Frisvad et al., ). Asperfuran is antifungal, but there are no reports on toxicity of this compound. Asperfuran production by authentic strains of A. oryzae has later been confirmed, and it has also been detected in Aspergillus sojae (Varga et al. ).

Aspergillic acids

These iron-chelating compounds have been used for discrimination between A. flavus and A. oryzae, in that Aspergillus oryzae sensu stricto has been claimed not to produce any of these pyrazine compounds. Testing Aspergillus flavus sensu stricto and Aspergillus oryzae sensu stricto has shown that it is only the former that can produce aspergillic acids (Bothast and Fennell; Hamsa and Ayres; Pitt et al.; Assante et al.; Liljegren et al.; Varga et al. ). However, compounds in this class have been reported from A. oryzae, including mutaaspergillic acid (Nakamura and Shiro,; Nakamura; Sugiyama et al.; Ohta and Ohta ), hydroxyaspergillic acid (Nakamura and Shiro,; Dutcher (as A. flavus); MacDonald; Ohta and Ohta; Sano et al. ), VI-2 (Ueno et al. ), A-2 (Sano et al. ), and aspergillic acid (Nishimura et al. ). Aspergillic acids have been evaluated for toxicity (Sasaki et al.; MacDonald; Perry et al. ), but Sano et al. suggest that the toxicity of aspergillic acids is so low that it can be present in fermented foods used for consumption. The strains producing aspergillic acid, indicated by the medium AFPA (Aspergillus flavus parasiticus agar), are probably representing Aspergillus flavus sensu stricto, but because of issues with potential aflatoxin production, they are called A. oryzae “short stipes.” The indicative red-orange color is caused by reaction of ferric ions with aspergillic acids (Assante et al. ) with none of these strains have been reported to produce aflatoxins (Sano et al. ).

Aspergillomarasmins

Aspergillomarasmin A, anhydroaspergillomarasmin A, and anhydromarasmic acid are polyamino acid compounds/phytotoxins related to lycomarasmin from Fusarium (Plattner and Clauson-Kaas; Hardegger et al. ), but they have also been found in Aspergillus oryzae or A. flavus (A. “flavus oryzae”) (Haenni et al. 1962; Haenni et al.; Robert et al. ). Aspergillomarasmin A is very interesting as it inhibits metallo-beta-lactamases and could thus help in overcoming bacterial resistance to penicillin (King et al.; Koteva et al. ). There are no data of toxicity of these compounds yet.

Asperopterins

Asperopterin A and B are compounds containing a pteridin ring system that were isolated from Aspergillus oryzae “T-17” (Kaneko and Sanada; Matsuura et al.; Hanaka et al. ) and have since been synthesized (Sugimoto et al.; Hanaka and Yamamoto ). Unfortunately, the original producer strain is not available, and there are no toxicity data available for the asperopterins. These compounds are blue fluorescing, so if they are produced by A. oryzae sensu stricto, these may be the compounds that could have been erroneously detected and identified as aflatoxins.

Aspirochlorines

Aspirochlorine is a halogenated diketopiperazine with a central disulfide bridge that was first isolated from Aspergillus oryzae IAM-2613 under the name oryzachlorin (Kato et al. ). The compound has also been chemically synthesized (Miknis and Williams; Wu et al. ). However, oryzachlorin was later shown to be the same as aspirochlorine and A30641 (Sakata et al.,,, ). It was isolated under the name A30641 from Aspergillus tamarii NRRL 8101, where it was co-occurring with canadensolide (Berg et al. ), as was also the case of a strain identified as A. flavus (Sakata et al. ). A strain of the latter was not available for more detailed studies. Another strain identified as A. flavus (“MDH-1420”) was shown to produce aspirochlorin and the related compound tetrathioaspirochlorine, and evidence for presence of the trithio analogue also (Klausmeyer et al. ). Furthermore, a bromoaspirochlorin, dechloroaspirochlorine, and O,O-dimethylaspirochlorine have been reported (Sakata et al. 1987). Aspirochlorin has been shown to be a highly selective and potent inhibitor of protein synthesis (Monti et al. ) and an effective inhibitor of fungi, bacteria, viruses, and murine tumor cells (Monti et al.; Chankhamjon et al. ). For these reasons and because epipolythiodiketopiperazines are generally toxic, the latter authors called aspirochlorin for a mycotoxin. The related mycotoxin gliotoxin was reported from 4 and 13% of clinical Aspergillus flavus strains (Lewis et al.; Kupfahl et al. ), but there is some doubt whether these data are correct (Patron et al.; Manzanares-Miralles et al.; Vidal-Garcia et al. ). On the other hand, Shaaban et al. isolated the reduced form of gliotoxin from A. “oryzae” MMAO1, and this latter isolate could be Aspergillus flavus sensu stricto. Gliotoxin-producing isolates have not been available for the scientific community (Varga et al. ). Aspirochlorin is a product of many species in section Flavi: A. avenaceus, A. caelatus, A. oryzae, A. parvisclerotigenus, A. sojae, and A. tamarii (Varga et al. ).

Asporyergosterol

Asporyergosterol and several other sterols were isolated from isolated from Aspergillus oryzae “cf-2” = CCTCC M 2010045, isolated from a marine alga (Qiao et al. ). The strain isolated could equally well be another Aspergillus, as A. oryzae in principle cannot be isolated from natural sources. An oxylipin and several sterols were isolated from A. flavus, isolated from an alga by the same authors (Qiao et al. ). The isolate also produced emeniveol and similar compounds and could probably in reality be A. cejpii, A. niveus, or A. striatus.

Avenaciolides and canadensolides

Canadensolides are formed via condensation of an acetate derived chain with a TCA cycle intermediate (Brookes et al.; Turner; Tanabe et al. ). It was first isolated from “Penicillium” canadense (McCorkindale et al. ), but it has been reported once from A. flavus (Sakata et al. ), and the related avenaciolide has been reported from A. avenaceus in Aspergillus section Flavi (Brookes et al.; Tanabem et al.; Varga et al. ). The avenaciolides are also present in Aspergillus glaber and A. stramenius from Aspergillus section Fumigati (Ellis et al.; Samson et al. ), and the avenaciolides are active against methicillin-resistant Staphylococci (Chang et al. ). Avenaciolide is also a specific inhibitor of glutamate transport in rat liver mitochondria (McGivan and Chappell ). Isoavenaciolide has been reported as an anti-cancer agent (Al-Tel et al. ). However, there are no indications that avenaciolide is a mycotoxin.

Csypyrones

Type III polyketides are rare among fungi, but more common in plants and bacteria (Juvvadi et al.; Hashimoto et al.; Shimizu et al. ). Aspergillus oryzae can, however, produce csypyrone B1, B2, and B3 and 3,5-dihydroxybenzoic acid (Seshime et al.,,; Hashimoto et al. ). Interestingly, Aspergillus niger produces protocatechuic acid, also a type III polyketide (Lv et al. ). Other fungi that can produce type III polyketides are and Botrytis cinerea (Hashimoto et al. ). There are no toxicity data for these secondary metabolites.

Drim-9(11)-en-8-ol (R and S)

This sesquiterpene compound has been isolated from A. oryzae strains that also produce sporogen AO1 and similar compounds, but very little is known on the bioactivity of this compound (Wada et al.; Leite et al.; Domíngues et al.; Shishido et al.; Armstrong et al.; Jansen and de Groot; ).

Flufuran

Flufuran, other related furans, and small molecular weight secondary metabolites, including 4-hydroxybenzoic acid, were isolated from Aspergillus oryzae and A. flavus (Evidente et al.; Lee et al.; Saldan et al. ). Flufuran has antifungal activity (Evidente et al. ).

Heptelidic acids

Heptelidic acid (=koningic acid), hydroheptelidic acid, gliocladic acid, and trichoderonic acid are sesquiterpenes that have antibiotic and anticancer properties (Itoh et al.; Nakazawa et al.; Kim and Lee ). Heptelidic acid has been reported from both Aspergillus oryzae and A. flavus (Lee et al.; Skóra et al. ).

Kojic acids

Kojic acid was the first compound to be isolated from Aspergillus oryzae (Yabuta,; Birkinshaw et al.; Jennings and Williams; Parrish et al.; Morton et al.; Marston; Bentley ). A dimer of kojic acid has been structure-elucidated as the bright greenish yellow flourescence pigment from Aspergillus flavus (Zeringue et al. ). Koji acid is common for nearly all species in Aspergillus section Flavi (Varga et al. ). However, kojic acid is not regarded as a mycotoxin (Bentley ). The gene cluster coding for kojic acid production is known (Terabayashi et al. ). 7-O-acetylkojic acid has also been isolated from A. flavus (Sun et al. ).

Kojistatins

An isolate of an industrial strain of Aspergillus oryzae (ATCC 20386 and FERM-15834) produced kojistatin A = CPI-4 and related cystein protease inhibitors, called CPI 1-5 (Sato et al.; Yamada et al. ). The kojistatins are nonribosomal peptide–polyketide hybride molecules. There are no data on the toxicity of these compounds.

Maltoryzin

The polyketide maltoryzin was reported from a strain of A. oryzae var. “microsporis” isolated from malting barley (Iizuka and Iida ). However, the fungus could also be an Aspergillus clavatus, which is very common in malting barley (Lopez Diaz and Flannigan ). A. oryzae or A. flavus has not been reported from malting barley. On the other hand, Bakhali et al. reported on maltoryzin production by A. flavus from walnuts.

Miyakamides

Miyakamides A1, A2, B1, and B2 (Shiomi et al. ), and oryzamide A1–2 (Rank et al. ) have been reported from both Aspergillus flavus “var. columnaris” FKI-0739 and A. oryzae RIB40 and are NRPs. The miyakamides are antimicrobial compounds, but there are no toxicity data on these compounds. Since the A. flavus strain FKI-0739 produced hydroxyaspergillic acid also (Shiomi et al. ), it was probably an A. flavus sensu stricto. As discussed earlier, RIB40 may also in reality be an A. flavus sensu stricto.

Oryzaeins

The polyketides oryzaein A–D, tabaisocoumarin A, caudacoumarin C, versicolol B, and exserolide D and F are antiviral and cytotoxic isocoumarin derivatives isolated from a fungus identified as A. oryzae isolated from the rhizome of the marine Paris polyphylla var. yunnanensis (Zhou et al. ), and thus, the producing strain is probably an A. flavus sensu stricto. However, compounds with isochroman chromophores have been found in extracts of some A. oryzae (Frisvad JC, “personal data”). The four oryzaeins had moderate to weak inhibitory effect against some human tumor cell lines (Zhou et al. ), but their actual toxicity is unknown.

Oryzines

Oryzines are maleidrides biosynthetically produced from acyl CoA thiolester and from oxaloacetic acid (Wasil et al. ). RIB 203, the producing strain, is from sake-koji and thus represents a real A. oryzae. There are no data on the bioactivity of these compounds as yet.

Parasiticolides

Parasiticolide A = astellolide A is a sesquiterpene that was first found in Aspergillus parasiticus from section Flavi (Hamasaki et al. ) and Aspergillus stellatus from section Nidulantes (Gould et al. ), and later parasiticolide A, dideacetylparasiticolide A, and 14-deacetyl parasiticolide A were isolated from A. oryzae RIB40 (Rank et al. ). Ren et al. found astellolides A, B, C–E, and F–I in Aspergillus oryzae QXPV-4 isolated from the insect Coccinella septempunctata. The origin of QXPV-4 indicates that this was also an A. flavus sensu stricto, rather than an A. flavus. Shinohara et al. also found parasiticolides = astellolides in A.oryzae RIB40: 14-deacetyl astellolide A = 14-deacetyl parasiticolide A (already found by Rank et al. ), and 14-deacetyl astellolide B. Depending on the opinion of the taxonomic status of A. flavus and A. oryzae, parasiticolides are secondary metabolites of one of these species or both.

Penicillins

Penicillins are non-ribosomally synthesized tripeptides (NRP) that have been reported from A. oryzae (Waksman and Bugie; Foster and Karow; Marui et al. ) and A. flavus originally as flavicidin (Bush and Goth; McKee and MacPhillamy; McKee et al.; Waksman and Bugie; RG Benedict, unpublished in Raper ). This important antibiotic is not regarded as a mycotoxin, but it is unwanted in industrial fermentations due to its wide use to treat microbial infections.

Pseurotins

Pseurotins are hybrid NRP/PKS compounds that have been found in A. leporis and A. nomius from Aspergillus section Flavi (Varga et al. ) and were also reported from A. “oryzae” MMAO1 (Shaaban et al. ) and A. flavus (Rodríguez et al. ). The pseurotins are not regarded as mycotoxins, but these compounds should be examined in more detail, as they have neuritogenic (Komagata et al. ), antibiotic (Mehedi et al.; Pinheiro et al. ), anti-inflammatory (Shi et al. ), chitin-synthase inhibitor (Wenke et al. ), and antileishmanial and anticancer (Martinez-Luis et al. ) characteristics.

Sporogens

Sporogen AO1 (=13-desoxyphomenone) is a sesquiterpenoid that was isolated from Aspergillus oryzae NOY-2, but the strain is not available to the scientific community. This compound induces conidiation in a less sporulating strain (Tanaka et al. 1984,b). Sporogen AO1 has later been found in strains of A. flavus (Frisvad and Larsen, unpublished). Phomenone, related to sporogen AO1, is a potent inhibitor of protein synthesis (Moule et al. ) and has moderate toxicity to shrimps (Capasso et al. ). Phomenone was recently shown to stimulate pro-inflammatory responses in murine cells and thus may exacerbate allergic reactions if inhaled (Rand et al. ). There are no direct data showing that these compounds are mycotoxins, but they are not unlike the mycotoxin PR-toxin in structure (Cole and Cox; Moule et al.; Capasso et al. ). Many of the sporogens are phytotoxins (Daengrot et al. ).

TMC-2A, -2B and -2C

The NRP-derived peptide-like compounds TMC-2A, -2B, and 2C were isolated from a strain identified as A. oryzae A374 = FERM P-14934 (Nonaka et al.; Asai et al. ). From the description of the strain, and as it was isolated from soil, it appears that the strain is rather an Aspergillus tamarii, as the conidia were large, distinctly roughened, and brown. These peptide-like compounds may be used as lead compounds to find better rheumatoid arthritis inhibitors, but toxicity data have not been presented.

Tryptophenalins

A fungus identified as A. oryzae (MMAO1) was isolated from rice hulls, and this fungus produced a dimeric diketopiperazine compound, ditryptophenaline, 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione, cyclo-(Trp-Tyr), cyclo-(Pro-Val), α-cyclopiazonic acid, (bismethylthio)gliotoxin, pseurotin A, kojic acid, linoleic acid, and uridine (Shaaban et al. ). Since the isolate was from rice hulls in a domesticated field, it was probably an A. flavus, but it could also be an A. nomius since pseurotin A has only been found once in A. flavus (see Varga et al.; Rodríguez et al. ). Ditryptoleucine, related to ditryptophenaline from A. flavus (Springer et al. ) was isolated from A. oryzae RIB40 (Rank et al. ). The toxicity of the diketopiperazines cyclo-(Trp-Tyr), cyclo-(Pro-Val) is unknown. The monomer of ditryptophenaline, cyclo-N-methylphenyl-alanyltryptophanyl has also been isolated (Kozlovskii et al. ).

Ustilaginoidins

The polyketide ustilaginoidin C was isolated as a suggested conidium pigment from A. parasiticus (Brown et al. ), and a compound with the same chromophore has been isolated from A. flavus (Frisvad, JC, unpublished data), so it could be representing the general naphtho-γ-pyrone pigment type produced in Aspergillus section Flavi. There are no toxicity data on these compounds.

Ustiloxin B

This ribosomally produced cyclic peptide (RIPS, ribosomally produced peptides) compound was isolated from Aspergillus flavus and A. oryzae (Umemura et al. 2013, b, 2014; Ye et al.; Yoshimi et al. ). The ustiloxins are phytotoxins first isolated from Villosiclava virens (= Ustilaginoidea virens), and they exibit potent antimitotic activity and inhibit microtubule assembly (Koiso et al. ), and they have also been called mycotoxins (Koiso et al. ). The ustiloxins are not established as mycotoxins. A. oryzae RIB40 does not produce ustiloxin B, probably because of the large deletion of the ustR gene encoding a transcriptional regulation that regulates ustiloxin B production (Umemura et al. ).

Secondary metabolites that are not produced by A. flavus or A. oryzae

Due to the close relatedness between A. flavus and A. oryzae as well as their similarity to other species, some reports have misleadingly described production of secondary metabolites in A. flavus or A. oryzae that they do not produce (Table 8).

Secondary metabolites described in T. reesei

Peptaibol non-ribosomal peptides (peptaibiotics) and similar peptides are produced by many Trichoderma species (Zeilinger et al. ), but it is only paracelsin A, C, and D in this class that have been reported from T. reesei (Brückner and Graf; Brückner et al.; Pócsfalvi et al.; Przybylski et al. ). The paracelsins were reported from an authentic strain of T. reesei (QM 9414 (mutant of QM 6a) = ATCC 26421 = CBS 392.92 and the wild ex type strain from cotton duck shelter, Bougainville Island QM 6a (= ATCC 13631 = CBS 383.78). Paracelsins are linear peptides containing a high level of uncommon amino acids, alphaaminoisobutyric acid (Aib), and isovaline (Iva), together with an acetylated N-terminal amino acid and a C-terminal amino alcohol (Pócsfalvi et al. ). These compounds have shown antimicrobial activity. There are no data on the toxicity of the paracelsins.

The sorbicillin biosynthetic family compounds have been reported from Trichoderma sp. USF 2690 (Abe et al. ) (strain not available in any culture collection), and it is only mentioned to be a product of T. reesei in the Antibase secondary metabolite database. The Trichodermatides (A–D) are produced by a fungus claimed to be a marine T. reesei (Sun et al.; Shigehisa et al. ), but the culture is unavailable in culture collections, and may be one of the many other known Trichoderma species. T. reesei may also produce some other non-ribosomal peptides, including intracellular and extracellular siderophores (Zeilinger et al. ). Siderophores such as ferricrocin have not been claimed to be toxic. Among the polyketides, the genes for a conidium pigment related to aurofusarin and bikaverin have been reported (Zeilinger et al. ). This polyketide compound (not structure elucidated) is probably a precursor for the green pigment (melanin) in the conidia of T. reesei, and generally, these conidium pigments have not been claimed to be toxic. T. reesei have PKS gene clusters for production of other polyketides, which are not unlike those for citrinin and fumonisins (Baker et al. ), but neither citrinin nor fumonisins have been detected in T. reesei. In conclusion, the only secondary metabolites that appear to be naturally produced by T. reesei are the paracelsins.

Based on genome sequencing data (Schmoll et al. ), several potential toxic secondary metabolites may be produced under special conditions. Such secondary metabolites have not been detected yet in T. reesei, however. Genome sequencing showed that there are 8 NRKS, 11 PKS, 2 NRPS-PKS hybrid, and 12 terpenoid synthase encoding genes (Schmoll et al.; Zeilinger et al. ). The LaeA and VELVET regulatory genes are important for the expression of secondary metabolites in T. reesei, but nevertheless, only few of the putative gene clusters for secondary metabolites seem to be actually expressed.

Conclusions

Aspergillus oryzae produce few recognized mycotoxins, and they are only produced by few strains. If they are produced, there are genetic means of inactivating the biosynthetic pathways, so isolates of the species can be exploited for production of enzymes and as a transformation host for industrially relevant secondary metabolites or enzymes. Some isolates of Aspergillus niger can produce three types of mycotoxins, ochratoxin A, fumonisin B2 (B4 and B6), and oxalic acid. Again, genetic means have been employed to inactivate the gene clusters for ochratoxins and fumonisins, while accumulation of the less toxic oxalic acid can be avoided by chosing an optimal substrate or use optimal procedures for the industrial products. Trichoderma reesei cannot produce any recognized mycotoxins and is one of the most important enzyme producers in the industry. All three species can produce interesting secondary metabolites, of which some are drug lead candidates and others, such as citric acid, are important bulk chemicals that are produced by fermentation.

References 529

  1. 1.

    Abarca ML, Bragulat MR, Castella G, Cabanes FJ. Ochratoxin A production by strains of Aspergillus niger var. niger. Appl Environ Microbiol. 1994;60:2650-2652.

    Not in our library10.1128/aem.60.7.2650-2652.1994

  2. 2.

    Abdelghany TM, El-Nagger MA, Ganash MA, Al Abboud MA. PCR identification of Aspergillus niger with using natural additives for controlling and detection of malformins and maltoryzine production by HPLC. BioNanoSci. 2017;7:588-596.

    Not in our library10.1007/s12668-017-0455-6

  3. 3.

    Abe K, Gomi K, Hasegawa F, Machida M. Impact of Aspergillus oryzae genomics on industrial production of metabolites. Mycopathologia. 2006;162:143-153.

    Not in our library10.1007/s11046-006-0049-2

  4. 4.

    Abe S, Saito T, Takayama KI, Furuya A (1961) L-Malic acid by fermentation. British patent no. 884,029, December 6

    Not in our library

  5. 5.

    Abe N, Sugimoto O, Arakawa T, Tanji K, Hirota A. Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690. Biosci Biotechnol Biochem. 2001;65:2271-2279.

    Not in our library10.1271/bbb.65.2271

  6. 6.

    Adler M, Wintersteiner O. A reinvestigation of flavacidin, the penicillin produced by Aspergillus flavus. J Biol Chem. 1948;176:873-891.

    Not in our library

  7. 7.

    Aiso K, Arai T, Shidara I, Kurihara H, Morita Y. A new broad spectrum antibiotic, violacetin. J Antibiot. 1955;8:33-38.

    Not in our library

  8. 8.

    Ali H, Ries MI, Lankhorst PP, van der Hoeven RAM, Schouten OL, Noga M, Hankemeier T, van Peij RAL, Vreeken RJ, Driessen AJM. A non-canonical NRPS is involved in the synthesis of fungisporin and related hydrophobic cyclic tetrapeptides in Penicillium chrysogenum. PLoS ONE. 2014;9:e98212.

    Not in our library10.1371/journal.pone.0098212

  9. 9.

    Almassi F, Ghisalberti EL, Rowland CY. Alkylcitrate-derived metabolites from Aspergillus niger. J Nat Prod. 1994;57:833-836.

    Not in our library10.1021/np50108a024

  10. 10.

    Al-Musallam A. Revision of the black Aspergillus species. 1980.

    Not in our library

  11. 11.

    Al-Tel TH, Al-Qawasmeyh R, Sabri SS, Voelter W. Differential use of anhydropyranosides for eantiomere routes to bis-g-butyrolactones: a new approach to the frameworks of antibiotic and anticancer agents isoavenaciolide and ethisolide. J Org Chem. 2009;74:4690-4696.

    Not in our library10.1021/jo900192a

  12. 12.

    Anderegg Robert J., Biemann Klaus, Buechi George, Cushman Mark. Malformin C, a new metabolite of Aspergillus niger. Journal of the American Chemical Society. 1976;98(11):3365-3370.

    Not in our library10.1021/ja00427a051

  13. 13.

    Andersen MR, Salazar MP, Schaap PJ, van de Vondervoort PJI, Culley D, Thykaer J, Frisvad JC, Nielsen KF, Albang R, Albermann K, Berka RM, Braus GH, Braus-Stromeyer SA, Corrochano LM, Dai Z, van Dijck PWM, Hofmann G, Lasure LL, Magnusson JK, Meijer SL, Nielsen JB, Nielsen ML, van Ooyen AJJ, Panther KS, Pel HJ, Poulsen L, Samson RA, Stam H, Tsang A, van den Brink JM, Atkins A, Aerts A, Shapiro H, Pangilinan J, Salamov A, Lou Y, Lindquist E, Lucas S, Grimwood J, Grigoriev IV, Kubicek CP, Martinez D, van Peij NNME, Roubos JA, Nielsen J, Baker S. Comparative genomics of citric-acid producing Aspergillus niger ATCC 1015 versus enzyme-producing CBS 513.88. Genome Res. 2011;21:885-897.

    Not in our library10.1101/gr.112169.110

  14. 14.

    Armstrong V, Cortes M, Lopez J. A revision of the absolute configuration of drim-9(11)-en-8-alfa-ol. Nat Prod Lett. 1996;8:225-229.

    Not in our library10.1080/10575639608044897

  15. 15.

    Asai Y, Nonaka N, Nishio M, Okamura K, Date T, Sugita T, Ohnuki T, Komatsubara S. TMC-2A, -2B and -2C, new dipeptidyl peptidase IV inhibitors produced by Aspergillus oryzae A374. II. Isolation and structure elucidation. J Antibiot. 1997;50:653-658.

    Not in our library10.7164/antibiotics.50.653

  16. 16.

    Asao T, Büchi G, Abdel-Kader MM, Chang SB, Wick EL, Wogan GN. Aflatoxins B and G. J Am Chem Soc. 1963;85:1706-1707.

    Not in our library10.1021/ja00894a050

  17. 17.

    Asao T, Büchi G, Abdel-Kader MM, Chang SB, Wick EL, Wogan GN. The structures of aflatoxins B and G1. J Am Chem Soc. 1965;87:882-886.

    Not in our library10.1021/ja01082a031

  18. 18.

    Assante G, Camarda L, Locci R, Merlini L, Nasini G, Papadopoulos E. Isolation and structure of red pigments from Aspergillus flavus and related species, growth on a differential medium. J Agric Food Chem. 1981;29:785-787.

    Not in our library10.1021/jf00106a023

  19. 19.

    Atalla MM, Hassanein NM, El-Beih AA, Youssef YAG. Mycotoxin production in wheat grains by different Aspergilli in relation to different relative humidities and storage periods. Nahrung. 2003;47:6-10.

    Not in our library10.1002/food.200390017

  20. 20.

    Ates S, Gökdere M. Effect of silicone oil on gibberellic acid production by Gibberella fujikuroi and Aspergillus niger. Appl Biochem Microbiol. 2006;42:500-501.

    Not in our library10.1134/s0003683806050097

  21. 21.

    Avalos J, Limon MC. Biological roles of fungal carotenoids. Curr Genet. 2015;61:309-324.

    Not in our library10.1007/s00294-014-0454-x

  22. 22.

    Awakawa T, Yang X-L, Wakimoto T, Abe I. Pyranonigrin E: a PKS-NRPS hybrid metabolite from Aspergillus niger identified by genome mining. ChemBioChem. 2013;14:2095-2099.

    Not in our library10.1002/cbic.201300430

  23. 23.

    Ayer WA, Nozawa K. Taxonomy and chemistry of a new fungus from bark beetle infested Pinus contorta var. latifolia. 2. Arthrographol, the metabolite inhibitory to Ophiostoma clavigerum. Can J Microbiol. 1990;36:83-85.

    Not in our library10.1139/m90-016

  24. 24.

    Baker SE. Aspergillus niger genomics: past, present and into the future. Med Mycol. 2006;44:S17-S21.

    Not in our library10.1080/13693780600921037

  25. 25.

    Baker SE, Perrone G, Richardson NM, Gallo A, Kubicek CP. Phylogenomic analysis of polyketide synthase encoding genes in Trichoderma. Microbiology-SGM. 2012;158:147-154.

    Not in our library10.1099/mic.0.053462-0

  26. 26.

    Bakhali A, El-Samawaty AMA, Abd El-Rahim MA, Yassin MA, El-Naggar MA, Muhammed MH (2015) Toxigenic fungal biota associated with walnut in Saudi Arabia. J Pure Appl Microbiol 7:1079–1086

    Not in our library

  27. 27.

    Baltz RH, Demain AL, Davies JE (eds) (2010) Manual of industrial microbiology and biotechnology. 3rd ed, ASM Press, Washington DC

    Not in our library

  28. 28.

    Bandara HMSKH, Kumar NS, Jayasinghe L, Masubuti H, Fujimoto Y. A 3-vinyl cephem derivative, a useful intermediate in the synthesis of cepham antibiotics, from Aspergillus awamori associated with banana fruit. Nat Prod Commun. 2015;10:1663-1666.

    Not in our library

  29. 29.

    Barbesgaard P, Heldt-Hansen HP, Diderichsen B. On the safety of Aspergillus oryzae: a review. Appl Microbiol Biotechnol. 1992;36:569-572.

    Not in our library10.1007/bf00183230

  30. 30.

    Barnes CL, Steiner JR, Torres E, Pacheco R, Marquez H. Structure and absolute configuration of pyrophen, a novel pyrone derivative of L-phenylalanine from Aspergillus niger. Int J Pept Prot Res. 1990;36:292-296.

    Not in our library10.1111/j.1399-3011.1990.tb00981.x

  31. 31.

    Bennett JW, Inamdar AA. Are some fungal volatile organic compounds (VOCs) mycotoxins? Toxins. 2015;7:3785-3804.

    Not in our library10.3390/toxins7093785

  32. 32.

    Bentley R. From miso, sake and shoyu to cosmetics: a century of science for kojic acid. Nat Prod Rep. 2006;23:1046-1062.

    Not in our library10.1039/b603758p

  33. 33.

    Berg DH, Massing RP, Hoehn MM, Boeck LD, Hamill RL. A30641, a new epidithiodiketopiperazine with antifungal activity. J Antibiot. 1976;29:394-397.

    Not in our library10.7164/antibiotics.29.394

  34. 34.

    Bertrand RL, Abdel-Hameed M, Sorensen JL. Lichen biosynthetic gene clusters part II: homology mapping suggests a functional diversity. J Nat Prod. 2018;81:732-748.

    Not in our library10.1021/acs.jnatprod.7b00770

  35. 35.

    Bills Gerald F, Yue Qun, Chen Li, Li Yan, An Zhiqiang, Frisvad Jens C. Aspergillus mulundensis sp. nov., a new species for the fungus producing the antifungal echinocandin lipopeptides, mulundocandins. The Journal of Antibiotics. 2015;69(3):141-148.

    Not in our library10.1038/ja.2015.105

  36. 36.

    Birkinshaw JH, Charles JHV, Lilly CH, Raistrick H. The biochemistry of microorganisms VII. Kojic acid (5-hydroxy-2-hydroxymethylpyrone). Phil Trans R Soc London. 1931;B220:127-138.

    Not in our library10.1098/rstb.1931.0018

  37. 37.
    antiSMASH 4.0—improvements in chemistry prediction and gene cluster boundary identification · 2017
    No notice
  38. 38.

    Blochwitz A. Die Gattung Aspergillus. Neue spezies. Diagnosen. Synonyme. Ann Mycol. 1929;27:205-240.

    Not in our library

  39. 39.

    Blumenthal CZ. Production of toxic metabolites in Aspergillus niger, Aspergillus oryzae and Trichoderma reesei: justification of mycotoxin testing in food grade enzymes derived from the three fungi. Reg Toxicol Pharmacol. 2004;39:214-228.

    Not in our library10.1016/j.yrtph.2003.09.002

  40. 40.

    Bothast RJ, Fennell DI. A medium for rapid identification and enumeration of Aspergillus flavus and related organisms. Mycologia. 1974;66:365-369.

    Not in our library10.1080/00275514.1974.12019615

  41. 41.

    Bouras N, Mathieu F, Coppel Y, Lebrihi A. Aurasperone F—a new member of the naphtho-gamma-pyrone class isolated from a cultures microfungus, Aspergillus niger C-433. Nat Prod Res. 2005;19:653-659.

    Not in our library10.1080/14786410412331286955

  42. 42.

    Bouras N, Mathieu F, Coppel Y, Strelkov SE, Lebrihi A. Occurrence of naphtho-gamma-pyrones- and ochratoxin A-producing fungi in French grapes and characterization of new naphtho-gamma-pyrone polyketide (aurasperone G) isolated from Aspergillus niger C-433. J Agric Food Chem. 2007;55:8920-8927.

    Not in our library10.1021/jf071406z

  43. 43.

    Braun MS, Wink M. Exposure, occurrence, and chemistry of fumonisins and their cryptic derivatives. Compr Rev Food Sci Food Saf. 2018;17:769-791.

    Not in our library10.1111/1541-4337.12334

  44. 44.

    Brookes D, Tidd BK, Turner WB. Avenaciolide, an antifungal lactone from Aspergillus avenaceus. J Chem Soc. 1963;1963:5385-5391.

    Not in our library10.1039/jr9630005385

  45. 45.

    Brown DW, Hauser FM, Tommasi R, Corlett SS, Salso JJ. Structural elucidation of a putative conidial pigment from Aspergillus parasiticus. Tetrahedron Lett. 2003;44:419-422.

    Not in our library10.1016/s0040-4039(02)02886-1

  46. 46.

    Brückner H, Graf H. Paracelsin, a peptide antibiotic containing α-aminobutyric acid, isolated from Trichodeerma reesei Simmons. Part A. Experientia. 1983;39:528-530.

    Not in our library10.1007/bf01965190

  47. 47.

    Brückner H, Graf H, Bokel M. Paracelsin; characterization by NMR spectroscopy and circular dichroism, and hemolytic properties of a peptaibol antibiotic from the cellulolytically active mold Trichoderma reesei. Part B. Experientia. 1984;40:1189-1197.

    Not in our library10.1007/bf01946646

  48. 48.

    Bugni TS, Abbanat D, Bernan VS, Maiese WM, Gereenstein M, van Wagoner RM, Ireland CM. Yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem. 2000;65:7195-7200.

    Not in our library10.1021/jo0006831

  49. 49.

    Burdock GA, Carabin IG, Madhusudan GS. Safety assessment of β-nitropropionic acid: a monograph in support of an acceptable daily intake in humans. Food Chem. 2001;75:1-27.

    Not in our library10.1016/s0308-8146(01)00194-7

  50. 50.

    Burkhardt HJ, Forgacs J. O-methylsterigmatocystin, a new metabolite from Aspergillus flavus, Link ex Fries. Tetrahedron. 1968;24:717-720.

    Not in our library10.1016/0040-4020(68)88020-2

  51. 51.

    Bush MT, Goth A. Flavicin: an antibacterial substance produced by an Aspergillus flavus. J Pharmacol Exptl Therap. 1943;78:164-169.

    Not in our library

  52. 52.

    Bush MT, Goth A, Dickison HL. Flavicin II: an antibacterial substance produced by an Aspergillus flavus. J Pharmacol Exp Ther. 1945;84:262-277.

    Not in our library

  53. 53.

    Bush MT, Touster O, Brockman JE. The production of β-nitropropionic acid by a strain of Aspergillus flavus. J Biol Chem. 1951;188:685-693.

    Not in our library

  54. 54.

    Caesar F, Jansson K, Mutschler E. Über Nigragillin, ein neues Alkaloid aus der Aspergillus niger-Gruppe. 1. Mitteilung. Isolierung and Strukturaufklärung des Nigragillins und eines Dioxopiparazine. Pharm Acta Helv. 1969;44:676-690.

    Not in our library

  55. 55.
    How a fungus shapes biotechnology: 100 years of Aspergillus niger research · 2018
    No notice
  56. 56.

    Capasso R, Iacobellis NS, Bottalico A, Randazzo G. Structure-toxicity relationships of the eremophilane phomenone and PR-toxin. Phytochemistry. 1984;23:2781-2784.

    Not in our library10.1016/0031-9422(84)83015-0

  57. 57.

    Cary JW, Ehrlich KC. Aflatoxigenicity in Aspergillus: molecular genetics, phylogenetic relationship and evolutionary implications. Mycopathologia. 2006;162:167-177.

    Not in our library10.1007/s11046-006-0051-8

  58. 58.

    Cary JW, Uka V, Han Z, Buyst D, Harris-Coward PY, Ehrlich KC, Wei Q, Bhatnagar D, Down PF, Martens SL, Calvo AM, Martins JC, Vanheaecke L, Coenye T, de Saeger S, di Mavungu JD. An Aspergillus flavus secondary metabolic gene cluster containing a hybrid PKS-NRPS is necessary for synthesis of the 2-pyridones, leporins. Fung Genet Biol. 2015;81:88-97.

    Not in our library10.1016/j.fgb.2015.05.010

  59. 59.

    Casadevall A, Pirofski L-A. The damage-response framework of microbial pathogenesis. Nat Rev Microbiol. 2003;1:17-24.

    Not in our library10.1038/nrmicro732

  60. 60.

    Cendoya E, Chiotta ML, Zachetti V, Chulze SN, Ramirez ML. Fumonisins and fumonisin producing Fusarium occurrence in wheat and wheat by products: a review. J Cer Sci. 2018;80:158-266.

    Not in our library10.1016/j.jcs.2018.02.010

  61. 61.

    Chang C.M, Chern J, Chen M-Y, Huang K-F, Chen CH, Yang YL, Wu SH (2015) Avenaciolides: potenatial Mur A-targeted inhibitors against peptidoglycan biosynthesis in methicillin-resistant Staphylococcus aureus (MRSA). J Am Chem Soc 137:267–275

    Not in our library10.1021/ja510375f

  62. 62.

    Chang P-K, Wilkinson JR, Horn BW, Uy J, Bhatnagar D, Cleveland TE. Genes differentially expressed by Aspergillus flavus strains after loss of aflatoxin production by serial transfers. Appl Microbiol Biotechnol. 2007;77:917-925.

    Not in our library10.1007/s00253-007-1224-1

  63. 63.

    Chankhamjon P, Hoettger-Schmidt D, Scherlach K, Urbansky B, Lackner G, Kalb D, Dahse H-M, Hoffmeister D, Hertweck C. Biosynthesis of the halogenated mycotoxin aspirochlorin in koji mold involves a cryptic amino acid conversion. Angew Chem Int Ed. 2014;53:13409-13413.

    Not in our library10.1002/anie.201407624

  64. 64.

    Chen AJ, Hubka V, Frisvad JC, Visagie CM, Houbraken J, Meijer M, Varga J, Rasine D, Jurjević Ž, Kubátová A, Sklenář F, Samson RA. Polyphasic taxonomy of Aspergillus section Aspergillus (formerly Eurotium) and its occurrence in indoor environment and food. Stud Mycol. 2017;88:37-135.

    Not in our library10.1016/j.simyco.2017.07.001

  65. 65.

    Chiang Y-M, Meyer KM, Praseuth M, Baker SE, Bruno KS, Wang CCC. Characterization of a polyketide synthase in Aspergillus niger whose product is a precursor for both dihydroxynaphthalene (DHN) melanin and naphtho-γ-pyrone. Fungal Genet Biol. 2011;48:430-437.

    Not in our library10.1016/j.fgb.2010.12.001

  66. 66.

    Chidananda C, Kumar CM, Sattur AP. Strain improvement of Aspergillus niger for the enhanced production of asperenone. Ind J Microbiol. 2008;48:274-278.

    Not in our library10.1007/s12088-008-0026-1

  67. 67.

    Choque E, El Rayess Y, Reaynal J, Mathieu F. Fungal naphtho-γ-pyrones—secondary metabolites of industrial interest. Appl Microbiol Biotechnol. 2015;99:1081-1096.

    Not in our library10.1007/s00253-014-6295-1

  68. 68.

    Christensen M. A synoptic key and evaluation of the species in the Aspergillus flavus group. Mycologia. 1981;73:1056-1084.

    Not in our library10.1080/00275514.1981.12021441

  69. 69.

    Christensen BE, Mølgaard H, Kaasgaard S, Lehmbeck J, Mølgaard MDLH (2000) Producing a polypeptide of interest such as a hormone or enzyme, comprising cultivating a mutant of a parent Aspergillus cell which produces less of at least one toxin of interest compared to the parent cell under the same conditions. Patent, WO200039322, July 6.

    Not in our library

  70. 70.

    Cihangir N. Stimulation of the gibberellic acid synthesis by Aspergillus niger in submerged culture using a precursor. World J Microbiol Biotechnol. 2002;18:727-729.

    Not in our library10.1023/a:1020401507706

  71. 71.

    Clevenger KD, Bok JW, Ye R, Miley GP, Verdan MH, Velk T, Chen C, Yang KH, Robey MT, Gao P, Lamprecht M, Thomas PM, Islam MN, Palmer JM, Wu CC, Keller NP. A scalable platform to identify fungal secondary metabolites and the gene clusters. Nat Chem Biol. 2017;13:895-901.

    Not in our library10.1038/nchembio.2408

  72. 72.

    Cole RJ, Cox RH. Handbook of toxic fungal metabolites. 1981.

    Not in our library

  73. 73.

    Cole RJ, Dorner JW, Springer JP, Cox RH. Indole metabolites from a strain of Aspergillus flavus. J Agric Food Chem. 1981;29:293-295.

    Not in our library10.1021/jf00104a019

  74. 74.

    Cole RJ, Kirksey JW, Schroeder HW. Dihydro-O-methylsterigmatocystin, a new metabolite from Aspergilus flavus. Tetrahedron Lett. 1970;11:3109-3112.

    Not in our library10.1016/s0040-4039(01)98427-8

  75. 75.

    Costa CP, Silva DG, Rudnitskaya A, Almeida A, Rocha SM. Shedding light on Aspergillus niger exometabolome. Sci Rep. 2016;6:27441.

    Not in our library10.1038/srep27441

  76. 76.

    Curtis RW, Tanaka H. Production of malformin by Aspergillus awamori. Appl Microbiol. 1967;15:1519-1520.

    Not in our library10.1128/am.15.6.1519-1520.1967

  77. 77.

    Cutler HG, Crumley FG, Cox RH, Hernandez O, Cole RJ, Dorner JW. Orlandin: a nontoxic fungal metabolite with plant growth inhabiting properties. J Agric Food Chem. 1979;27:592-595.

    Not in our library10.1021/jf60223a043

  78. 78.

    Daengrot C, Rukachairisikul V, Tansakul C, Thongpanchang T, Phongpaichit S, Bowornwiriyapan K, Sakayaroj J. Eremophilane sesquiterpenes and diphenyl thioethers from the soil fungus Penicillium copticola PSU-RSPG138. J Nat Prod. 2015;78:615-622.

    Not in our library10.1021/np5005328

  79. 79.

    Dey NC. A preliminary note on the antibacterial substance from Aspergillus flavus. Curr Sci (India). 1945;14:265-267.

    Not in our library

  80. 80.
    Carcinogenic Activity of a Series of Reactive Lactones and Related Substances · 1961
    No notice
  81. 81.

    Ding G, Jiang L, Guo L, Chen X, Zhang H, Che Y. Pestalazines and pestalamides, bioactive metabolites from the plant pathogenic fungus Pestalotiopsis theae. J Nat Prod. 2008;71:1861-1865.

    Not in our library10.1021/np800357g

  82. 82.

    Domíngues G, Hueso-Rodríguez JA, de la Torre MC, Rodríguez B. Synthesis and absolute configuration of drim-9(11)-en-8-ols from Aspergillus oryzae. Tetrahedron Lett. 1991;32:4765-4768.

    Not in our library10.1016/s0040-4039(00)92302-5

  83. 83.

    Domsch KH, Gams W, Anderson T-H. Compendium of soil fungi. 2007.

    Not in our library

  84. 84.

    Dunn G, Newbold GT, Spring FS. Synthesis of flavacol, a metabolic product of Aspergillus flavus. J Chem Soc. 1949;1949:2586-2587.

    Not in our library10.1039/jr9490002586

  85. 85.

    Duran RM, Cary JW, Calvo AM. Production of cyclopiazonic acid, aflatrem, and aflatoxin by Aspergillus flavus is regulated by veA, a gene necessary for sclerotial formation. Appl Microbiol Biotechnol. 2007;73:1158-1168.

    Not in our library10.1007/s00253-006-0581-5

  86. 86.

    Dutcher JD. Aspergillic acid: an antibiotic substance produced by Aspergillus flavus. I. General properties, formastion of desoxyaspergillic acid and structural conclusions. J Biol Chem. 1947;171:321-339.

    Not in our library

  87. 87.

    Dutcher JD. Aspergillic acid: an antibiotic substance produced by Aspergillus flavus. III. The structure of hydroxyaspergillic acid. J Biol Chem. 1958;232:785-796.

    Not in our library

  88. 88.

    Dutton MF, Heathcote JG. Structure biochemical properties and origin of aflatoxins B2a and G2a. Chem Ind. 1968;1968:418-420.

    Not in our library

  89. 89.

    Ehrlich KC, Mack BM. Comparison of expression of secondary metabolite biosynthesis cluster genes in Aspergillus flavus, A. parasiticus, and A. oryzae. Toxins. 2014;6:1916-1928.

    Not in our library10.3390/toxins6061916

  90. 90.

    El-Hag N, Morse RE. Aflatoxin production by a variant of Aspergillus oryzae (NRRL strain 1988) on cowpeas (Vigna sinensis). Science. 1976;192:1345-1346.

    Not in our library10.1126/science.1273594

  91. 91.

    El-Kady I, El-Maraghy S, Zohri A. Mycotoxin producing potential of some isolates of Aspergillus flavus and Eurotium groups from meat-products. Microbiol Res. 1994;149:297-307.

    Not in our library10.1016/s0944-5013(11)80073-x

  92. 92.

    Ellis JJ, Stodola FH, Vesonder RF, Glass CA. A C15H22O4 compound produced by the fungus Aspergillus fischeri var. glaber. Nature. 1964;203:1382.

    Not in our library10.1038/2031382a0

  93. 93.

    Elsahrkawy SH, Abbas HK. Metabolism of T-2 toxin by Mucor and Aspergillus sp. Acta Pharm Jugos. 1991;41:191-201.

    Not in our library

  94. 94.

    El-Sayed Ashraf S.A., Safan Samia, Mohamed Nabil Z., Shaban Lamis, Ali Gul Shad, Sitohy Mahmoud Z. Induction of Taxol biosynthesis by Aspergillus terreus, endophyte of Podocarpus gracilior Pilger, upon intimate interaction with the plant endogenous microbes. Process Biochemistry. 2018;71:31-40.

    Not in our library10.1016/j.procbio.2018.04.020

  95. 95.

    Enomoto M, Saito M. Carcinogens produced by fungi. Annu Rev Microbiol. 1972;26:279-312.

    Not in our library10.1146/annurev.mi.26.100172.001431

  96. 96.

    Esaki H, Onozaki H, Kawakishi S, Ozawa T. New antioxidant isolated from tempeh. J Agric Food Chem. 1996;44:696-700.

    Not in our library10.1021/jf950454t

  97. 97.

    Evidente A, Cristinzio G, Punzo B, Andolfi A, Testa A, Melck D. Flufuran, an antifungal 3,5-disubstituted furan produced by Aspergillus flavus Link. Chem Biodiver. 2009;6:328334.

    Not in our library10.1002/cbdv.200800292

  98. 98.

    Faustinelli PC, Wang XM, Palencia ER, Arias RS. Genome sequences of eight Aspergillus flavus spp., and one A. parasiticus sp., isolated from peanut seeds in Georgia. Genome Announc. 2016;4:e00278-e00216.

    Not in our library10.1128/genomea.00278-16

  99. 99.

    Fennell DI. Aspergillus oryzae (NRRL strain 1988): a clarification. Science. 1976;194:1188.

    Not in our library10.1126/science.996551

  100. 100.

    Fernagut PO, Diguet E, Stefanova N, Biran M, Wenning GK, Canioni P, Bioulac B, Tison F. Subacute systemic 3-nitropropionic acid intoxication induced a distinct motor disorder in adult C57B1/6 mice: behavioural and histopathological characterization. Neuroscience. 2002;114:1005-1017.

    Not in our library10.1016/s0306-4522(02)00205-1

  101. 101.

    Foster JW, Karow EO. Microbiological aspects of penicillin. VIII. Penicillin from different fungi. J Bacteriol. 1945;49:19-29.

    Not in our library10.1128/jb.49.1.19-29.1945

  102. 102.

    Frisvad JC. The connection between the penicillia and aspergilli and mycotoxins with special emphasis on misidentified isolates. Arch Environ Contam Toxicol. 1989;18:452-467.

    Not in our library10.1007/bf01062373

  103. 103.

    Frisvad JC, De Saeger S. Rational for a polyphasic approach in the identification of mycotoxigenic fungi. Determining mycotocins and mycotoxigenic fungi in food and feed. 2011;279-297.

    Not in our library

  104. 104.

    Frisvad JC, Hubka V, Ezekiel CN, Hong S-B, Nováková A, Chen AL, Arzanlou M, Larsen TO, Sklenár F, Mahakarnchanakul W, Samson RA, Houbraken J. Taxonomy of Aspergillus section Flavi and their production of aflatoxins, ochratoxins and other mycotoxins. Stud Mycol. 2019;93:1-63.

    Not in our library10.1016/j.simyco.2018.06.001

  105. 105.

    Frisvad JC, Larsen TO. Chemodiversity in the genus Aspergillus. Appl Microbiol Biotechnol. 2015;99:7859-7877.

    Not in our library10.1007/s00253-015-6839-z

  106. 106.

    Frisvad JC, Larsen TO, Dalsgaard PW, Seifert KA, Louis-Seize G, Lyhne EK, Jarvis BB, Fettinger JC, Overy DP. Four psychrotolerant species with high chemical diversity consistently producing cycloaspeptide A, P. jamesonlandense sp. nov., P. ribium sp. nov., P. soppii and P. lanosum. Int J Syst Evol Microbiol. 2006;56:1427-1437.

    Not in our library10.1099/ijs.0.64160-0

  107. 107.
    Fumonisin and Ochratoxin Production in Industrial Aspergillus niger Strains · 2011
    No notice
  108. 108.

    Frisvad JC, Petersen LM, Lyhne EK, Larsen TO. Formation of sclerotia and production of indoloterpenes by Aspergillus niger and other species in section Nigri. PLoS ONE. 2014;9:e94857.

    Not in our library10.1371/journal.pone.0094857

  109. 109.

    Frisvad JC, Smedsgaard J, Larsen TO, Samson RA. Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium. Stud Mycol. 2004;49:201-241.

    Not in our library

  110. 110.

    Frisvad JC, Smedsgaard J, Samson RA, Larsen TO, Thrane U. Fumonisin B2 production by Aspergillus niger. J Agric Food Chem. 2007;55:9727-9732.

    Not in our library10.1021/jf0718906

  111. 111.

    Fu Y, He F, Zhang S, Jiao X. Consistent striatal damage in rats induced by 3-nitropropionic acid and cultures of Arthrinium fungus. Neurotoxicol Teratol. 1995;17:413-418.

    Not in our library10.1016/0892-0362(94)00078-r

  112. 112.

    Fujii R, Ugai T, Ichonose H, Hatakeyama M, Kosaki T, Gomio K, Fujii I, Minami A, Oikawa H. Reconstitution of biosynthetic intermediates by expression host. Biosci Biotechnol Biochem. 2016;80:426-431.

    Not in our library10.1080/09168451.2015.1104234

  113. 113.

    Fujimoto Y, Miyagawa H, Tsurushima T, Irie H, Okamura K, Ueno T. Structures of antafumicins A and B, novel antifungal substances produced by the fungus Aspergillus niger NH-401. Biosci Biotechol Biochem. 1993;57:1222-1224.

    Not in our library10.1271/bbb.57.1222

  114. 114.

    Fukuda T, Hasegawa Y, Hagimori K, Yamaguchi Y, Masuma R, Tomoda H, Omura S. Tensidols, new potentiators of antifungal miconazol activity, produced by Aspergillus niger FKI-2342. J Antibiot. 2006;59:480-485.

    Not in our library10.1038/ja.2006.67

  115. 115.

    Fukui S, Tani Y, Kishibe T. The role of B vitamins in sake brewing, II, The nature of a growth-stimulating factor produced by Aspergillus oryzae for Saccharomyces sake and its relationship to pantothenic acid. J Ferment Technol. 1955;33:59-64.

    Not in our library

  116. 116.

    Fukui S, Tani Y, Kishibe T. The role of B vitamins in sake brewing, IV. Biosynthesis and decompositions of B vitamins by Saccharomyces sake and Aspergillus oryzae. J Ferment Technol. 1955;33:175-179.

    Not in our library

  117. 117.

    Galagan JE, Calvo SE, Cuomo C, Ma L-J, Wortman JR, Batzoglou S, Lee S-I, Bastürkmen M, Spevak CC, Clutterbuck J, Kapitonov V, Jurka J, Scazzocchio C, Farman M, Butler J, Purcell S, Harris S, Braus GH, Draht O, Busch S, D’Enfert C, Bouchier C, Goldman GH, Bell-Pedersen D, Griffith-Jones S, Doonan JH, Yu J, Vienken K, Pain A, Freitag M, Selker EU, Archer DB, Penalva MA, Oakley BR, Momany M, Tanaka T, Kumagai T, Asai K, Machida M, Nierman WC, Denning DW, Caddick M, Hynes M, Paoletti NM, Fischer R, Miller B, Dyer P, Sachs MS, Osmani SA, Birren BW. Sequencing of Aspergillus nidulans and comparative analysis with A. fumigatus and A. oryzae. Nature. 2005;438:1105-1115.

    Not in our library10.1038/nature04341

  118. 118.

    Gallagher RT, Clardy J, Wilson BJ. Aflatrem, a tremorgenic toxin from Aspergillus flavus. Tetrahedron Lett. 1980;21:239-242.

    Not in our library10.1016/s0040-4039(00)71178-6

  119. 119.

    Gallagher RT, McCabe T, Hirotsu K, Clardy J, Nicholson J, Wilson BJ. Aflavinine, a novel indole-mevanolate metabolite from tremorgen-producing Aspergillus flavus species. Tetrahedron Lett. 1980;21:243-246.

    Not in our library10.1016/s0040-4039(00)71179-8

  120. 120.

    Gallagher RT, Richard JL, Stahr HM, Cole RJ. Cyclopiazonic acid production by aflatoxigenic and non-aflatoxigenic strains of Aspergillus flavus. Mycopathologia. 1978;66:31-36.

    Not in our library10.1007/bf00429590

  121. 121.

    Gallagher RT, Wilson BJ. Aflatrem, the tremorgenic mycotoxin from Aspergillus flavus. Mycopathologia. 1980;66:183-185.

    Not in our library10.1007/bf00683969

  122. 122.

    Gallo A, Ferrara M, Perrone G. Recent advances on the molecular aspects of ochratoxin A biosynthesis. Curr Op Food Sci. 2017;17:49-56.

    Not in our library10.1016/j.cofs.2017.09.011

  123. 123.

    Gardner SN, Slezak T, Hall BG. kSNP3.0: SNP detection and phylogenetic analysis of genomes without genome alignment or reference genome. Bioinformatics. 2015;31:2877-2878.

    Not in our library10.1093/bioinformatics/btv271

  124. 124.

    Garson MJ, Jenkins SM, Staunton J, Chaloner PA. Isolation of some new 3,6-dialkyl-1,4-dihydroxypiperazine-2,5-diones from Aspergillus terreus. J Chem Soc Perkin Trans I. 1986;1986:901-903.

    Not in our library10.1039/p19860000901

  125. 125.

    Geiser DM, Dorner JW, Horn BW, Taylor JW. The phylogenetics of mycotoxin and sclerotium production in Aspergillus flavus and Aspergillus oryzae. Fungal Genet Biol. 2000;31:169-179.

    Not in our library10.1006/fgbi.2000.1215

  126. 126.
    Cryptic speciation and recombination in the aflatoxin-producing fungus Aspergillus flavus · 1998
    Not checked
  127. 127.

    Georgianna D, Fedorova ND, Yu J, Machida M, Rokas A, Baker S, Dean R, Brown D, Dolexal A, Bhatnagar D, Cleveland T, Wortman J, Maiti R, Joardar V, Amedeo P, Denning D, Woloshuk C, Nierman W, Payne G. Comparative genomics of Aspergillus flavus and A. oryzae revealed nearly identical genomes but differences in gene expression. Phytopathol. 2009;99:S42.

    Not in our library

  128. 128.

    Ghosal S, Boswas K, Chakrabarti DK. Toxic naphtho-γ-pyrones from Aspergillus niger. J Agric Food Chem. 1979;27:1347-1351.

    Not in our library10.1021/jf60226a018

  129. 129.

    Gibbons JG, Salichos L, Slot JC, Rinker DC, McGary KL, King JG, Klich MA, Tabb DL, McDonald WH, Rokas A. The evolutionary imprint of domestication on genome variation and function of the filamentous fungus Aspergillus oryzae. Curr Biol. 2012;22:1403-1409.

    Not in our library10.1016/j.cub.2012.05.033

  130. 130.
    Whole genome comparison of Aspergillus flavus L-morphotype strain NRRL 3357 (type) and S-morphotype strain AF70. · 2018
    Not checked
  131. 131.

    Gilbert MK, Mack BM, Wei Q, Bland JM, Bhatnagar D, Cary JW. RNA sequencing of an nsdC mutant reveals global regulation of secondary metabolite clusters in Aspergillus flavus. Microbiol Res. 2016;182:150-161.

    Not in our library10.1016/j.micres.2015.08.007

  132. 132.

    Gill-Serna J, García-Díaz M, González-Jaén M, Vázquez C, Patino B. Description of an orthologous cluster of ochratoxin A biosynthetic genes in Aspergillus and Penicillium species. Int J Food Microbiol. 2018;268:35-43.

    Not in our library10.1016/j.ijfoodmicro.2017.12.028

  133. 133.

    Girol CG, Fisch KM, Heinekamp T, Günther S, Hüttel W, Piel J, Brakhage AA, Müller M. Regio- and stereoselective oxidative phenol coupling in Aspergillus niger. Angew Chem Int Ed. 2012;51:9788-9791.

    Not in our library10.1002/anie.201203603

  134. 134.

    Gloer JB, TePaske MR, Sima JS, Wicklow DT, Dowd PF. Antiinsectan aflavinine derivatives from the sclerotia of Aspergillus flavus. J Org Chem. 1988;53:5457-5460.

    Not in our library10.1021/jo00258a011

  135. 135.

    Godet M, Munaut F. Molecular strategy for identification in Aspergillus section Flavi. FEMS Microbiol Lett. 2010;304:157-168.

    Not in our library10.1111/j.1574-6968.2009.01890.x

  136. 136.

    Goris J, Konstantinidis KT, Klappenbach JA, Coenye T, Vandamme P, Tiedje JM. DNA-DNA hybridization values and their relationship to whole-genome sequence similarities. Int J Syst Evol Microbiol. 2007;57:81-91.

    Not in our library10.1099/ijs.0.64483-0

  137. 137.

    Gould RO, Simpson TJ, Walkinshaw MD. Isolation and X-ray crystal structures of astellolides A and B, sesquiterpenoid metabolites of Aspergillus variecolor. Tetrahedron Lett. 1981;22:1047-1050.

    Not in our library10.1016/s0040-4039(01)82862-8

  138. 138.

    Grove JF. New metabolic products of Aspergillus flavus. Part. I. Asperentin, its methyl esters, and 5′-hydroxyasperentin. J Chem Soc Perkin Trans. 1972;1(1972):2400-2406.

    Not in our library10.1039/p19720002400

  139. 139.

    Grove JF. New metabolic products of Aspergillus flavus. Part. II. Asperflavin, anhydroasperflavin, and 5,7-dihydroxy-4-methylphthalide. J Chem Soc Perkin Trans. 1972;1(1972):2406-2411.

    Not in our library10.1039/p19720002406

  140. 140.

    Grove JF. New metabolic products of Aspergillus flavus. Part. III. Biosynthesis of asperentin. J Chem Soc Perkin Trans. 1973;1(1973):2626-2429.

    Not in our library10.1039/p19730002626

  141. 141.

    Grove JF. New metabolic products of Aspergillus flavus. Part. IV. 4′-Hydroxyasperentin and 5′-hydroxyasperentin 8-methyl ether. J Chem Soc Perkin Trans. 1973;1(1973):2704-2706.

    Not in our library10.1039/p19730002704

  142. 142.

    Guida VO. Activades antibioticas do Aspergillus flavus. Sobre diversas bacterias. Bol Soc Paulista Med Vet (Sao Paolo). 1948;8:70-73.

    Not in our library

  143. 143.

    Gurupavithra S, Rajalakshmi A, Jayachitra A. Optimization of fermentation conditions for red pigment production from Aspergillus flavus under submerged cultivation analyse its antioxidant properties. Indo Am J P Sci. 2017;2:2185-2194.

    Not in our library

  144. 144.

    Haenni AL, Lederer E, Barbier M (1962) Chimique biologique - sur la structure de l'aspergillomarasmine A. Compt Rend Hebd Scean Acad Sci 255:1476–1480

    Not in our library

  145. 145.

    Haenni AL, Robert M, Vetter W, Roux L, Barbier M, Lederer E. Structure chimique des aspergillomarasmins A et B. Helv Chim Acta. 1965;48:729-750.

    Not in our library10.1002/hlca.19650480409

  146. 146.

    Hamasaki T, Kuwano H, Isono K, Hatsuda Y, Fukuyama K, Tsukihara T, Katsube Y (1975) New metabolite parasiticolide A, from Aspergillus parasiticus. Agric Biol Chem 39:749–751

    Not in our library

  147. 147.

    Hamsa TAP, Ayres JC. A differential medium for the isolation of Aspergillus flavus from cottonseed. J Food Sci. 1977;42:449-453.

    Not in our library10.1111/j.1365-2621.1977.tb01520.x

  148. 148.
    Dynamic Fumonisin B2 Production by Aspergillus niger Intented Used in Food Industry in China · 2017
    Not checked
  149. 149.

    Hanaka T, Ejiri K, Yamamoto H. First synthesis of a natural isoxanthopterin glycoside, asperopterin A. Heterocycles. 2012;84:801-813.

    Not in our library10.3987/com-11-s(p)57

  150. 150.

    Hanaka T, Yamamoto H. First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae. Pteridines. 2013;24(special issue):3-6.

    Not in our library

  151. 151.

    Hanson JR. The chemistry of fungi. 2008.

    Not in our library

  152. 152.

    Happi GM, Kouam SF, Talontsi FM, Nkenfou CN, Longo F, Zuhlke S, Dounla-Meli C, Spiteller M. A new dimeric naphtho-gamma-pyrone from an endophytic fungus Aspergillus niger AKRN associated with the roots of Entandrophragma congoense collected in Cameroun. Z Naturforsch Sect B J Chem Sci. 2015;70:625-630.

    Not in our library10.1515/znb-2015-0036

  153. 153.

    Hardegger E, Liecht P, Jackman LM, Boller A, Plattner PA. Welkstoffe und Antibiotika. 24. Mitteilung. Die Konstitution des Lycomarasmins. Helv Chim Acta. 1963;46:60-74.

    Not in our library10.1002/hlca.19630460109

  154. 154.

    Hartley RD, Nesbitt BF, O’Kelley J. Toxic metabolites of Aspergillus flavus. Nature. 1963;198:1056-1058.

    Not in our library10.1038/1981056a0

  155. 155.

    Hasegawa Y, Fukuda T, Hagimori K, Tomoda H, Omura S. Tensyic acids, new antibiotics produced by Aspergillus niger FKI-2342. Chem Pharm Bull. 2007;55:1338-1341.

    Not in our library10.1248/cpb.55.1338

  156. 156.

    Hashimoto M, Nonaka T, Fujii I. Fungal type III polyketide synthases. Nat Prod Rep. 2014;31:1306-1317.

    Not in our library10.1039/c4np00096j

  157. 157.

    Hashimoto M, Seshime Y, Kitamoto K, Uchhiyama N, Goda Y, Fujii I. Identification of csypyrone B2 and B3 as the minor products of Aspergillus oryzae type III polyketide synthase CsyB. Biomed Med Chem Lett. 2013;23:650-653.

    Not in our library10.1016/j.bmcl.2012.11.119

  158. 158.

    Hautbergue T, Puel O, Tadrist S, Meneghetti L, Pean M, Delaforge M, Debrauwer L, Oswald IP, Jamin EL. Evidencing 98 secondary metabolites of Penicillium verrucosum using substrate isotopic labelling and high-resolution mass spectrometry. J Chromatogr B Anal Technol Biomed Life Sci. 2017;1071:29-43.

    Not in our library10.1016/j.jchromb.2017.03.011

  159. 159.

    He Y, Tain J, Chen X, Sun W, Zhu H, Li Q, Lei L, Yao G, Xue Y, Wang J, Li H, Zhang Y. Fungal naphtho-γ-pyrones: potent antibiotics for drug-resistant microbial pathogens. Sci Rep. 2016;6:24291.

    Not in our library10.1038/srep24291

  160. 160.

    He Y, Wang B, Chen W, Cox RJ, He J, Chen F. Recent advances in reconstructing microbial secondary metabolites biosynthesis in Aspergillus spp. Biotechnol Adv. 2018;36:739-783.

    Not in our library10.1016/j.biotechadv.2018.02.001

  161. 161.

    He FS, Zhang S, Qian FY, Zhang CL. Delayed dystonia with striatal CT lucencies induced by a mycotoxin (3-nitropropionic acid). Neurology. 1995;456:2178-2183.

    Not in our library10.1212/wnl.45.12.2178

  162. 162.

    Heathcote JG, Dutton MF. New metabolites of Aspergillus flavus. Tetrahedron. 1969;10:1497-1500.

    Not in our library10.1016/s0040-4020(01)82721-6

  163. 163.

    Henrikson JC, Ellis TK, King JB, Cichewicz RH. Reappraising the structures and distribution of metabolites from the black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one systems. J Nat Prod. 2011;74:1959-1964.

    Not in our library10.1021/np200454z

  164. 164.

    Henrikson JC, Hoover AR, Joyner PM, Cichewicz RH. A chemical epigenetics approach for engineering the in situ biosynthesis of a cryptic natural product from Aspergillus niger. Org Biomol Chem. 2009;7:435-438.

    Not in our library10.1039/b819208a

  165. 165.

    Henry MH, Wyatt RD. The toxicity of fumonisin B1, B2 and B3, individually and in combination, in chicken embryos. Poultry Sci. 2001;80:401-407.

    Not in our library10.1093/ps/80.4.401

  166. 166.

    Hesseltine CW, Shotwell OL, Smith M, Ellis JJ, Vandegraft E, Shannon G (1970). Production of various aflatoxins by strains of the Aspergillus flavus series. In: Herzberg M (ed) Proceedings of the first joint U.S.–Japan conference on toxic micro-organisms. Mycotoxins. Botulism. UJNR Joint Panels on Toxic Micro-organisms and the U.S. Department of the Interior, Washington D.C., USA, 202–210

    Not in our library

  167. 167.
    Comparative Ochratoxin Toxicity: A Review of the Available Data · 2015
    No notice
  168. 168.

    Higuchi R. Biosynthesis and destruction of flavin mononucleotide and flavine adenine dinucleotide by Aspergillus oryzae. I. Comparison of riboflavine and its derivatives biosynthesized by some species of Aspergillus oryzae. Vitamins (Kyoto). 1956;11:559-561.

    Not in our library

  169. 169.

    Hiort J, Maksimenka K, Reichert M, Perović-Ottstadt S, Lin WH, Wray V, Steube K, Schaumann K, Weber H, Proksch P, Ebel R, Müller WEG, Bringmann G. New natural products from the sponge-derived fungus Aspergillus niger. J Nat Prod. 2004;67:1532-1543.

    Not in our library10.1021/np030551d

  170. 170.

    Holker JSE, Kagal SA, Mulheirn LJ, White PM. Some new metabolites of Aspergillus versicolor and a revised structure for averufin. J Chem Soc Chem Commun. 1966;1966:911-913.

    Not in our library

  171. 171.

    Holm DK, Petersen LM, Klitgaard A, Knudsen PB, Jarzynska ZD, Nielsen KF, Gotfredsen CH, Larsen TO, Mortensen UH. Molecular and chemical characterization of the biosynthesis of the 6-MSA-derived meroterpenoid yanuthone D in Aspergillus niger. Chem Biol. 2014;21:519-529.

    Not in our library10.1016/j.chembiol.2014.01.013

  172. 172.

    Holzapfel Cedric W., Bredenkamp Martin W., Snyman Renske M., Boeyens Jan C.A., Allen Christine C. Cyclopiamide, an isoindolo[4,6-cd]indole from Penicillium cyclopium. Phytochemistry. 1990;29(2):639-642.

    Not in our library10.1016/0031-9422(90)85133-z

  173. 173.

    Hong S-B, Lee M, Kim D-H, Chung S-H, Shin H-D, Samson RA. The proportion of non-aflatoxigenic strains of the Aspergillus flavus/oryzae complex from Meju by analyses of the aflatoxin biosynthetic genes. J Microbiol. 2013;51:766-772.

    Not in our library10.1007/s12275-013-3128-3

  174. 174.
    ASPERGILLUS LUCHUENSIS, AN INDUSTRIALLY IMPORTANT BLACK ASPERGILLUS IN EAST ASIA · 2013
    No notice
  175. 175.

    Horn BW, Dorner JW. Effect of competition and adverse culture conditions on aflatoxin production by Aspergillus flavus through successive generations. Mycologia. 2001;94:741-751.

    Not in our library10.1080/15572536.2003.11833167

  176. 176.

    Houbraken J, de Vries RP, Samson RA. Modern taxonomy of biotechnologically important Aspergillus and Penicillium species. Adv Appl Microbiol. 2014;86:199-249.

    Not in our library10.1016/b978-0-12-800262-9.00004-4

  177. 177.

    Hu X, Xia Q-W, Zhao Y-Y, Zheng Q-H, Liu Q-Y, Chen L, Zhang Q-Q. Speradines B-E, four novel tetracyclic oxindole alkaloids from the marine-derived fungus Aspergillus oryzae. Heterocycles. 2014;89:1662-1669.

    Not in our library10.3987/com-14-13004

  178. 178.

    Hu X, Xia Q-W, Zhao Y-Y, Zheng Q-H, Liu Q-Y, Chen L, Zhang Q-Q. Speradines F-H, three new oxindole alkaloids from the marine-derived fungus Aspergillus oryzae. Chem Pharm Bull. 2014;62:942-946.

    Not in our library10.1248/cpb.c14-00312

  179. 179.

    Hummel BCW. Isolation and partial characterization of flavicidic acid, phytotoxic metabolite of Aspergillus flavus. Dissertation Abstr. 1956;16:1332-1333.

    Not in our library

  180. 180.

    Huson DH, Scornavacca C. Dendroscope 3: an interactive tool for rooted phylogenetic trees and networks. Syst Biol. 2012;61:1061-1067.

    Not in our library10.1093/sysbio/sys062

  181. 181.

    Hüttel W, Müller M. Regio- and steroselective intermolecular oxidative phenol coupling in kotanin biosynthesis by Aspergillus niger. ChemBioChem. 2007;8:521-529.

    Not in our library10.1002/cbic.200600434

  182. 182.

    Iizuka A, Iida M. Maltoryzin, a new toxic metabolite produced by a strain of Aspergillus oryzae var. microsporus isolated from the poisonous malt sprout. Nature. 1962;196:681-682.

    Not in our library10.1038/196681a0

  183. 183.

    Inokoshi J, Shiomi K, Masuma R, Tanaka H, Yamada H, Omura S. Funalenone, a novel collagenase inhibitor produced by Aspergillus niger. J Antibiot. 1999;52:1095-1100.

    Not in our library10.7164/antibiotics.52.1095

  184. 184.

    Itoh Y, Takahashi S, Haneishi T, Arai M. Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi. J Antibiot. 1989;33:525-526.

    Not in our library10.7164/antibiotics.33.525

  185. 185.

    Iwamoto T, Hirota A, Shima S, Sakai H, Isogai A. Nigerazine A, an isomer of nigerazine B, from Aspergillus niger. Agric Biol Chem. 1985;49:3323-3325.

    Not in our library

  186. 186.

    Iwamoto T, Shima S, Hirota A, Isogai A, Sakai H. Nigerazine B, a new metabolite from Aspergillus niger screening, isolation, and chemical and biological properties. Agric Biol Chem. 1983;47:739-743.

    Not in our library

  187. 187.

    Iwasaki T, Kosikowski FV. Production of β-nitropropionic acid in foods. J Food Sci. 1973;38:1162-1165.

    Not in our library10.1111/j.1365-2621.1973.tb07228.x

  188. 188.

    Jahn F. Toxicity and production of oxalic acid of an Aspergillus niger strain from mold hay. Wien Tierartl Monatschr. 1977;64:79-82.

    Not in our library

  189. 189.

    Jansen BJM, de Groot A. The occurrence and biological activity of drimane sesquiterpenoids. Nat Prod Rep. 1990;8:309-318.

    Not in our library10.1039/np9910800309

  190. 190.

    Jansen BJM, de Groot A. The occurrence and biological activity of drimane sesquiterpenoids. Nat Prod Rep. 2004;21:449-477.

    Not in our library10.1039/b311170a

  191. 191.

    Jarvis BB, Miller JD. Mycotoxins as harmful indoor air contaminants. Appl Microbiol Biotechnol. 2005;66:367-372.

    Not in our library10.1007/s00253-004-1753-9

  192. 192.

    Jefferson WE. Steroids and other factors influencing the accumulation of asperenone and fermentation acids by Aspergillus niger in replacement cultures. Biochem. 1967;6:3484-3488.

    Not in our library10.1021/bi00863a020

  193. 193.

    Jefferson WE. The isolation and characterization of asperenone, a new phenylpolyene from Aspergillus niger. Biochemistry. 1967;6:3479-3484.

    Not in our library10.1021/bi00863a019

  194. 194.

    Jennings MA, Williams TI. Production of kojic acid by Aspergillus effusus Tiraboschi. Nature. 1945;155:302.

    Not in our library10.1038/155302a0

  195. 195.

    Johnson JR, Robinson BL, Ali SF, Binienda Z. Dopamine toxicity following long term exposure to low doses of 3-nitropropionic acid (3-NPA) in rats. Toxicol Lett. 2000;116:113-118.

    Not in our library10.1016/s0378-4274(00)00214-9

  196. 196.

    Jørgensen TR. Identification and toxigenic potential of the industrally important fungi, Aspergillus oryzae and Aspergillus sojae. J Food Prot. 2007;70:2916-2934.

    Not in our library10.4315/0362-028x-70.12.2916

  197. 197.

    Jørgensen TR, Park J, Arentshorst M, van Welzen AM, Lamers G, vanKuyk PA, Damvel RA, van den Hondel CAM, Nielsen KF, Frisvad JC, Ram AFJ. The molecular and genetic basis of conidial pigmentation in Aspergillus niger. Fungal Gen Biol. 2011;48:544-553.

    Not in our library10.1016/j.fgb.2011.01.005

  198. 198.

    Juvvadi PR, Seshime Y, Kitamoto K. Genomics reveal traces of fungal phenylpropanoid-flavanoid metabolic pathway in the filamentous fungus Aspergillus oryzae. J Microbiol. 2005;43:457-486.

    Not in our library

  199. 199.

    Kaneko Y, Sanada M. Studies on the fluorescent substances produced by Aspergillus fungi. VIII. Purification and isolation of asperopterin B and chemical properties of asperopterin B and A. J Ferment Technol. 1969;47:8-19.

    Not in our library

  200. 200.

    Kang D, Kim J, Choi JN, Liu K-H, Lee CH. Chemotaxonomy of Trichoderma spp. using mass spectrometry metabolite profiling. J Microbiol Biotechnol. 2011;21:5-13.

    Not in our library10.4014/jmb.1008.08018

  201. 201.

    Kato A, Saeki T, Suzuki S, Ando K, Tamura G, Arima K. Oryzachlorin, a new antifungal antibiotic (Studies on antiviral and antitumor Antibiotics XVIII). J Antibiot. 1969;22:322-326.

    Not in our library10.7164/antibiotics.22.322

  202. 202.

    Kato N, Tokuoka M, Shinohara Y, Kaeatani M, Uramoto M, Seshime Y, Fujii I, Kitamoto K, Takahashi T, Takahashi S, Koyama Y, Osada H. Genetic safeguard against mycotoxin cyclopiazonic acid production in Aspergillus oryzae. ChemBioChem. 2011;12:1376-1382.

    Not in our library10.1002/cbic.201000672

  203. 203.

    Kayoko M. Reduction of ochratoxin a toxicity in mice treated with phenylalanine and phenobarbital. Toxicol Lett. 1985;25:1-5.

    Not in our library10.1016/0378-4274(85)90092-x

  204. 204.

    Kim JH, Lee CH. Heptelidic acid, a sesquiterpene lactone, inhibits apoptosis in human leukemia U937 cells. J Microbiol Biotechnol. 2009;19:787-791.

    Not in our library

  205. 205.

    Kim K-W, Sugawara F, Yoshida S, Murofuschi N, Takahashi N, Curtis RW. Structure of malformin B, a phytotoxic metabolite produced by Aspergillis niger. Biosci Biotech Biochem. 1993;57:787-791.

    Not in our library10.1271/bbb.57.787

  206. 206.

    Kimura Y, Nishibe M, Nakajima H, Hamasaki T, Shigemitsu N, Sugawara F, Stout TJ, Clardy J. Emeniveol; a new pollen growth inhibitor from the fungus, Emericella nivea. Tetrahedron Lett. 1992;33:6987-6990.

    Not in our library10.1016/s0040-4039(00)60913-9

  207. 207.

    King AM, Reid-Yu SA, Wang W, King DT, De Pascale G, Strynadka NC, Walsch TR, Coombes BK, Wright GD. Aspergillomarasmine A overcomes metallo-β-lactamase antibiotic resistance. Nature. 2014;510:503-506.

    Not in our library10.1038/nature13445

  208. 208.

    Kinoshita S, Akita S, Saito K (1961) L-glutamic acid. Japanese patent no. 3171, Apr. 14.

    Not in our library

  209. 209.

    Kishimoto S, Tsunematsu Y, Sato M, Watanabe K. Elucidation of biosynthetic pathways of natural products. Chem Rec. 2017;17:1095-1108.

    Not in our library10.1002/tcr.201700015

  210. 210.

    Kistner HE Sr (1962) Sucrose fermentation of Aspergillus flavus-oryzae. U.S. patent no. 3,043,748, July 10.

    Not in our library

  211. 211.

    Kiyota T, Hamada R, Sakamoto K, Iwashita K, Yamada O, Mikami S. Aflatoxin non-productivity of Aspergillus oryzae caused by loss of function of the aflJ gene product. J Biosci Bioeng. 2011;111:512-517.

    Not in our library10.1016/j.jbiosc.2010.12.022

  212. 212.

    Kjærbølling I, Vesth TC, Frisvad JC, Nybo JL, Theobald S, Kuo A, Bowyer P, Matsuda Y, Mondo S, Lyhne EK, Kogle M, Clum A, Lipzen A, Salamov A, Ngan C, Daum C, Chiniquy J, Barry K, LaButti K, Haridas S, Simmons B, Magnuson J, Mortensen U, Larsen T, Grigoriev I, Baker S, Andersen MR. Linking secondary metabolites to gene clusters through genome sequencing of six diverse Aspergillus species. Proc Nat Acad Sci, USA. 2018;115:E753-E761.

    Not in our library10.1073/pnas.1715954115

  213. 213.

    Klausmeyer P, McCloud TG, Tucker KD, Cardellina JH, Shoemaker RH. Aspirochlorine class compounds from Aspergillus flavus inhibit azole-resistant Candida albicans. J Nat Prod. 2005;68:1300-1302.

    Not in our library10.1021/np050141k

  214. 214.

    Klich MA, Mullaney EJ. DNA restriction enzyme gragment polymorphiosms as a tool for rapid differentiation of Aspergillus flavus from Aspergillus oryzae. Exp Mycol. 1987;11:170-175.

    Not in our library10.1016/0147-5975(87)90002-8

  215. 215.

    Klich MA, Pitt JI, Samson RA, Pitt JI. The theory and practice of distinguishing species of the Aspergillus flavus group. Advances in Penicillium and Aspergillus systematics. 1985;211-220.

    Not in our library

  216. 216.

    Klich MA, Pitt JI. Differentiation of Aspergillus flavus from A. parasiticus and other closely related species. Trans Brit Mycol Soc. 1988;91:99-108.

    Not in our library10.1016/s0007-1536(88)80010-x

  217. 217.

    Klitgaard A, Nielsen JB, Frandsen RJN, Andersen MR, Nielsen KF. Combining stabel isotope labelling and molecular networking for biosynthetic pathway characterization. Anal Chem. 2015;87:6520-6526.

    Not in our library10.1021/acs.analchem.5b01934

  218. 218.

    Kobayashi T. Food poisoning. Chiba Daikage Fuhai Kenkyosho Hokoku. 1966;19:92-107.

    Not in our library

  219. 219.

    Kobayashi T, Abe K, Asai K, Gomi K, Juvvadi PR, Kato M, Kitamoto K, Takeuchi M, Machida M. Genomics of Aspergillus oryzae. Biosci Biotechnol Biochem. 2007;71:646-670.

    Not in our library10.1271/bbb.60550

  220. 220.

    Kobayashi K, Shimizu H, Itho M, Suginome H. An efficient synthesis of 5,7-dihydroxy-4-methylisobenzofuran-1-(3H)-one, a metabolite of Aspergillus flavus and a key intermediate in the synthesis of mycophenolic acid. Bull Chem Soc Japan. 1990;63:2435-2437.

    Not in our library10.1246/bcsj.63.2435

  221. 221.

    Kobbe B, Cushman M, Wogan GN, Demain AL. Production and bacterial activity of malformin C, a toxic metabolite of Aspergillus niger. Appl Environ Microbiol. 1977;33:996-997.

    Not in our library10.1128/aem.33.4.996-997.1977

  222. 222.

    Koch L, Lodin A, Herold I, Ilan M, Carmeli S, Yarden O. Sensitivity of Neurospora crassa to a marine-derived Aspergillus tubingensis anhydride exhibiting antifungal activity that is mediated by the MAS1 protein. Mar Drugs. 2014;12:4713-4731.

    Not in our library10.3390/md12094713

  223. 223.

    Kocsubé S, Perrone G, Magistà D, Houbraken J, Varga J, Szigeti G, Hubka V, Hong S-B, Frisvad JC, Samson RA. Aspergillus is monophyletic: evidence from multiple gene phylogenies and extrolite profiles. Stud Mycol. 2016;85:199-213.

    Not in our library10.1016/j.simyco.2016.11.006

  224. 224.

    Kodukula K, Arcuri M, Cutrone JQ, Hugill RM, Lowe SE, Pirnik DM, Shu Y-Z, Fernandes PV, Seethala R. BMS-192548, a tetracyclic binding inhibitor of neuropeptide Y receptors, from Aspergillus niger WB2346. II. Taxonomy, fermentation, isolation and biological activity. J Antibiot. 1995;48:1055-1059.

    Not in our library10.7164/antibiotics.48.1055

  225. 225.

    Koiso Y, Iwasaki S, Hanaoka K, Kobayashi T, Sonoda R, Fujita Y, Yaegashi H, Sato Z. Ustiloxins, antimitotic cyclic peptides from false smut balls on rice panicles caused by Ustilaginoidea virens. J Antibiot. 1994;47:765-773.

    Not in our library10.7164/antibiotics.47.765

  226. 226.

    Koiso Y, Natori M, Iwasaki S, Sato S, Sonoda R, Fujita Y, Yaegashi H, Sato Z. Ustiloxin: a phytotoxin and a mycotoxin from false smut balls on rice panicles. Tetrahedron Lett. 1992;33:4157-4160.

    Not in our library10.1016/s0040-4039(00)74677-6

  227. 227.

    Komagata D, Fujita S, Yamashita N, Saito S, Morino T. Novel neuritogenic activities of pseurotin A and penicillic acid. J Antibiot. 1996;49:958-959.

    Not in our library10.7164/antibiotics.49.958

  228. 228.

    Koteva K, King AM, Capretta A, Wright GD. Total synthesis and activity of the metallo-β-lactamase inhibitor aspergillomarasmin A. Angew Chem Ind Ed. 2016;55:2210-2212.

    Not in our library10.1002/anie.201510057

  229. 229.

    Kozakiewicz Z, Frisvad JC, Hawksworth DL, Pitt JI, Samson RA, Stolk AC. Proposals for nomina specifica conservanda and rijicienda in Aspergillus and Penicillium (Fungi). Taxon. 1992;41:109-113.

    Not in our library10.2307/1222500

  230. 230.
    Ochratoxin A: Molecular Interactions, Mechanisms of Toxicity and Prevention at the Molecular Level · 2016
    No notice
  231. 231.

    Kredics László, Varga János, Antal Zsuzsanna, Samson Robert A, Kocsubé Sándor, Narendran Venkatapathy, Bhaskar Madhavan, Manoharan Chockaiya, Vágvölgyi Csaba, Manikandan Palanisamy. Black aspergilli in tropical infections. Reviews in Medical Microbiology. 2008;19(3):65-78.

    Not in our library10.1097/mrm.0b013e3283280391

  232. 232.

    Kozlovskii AG, Solov’yeva TF, Bukhtiyarov YE, Shurukhin YV, Sakharovskii VG, Adanin VM, Nefedova MY, Pertsova RN, Tokarev VG, Golovleva LE. Secondary metabolites of new soil strains of microscopic fungi from the genera Aspergillus and Penicillium. Microbiology (Moscow). 1990;59:409-415.

    Not in our library

  233. 233.

    Kubicek CP, Druzhinina IS, Paterson RRM, Lima N. Trichoderma mycoses and mycotoxins. Molecular biology of food and water borne mycotoxigenic and mycotic fungi. 2016;521-538.

    Not in our library

  234. 234.

    Kupfahl C, Michalka A, Lass-Flörl C, Fischer G, Haase G, Ruppert T, Geginat G, Hof H. Gliotoxin production by clinical and environmental Aspergillus fumigatus strains. Int J Med Microbiol. 2008;298:319-327.

    Not in our library10.1016/j.ijmm.2007.04.006

  235. 235.

    Lallouette P (1962) Extraction and purification of a growth factor. French patent no. 1,284,511 (June 18)

    Not in our library

  236. 236.

    Larsen TO, Smedsgaard J, Nielsen KF, Hansen ME, Frisvad JC. Phenotypic taxonomy and metabolite profiling in microbial drug discovery. Nat Prod Rep. 2005;22:672-695.

    Not in our library10.1039/b404943h

  237. 237.

    Lederer E. Chimie biologique –sur la structure de l’aspergillomarasmine A. C R Hebd Seance Acad Sci. 1962;255:1476-1485.

    Not in our library

  238. 238.

    Lee M, Cho J-Y, Lee YG, Lee HJ, Lim S-I, Lee S-Y, Nam Y-D, Moon J-H. Furan, phenolic, and heptelidic acid derivatives produced by Aspergillus oryzae. Food Sci Biotechnol. 2016;25:1259-1264.

    Not in our library10.1007/s10068-016-0199-z

  239. 239.

    Lee JH, Jo EH, Hong EJ, Kim KM, Lee I. Safety evaluation of filamentous fungi isolated from industrial Doenjang Koji. J Microbiol Biotechnol. 2014;24:1397-1404.

    Not in our library10.4014/jmb.1403.03007

  240. 240.

    Lee CZ, Liou GY, Yuan GF. Comparison of aflR gene sequences of strains in Aspergillus section Flavi. Microbiology-SGM. 2006;152:161-170.

    Not in our library10.1099/mic.0.27618-0

  241. 241.

    Lee KC, Tam EWT, Lo KC, Tsang AKL, Lau CCY, To KKW, Chan JFW, Lam CW, Yuen KY, Lau SKP, Woo PCY. Metabolomics analysis reveals specific novel tetrapeptide and potential anti-inflammatory metabolites in pathogenic Aspergillus species. Int J Mol Sci. 2015;16:13850-13867.

    Not in our library10.3390/ijms160613850

  242. 242.

    Lee YH, Tominaga M, Hayashi R, Sakamoto K, Yamado O, Akito O. Aspergillus oryzae strains with a large deletion of the aflatoxin biosynthetic homologous gene cluster differentiated by chromosomal breakage. Appl Microbiol Biotechnol. 2006;72:339-345.

    Not in our library10.1007/s00253-005-0282-5

  243. 243.

    Leite MAF, Sarragiotto MH, Imamura PM, Marsaioli AJ. Absolute configuration of drim-9(11)-en-8-ol from Aspergillus oryzae. J Org Chem. 1986;51:5409-5410.

    Not in our library10.1021/jo00376a066

  244. 244.

    Leutou AS, Yun K, Son BW. Induced production of 6,9-dibromoflavasperone, a new radical scavenging naphthopyranone in the marine-mitflat-derived fungus Aspergillus niger. Arch Pharm Res. 2016;39:806-810.

    Not in our library10.1007/s12272-016-0764-2

  245. 245.

    Lewis RE, Wiederhold NP, Lionakis MS, Prince RA, Kontoyiannis DP. Frequency and species distribution of gliotoxin-producing Aspergillus isolates recovered from patients at a tertiary-care cancer center. J Clin Microbiol. 2005;43:6120-6122.

    Not in our library10.1128/jcm.43.12.6120-6122.2005

  246. 246.

    Li Y, Chooi Y-H, Sheng Y, Valentine JS, Tang Y. Comparative characterization of fungal anthracenone and naphthacenedione biosynthetic pathways reveals an α-hydroxylation-dependent Claisen-like cyclization catalyzed by a dimanganese thioesterase. J Amer Chem Soc. 2011;133:15773-17785.

    Not in our library10.1021/ja206906d

  247. 247.

    Li D-H, Han T, Guan L-P, Bai J, Zhao N, Li Z-L, Wu X, Hua H-M. New naphthopyrones from the marine-derived fungus Aspergillus niger 2HL-M-8 and their in vitro antiproliferative activity. Nat Prod Res. 2016;30:1116-1122.

    Not in our library10.1080/14786419.2015.1043553

  248. 248.

    Li X-B, Li Y-L, Zhou J-C, Yuan H-Q, Wang X-N, Lou H-X. A new diketopiperazine heterodimer from an endophytic fungus Aspergillus niger. J Asian Nat Prod Res. 2015;17:182-187.

    Not in our library10.1080/10286020.2014.959939

  249. 249.

    Li X-B, Xie F, Liu S-S, Li Y, Zhou JC, Liu YQ, Yuan H-Q, Lou H-X. Naphtho-γ-pyrones from endophyte Aspergillus niger occurring in the liverwort Heteroscyphus tener (Steph.) Schiffn. Chem Biol. 2013;10:1193-2001.

    Not in our library10.1002/cbdv.201300042

  250. 250.

    Liljegren K, Svendsen A, Frisvad JC. Mycotoxins and exoenzyme production by members of Aspergillus section Flavi: an integrated taxonomic approach to their classification. Proc Jpn Assoc Mycotoxicol Suppl. 1988;1:35-36.

    Not in our library10.2520/myco1975.1988.1supplement_35

  251. 251.
    Drivers of genetic diversity in secondary metabolic gene clusters within a fungal species · 2017
    No notice
  252. 252.

    Lind AL, Wisecaver JH, Smith TD, Feng X, Calvo AM, Rokas A. Examining the evolution of the regulatory circuit controlling secondary metabolism and development in the fungal genus Aspergillus. PLoS Genet. 2015;11:e1005096.

    Not in our library10.1371/journal.pgen.1005096

  253. 253.

    Liu L, Bao L, Wang L, Ma K, Han J, Yang Y, Liu R, Ren J, Yin W, Wang W, Liu H. Asperorydines A-M: Prenylated tryptophan-derived alkaloids with neurotropic effects from Aspergillus oryzae. J Org Chem. 2018;83:812-822.

    Not in our library10.1021/acs.joc.7b02802

  254. 254.

    Liu D, Li X-M, Li C-S, Gao S-S, Shang Z, Proksch P, Huang C-G, Wang B-G. Nigerapyrones A-H, α-pyrone derivatives from the marine mangrove-derived endophytic fungus Aspergillus niger MA-132. J Nat Prod. 2011;74:1787-1791.

    Not in our library10.1021/np200381u

  255. 255.

    Liu D, Li X-M, Li C-S, Wang B-G. Nigerasterols A and B, antiproliferative sterols from the mangrove-derived endophytic fungus Aspergillus niger MA-132. Helv Chim Acta. 2013;96:1055-1061.

    Not in our library10.1002/hlca.201200332

  256. 256.

    Liu XJ, Luo XY, Hu WJ, Natori S, Ueno Y. Arthrinium spp and the etiology of deteriorated sugarcane poisoning. Mycotoxins and phycotoxins 88. 1989;109-118.

    Not in our library

  257. 257.

    Liu C, Tagami K, Minami A, Matsumoto T, Frisvad JC, Suzuki H, Ishikawa J, Gomi K, Oikawa H. Reconstitution of biosynthetic machinery for highly elaborated indole diterpene penitrem. Angew Chem Int Ed. 2015;54:5748-5752.

    Not in our library10.1002/anie.201501072

  258. 258.

    Logrieco A., Ferracane R., Haidukowsky M., Cozzi G., Visconti A., Ritieni A. Fumonisin B2production byAspergillus nigerfrom grapes and natural occurrence in must. Food Additives & Contaminants: Part A. 2009;26(11):1495-1500.

    Not in our library10.1080/02652030903148322

  259. 259.

    Lopez Diaz TM, Flannigan B. Production of patulin and cytochalasin E by Aspergillus clavatus during malting of barley and wheat. Int J Food Microbiol. 1997;35:129-136.

    Not in our library10.1016/s0168-1605(96)01211-1

  260. 260.
    Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities · 2014
    Not checked
  261. 261.

    Lu X-T, Zhang E-X, Yin S-T, Fan L-H, Hu H-B. Methylseleninic acid prevents patulin-induced hepatotoxicity and nephrotoxicity via the inhibition of oxidative stress and inactivation of p53 and MAPKs. J Agric Chem. 2017;65:5299-5305.

    Not in our library10.1021/acs.jafc.7b01338

  262. 262.

    Lubna AS, Hamayun M, Gul H, Lee I-J, Hussain A. Aspergillus niger CSR3 regulates plant hormones and secondary metabolites by producing gibberellins and indoleacetic acid. J Plant Interact. 2018;13:100-111.

    Not in our library10.1080/17429145.2018.1436199

  263. 263.

    Luk KC, Kobbe B, Townsend JM. Production of cyclopiazonic acid by Aspergillus flavus Link. Appl Environ Microbiol. 1977;33:211-212.

    Not in our library10.1128/aem.33.1.211-212.1977

  264. 264.

    Lv Y, Xiao J, Pan L. Type III polyketide synthase is involved in the biosynthesis of protocatechuic acid in Aspergillus niger. Biotechnol Lett. 2014;36:2303-2310.

    Not in our library10.1007/s10529-014-1609-z

  265. 265.

    Lv Y, Zhou F, Wang B, Pam L. Morphological transitions under oxidative stress in response to metabolite formation in Aspergillus niger. Biotechnol Lett. 2015;37:6012-6018.

    Not in our library10.1007/s10529-014-1713-0

  266. 266.

    Ma Y, Li T, Ma C. A new pyrone derivative from an endophytic Aspergillus tubingensis of Lycium ruthenicum. Nat Prod Res. 2016;30:1499-1503.

    Not in our library10.1080/14786419.2015.1114939

  267. 267.

    Ma X, Peng J, Wu G, Zhu T, Li G, Gu Q, Li D. Speradines B-D, oxygenated cyclopiazonic acid alkaloids from the sponge-derived fungus Aspergillus flavus MXH-X104. Tetrahedron. 2015;71:3522-3527.

    Not in our library10.1016/j.tet.2015.03.050

  268. 268.

    MacDonald JC. Biosynthesis of aspergillic acid. J Biol Chem. 1961;236:512-514.

    Not in our library

  269. 269.

    MacDonald JC. Biosynthesis of hydroxyaspergillic acid. J Biol Chem. 1962;237:1977-1981.

    Not in our library

  270. 270.

    MacDonald JC. Toxicity, analysis, and production of aspergillic acid and its analogs. Can J Biochem. 1973;51:1311-1315.

    Not in our library10.1139/o73-172

  271. 271.

    Machida M, Asai K, Sano M, Tanaka T, Kumagai T, Terai G, Kusumoto K, Arima T, Akita O, Kashiwagi Y, Abe K, Gomi K, Horiuchi H, Kitamoto K, Kobayashi T, Takeuchi M, Denning DW, Galaghan JE, Nierman WC, Yu JJ, Archer DB, Bennett JW, Bhatnagar D, Cleveland TE, Fedorova ND, Gotoh O, Horikawa H, Hosoyama A, Ichinomaya M, Igarashi R, Iwashita K, Juvvadi PR, Kato M, Kato Y, Kin T, Kokubun A, Maede H, Maeyama N, Maruyama J, Nagasaki H, Nakajima T, Oda K, Okada K, Paulsen I, Sakamoto K, Sawano T, Takahashi M, Takase K, Terabayashi Y, Wortman JR, Yamada O, Yamagata Y, Anazawa H, Hata Y, Koide Y, Komori T, Koyama Y, Minetoki T, Suharnan S, Taanaka A, Isono K, Kuhara S, Ogasawara N, Kukuchi H. Genome sequencing and analysis of Aspergillus oryzae. Nature. 2005;438:1157-1161.

    Not in our library10.1038/nature04300

  272. 272.

    Machida M, Yamada O, Gomi K. Genomics of Aspergillus oryzae: learning from the history of koji mold and exploration of its future. DNA Res. 2008;15:173-183.

    Not in our library10.1093/dnares/dsn020

  273. 273.

    Manonmani HK, Sreektaniah KR. Pigment production by a strain of Aspergillus sp. J Food Sci Technol. 1984;21:195-197.

    Not in our library

  274. 274.

    Månsson M, Klejnstrup ML, Phipps RK, Nielsen KF, Frisvad JC, Gotfredsen CH, Larsen TO. Isolation and NMR characterization of fumonisin B2 and B6, a new fumonisin from Aspergillus niger. J Agric Food Chem. 2010;58:949-953.

    Not in our library10.1021/jf902834g

  275. 275.

    Manzanares-Miralles L, Sarikaya-Bayram Ö, Smith EB, Dolan SK, Bayram Ö, Jones GW, Doyle S. Quantitative proteomcis revelas the mechanism and consequence of gliotoxin-mediates dysregulation of the methionine cycle in Aspergillus niger. J Proteomics. 2016;131:149-162.

    Not in our library10.1016/j.jprot.2015.10.024

  276. 276.

    Marston RQ. Production of kojic acid from Aspergillus lutescens. Nature. 1949;164:961.

    Not in our library10.1038/164961b0

  277. 277.

    Martinez D, Berka RM, Henrissat B, Saloheimo M, Arvas M, Baker SE, Chapman J, Chertkov O, Coutinho PM, Cullen D, Danchin EG, Grigoriev IV, Harris P, Jackson M, Kubicek CP, Han CS, Ho I, Larrondo LF, de Leon AL, Magnuson JK, Merino S, Misra M, Nelson B, Putnam M, Robbertse B, Salamov AA, Scmoll M, Terry A, Thayer N, Westerhom-Parvinen A, Sloch CL, Yao J, Barbote R, Nelson MA, Detter C, Bruce D, Kuske CR, Xie G, Richardson P, Rokshar H, Lucas SM, Rubin EM, Dunn-Coleman N, Ward M, Brettin TS. Genome sequencing and analysis of the biomass-degrading fungus Trichoderme reesei (syn. Hyprocrea jecorina). Nat Biotechnol. 2008;26:553-560.

    Not in our library10.1038/nbt1403

  278. 278.

    Martinez-Luis S, Cherigo L, Arnold E, Spadafora C, Gerwick WH, Cubila-Rios L. Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544. Nat Prod Commun. 2012;7:165-168.

    Not in our library

  279. 279.

    Marui J, Ohashi-Kunihiro S, Ando T, Nishimura M, Koike H, Machida M. Penicillin biosynthesis in Aspergillus oryzae and its overproduction by genetic engineering. J Biosci Bioeng. 2010;110:8-11.

    Not in our library10.1016/j.jbiosc.2010.01.001

  280. 280.

    Massi FP, Sartori D, Ferranti L d S, Iamanaka BT, Taniwaki MH, Vieira MKLC, Fungaro MHP. Prospecting for the incidence of genes involved in ochratoxin and fumonisin biosynthesis in Brazilian strains of Aspergillus niger and A. welwitschiae. Int J Food Microbiol. 2016;221:19-28.

    Not in our library10.1016/j.ijfoodmicro.2016.01.010

  281. 281.

    Matsumaru Takanori, Sunazuka Toshiaki, Hirose Tomoyasu, Ishiyama Aki, Namatame Miyuki, Fukuda Takashi, Tomoda Hiroshi, Otoguro Kazuhiko, Ōmura Satoshi. Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B. Tetrahedron. 2008;64(30-31):7369-7377.

    Not in our library10.1016/j.tet.2008.05.035

  282. 282.

    Matsuo M. In vivo antioxidant activity of Okara koji, a fermented okara, by Aspergillus oryzae. Biosci Biotech Biochem. 1997;61:1968-1972.

    Not in our library10.1271/bbb.61.1968

  283. 283.

    Matsuura S, Yamamoto M, Kaneko Y. The structure of the pteridine glycoside from Aspergillus oryzae. Bull Chem Soc Japan. 1972;45:492-495.

    Not in our library10.1246/bcsj.45.492

  284. 284.

    Mazzaferro LS, Hüttel W, Fries A, Müller M. Cytochrome P450-catalyzed region- and stereoselective phenol coupling of fungal natural products. J Am Chem Soc. 2015;137:12289-12295.

    Not in our library10.1021/jacs.5b06776

  285. 285.

    McCorkindale NJ, Wright JLC, Brian PW, Clarke SM, Hutchinson SA. Canadensolide – an antifungal metabolite of Penicillium canadense. Tetrahedron Lett. 1968;9:727-730.

    Not in our library10.1016/s0040-4039(00)75621-8

  286. 286.

    McGivan JD, Chappell JB. Avenaciolide—a specific inhibitor of glutamate transport in rat liver mitochondria. Biochem J. 1970;116:P37.

    Not in our library10.1042/bj1160037pb

  287. 287.

    McKean C, Tang L, Tang M, Billam M, Wang Z, Theodorakis CW, Kendall RJ, Wang JS. Comparative acute and combinative toxicity of aflatoxin B1 and fumonisin B1 in animals and human cells. Food Chem Toxicol. 2006;44:868-876.

    Not in our library10.1016/j.fct.2005.11.011

  288. 288.

    McKee CM, MacPhillamy HB. An antibiotic substance produced by submerged cultivation of Aspergillus flavus. Proc Soc Exptl Biol Med. 1943;53:247-248.

    Not in our library10.3181/00379727-53-14268p

  289. 289.

    McKee CM, Rake G, Houck CL. Studies on Aspergillus flavus. II. The production and properties of a penicillin-like substance—flavididin. J Bacteriol. 1944;47:187-197.

    Not in our library10.1128/jb.47.2.187-197.1944

  290. 290.

    Mehedi MAU, Molla AH, Khondar P, Sultana S, Islam MA, Rashid MA, Chowdhury R. Pseurotin A: an antibacterial secondary metabolite from Aspergillus fumigatus. Asian J Chem. 2010;22:2611-2614.

    Not in our library

  291. 291.

    Meng J, Sun W, Mao Z, Xu D, Wang X, Lu S, Lai D, Liu Y, Zhou L, Zhang G. Main ustilaginoidins and their distribution in rice false smut balls. Toxins. 2015;7:4023-4034.

    Not in our library10.3390/toxins7104023

  292. 292.

    Miknis GF, Williams RW. Total synthesis of (+)-aspirochlorin. J Am Chem Soc. 1993;115:536-547.

    Not in our library10.1021/ja00055a025

  293. 293.

    Minami A, Liu CW, Oikawa H. Total biosynthesis of fungal indole terpenes using cell factories. Heterocycles. 2016;92:397-421.

    Not in our library10.3987/rev-15-830

  294. 294.

    Ming L. Moldy sugarcane poisoning—a case report with a brief review. J Toxicol Clin Toxicol. 1995;33:363-367.

    Not in our library10.3109/15563659509028924

  295. 295.

    Mituzani S, Komori K, Taniguchi T, Monde K, Kuramochi K, Tsubaki K. A bioinspired synthesis of (+)-rubramide, (+)-flavipucine, and (+)-isoflavipucine. Angew Chem Int Ed. 2016;55:9553-9556.

    Not in our library10.1002/anie.201602910

  296. 296.

    MIYAKE Yoshiaki, ITO Chihiro, ITOIGAWA Masataka, OSAWA Toshihiko. Isolation of the Antioxidant Pyranonigrin-A from Rice Mold Starters Used in the Manufacturing Process of Fermented Foods. Bioscience, Biotechnology, and Biochemistry. 2007;71(10):2515-2521.

    Not in our library10.1271/bbb.70310

  297. 297.

    Miyake Y, Mocchizuki M, Ito C, Itoigawa M, Osawa T. Antioxidative pyranonigrins in rice mold starters and their suppressive effect on the expression of blood adhesion molecules. Biosci Biotech Biochem. 2008;72:1580-1585.

    Not in our library10.1271/bbb.80077

  298. 298.

    Mogensen JM, Frisvad JC, Thrane U, Nielsen KF. Production of fumonisin B2 and B4 by Aspergillus niger on grapes and raisins. J Agric Food Chem. 2010;58:954-958.

    Not in our library10.1021/jf903116q

  299. 299.

    Mogensen JM, Varga J, Thrane U, Frisvad JC. Aspergillus acidus from Puerh tea and black tea does not produce ochratoxin A and fumonisin B2. Int J Food Microbiol. 2009;132:141-144.

    Not in our library10.1016/j.ijfoodmicro.2009.04.011

  300. 300.

    Mogi M, Nakayima S, Iguchi N. Fortified miso (fermented soybean paste). II. Riboflavin production by ultraviolet-induced mutants of Aspergillus oryzae. J. Ferment Technol. 1952;30:363-369.

    Not in our library

  301. 301.

    Mogi M, Nakayima S, Yoshida F. Fortified miso (fermented soybean paste). I. Trial brewing of miso with riboflavine-producing strain of Aspergillus oryzae. J Ferment Technol. 1951;29:302-310.

    Not in our library

  302. 302.

    Monti F, Ripamonti F, Hawser SP, Islam K. Aspirochlorine: a highly selective and potent inhibitor of fungal protein synthesis. J Antibiot. 1999;52:311-318.

    Not in our library10.7164/antibiotics.52.311

  303. 303.

    Morton HE, Kocholaty W, Junowicz-Kocholaty R, Kelner A. Toxicity and antibiotic activity of kojic acid produced by Aspergillus luteo-virescens. J Bacteriol. 1945;50:579-583.

    Not in our library

  304. 304.

    Moule Y, Moreau S, Bousquet JF. Relationship between the chemical structure and the biological properties of some ermophilane compounds related to PR-toxin. Chem Biol Interact. 1977;17:185-192.

    Not in our library10.1016/0009-2797(77)90083-7

  305. 305.

    Munkvold GP, Weieneth L, Proctor RH, Busman M, Blandino M, Susca A, Logrieco A, Moretti A. Pathogenicity of fumonisin-producing and nonproducing strains of Aspergillus species in section Nigri to maize ears and seedlings. Plant Dis. 2018;102:282-291.

    Not in our library10.1094/pdis-01-17-0103-re

  306. 306.

    Murakami H. Classification of the koji mould. J Gen Appl Microbiol. 1971;17:281-309.

    Not in our library10.2323/jgam.17.281

  307. 307.

    Murakami H. Summary and description of species of the black aspergilli. Taxonomic studies on Japanese Industrial strains of the Aspergillus (Part 33). J Brew Soc Japan. 1979;74:854-858.

    Not in our library10.6013/jbrewsocjapan1915.74.854

  308. 308.
    Natural products as reservoirs of novel therapeutic agents · 2018
    No notice
  309. 309.

    Nagano N, Umemura M, Izumikawa M, Kawano J, Ishii T, Kikuchi M, Tomii K, Kumagai T, Yoshimi A, Machida M, Abe K, Shin-ya K, Asai K. Class of cyclic ribosomal peptide synthetic genes in filamentous fungi. Fungal Genet Biol. 2016;86:58-70.

    Not in our library10.1016/j.fgb.2015.12.010

  310. 310.

    Nair MG. Fumonisin and human health. Ann Tropic Paed. 1998;18:S47-S52.

    Not in our library10.1080/02724936.1998.11747980

  311. 311.

    Nakamura S. Muta-aspergillic acid, a new growth inhibitant against hiochi-bacteria. Bull Agric Chem Soc Jpn. 1960;24:629-630.

    Not in our library10.1080/03758397.1960.10857723

  312. 312.

    Nakamura S. The structure of muta-aspergillic acid. Agric Biol Chem. 1961;25:74-75.

    Not in our library

  313. 313.

    Nakamura S, Shimoda C. Studies on antibiotic substance oryzacidin, produced by Aspergillus oryzae. Part 5. Existence of β-nitropropionic acid. J Agr Chem Soc Japan. 1954;28:909-913.

    Not in our library

  314. 314.

    Nakamura S, Shiro T. Studies on growth inhibition of hiochi-bacteria, specific saprophytes of sake. 4. Hydroxyaspergillic acid as a growth inhabitant against hiochi-bacteria. Bull Agric Chem Soc Jpn. 1959;23:418-427.

    Not in our library10.1080/03758397.1959.10857595

  315. 315.

    Nakamura S, Shiro T. Hydroxyaspergillic acid as growth inhabitant against hiochi-bacteria (Studies on growth inhibition of hiochi-bacteria, specific saprophytes of sake. 4). Bull Agric Chem Soc Jpn. 1959;23:65-67.

    Not in our library10.1080/03758397.1959.10857595

  316. 316.

    Nakazawa R (1907) On the koji fungus. Aspergillus awamori. Rept Inst Gov Res Formosa 1

    Not in our library

  317. 317.

    Nakazawa M, Uehara T, Nomura Y. Koningic acid (a potent glyceraldehyde-3-phosphate dehydrogenase inhibitor) induced fragmentation and condensation of DNA in NG108-15 cells. J Neurochem. 1997;68:24932499.

    Not in our library10.1046/j.1471-4159.1997.68062493.x

  318. 318.

    Nicholson MJ, Koulman A, Monahan BJ, Pritchard BL, Payne GA, Scott B. Identification of two aflatrem biosynthesis gene loci in Aspergillus flavus and metabolic engineering of Penicillium paxilli to elucidate their function. Appl Environ Microbiol. 2009;75:7469-7481.

    Not in our library10.1128/aem.02146-08

  319. 319.

    Nielsen KF, Gräfenham T, Zafari D, Thrane U. Trichothecene production by Trichoderma brevicompactum. J Agric Food Chem. 2005;53:8190-8196.

    Not in our library10.1021/jf051279b

  320. 320.

    Nielsen JC, Grijseels S, Prigent S, Ji B, Dainat J, Nielsen KF, Frisvad JC, Workman M, Nielsen J. Global analysis of biosynthetic gene clusters reveals vast potential of secondary metabolite production in Penicillium species. Nat Microbiol. 2017;2:17044.

    Not in our library10.1038/nmicrobiol.2017.44

  321. 321.

    Nielsen KF, Mogensen JM, Johansen M, Larsen TO, Frisvad JC. Review of secondary metabolites and mycotoxins from the Aspergillus niger group. Anal Bioanal Chem. 2009;395:1225-1246.

    Not in our library10.1007/s00216-009-3081-5

  322. 322.

    Nierman WC, Yu J, Fedorova-Adams ND, Losada L, Cleveland TE, Bhatnagar D, Bennett JW, Dean R, Payne GA. Genome sequence of Aspergillus flavus NRRL 3357, a strain that causes aflatoxin contamination of food and feed. Genome Announc. 2015;3:e00168-e00115.

    Not in our library10.1128/genomea.00168-15

  323. 323.

    Nishie K, Porter JK, Cole RJ, Dorner JW. Neurochemical and pharmacological effects of cyclopiazonic acid, chlorpromazine and reserpine. Res Commun Psychol Psych Behav. 1985;10:291-302.

    Not in our library

  324. 324.

    Nishimura A, Okamoto S, Yoshizako F, Morishima I, Ueno T. Stimulatory effect of acetate and propionate on aspergillic acid formation by Aspergillus oryzae A21. J Ferment Bioeng. 1991;72:461-464.

    Not in our library10.1016/0922-338x(91)90055-l

  325. 325.

    Nishimura I, Shinohara Y, Oguma T, Koyama Y. Survival strategy of the salt-tolerant lactic acid bacterium, Tetragenococcus halophilus, to counteract koji mold, Aspergillus oryzae, in soy sauce brewing. Biosci Biotechnol Biochem. 2018;82:1437-1443.

    Not in our library10.1080/09168451.2018.1460574

  326. 326.

    Niu J, Arenthorst M, Nair PDS, Dai Z, Baker S, Frisvad JC, Nielsen KF, Punt PJ, Ram A. Identification of a classical mutant in the industrial host Aspergillus niger by systems genetics: LaeA is required for citric acid production and regulates the formation of some secondary metabolites. G3: Gen Genom Genet. 2016;6:193-204.

    Not in our library10.1534/g3.115.024067

  327. 327.

    Nonaka N, Asai Y, Nishio M, Takahashi K, Okuda T, Tanaka S, Suita T, Ohnuki T, Komatsubara S. TMC-2A, -2B and -2C, new dipeptidyl peptidase IV inhibitors produced by Aspergillus oryzae A374. I. Taxonomy of producing strain, fermentation, and biochemical properties. J Antibiot. 1997;50:646-652.

    Not in our library10.7164/antibiotics.50.646

  328. 328.

    Nozawa K, Nakajima S, Kawai K. Isolation and structures of indoloterpenes, possible biosynthetic intermediates to the tremorgenic mycotoxin, paxilline, from Emericella striata. J Chem Soc Perkin Trans I. 1988;1988:2607-2610.

    Not in our library10.1039/p19880002607

  329. 329.

    Nozawa K, Sekita S, Harada M, Udagawa S, Kawai K. Isolation and structures of two new indoloterpenes related to aflavinine from a microsclerotium-producing strain of Aspergillus flavus. Chem Pharm Bull. 1989;37:626-630.

    Not in our library10.1248/cpb.37.626

  330. 330.

    Oda M, Saraya T, Wakayama M, Shibuya K, Ogawa Y, Ihui T, Yokoyama E, Inoue M, Shimayamada H, Fujiwara M, Ota T, Takizawa H, Goto H (2013) Calcium oxalate crystal deposition in a patient with aspergilloma due to Aspergillus niger. J Thorac Dis 5:E174–E178

    Not in our library10.3978/j.issn.2072-1439.2013.08.45

  331. 331.

    Ohmomo S, Sugita M, Abe M. Isolation of cyclopiazonic acid, cyclopiazonic acid imine and bissecodehydrocyclopiazonic acid from the cultures of Aspergillus versicolor (Vuill.) Tiraboschi. J Agric Chem Soc Japan. 1973;47:57-93.

    Not in our library

  332. 332.

    Ohta A, Ohta M. Synthesis of mutaaspergillic and dl-hydroxyaspergillic acids. Chem Pharm Bull. 1983;31:20-24.

    Not in our library10.1248/cpb.31.20

  333. 333.

    Orth R. Mycotoxins of Aspergillus oryzae strains for use in the food industry as starters and enzyme producing strains. Ann Nutr Aliment. 1977;31:617-624.

    Not in our library

  334. 334.

    Ovenden SPB, Sberna G, Tait RM, Wildman HG, Patel R, Li B, Steffy K, Nguyen N, Meurer-Grimes BM. A diketopiperazine dimer from a marine-derived isolates of Aspergillus niger. J Nat Prod. 2004;67:2093-2095.

    Not in our library10.1021/np0497494

  335. 335.

    Park H-S, Jun S-C, Han K-H, Hong S-B, Yi J-H. Diversity, application, and synthetic biology of industrially important Aspergillus fungi. Adv Appl Microbiol. 2017;100:161-202.

    Not in our library10.1016/bs.aambs.2017.03.001

  336. 336.

    Park SY, Oh HH, Park YL, Yu HM, Myung DS, Ch SB, Lee WS, Park D, Joo YE. Malformin A1 treatment alters invasive and oncogenic phenotypes of human colorectal cancer cells through stimulation of the p38 singaling pathway. Int J Oncol. 2017;51:959-966.

    Not in our library10.3892/ijo.2017.4070

  337. 337.

    Parrish FW, Wiley BJ, Simmons EG, Lang L. Production of aflatoxins and kojic acid by species of Aspergillus and Penicillium. Appl Microbiol. 1966;14:139.

    Not in our library10.1128/am.14.1.139-.1966

  338. 338.

    Patron NJ, Waller RF, Cozijnsen AJ, Straney DC, Gardiner DM, Nierman WC, Howlett BJ. Origin and distribution of epipolythiodioxopiperazine (ETP) gene clusters in filamentous ascomycetes. BMC Evol Biol. 2007;7:174.

    Not in our library10.1186/1471-2148-7-174

  339. 339.

    Pattenden G. Synthesis of asperenone, a new pigment from Aspergillus niger and Aspergillus awamori. Tetrahedron Lett. 1969;9:4049-4052.

    Not in our library10.1016/s0040-4039(01)88611-1

  340. 340.

    Pattenden G. Synthesis of asperenone [all-trans(E)-8-methyl-13-phenyltrideca-4,6,8,10,12-pentaen-3-one], a pigment of Aspergillus species of fungi. J Chem Soc (C). 1970;1970:1404-1409.

    Not in our library

  341. 341.

    Payne GA, Nierman WC, Wortman JR, Pritchard BL, Brown D, Dean RA, Bhatnagar D, Cleveland TE, Machida M, Yu Y. Whole genome comparison of Aspergillus flavus and A. oryzae. Med Mycol. 2006;44:S9-S11.

    Not in our library10.1080/13693780600835716

  342. 342.

    Pel HJ, van de Winde JH, Archer DB, Dyer PS, Hofmann G, Schaap PJ, Turner G, de Vries RP, Albang R, Alberman K, Andersen MR, Bendtsen JD, Benen JA, van den Berg M, Breetstraat S, Caddick MS, Contreras R, Cornell M, Coutinho PM, Dancnin EG, Debets AJ, Dekker P, van Dijck PW, van Dijk A, Dijkhuizen L, Driessen AJ, d’Enfert C, Geysens S, Goosen C, Groot GS, de Groot PW, Guillemette T, Henrissat B, Herweijer M, van den Homberg JP, van den Hondel CA, van der Heijden RT, van der Kaaij RM, Klis FM, Kools HJ, Kubicek CP, van Kuyk PA, Lauber J, Lu X, van der Marel MJ, Meulenberg R, Menke H, Mortimer MA, Nielsen J, Oliver SG, Olsthoorn M, Pal K, van Peij NN, Ram AF, Rinas U, Troubos JA, Sagt CM, Schmoll M, Sun J, Ussery D, Varga J, Vervecken W, van de Vondervoort PJ, Wedler H, Wosten HA, Zeng AP, van Oorwen AJ, Visser J, Stam H. Genome sequencing and analysis of the versatile cell factory Aspergillus niger CBS 513.88. Nat Biotechnol. 2007;25:221-231.

    Not in our library10.1038/nbt1282

  343. 343.

    Perrone G, Stea G, Epifani F, Varga J, Frisvad JC, Samson RA. Aspergillus niger contains the cryptic phylogenetic species A. awamori. Fungal Biol. 2011;115:1138-1150.

    Not in our library10.1016/j.funbio.2011.07.008

  344. 344.

    Perry MJ, Makins JF, Adlard MW, Holt G. Aspergillic acids produced by mixed cultures of Aspergillus flavus and Aspergillus nidulans. J Gen Microbiol. 1984;130:319-323.

    Not in our library10.1099/00221287-130-2-319

  345. 345.

    Petersen LM, Holm DK, Knudsen PB, Nielsen KF, Gotfredsen CH, Mortensen UH, Larsen TO. Characterization of four new yanuthones from Aspergillus niger. J Antibiot. 2015;68:201-205.

    Not in our library10.1038/ja.2014.130

  346. 346.

    Pfefferle W, Anka H, Bross M, Steffan B, Vianden R, Steglich W. Asperfuran, a novel antifungal metabolite from Aspergillus oryzae. J Antibiot. 1990;43:648-654.

    Not in our library10.7164/antibiotics.43.648

  347. 347.

    Pinheiro EAA, Carvalho JM, dos Santos DCP, Feitosa AD, Marinho PSB, Guilhon GMSP, de Souza ADL, da Silva FMA, Marinho AMD. Antibacterial activity of alkaloids produced by endophytic fungus Aspergillus sp EJC08 isolated from medical plant Bauhinia guianensis. Nat Prod Res. 2013;27:1633-1638.

    Not in our library10.1080/14786419.2012.750316

  348. 348.

    Pitt JI, Hocking AD, Glenn DR. An improved medium for the detection of Aspergillus flavus and Aspergillus parasiticus. J Appl Bacteriol. 1983;54:109-114.

    Not in our library10.1111/j.1365-2672.1983.tb01307.x

  349. 349.

    Plattner PA, Clauson-Kaas N. Űber ein Welke erzeugendes Stoffwechselproducte von Fusarium lycopersici Sacc. Helv Chim Acta. 1945;28:188-195.

    Not in our library10.1002/hlca.660280121

  350. 350.

    Pócsfalvi G, Ritieni A, Ferranti P, Randazzo G, Vékey K, Malorni A. Microheterogeneity characterization of a paracelsin mixture from Trichoderma reesei using high-energy collision-induced dissociation tandem mass spectrometry. Rap Commun Mass Spectrom. 1997;11:922-930.

    Not in our library10.1002/(sici)1097-0231(199705)11:8<922::aid-rcm927>3.0.co;2-n

  351. 351.

    Pontovich VE. Aspergillus flavus as a source of flavin. Biokhimiya. 1943;8:297-301.

    Not in our library

  352. 352.

    Powell Amy J, Conant Gavin C, Brown Douglas E, Carbone Ignazio, Dean Ralph A. Altered patterns of gene duplication and differential gene gain and loss in fungal pathogens. BMC Genomics. 2008;9(1):147.

    Not in our library10.1186/1471-2164-9-147

  353. 353.

    Poulsen L, Andersen MR, Lantz AE, Thykaer J. Identification of a transcription factor controlling pH-dependent organic response in Aspergillus niger. PLoS ONE. 2012;7:e50596.

    Not in our library10.1371/journal.pone.0050596

  354. 354.

    Price MN, Dehal PS, Arkin AP. FastTree: computing large minimum evolution trees with profiles instead of a distance matrix. Mol Biol Evol. 2009;26:1641-1650.

    Not in our library10.1093/molbev/msp077

  355. 355.

    Priegnitz B-E, Brandt U, Pahirulzaman AK, Dickschat JS, Fleissner A. The AngFus3 mitogen-activated protein kinase controls hyphal differentiation and secondary metabolism in Aspergillus niger. Euk Cell. 2015;14:602-615.

    Not in our library10.1128/ec.00018-15

  356. 356.

    Przybylski M, Dietrich I, Manz I, Brückner H. Elucidation of structure and microheterogeneity of the polypeptide antibiotics paracelsin and trichotoxin A-50 by fast atom bombardment mass spectrometry in combination with selective in situ hydrolysis. Biomed Mass Spectrom. 1984;11:569-582.

    Not in our library10.1002/bms.1200111105

  357. 357.

    Purchase IFH. The acute toxicity of the mycotoxin cyclopiazonic acid to rats. Toxicol Appl Pharmacol. 1971;18:114-123.

    Not in our library10.1016/0041-008x(71)90320-6

  358. 358.

    Purchase IFH, Theron JJ. The acute toxicity of ochratoxin A to rats. Food Cosmet Toxicol. 1968;6:479-480.

    Not in our library10.1016/0015-6264(68)90138-7

  359. 359.

    Qiao M-F, Ji N-Y, Liu X-H, Li F, Xue Q-Z. Asporyergosterol, a new steroid from an algicolous isolate of Aspergillus oryzae. Nat Prod Commun. 2010;5:1575-1578.

    Not in our library

  360. 360.

    Qiao M-F, Ji N-Y, Liu X-H, Li K, Zhu Q-M. Indoloterpenes from an algicolous isolate of Aspergillus oryzae. Bioorg Med Chem Lett. 2010;20:5677-5680.

    Not in our library10.1016/j.bmcl.2010.08.024

  361. 361.

    Qiao M-F, Ji N-Y, Miao F-P, Yin X-L. Steroids and an oxylipin from an algicolous isolate of Aspergillus flavus. Magn Res Chem. 2011;49:366-369.

    Not in our library10.1002/mrc.2748

  362. 362.

    Rabache M, Neuman J, Lavollay J. Phenylpolyenes d’Aspergillus niger: structure et proprietes de l’asperrubrol. Phytochem. 1974;13:637-642.

    Not in our library10.1016/s0031-9422(00)91366-9

  363. 363.

    Rahssaparpoor P. An investigation on the patterns of deoxunivalenol (DON) mean values in Aspergillus isolates, based on subgenus and species correlations. Ind J Fund Appl Life Sci. 2014;4:143-154.

    Not in our library

  364. 364.

    Raistrick H, Clark AB. On the mechanism of oxalic acid formation by Aspergillus niger. Biochem J. 1919;13:329-344.

    Not in our library10.1042/bj0130329

  365. 365.

    Ramakrishnan CV, Desai PJ. Effect of addition of iron, cobalt, and ascorbic acid to the medium on the synthesis of ascorbic acid in molds. Curr Sci (India). 1956;25:189-190.

    Not in our library

  366. 366.

    Ramakrishnan CV, Sathe V. Effect of vitamin K3 on inducing its biosynthesis in moulds. Sci Cult (Calcutta). 1956;22:340.

    Not in our library

  367. 367.

    Rand TG, Chang CT, McMullin DR, Miller JD. Inflammation-associated gene expression in RAW 264.7 macrophages induced by toxins from fungi common on damp building materials. Toxicol in Vitro. 2017;43:16-20.

    Not in our library10.1016/j.tiv.2017.05.015

  368. 368.

    Rank C, Klejnstrup ML, Petersen LM, Kildegaard S, Frisvad JC, Gotfredsen CH, Larsen TO. Comparative chemistry of Aspergillus oryzae (RIB40) and A. flavus (NRRL 3357). Metabolites. 2012;2:39-56.

    Not in our library10.3390/metabo2010039

  369. 369.

    Rao KCS, Divakar S, Babu KN, Rao AGA, Karanth NG, Sattur AP. Nigerloxin, a novel inhibitor of aldose reductase and lipoxygenase with free radical scavenging activity from Aspergillus niger CFR-W-105. J Antibiot. 2002;55:789-793.

    Not in our library10.7164/antibiotics.55.789

  370. 370.

    Rao KCS, Divakar S, Rao AGA, Karanth NG, Suneetham WJ, Krishnakantha TP, Sattur AP. Asperenone: an inhibitor of 15-lipoxygenase and of human platelet aggregation from Aspergillus niger. Biotechnol Lett. 2002;24:1967-1970.

    Not in our library10.1023/a:1016066617891

  371. 371.

    Rao K.C. Sekhar, Karanth N.G., Sattur A.P. Production of nigerloxin, an enzyme inhibitor and a free radical scavenger, by Aspergillus niger using solid state fermentation. Process Biochemistry. 2005;40(7):2517-2522.

    Not in our library10.1016/j.procbio.2004.10.008

  372. 372.

    Raper KB. The development of improved penicillin-producing molds. Ann NY Acad Sci. 1946;48:41-52.

    Not in our library10.1111/j.1749-6632.1946.tb31753.x

  373. 373.

    Raper KB, Fennell DI. The genus Aspergillus. 1965.

    Not in our library

  374. 374.

    Ray AC, Eakin RE. Studies on the biosynthesis of aspergillin by Aspergillus niger. Appl Microbiol. 1975;30:909-915.

    Not in our library10.1128/am.30.6.909-915.1975

  375. 375.

    Ren R, Chen C-J, Hu S-S, Ge H-M, Zhu W-Y, Tan R-X, Jiao R-H. Drimane sesquiterpenoids from the Aspergillus oryzae QXPC-4. Chem Biodiv. 2015;12:371-379.

    Not in our library10.1002/cbdv.201400119

  376. 376.

    Robert M, Barbier M, Lederer E, Roux L, Biemann K, Vetter W. Two new natural phytotoxins: Aspergillomarasmines A and B and their identity to lycomarasmine and its derivatives. Bull Soc Chim Fr. 1962;1962:187-188.

    Not in our library

  377. 377.

    Rodricks JV, Lustig E, Campbell AD, Stoloff L. Aspertoxin, a hydroxyl derivative of O-methylsterigmatocystin from aflatoxin producintg cultures of Aspergillus flavus. Tetrahedron Lett. 1968;9:2975-2978.

    Not in our library10.1016/s0040-4039(00)89626-4

  378. 378.

    Rodrigues BSF, Sahm BDB, Jimenez PC, Pinto FCL, Mafezoli J, Mattos MC, Rodrigues-Filho E, Pfenning LH, Abreau LM, Costa-Lotufo LV, Oliveira MCF. Bioprospection of cytotoxic compounds in fungal strains recovered from sediments of the Brazilian coast. Chem Biodiv. 2015;12:432-442.

    Not in our library10.1002/cbdv.201400193

  379. 379.

    Rodriguez RLM, Konstantinidis KT. Bypassing cultivation to identify bacterial species. Microbe. 2014;9:111-118.

    Not in our library

  380. 380.

    Rodríguez A, Rodríguez M, Luque MI, Martín A, Córdoba JJ. Real-tine PCR assays for detection and quantification of aflatoxin-producing molds in foods. Food Microbiol. 2012;31:89-99.

    Not in our library10.1016/j.fm.2012.02.009

  381. 381.

    Rokas A. The effect of domestication on the fungal proteome. Trends Genet. 2009;23:60-63.

    Not in our library10.1016/j.tig.2008.11.003

  382. 382.

    Rokas A, Payne G, Fedorova ND, Baker SE, Machida M, Yu J, Georgianna DR, Dean RA, Bhatnagar D, Cleveland TE, Wortman JR, Maiti R, Joardar V, Denning DW, Nierman WC. What can comparative genomics tell us about species concepts in the genus Aspergillus? Stud Mycol. 2007;59:11-17.

    Not in our library10.3114/sim.2007.59.02

  383. 383.

    Saito K. Űber die Säurebildung bei Aspergillus oryzae. Botan Mag (Tokyo). 1907;21:7-11.

    Not in our library10.15281/jplantres1887.21.240_7

  384. 384.

    Saito M, Tsuruta O. A new variety of Aspergillus flavus from tropical soil in Thailand and its aflatoxin productivity. Proc Jpn Assoc Mycotoxicol. 1993;37:31-36.

    Not in our library10.2520/myco1975.1993.31

  385. 385.

    Sakaguchi K, Iizuka H, Yamazaki S. A study on the black aspergilli. J Agric Chem Soc Japan. 1951;24:138-142.

    Not in our library

  386. 386.

    Sakaguchi K, Takahashi H, Morino H. Production of α-ketoglutaric acid by molds. J Agr Chem Soc Japan. 1953;27:591-595.

    Not in our library

  387. 387.

    Sakai H. On vitamin B12 production by fermentation. Part. 2. Production test of B12 by various microorganisms. J Agr Chem Soc Japan. 1953;27:405-407.

    Not in our library

  388. 388.

    Sakai K, Kinioshita H, Shimuzu T, Nihira T. Construction of a citrinin gene cluster expression system in heterologous Aspergillus oryzae. J Biosci Bioeng. 2008;106:466-472.

    Not in our library10.1263/jbb.106.466

  389. 389.

    Sakata K, Kuwatsuka T, Sakurai A, Takahashi N, Tamura G. Isolation of aspirochlorine (= antibiotic A 30641) as a true antimicrobial constituent of the antibiotic oryzachlorin, from Aspergillus oryzae. Agric Biol Chem. 1983;47:2673-2674.

    Not in our library

  390. 390.

    Sakata K, Maruyama M, Uzawa J, Sakurai A, Lu HSM, Clardy J. Structural revision of aspirochlorine (= antibiotic A 30641), a novel epidithiopiperazine-2,5-dione produced by Aspergillus spp. Tetrahedron Lett. 1987;28:5607-5610.

    Not in our library10.1016/s0040-4039(00)96792-3

  391. 391.

    Sakata K, Masago H, Sakurai A, Takahashi N. Isolation of aspirochlorine (= antibiotic A 30641) possessing a novel dithiodiketopiperazine structure from Aspergillus flavus. Tetrahedron Lett. 1982;23:2095-2098.

    Not in our library10.1016/s0040-4039(00)87270-6

  392. 392.

    Sakata K, Masahito M, Kuwatsuka T, Uzawa J, Sakurai A, Lu HSM, Clardy J (1987b) Structure of aspirochlorine, a novel epidithiopiperazine-2,5-dione, and related compounds produced by Aspergillus spp. 29th Symp Chem Nat Prod 29:685–691

    Not in our library

  393. 393.

    Saldan NC, Almeida RTR, Avíncola A, Porot C, Galuch MB, Magon TFS, Pilau EJ, Svidzinski TIE, Oliveira CC. Development of an analytical method for identification of Aspergillus flavus based on chemical markers using HPLC-MS. Food Chem. 2018;241:113-121.

    Not in our library10.1016/j.foodchem.2017.08.065

  394. 394.

    Samson RA, Hong S-B, Peterson SW, Frisvad JC, Varga J. Polyphasic taxonomy of Aspergillus section Fumigati and its teleomorph Neosartorya. Stud Mycol. 2007;59:147-203.

    Not in our library10.3114/sim.2007.59.14

  395. 395.

    Samson RA, Visagie CM, Houbraken J, Hong S-B, Hubka V, Klaassen CHW, Perrone G, Seifert KA, Susca A, Tanney JB, Varga J, Kocsubé S, Szigeti G, Yaguchi T, Frisvad JC. Phylogeny, identification and nomenclature of the genus Aspergillus. Stud Mycol. 2014;78:141-173.

    Not in our library10.1016/j.simyco.2014.07.004

  396. 396.

    Samuels GJ, Ismaiel A, Mulaw TB, Szakacs G, Druzhinina IS, Kubicek CP, Jaklitsch WM. The Longibrachiatum clade of Trichoderma: a revision with new species. Fungal Divers. 2012;55:77-108.

    Not in our library10.1007/s13225-012-0152-2

  397. 397.

    Samuels GJ, Petrini O, Kuhls K, Lieckfeldt E, Kubicek CP. The Hypocrea schweinitzii complex and Trichoderma sect. Longibrachiatum. Stud Mycol. 1998;41:1-54.

    Not in our library

  398. 398.

    Sano Y, Ishikawa TY, Muramatsu S, Uzuka Y, Kokubo S, Omata S, Kitamura T, Matsugo S. Study on the Koji mold producing substrate – possible application as a food supplement. Food Sci Technol. 2007;13:13-19.

    Not in our library

  399. 399.

    Sasaki M, Asoa Y, Yokotsuka T (1968) Studies of the compounds produced by molds part V. Isolation of non-fluorescent pyrazine compounds (2). J Agric Chem Soc Jpn 42:351–355 (in Japanese)

    Not in our library

  400. 400.

    Sato N, Horiuchi T, Hamano M, Sekine H, Chiba S, Yamamoto H, Yoshioka T, Kimura I, Satake M, Ida Y. Kojistatin A, a new cysteine protease inhibitor produced by Aspergillus oryzae. Biosci Biotech Biochem. 1996;60:1747-1748.

    Not in our library10.1271/bbb.60.1747

  401. 401.

    SCCS (Scientific Committee on Consumer Safety) (2012) Opinion on kojic acid, 26–27 June 2012.

    Not in our library

  402. 402.

    Schlingmann G, Taniguchi T, He H, Bigelis R, Yang HY, Koehn FE, Carter GT, Berova N. Reassessing the structure of pyranonigrin. J Nat Prod. 2007;70:1180-1187.

    Not in our library10.1021/np070175n

  403. 403.

    Schmoll M, Dattenböck C, Carreras-Villaseñor N, Mendoza-Mendoza A, Tisch D, Alemán MI, Baker SE, Brown C, Cervantes-Badillo MG, Cetz-Chel J, Cristobal-Mondragon GR, Delaye H, Esquivel-Naranjo EU, Frischmann A, Gallardo-Negrete JD, Garca-Esquivel M, Gomez-Rodriguez E, Greenwood DR, Hernandez-Onata M, Kruszewska JS, Lawrey R, Mora-Montes HM, Munoz-Centeno T, Nieto-Jacobo MF, Lopez GN, Olmedo-Nonfil V, Osoroa-Conceosion M, Pilsyk S, Pomraning KR, Rodriguez-Iglesias A, Rosales-Saavedra MT, Sanchez-Arregyúin JA, Sedl-Seiboth V, Stewart A, Iresti-Rivera EE, Wang CL, Wang TF, Zeilinger S, Casas-Flores S, Herrera-Estrella A. The genomes of three uneven siblings: Footprints of the lifestyles of three Trichoderma species. Microbiol Mol Biol Rev. 2016;80:205-327.

    Not in our library10.1128/mmbr.00040-15

  404. 404.

    Schroeder HW, Kelton WH. Production of sterigmatocystin by some species of the genus Aspergillus and its toxicity to chicken embryos. Appl Microbiol. 1975;30:589-591.

    Not in our library10.1128/am.30.4.589-591.1975

  405. 405.

    Schuster E, Dunn-Coleman N, Frisvad JC, van Dijck PWM. On the safety of Aspergillus niger—a review. Appl Microbiol Biotechnol. 2002;59:426-435.

    Not in our library10.1007/s00253-002-1032-6

  406. 406.

    Seshime Y, Juvvadi PR, Fujii I, Kitamoto K. Discovery of a novel superfamily of type III polyketide synthases in Aspergillus oryzae. Biochem Biophys Res Commun. 2005;331:253-260.

    Not in our library10.1016/j.bbrc.2005.03.160

  407. 407.

    Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Fujii I. Identification of csypyrone B1 as the novel product from Aspergillus oryzae type III polyketide synthase CsyB. Biomed. Med Chem. 2010;18:4542-4546.

    Not in our library10.1016/j.bmc.2010.04.058

  408. 408.

    Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Nonaka T, Fujii I. Aspergillus oryzae type III polyketide synthase csyA is involved in the biosynthesis of 3,5-dihydroxy-benzoic acid. Biomed. Med Chem Lett. 2010;20:4785-4788.

    Not in our library10.1016/j.bmcl.2010.06.119

  409. 409.

    Shaaban M, El-Metwally MM, Nasr H. A new diketopiperazine alkaloid from Aspergillus oryzae. Nat Prod Res. 2014;28:86-94.

    Not in our library10.1080/14786419.2013.841687

  410. 410.

    Shen L, Ye Y-H, Wang X-T, Zhu H-L, Xu C, Song YC, Li H, Tan R-X. Structure and total synthesis of aspernigerin: a novel cytotoxic endophyte metabolite. Chem Eur J. 2006;2006:4393-4396.

    Not in our library10.1002/chem.200501423

  411. 411.

    Shi YS, Zhang Y, Chen XZ, Zhang N, Liu YB. Metabolites produced by the endophytic fungus Aspergillus fumigatus from the stem of Erythrophloeum fordii Oliv. Molecules. 2015;20:10793-10799.

    Not in our library10.3390/molecules200610793

  412. 412.

    Shigehisa H, Kikuchi H, Suzuki T, Hiroya K. The revised structure of trichodermatide A. Eur J Org Chem. 2015;2015:7670-7673.

    Not in our library10.1002/ejoc.201501281

  413. 413.

    Shimizu Y, Ogata H, Goto S. Type III polyketide synthases: functional classification and phylogenomics. ChemBioChem. 2017;18:50-65.

    Not in our library10.1002/cbic.201600522

  414. 414.

    Shimoda C. An antibacterial substance, oryzacidin, against sake-putryfying bacteria, produced by Aspergillus oryzae. J Agric Chem Soc Japan. 1951;25:254-260.

    Not in our library

  415. 415.

    Shinohara Y, Kawatani M, Futamura Y, Osada H, Koyama Y. An overproduction of astellolides induced by genetic disruption of chromatin-remodeling factors in Aspergillus oryzae. J Antibiot. 2016;69:4-8.

    Not in our library10.1038/ja.2015.73

  416. 416.

    Shiomi K, Hatae K, Yamaguchi Y, Masuma R, Tomoda H, Kobayashi S, Omura S. New antibiotics miyakamides produced by a fungus. J Antibiot. 2002;55:952-961.

    Not in our library10.7164/antibiotics.55.952

  417. 417.

    Shishido K, Omodani T, Shibuya M. Novel and enantioselective total synthesis of drimane type sesquiterpenes. J Chem Soc Perkin Trans. 1991;1(1991):2285-2287.

    Not in our library10.1039/p19910002285

  418. 418.

    Shu Y-Z, Cutrone JQ, Klohr SE, Huang S. BMS-192548, a tetracyclic binding inhibitor of neuropeptide Y receptors, from Aspergillus niger WB2346. II Physicochemical properties and structural characterization. J Antibiot. 1995;48:1060-1065.

    Not in our library10.7164/antibiotics.48.1060

  419. 419.

    Skóra J, Sulyok M, Nowak A, Otlewska A, Gutarowska B. Toxinogenicity and cytotoxicity of Alternaria, Aspergillus and Penicillium moulds isolated from working environments. Int J Environ Sci Technol. 2017;14:595-608.

    Not in our library10.1007/s13762-016-1172-3

  420. 420.

    Son SY, Lee S, Singh D, Lee N-R, Lee D-Y, Lee CH (2018) Comprehensive secondary metabolite profiling toward delineating the solid and submerged-state fermentation of Aspergillus oryzae KCCM 12698. Front Microbiol 9 Art 1076

    Not in our library10.3389/fmicb.2018.01076

  421. 421.

    Sørensen LM, Lametsch R, Andersen MR, Nielsen PV, Frisvad JC. Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism. BMC Microbiol. 2009;9:255.

    Not in our library10.1186/1471-2180-9-255

  422. 422.

    Springer JP, Büchi G, Kobbe B, Demain AL, Clardy J. The structure of ditryptophenaline—a new metabolite of Aspergillus flavus. Tetrahedron Lett. 1977;18:2403-2406.

    Not in our library10.1016/s0040-4039(01)83777-1

  423. 423.

    Srinisavan KS, Ramakrishnan CV. Synthesis of thiamine by molds. Biochem Biophys Acta. 1952;9:156-160.

    Not in our library10.1016/0006-3002(52)90142-x

  424. 424.

    Stockmann-Juvala H, Savolainen K. A review of the toxic effects and mechanisms of action of fumonisin B1. Hum Exp Toxicol. 2008;27:799-809.

    Not in our library10.1177/0960327108099525

  425. 425.

    Sugawara F, Kim K-W, Uzawa J, Yoshida S, Takahashi N, Curtis RW. Structure of malformin A2, reinvestigation of phytotoxic metabolites produced by Aspergillus niger. Tetrahedron Lett. 1990;31:4337-4340.

    Not in our library10.1016/s0040-4039(00)97615-9

  426. 426.

    Sugimoto T, Murata S, Matsuura S, Pfleiderer W. Synthesis of asperopterin B and some analogues. Tetrahedron Lett. 1986;27:4179-4180.

    Not in our library10.1016/s0040-4039(00)84942-4

  427. 427.

    Sugiyama M, Masaki M, Ohta M. Synthesis of 1-hydroxy-3-isobutyl-6-(1-hydroxy-1-methylethyl)-2-pyrazinone and the structure of muta-aspergillic acid. Tetrahedron Lett. 1967;8:845-848.

    Not in our library10.1016/s0040-4039(00)71575-9

  428. 428.

    Sun Y, Laian T, Huangn J, Ma H-Y, Lv A-L, Yasukawa K, Pei Y-H. Trichodermatides A-D, novel polyketides from the marine-derived fungus Trichoderma reesei. Org Lett. 2008;10:393-396.

    Not in our library10.1021/ol702674f

  429. 429.

    Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W. Indole diterpenoids and isocoumarin from the fungus Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014;12:3970-3981.

    Not in our library10.3390/md12073970

  430. 430.

    Suresha BS, Srinivasan K. Antioxidant properties of fungal metabolite nigerloxin in vitro. Appl Biochem Microbiol. 2013;49:587-591.

    Not in our library10.1134/s0003683813060173

  431. 431.

    Susca A, Proctor RH, Butchko RAE, Haidukowski M, Stea G, Logrieco A, Moretti A. Variation in the fumonisin biosynthetic gene cluster in fumonisin-producing and nonproducing black aspergilli. Fungal Genet Biol. 2014;73:39-52.

    Not in our library10.1016/j.fgb.2014.09.009

  432. 432.

    Taevernier L, Wynendaele E, de Vreese L, Burvenich C, de Spiegeleer B. The mycotoxin definition reconsidered towards fungal cyclic depsipeptides. J Environ Sci Health, Part C. 2016;34:114-135.

    Not in our library10.1080/10590501.2016.1164561

  433. 433.

    Tagami Koichi, Minami Atsushi, Fujii Ryuya, Liu Chengwei, Tanaka Mizuki, Gomi Katsuya, Dairi Tohru, Oikawa Hideaki. Rapid Reconstitution of Biosynthetic Machinery for Fungal Metabolites inAspergillus oryzae: Total Biosynthesis of Aflatrem. ChemBioChem. 2014;15(14):2076-2080.

    Not in our library10.1002/cbic.201402195

  434. 434.

    Takagi M, Motohashi K, Hwang J-H, Nagai A, Shin-ya K. New tensidols, JBIR-86 and JBIR-87, isolated from Aspergillus sp. fJ80. J Antibiot. 2010;63:371-373.

    Not in our library10.1038/ja.2010.45

  435. 435.

    Takahashi T, Jin FJ, Sunagawa M, Machida M, Koyama Y. Generation of large chromosomal deletions in koji molds Aspergillus oryzae and Aspergillus sojae via loop-out recombination. Appl Environ Microbiol. 2008;74:7684-7693.

    Not in our library10.1128/aem.00692-08

  436. 436.

    Takahashi T, Ogawa M, Koyama Y. Analysis of the functions of recombination-related genes in the generation of large chromosomal deletions by loop-out recombination in Aspergillus oryzae. Euk Cell. 2012;11:507-517.

    Not in our library10.1128/ec.05208-11

  437. 437.

    Talontsi FM, Tatong MD, Dittrich B, Douanla-Meli C, Laatsch H. Structures and absolute configuration of three α-pyrones from an endophytic fungus Aspergillus niger. Tetrahedron. 2013;69:7147-7151.

    Not in our library10.1016/j.tet.2013.05.098

  438. 438.

    Tamiya H. Studien über die Stoffwechselprodukte von Aspergillus oryzae. I. Metabolic physiology of Aspergillus oryzae. I. Acta Phytochim Jpn. 1927;3:51-173.

    Not in our library

  439. 439.

    Tamogami S, Katayama M, Marumo S, Isobe M. Synthesis of the 5-demethyl-6-deoxy analogue of sporogen AO1, a sporogenic substance of Aspergillus oryzae. Biosci Biotech Biochem. 1996;60:1372-1374.

    Not in our library10.1271/bbb.60.1372

  440. 440.

    Tan Q-W, Gao F-L, Wang F-R, Chen Q-J. Anti-TMV activity of malformin A1, a cyclic penta-peptide produced by an endophytic fungus Aspergillus tubingensis FJBJ11. Int J Mol Sci. 2015;16:5750-5761.

    Not in our library10.3390/ijms16035750

  441. 441.

    Tanabe M, Hamasaki T, Suzuki Y, Johnson LF. Biosynthetic studies with carbon-13: Fourier nuclear magnetic resonance spectra of the metabolite avenaciolide. J Chem Soc Chem Commun. 1973;1973:212-213.

    Not in our library10.1039/c3973000212b

  442. 442.

    Tanaka K, Goto T, Manabe M, Matsuura S. Traditional japanese fermented foods free from mycotoxin contamination. Jpn Agric Res Quart. 2002;236:45-50.

    Not in our library10.6090/jarq.36.45

  443. 443.

    Tanaka T, Hasegawa A, Aoki N, Yamamoto S, Udagawa S, Sekita S, Harada M, Nozawa K, Kawai K. Production of aflatrem and its related indoloterpenes by microsclerotium-producing strains of Aspergillus flavus. Proc Jpn Assoc Mycotoxicol. 1989;30:19-23.

    Not in our library10.2520/myco1975.1989.30_19

  444. 444.

    Tanaka S, Wada K, Katayama M, Marumo S. Isolation of sporogen-AO1, a sporogenic substance from Aspergillus oryzae. Agric Biol Chem. 1984;48:3189-3191.

    Not in our library

  445. 445.

    Tanaka S, Wada K, Marumo S, Hattori H. Structure of sporogen-AO1, a sporogenic substance. Tetrahedron Lett. 1984;25:5907-5910.

    Not in our library10.1016/s0040-4039(01)81717-2

  446. 446.

    Tang M-C, Lin H-C, Li D, Zou Y, Li J, Xu W, Cacho RA, Hillenmeyer ME, Garg NK, Tang Y. Discovery of unclustered fungal indole diterpene biosynthetic pathways through combinatorial pathway reassembly in engineered yeast. J Am Chem Soc. 2015;137:13724-13727.

    Not in our library10.1021/jacs.5b06108

  447. 447.

    Tao L, Chung SH. Non-aflatoxigenicity of commercial Aspergillus oryzae strains due to genetic defects compared to aflatoxigenic strains. J Microbiol Biotechnol. 2014;24:1081-1087.

    Not in our library10.4014/jmb.1311.11011

  448. 448.

    TePaske MR, Gloer JB, Wicklow DT, Dowd PF. Aflavazole: a new antiinsectan carbazole metabolite from the sclerotia of Aspergillus flavus. J Org Chem. 1990;55:5299-5301.

    Not in our library10.1021/jo00305a030

  449. 449.

    TePaske MR, Gloer JB, Wicklow DT, Dowd PF. Leporin A—an antiinsectan N-alkoxypyridone from the sclerotia of Aspergillus leporis. Tetrahedron Lett. 1991;32:5687-5690.

    Not in our library10.1016/s0040-4039(00)93530-5

  450. 450.

    TePaske MR, Gloer JB, Wicklow DT, Dowd PF. Aflavarin and beta-aflatrem—new anti-insectan metabolites from the sclerotia of Aspergillus flavus. J Nat Prod. 1992;55:1080-1086.

    Not in our library10.1021/np50086a008

  451. 451.

    Terabayashi Y, Sano M, Yamane N, Maruui J, Tamano K, Sagara J, Dohmoto M, Oda K, Ohshima E, Tachibana K, Higa Y, Ohashi S, Koike H, Machida M. Identification and characterization of genes responsible for biosynthesis of kojic acid, an industrially important compound from Aspergillus oryzae. Fungal Genet Biol. 2010;47:953-961.

    Not in our library10.1016/j.fgb.2010.08.014

  452. 452.

    Thom C, Church MB. Aspergillus flavus, A. oryzae, and associated species. Amer J Bot. 1921;8:103-126.

    Not in our library10.1002/j.1537-2197.1921.tb05609.x

  453. 453.

    Tokuoda M, Seshime Y, Fujii I, Kitamoto K, Takahashi T, Koyama Y. Identification of a novel polyketide synthase-nonribosomal peptide synthase (PKS-NRPS) gene required for the biosynthesis of cyclopiazonic acid in Aspergillus oryzae. Fungal Genet Biol. 2008;45:1608-1615.

    Not in our library10.1016/j.fgb.2008.09.006

  454. 454.

    Tokuoka M, Kukuchi T, Shinohara Y, Koyama A, Iio S, Kubota T, Kabayashi J, Kayama A, Shindo H, Sato K. Cyclopiazonic acid biosynthesis gene cluster cpaM is required for speradine A biosynthesis. Biosci Biotechnol Biochem. 2015;79:2081-2085.

    Not in our library10.1080/09168451.2015.1065167

  455. 455.

    Tominaga M, Lee Y-H, Hayashi R, Suzuki Y, Yamada O, Sakamoto K, Gotoh K, Akita O. Molecular analysis of an inactive aflatoxin biosynthesis gene cluster in Aspergillus oryzae RIB strains. Appl Environ Microbiol. 2006;72:484-490.

    Not in our library10.1128/aem.72.1.484-490.2006

  456. 456.

    Torres J, Guarro J, Suarez G, Sune N, Ramírez C. Morphological changes in strains of Aspergillus flavus Link ex Fries and Aspergillus parasiticus Speare related with aflatoxin production. Mycopathologia. 1980;72:171-174.

    Not in our library10.1007/bf00572660

  457. 457.

    Tsuda M, Mugishima T, Komatus K, Sone T, Tanaka M, Mikami Y, Shiro M, Hirai M, Ohizumi Y, Kobayashi J. Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii. Tetrahedron. 2003;59:3227-3230.

    Not in our library10.1016/s0040-4020(03)00413-7

  458. 458.

    Tsukui T, Nagano N, Umemura M, Kumagai T, Terai G, Machida M, Asai K. Ustiloxins, fungal cyclic peptides, are ribosomally synthesized in Ustilaginoidea virens. Bioinformatics. 2015;31:981-985.

    Not in our library10.1093/bioinformatics/btu753

  459. 459.

    Turner WB. Fungal metabolites. 1971.

    Not in our library

  460. 460.

    Turner WB, Aldridge DC. Fungal metabolites II. 1983.

    Not in our library

  461. 461.

    Uchoa Paula Karina S., Pimenta Antonia T. A., Braz-Filho Raimundo, de Oliveira Maria da Conceição F., Saraiva Natália N., Rodrigues Barbara S. F., Pfenning Ludwig H., Abreu Lucas M., Wilke Diego V., Florêncio Katharine G. D., Lima Mary Anne S. New cytotoxic furan from the marine sediment-derived fungi Aspergillus niger. Natural Product Research. 2017;31(22):2599-2603.

    Not in our library10.1080/14786419.2017.1283499

  462. 462.

    Ueno T, Nishimura A, Yoshizako F. Isolation and identification of a new analogue of aspergillic acid derived from valine and isoleucine. Agric Biol Chem. 1977;41:901-902.

    Not in our library

  463. 463.

    Ui H, Shiomi K, Yamaguchi Y, Masuma R, Nagamitsu T, Takano D, Sunazuka T, Namikoshi M, Omura S. Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554. J Antibiot. 2001;54:234-238.

    Not in our library10.7164/antibiotics.54.234

  464. 464.

    Uka V, Moore GG, Arroyo-Manzanares N, Nebija D, De Saeger S, Mavungu JDD. Unravelling the diversity of the cyclopiazonic acid family of mycotoxins in Aspergillus flavus by UHPLC triple-TOF HRMS. Toxins. 2017;9:35.

    Not in our library10.3390/toxins9010035

  465. 465.
    MIDDAS-M: motif-independent de novo detection of secondary metabolite gene clusters through the integration of genome sequencing and transcriptome data. · 2013
    Not checked
  466. 466.

    Umemura M, Koike H, Yamane N, Koyama Y, Satou Y, Kikuzato I, Teruya M, Tsukahara M, Imada Y, Wachi Y, Miwa Y, Yano S, Tamano K, Kawarabayasi Y, Fujimoro KE, Machida M, Hirano T. Comparative genome analysis between Aspergillus oryzae strains reveals close relationship between sites of mutation localization and regions of highly divergent genes among Aspergillus species. DNA Res. 2012;19:375-382.

    Not in our library10.1093/dnares/dss019

  467. 467.

    Umemura M, Koyama Y, Takeda I, Hagiwara H, Ikegami T, Koike H, Machida M. Fine de novo sequencing of a fungal genome using only SOLiD short read data: verfication on Aspergillus oryzae RIB40. PLoS ONE. 2013;8:e63673.

    Not in our library10.1371/journal.pone.0063673

  468. 468.

    Umemura M, Nagano N, Koike H, Kawano J, Ishii T, Miyamura Y, Kikuchi M, Tamano K, Yu J, Shin-ya K, Machida M. Characterization of the biosynthetic gene cluster for the ribosomally synthesized cyclic peptide ustiloxin B in Aspergillus flavus. Fungal Genet Biol. 2014;68:23-30.

    Not in our library10.1016/j.fgb.2014.04.011

  469. 469.

    Umezawa H, Tobe H, Shibamoto N, Nakamura F, Nakamura K, Matzusaki M, Takeuchi T. Isolation of isoflavones inhibiting DOPA decarboxylase from fungi and Streptomyces. J Antibiot. 1975;28:947-952.

    Not in our library10.7164/antibiotics.28.947

  470. 470.

    Valdes JJ, Cameron JE, Cole RJ. Aflatrem: a tremorgenic mycotoxin with acute neurotoxic effects. Environ Health Perspec. 1985;62:459-463.

    Not in our library10.1289/ehp.8562459

  471. 471.

    Van der Merwe KJ, Fourie L, Scott de B. On the structure of the aflatoxins. Chem Ind. 1963;1963:1660-1661.

    Not in our library

  472. 472.

    Varga J, Due M, Frisvad JC, Samson RA. Taxonomic revision of Aspergillus section Clavati based on molecular, morphological and physiological data. Stud Mycol. 2007;59:89-106.

    Not in our library10.3114/sim.2007.59.11

  473. 473.

    Varga J, Frisvad JC, Kocsubé S, Brankovics B, Tóth B, Szigeti G, Samson RA. New and revisited species in Aspergillus section Nigri. Stud Mycol. 2011;69:1-17.

    Not in our library10.3114/sim.2011.69.01

  474. 474.

    Varga J, Frisvad JC, Samson RA. A reappraisal of fungi producing aflatoxin. World Mycotoxin J. 2009;2:263-277.

    Not in our library10.3920/wmj2008.1094

  475. 475.

    Varga J, Frisvad JC, Samson RA. Two new aflatoxin producing species and an overview of Aspergillus section Flavi. Stud Mycol. 2011;69:57-80.

    Not in our library10.3114/sim.2011.69.05

  476. 476.

    Varoglu M, Corbett TH, Valeriote FA, Crews P. Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of Aspergillus niger. J Org Chem. 1997;62:7078-7079.

    Not in our library10.1021/jo970568z

  477. 477.

    Varoglu M, Crews P. Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger. J Nat Prod. 2000;63:41-43.

    Not in our library10.1021/np9902892

  478. 478.

    Vasantha KY, Singh RP, Sattur AP. A preliminary pharmacokinetic and toxicity study of nigerloxin. Ind J Biochem Biophys. 2018;55:44-51.

    Not in our library

  479. 479.

    Vernot EH, MacEwen CC, Kinkead ER. Acute toxicity and skin corrosion data for some organic and inorganic compounds and aqueous solutions. Toxicol Appl Pharmacol. 1977;42:417-423.

    Not in our library10.1016/0041-008x(77)90019-9

  480. 480.

    Vesth TC, Nybo JL, Theobald S, Frisvad JC, Larsen TO, Nielsen KF, Hoof JB, Brandl J, Salamov A, Ryley R, Gladden JM, Phatale P, Nielsen MT, Lyhne EK, Kogle ME, Strasser K, McDonald E, Berrey K, Clun A, Chen C, Nolan M, Sandor L, Kuo A, Lipzen A, Hainaut M, Drula E, Tsang A, Magnuson JK, Henrissat B, Wiebenga A, Simmons BA, Mäkelä MR, de Vries RP, Grigoriev IV, Mortensen UH, Baker SE, Andersen MR (2018) Section-level genome sequencing of Aspergillus section Nigri to investigate inter- and intra-species variation. Nature Genetics in press

    Not in our library10.1038/s41588-018-0246-1

  481. 481.

    Vidal-Garcia M, Redrado S, Domingo MP, Marquina P, Colmemarejo C, Meis JF, Rezusta A, Pardo J, Galvez EM. Production of the invasive aspergillosis biomarker bis(methylthio)gliotoxin within the genus Aspergillus: in vitro and in vivo metabolite quantification and genomic analysis. Front Microbiol. 2018;9:1246.

    Not in our library10.3389/fmicb.2018.01246

  482. 482.

    Voss KA, Riley RT. Fumonisin toxicity and mechanism action: overview and current perspectives. Food Saf. 2013;1:50-69.

    Not in our library

  483. 483.

    Wada K, Tanaka S, Marumo S. Structures of two new sesquiterpenes from Aspergillus oryzae. Agric Biol Chem. 1983;47:1075-1078.

    Not in our library

  484. 484.

    Waiss AC, Wiley M, Black DR, Lundin RE. 3-Hydroxy-6,7-dimethoxydifuroxanthone—a new metabolite from Aspergillus flavus. Tetrahedron Lett. 1968;9:3207-3210.

    Not in our library10.1016/s0040-4039(00)89525-8

  485. 485.

    Waksman SA, Bugie E. Strain specificity and production of antibiotic substances. II. Aspergillus flavus-oryzae group. Proc Nat Acad Sci U S A. 1943;29:282-288.

    Not in our library10.1073/pnas.29.9.282

  486. 486.

    Wang D, Bao Y-R, Yang X-X, Meng X-S, Chen G. A new alkaloid from Penicillium dipodomyicola. Chem Nat Comp. 2015;51:733-735.

    Not in our library10.1007/s10600-015-1395-4

  487. 487.
    Ochratoxin A Producing Fungi, Biosynthetic Pathway and Regulatory Mechanisms · 2016
    Not checked
  488. 488.

    Wani MA, Sanjana K, Kumar DM, Lal DK. GC-MS analysis reveals production of 2-phenylethanol from Aspergillus niger endophytic in rose. J Basic Microbiol. 2010;50:110-114.

    Not in our library10.1002/jobm.200900295

  489. 489.

    Wasil Z, Huhnert E, Simpson TJ, Cox RJ. Oryzines A & B, maleidride congeners from Aspergillus oryae and their putative biosynthesis. J Fungi. 2018;4:96.

    Not in our library10.3390/jof4030096

  490. 490.

    Watts R, Dahiya J, Chanhary K, Tauro P. Isolation of a new antifungal metabolite of Trichoderma reesei. Plant Soil. 1988;107:81-84.

    Not in our library10.1007/bf02371547

  491. 491.

    Wenke J, Anke H, Sterner O. Pseurotin A and 8-O-demethylpseurotin A from Aspergillus fumigatus and their inhibitory activities on chitin synthase. Biosci Biotechnol Biochem. 1993;57:961-964.

    Not in our library10.1271/bbb.57.961

  492. 492.

    White EC. Bactericidal filtrates from a mold culture. Science. 1940;92:127.

    Not in our library10.1126/science.92.2380.127

  493. 493.

    White EC, Hill JH. Studies on antibacterial products formed by molds. I. Aspergillic acid, a product of a strain of Aspergillus flavus. J Bacteriol. 1943;45:433-444.

    Not in our library10.1128/jb.45.5.433-443.1943

  494. 494.

    Wicklow DT, Kurata H, Ueno Y. Adaptation in wild and domesticated yellow-green aspergilli. Toxigenic fungi—their toxins and health hazard. 1984;78-85.

    Not in our library

  495. 495.

    Wicklow DT, Cole RJ. Tremorgenic indole metabolites and aflatoxins in sclerotia of Aspergillus flavus—an evolutionary perspective. Can J Bot. 1982;60:525-528.

    Not in our library10.1139/b82-070

  496. 496.

    Wiemann P, Guo C-J, Palmer JM, Sekonyela R, Wang CCC, Keller NP. Prototype of an intertwined secondary metabolite gene cluster. Proc Nat Acad Sci U S A. 2013;110:17065-17070.

    Not in our library10.1073/pnas.1313258110

  497. 497.

    WU Zu-Jian, OUYANG Ming-An, SU Ren-Kuan, GUO Yue-Xiong. Two New Cerebrosides and Anthraquinone Derivatives from the Marine FungusAspergillus niger. Chinese Journal of Chemistry. 2008;26(4):759-764.

    Not in our library10.1002/cjoc.200890142

  498. 498.

    Wu ZC, Williams LJ, Danischefsky SJ. A tree-step entry to the aspirochlorine family of antifungal agents. Angew Chem Int Ed. 2000;39:3866-3869.

    Not in our library10.1002/1521-3773(20001103)39:21<3866::aid-anie3866>3.0.co;2-e

  499. 499.

    Xu X, Zhang X, Nong X, Wei X, Shuhua Q. Oxindole alkaloids from the fungus Penicillium commune DFFSCS026 isolated from deep-sea-derived sediments. Tetrahedron. 2015;71:610-615.

    Not in our library10.1016/j.tet.2014.12.031

  500. 500.

    Yabuta T. On kojic acid, a new organic acid produced by Aspergillus oryzae. J Coll Agr, Imp Univ Tokyo. 1912;5:51-58.

    Not in our library

  501. 501.

    Yabuta T. A new organic acid (kojic acid) formed by Aspergillus oryzae. J Chem Soc. 1922;122:939-941.

    Not in our library

  502. 502.

    Yamada T, Hiratake J, Aikawa M, Suizu T, Saito Y, Kawato A, Suginami K, Oda J. Cysteine protease inhibitors produced by the industrial koji mold, Aspergillus oryzae O-1018. Biosci Biotechnol Biochem. 1998;62:907-914.

    Not in our library10.1271/bbb.62.907

  503. 503.

    Yamaji K, Fukushi Y, Hashidoko Y, Yoshida T, Tahara S. Characterization of antifungal metabolites produced by Penicillium species isolated from seeds of Picea glehnii. J Chem Ecol. 1999;25:1643-1653.

    Not in our library10.1023/a:1020849202413

  504. 504.

    Yang X-L, Awakara T, Wakimoto T, Abe I. Three acyltetronic acid derivatives: noncanonical cryptic polyketides from Aspergillus niger identified by genome mining. ChemBioChem. 2014;15:1578-1583.

    Not in our library10.1002/cbic.201402172

  505. 505.

    Yang G, Sandjo L, Yun K, Leutou AS, Kim GD, Choi HD, Kang JS, Hong J, Son BW. Flavusides A and B, antibacterial cerebrosides from the marine-derived fungus Aspergillus flavus. Chem Pharm Bull. 2011;59:1174-1177.

    Not in our library10.1248/cpb.59.1174

  506. 506.

    Yassin MA, El-Rahim A, El-Samawaty MA, Moslem AA, Al-Arfaj AA. Coffee bean myco-contaminants and oxalic acid producing Aspergillus niger. Ital J Food Sci. 2015;27:1.

    Not in our library

  507. 507.

    Ye Y, Minami A, Igarashi Y, Izumikawa M, Umemura M, Nagano N, Machida M, Kawahara T, Shin-ya K, Gomi K, Oikawa H. Unveiling the biosynthetic pathway of the ribosomally synthesized and post-translationally modified peptide ustiloxin B in filamentous fungi. Angew Chem Int Ed. 2016;55:8072-8075.

    Not in our library10.1002/anie.201602611

  508. 508.

    Ye YH, Zhu HL, Song YC, Liu JY, Tan RX. Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFB-E002. J Nat Prod. 2005;68:1106-1108.

    Not in our library10.1021/np050059p

  509. 509.

    Yoshimi A, Umemura M, Nagano N, Koike H, Machida M, Abe K. Expression if ustR and the Golgi protease KexB are required for ustiloxin B biosynthesis in Aspergillus oryzae. AMB Express. 2016;6:9.

    Not in our library10.1186/s13568-016-0181-4

  510. 510.

    Yoshizawa T, Tsuchiya Y, Morooka N, Sawada Y. Malformin A1 as a mammalian toxicant from Aspergillus niger. Agric Biol Chem. 1975;39:1325-1326.

    Not in our library

  511. 511.

    Yu J, Tamura G, Takahashi N, Arima K. Asperyellone, a new pigment of Aspergillus awamori. Agric Biol Chem. 1967;31:831-836.

    Not in our library

  512. 512.

    Zabala AO, Xu W, Chooi Y-H, Tang Y. Charactrization of a silent azaphilone gene cluster from Aspergillus niger ATCC 1015 reveals a hydroxylation-mediate pyran-ring formation. Chem Biol. 2012;19:1049-1059.

    Not in our library10.1016/j.chembiol.2012.07.004

  513. 513.

    Zalesskaya MI. Riboflavin formation in Aspergillus flavus mycelium grown in filtered cereal mashes. Mikrobiologiya. 1950;19:127-136.

    Not in our library

  514. 514.

    Zeilinger S, Gruber S, Bansal R, Mukherjee PK. Secondary metabolism in Trichoderma—chemistry meets genomics. Fungal Biol Rev. 2016;30:74-90.

    Not in our library10.1016/j.fbr.2016.05.001

  515. 515.

    Zeiliger S, Martin J-F, García-Estrada C (eds) (2015) Biosynthesis and molecular genetics of fungal secondary metabolites. vol. 2. Springer, New York

    Not in our library

  516. 516.

    Zeringue HJ, Shih BY, Moskos K, Grimm D. Identification of the bright-greenish-yellow-fluorescence (BGY-F) compound on cotton lint associated with aflatoxin contamination in cottonseed. Phytochemistry. 1999;52:1391-1397.

    Not in our library10.1016/s0031-9422(99)00432-x

  517. 517.

    Zhang Y, Li X-M, Feng Y, Wang B-G. Phenetyl-α-pyrone derivatives and cyclodipeptides from a marine algous endophytic fungus Aspergillus niger EN-13. Nat Prod Res. 2010;24:1036-1043.

    Not in our library10.1080/14786410902940875

  518. 518.

    Zhang Y, Li X-M, Proksch P, Wang B-G. Ergosterimide, a new natural Diels-Alder adduct of a steroid and maleimide in the fungus Aspergillus niger. Steroids. 2007;72:723-727.

    Not in our library10.1016/j.steroids.2007.05.009

  519. 519.

    Zhang Y, Li X-M, Wang B-G. Nigerasperones A-C, new monomeric and dimeric naphtho-γ-pyrones from marine alga-derived endophytic fungus Aspergillus niger EN-13. J Antibiot. 2007;60:204-210.

    Not in our library10.1038/ja.2007.24

  520. 520.

    Zhang Y, Li XM, Wang CY, Wang BG. A new naphthoquinoneimide derivative from the marine algal-derived endophytic fungus Aspergillus niger EN-13. Chin Chem Lett. 2007;18:951-953.

    Not in our library10.1016/j.cclet.2007.05.054

  521. 521.

    Zhang S, Monahan BJ, Tkacz JS, Scott B. Indole-diterpene gene cluster from Aspergillus flavus. Appl Environ Microbiol. 2004;70:6875-6883.

    Not in our library10.1128/aem.70.11.6875-6883.2004

  522. 522.

    Zhang Y, Wang S, Li X, Cui CM, Feng C, Wang BG. New sphingolipids with a previously unreported 9-methyl-C20-sphingosine moiety from a marine algous endophytic fungus Aspergillus niger EN-13. Lipids. 2007;42:759-764.

    Not in our library10.1007/s11745-007-3079-8

  523. 523.

    Zhao G, Yao Y, Chen W, Cao X. Comparison and analysis of the genomes of two Aspergillus oryzae strains. J Agric Food Chem. 2013;61:7805-7809.

    Not in our library10.1021/jf400080g

  524. 524.

    Zhao G, Yao Y, Hou L, Wang C, Cao X (2014a) Draft genome sequence of Aspergillus oryzae 100-8, an increased acid protease production strain. Genome Announc 2: e00548–14

    Not in our library10.1128/genomea.00548-14

  525. 525.

    Zhao G, Yao Y, Hou L, Wang C, Cao X. Comparison of the genomes and transcriptomes associated with the different protease secretions of Aspergillus oryzae 100-8 and 3.042. Biotechnol Lett. 2014;36:2053-2058.

    Not in our library10.1007/s10529-014-1574-6

  526. 526.

    Zhao G, Yao Y, Wang C, Hou L, Cao X. Comparative genomic analysis of Aspergillus oryzae strains 3.042 and RIB40 for soy sauce fermentation. Int J Food Microbiol. 2013;164:148-154.

    Not in our library10.1016/j.ijfoodmicro.2013.03.027

  527. 527.

    Zhao G, Yao W, Wang C, Hou L, Zeng B, Cao X. Draft genome sequence of Aspergillus oryzae strain 3-042. Euk Cell. 2012;11:1178.

    Not in our library10.1128/ec.00160-12

  528. 528.

    Zhou X, Fang W, Tan S, Lin X, Xun T, Yang B, Liu S, Liu Y. Aspernigrins with anti-HIV-1 activities from the marine-derived fungus Aspergillus niger SCSIO Jcsw6F30. Bioorg Med Chem Lett. 2016;26:361-365.

    Not in our library10.1016/j.bmcl.2015.12.005

  529. 529.

    Zhuravleva OI, Kirichuk NN, Denisenko VA, Dmetrenok PS, Pivkin MV, Afiatullov SS. New kipukasin from marine isolate of the fungus Aspergillus flavus. Chem Nat Comp. 2016;52:266-268.

    Not in our library10.1007/s10600-016-1610-y

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