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The Hunt for Natural Skin Whitening Agents

Nico Smit, Jana Vicanova, Stan Pavel

International Journal of Molecular Sciences · 2009 · Review · CC BY

doi:10.3390/ijms10125326

Abstract

Skin whitening products are commercially available for cosmetic purposes in order to obtain a lighter skin appearance. They are also utilized for clinical treatment of pigmentary disorders such as melasma or postinflammatory hyperpigmentation. Whitening agents act at various levels of melanin production in the skin. Many of them are known as competitive inhibitors of tyrosinase, the key enzyme in melanogenesis. Others inhibit the maturation of this enzyme or the transport of pigment granules (melanosomes) from melanocytes to surrounding keratinocytes. In this review we present an overview of (natural) whitening products that may decrease skin pigmentation by their interference with the pigmentary processes.

Full text

From PubMed Central, U.S. National Library of Medicine, as current on Oct 23, 2026. Paragraph numbers are ours, so an answer can point at one.

Introduction

In the skin, melanocytes are situated on the basal layer which separates dermis and epidermis. One melanocyte is surrounded by approximately 36 keratinocytes. Together, they form the so-called epidermal melanin unit. The melanin produced and stored inside the melanocyte in the melanosomal compartment is transported via dendrites to the overlaying keratinocytes. The melanin pigment is a polymer produced inside the melanosomes and synthesised from the amino acid l-tyrosine that is converted by the enzyme tyrosinase to dopaquinone. This reaction continues spontaneously via dopachrome to the monomeric indolic precursors (5,6-dihydroxyindole and 5,6-dihydroxyindole 2-carboxylic acid) of the black-brown pigment eumelanin. However, some other enzymes, like the tyrosinase related proteins (TRP-1 and dopachrome tautomerase (TRP-2) may also play an important role in melanogenesis in vivo. Upon reaction with cysteine, dopaquinone forms 2- or 5-S-cysteinyldopa that generates the benzothiazine precursors of the red/yellow pheomelanin polymer. In general, a mixed type of pheo- and eumelanin polymer is produced and deposited onto the melanosomal matrix proteins. Considering the many colour variations that can be seen in the skin and hair, one may expect that the composition of the mixed melanins is regulated in many different ways. However, altered production of cutaneous melanin may cause considerable problems of esthetic nature, especially in hyperpigmentary conditions, like melasma, postinflammatory hyperpigmentation, freckles or lentigines. But also depigmenting conditions, like vitiligo, have high impact on the quality of life of the patients.

In the Western culture it is still considered desirable to obtain a (bronze) tan. Despite warnings about the consequences of excessive sun or UV exposure, the artificial tanning business has expanded strongly in the last decades. In the Eastern world, however, a centuries long tradition exists whereby a light complexion is regarded as equivalent to youth and beauty. Development of preparations for bleaching hyperpigmented lesions or to safely achieve overall whitening is one of the challenges for cosmetic industry. In recent years, the interest in skin whitening has grown tremendously.

Targeting Tyrosinase as the Key Enzyme of Melanogenesis

One of the most obvious cellular targets for depigmenting agents is the enzyme tyrosinase. The scientific literature on tyrosinase inhibition shows that a large majority of the work has been conducted since 2000 and has mostly been devoted to the search for new depigmenting agents. Notably, many of these studies deal with tyrosinase inhibitors from natural sources and are mostly of Asian origin (see Tables 1 and 2). However, early pioneering work in the field has been performed much earlier using 4-hydroxyanisole. This compound could serve as an alternative substrate for tyrosinase causing depigmentation both in vivo and in vitro. Since this and various other substituted phenolic compound can generate potentially toxic quinone products they were used in various studies aimed at the induction of toxicity mediated by tyrosinase in melanoma cells.

Considerable interest in tyrosinase inhibitors exists also in the food industry because the activity of this enzyme is responsible for the browning of fruit and vegetables. Cysteine or ascorbic acid can be used to prevent the enzymatic browning of fruit and vegetables by binding the o-dopaquinone intermediates. More recently also 4-hexylresorcinol has been utilized for this purpose. Since safety considerations are very strict in food industry, the search for new, natural tyrosinase inhibitors without negative side effects is of utmost importance in this field of research.

Work on synthetic and natural tyrosinase inhibitors has been recently reviewed in several papers. The tyrosinase inhibitors can be classified as competitive, uncompetitive, mixed type and non-competitive inhibitors. The nature of tyrosinase inhibition can be disclosed by measuring enzyme inhibition kinetics using Lineweaver-Burk plots with varying concentrations of l-DOPA as the substrate. This can be seen on example of polyphenol extracts from acerola (West Indian cherry) or a chalcone derivative isolated from Morus nigra (black mulberry) which has been described in recent work of Hanamura et al. and Zhang et al.. Knowledge of the type of inhibition may be important in order to achieve better skin lightening effects since combined treatments may result in synergistic effects. This has been shown in case of the competitive tyrosinase inhibitor, arbutin and the noncompetitive inhibitor, aloesin.

A 2009 paper by Chang states that a large majority of tyrosinase inhibitors show reversible inhibition. In irreversible inhibition, covalent binding with the enzyme may cause its inactivation by altering the active site of the enzyme and/or by conformational changes to the protein molecule. Irreversible inhibition may also occur via the so-called suicide inhibition mechanism as described in the model by Land et al.. Also, two 8-hydroxy isoflavones isolated from soygerm koji showed suicide inhibition of tyrosinase and have been tested with promising results in an in vivo assay with 60 volunteers. In Table 1 we summarize the large number of studies using tyrosinase inhibitors from natural sources that have appeared, mostly in the last decade. In many of the investigations, the active ingredients from extracts of various species have been isolated and identified. In case the mode of tyrosinase inhibition was established, a comparison with IC50 values of well known inhibitors such as kojic acid and arbutin was often made. In some of the studies specific side groups (with substitutions to C4, C5 or C8 position) of recorcinols isolated from the breadfruit (Artocarpus incisus) or from a ‘bitter root’ (Sophora flavescens) proved of great importance to their inhibitory potential. In some cases modifications to the natural compounds were made, e.g., the deglycosylation of stilbene compounds by cellulase treatment of the Veratrum patulum extract resulted in improved tyrosinase inhibition. Thus, exact knowledge on enzyme inhibition mechanisms is helpful for designing new whitening products based on targeting the key enzyme of melanogenesis, tyrosinase. Although tyrosinase plays a major role in melanin synthesis, one should realize that the regulation of skin pigmentation exists at various levels and therefore, different modes of interference are possible. There are indications that combined approaches could be more successful than targeting tyrosinase only.

TI; tyrosinase inhibition, (c) competitive mode (nc) non competitive mode of inhibition. SB; Streptomyces bikiniensis. MMS; molecular modeling studies on TI. SAR; structure activity relationship. PI; pigment inhibition.

Tyrosinase inhibition among different studies is difficult to compare for several reasons (see also Chang) because of different sources of tyrosinase used (see Parvez,) and IC50 values that are found using either tyrosinase or l-DOPA as the substrate. In the table comparison to kojic acid (KA) for some of the component (number) is indicated as < or > or compounds are compared among each other (1 > 2).

Extraction procedures for isolation and identification are highly important for good yield of the active ingredients. Many of the papers in Table 1 describe different extraction procedures. An overview of TI from natural and synthetic sources has been presented earlier in the review by Kim and Ujama.

Different Modes of Reducing Melanin Production in Melanocytes and Skin

As proposed by Briganti et al. all depigmenting agents may be divided on the basis of interference in melanin synthesis, transport and removal by skin turnover. In Table 2, we sum up a large number of studies that describe new whitening agents from natural sources with some extra information on their mode of action besides the inhibition of tyrosinase. Next to tyrosinase inhibition (TI) the extracts or their isolated active components were demonstrated to exhibit pigment inhibition (PI). For this purpose, some studies make use of the pigment-producing S. bikiniensis (SB) system or transformed E.coli. In most cases, however B16 melanoma cells are used for demonstrating PI. In addition, PI is demonstrated in the mouse melan-a or mel-ab melanocyte cultures or in normal human melanocytes (nHEM). Obviously, the use of the nHEM may better simulate the in vivo situation. On the other hand, the melanocytes are more difficult to maintain in culture. These cells, also show variations in melanin content from donor to donor and from one passage to the other. Cocultures of melanocytes and keratinocytes from mouse or human skin more closely mimic the in vivo situation and, eventually, a skin equivalent model (SEM) may be the preferred in vitro system for testing skin whitening agents. In this respect, recently commercially available SEM have already been applied for skin whitening studies. Next to this, the brownish guinea pig (GP) model is used in several studies (Table 2) where the pigmentation is induced by either UV or α-MSH. In case of in vivo studies, prevention of the induction of pigment by the whitening agents could be demonstrated using a Minolta chromameter or by histochemical investigations showing a decrease in DOPA positive cells. Another animal model used for whitening studies is the zebrafish that also proved useful for demonstrating the in vivo toxicity of the whitening agents. So far, only limited numbers of clinical trials (CT) with skin whitening agents or formulations have been performed.

Preventing the maturation or intracellular trafficking of tyrosinase is an alternative way to reduce the effect of the enzyme on pigmentation. Various natural extracts can also influence tyrosinase mRNA at the transcription level; also mRNA of the other tyrosinase-related proteins or microphtalmia transcription factor (MITF) can be affected (see refs. and others in Table 2). From the work of Sharlow et al. and Seiberg we learned that the protease activated receptor 2 (PAR-2) is important for melanosomal transfer from melanocytes to keratinocytes and that this transfer can be used as a target for skin lightening. The vitamin B3 derivative niacinamide is one of the agents used for inhibiting melanosomal transfer. Melanocytes express high levels of sAPP, the soluble N-terminal ectodomain of the β-amyloid precursor protein. sAPP may play a role in the release of melanin particles via dendritic tips. Blocking the sAPP signalling could thus be another way to influence melanosome transport.

Mammone et al. (Estee Lauder) proposed that melanin can be degraded enzymatically in keratinocytes and application of melanin degrading enzymes could be used to prevent UVB induced pigmentation in human skin.

Reduction of ROS levels in melanocytes may prevent activation of melanogenesis. In various studies, extracts from plants or fruit or other species were tested for their antioxidant capacity by using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay or the oxygen radical absorbance capacity (ORAC) (e.g., Rangkadilok et al.). Fujiwara and colleagues showed that daily oral administration of vitamin C (ascorbic acid) and vitamin E and cysteine to brownish guinea pigs reduced UVB-induced pigmentation. Ascorbic acid is considered a skin whitening agent and more stable derivatives such as ascorbyl glucoside and ascorbyl palmitate are already being used in different skin whitening formulations. As known from many cases of post-inflammatory hyperpigmentation, melanogenesis can be stimulated by some inflammatory mediators. Inhibition of the production of inflammatory mediators (Il1α and TNF-α) was reported for sea grape extracts. Via this indirect way stimulation of melanogenesis in the pigment cells could be prevented.

Induction of Pigmentation

For the development of effective skin whitening, we also need to understand processes that regulate the induction of pigmentation. Constitutive pigmentation is reflected by the phenotypes of the different skin types with varying pigmentation based on their genetic diversity. The facultative pigmentation acquired on top of the constitutive level can be obtained via different stimuli of which ultraviolet radiation (UVR) is well known as provoking the “tanning response”. An overview of the signalling pathways and intrinsic and extrinsic factors (inclusive UV) that influence melanocyte proliferation or metabolism can be found in the paper by Brenner and Hearing. In brief, the UV response increases the microphtalmia-associated transcription factor (MITF) that is on its turn regulated by another transcription factor SOX9. MI is the main switch for induction of the melanogenic proteins responsible for the final increase of the melanin content in skin after UV exposure. Various pathways can be induced by the signalling through basic fibroblast growth factor (bFGF), hepatocyte growth factor (HGF), stem cell factor (SCF), endothelin-1 (ET-1), adrenocorticotropic hormone and α-melanocyte stimulating hormone (ACTH and α-MSH) via their respective receptors present on melanocytes and thus stimulating their pigment production. These signalling pathways could also serve as a means of specific targeting the melanogenic pathway. In this way, the presence of melanocortin-1 receptor (MC1R) on (B16) melanoma cells has been often used for induction of pigmentation and for testing the depigmenting effects of natural skin lighteners (see examples in Table 2).

Several authors focus on factors that were not directly involved in melanin synthesis but could affect proteins indirectly connected with skin pigmentation. For instance, the endothelin-1 induction of pigmentation in melanocytes could be prevented by 3’antisense S-oligo for tyrosinase that also reduced UV induced pigmentation.

The Wnt/β-catenin pathway is known to play an important role in developmental processes. Binding of Wnt proteins to their receptors (the frizzled family of transmembrane proteins)can be inhibited by Dikkopf 1 (DKK1), a factor secreted by fibroblasts which can suppress growth of melanocytes and strongly inhibit melanin production. Thus, some of the natural whitening agents presented in Table 1 or 2 are not direct inhibitors of tyrosinase but downregulate expression of melanogenic proteins and in this way they may interfere with the complex regulation of melanocyte signalling cascades. Stem cell factor is a cytokine that binds to the c-kit receptor (CD117) and the activation of c-Kit leads to the activation of multiple signaling cascades, including the RAS/ERK, PI3-Kinase, Src kinase, and JAK/STAT pathways. Na and coworkers have used the signalling via SCF/c-kit for the evaluation of new whitening agents by high throughput screening with approximately 10.000 synthetic compounds. They found that phenyl-imidazole sulfonamide derivatives prevented stem cell factor induced c-kit phosphorylation in (501mel) human melanoma cells and also the UV induced pigmentation on brownish guinea pigs. Furthermore, the SCF/c-kit pathway was used to induce pigmentation in case of vitiligo. Geniposide (from the fruit of Gardenia jasminoides Ellis) is used in traditional Chinese medicine for treatment of generalized vitiligo. This compound was shown to increase pigmentation via SCF/c-kit in normal human melanocytes where melanogenesis was suppressed by norepinephrine. In the case of SOX9 and MITF, signalling is mediated via cAMP and PKA, but also the stimulation of PKC (via diacylglycerol and calcium) may results in activation of tyrosinase. Inhibition of PKC by the specific PKC inhibitor bisindolylmaleimide (bis) resulted in a reduced tanning response in pigmented guinea pigs and in a marked lightening of freshly depilated hairs in mice.

Furthermore, Yaar et al. proposed bone morphogenetic proteins (BMPs) to be involved in modulating melanogenesis since melanocytes express the BMP receptors and produce BMP-4, that is able to decrease melanin synthesis in human melanocytes in culture. Another mechanism of pigment regulation is suggested for the peroxisome proliferator- activated receptor (PPAR) since binding of octadecenedioic acid to this PPAR leads to reduced melanogenesis and tyrosinase expression. The same was found for a known pharmaceutical PPAR agonist rosiglitazone.

Another pathway indicated in several papers by Kim et al. is the signalling via extracellular signal-regulated kinases (ERK). This pathway can be triggered by different stimuli, like growth factors (bFGF and HGF) and cytokines (SCF), as indicated above. The authors first reported that c2-ceramide inhibits melanogenesis by activation of ERK and they showed that inhibition of ERK (and AKT/PKB) caused an increase in pigmentation in human melanocytes. As a follow-up they described a new 2-imino-1,3-thiazoline derivative that decreased melanin production in B16 melanoma cells via induction of ERK. More recently they showed that terrein, which acted on ERK and downregulated MITF, in combination with a new tyrosinase inhibitor, KI-063, caused additive effects on depigmentation in the Mel-ab melanocytes. They also described a new imidazole derivative AVS-1357 that reduced pigmentation by activation of ERK and the downregulation of MITF and tyrosinase. Similar results were achieved with haginin A that inhibited tyrosinase and also activated ERK and thus downregulated MITF and tyrosinase and TRP-1. Haginin A effectively reduced pigmentation in the brownish guinea pig and the zebrafish model systems.

The effects of ceramide on pigmentation is of interest as well since it has been reported that glycosylation of lipids could be of importance for proper sorting of the melanogenic proteins to the melanosomes. A glycosphingolipid-deficient melanoma culture was not pigmented and by transfection with ceramide glucosyltransferase, pigmentation could be restored. We found that reducing the levels of glucosylceramide may affect pigment production in normal human melanocytes. In this respect it is interesting to note that 1-deoxynojirimycin (DNJ) is a glycosidase inhibitor and one of the main components in mulberry leaves (from Morus alba) and personal communication Aerts JMG, Academic Medical Center, University of Amsterdam). As shown in Tables 1 and 2 the compounds isolated from Morus alba (oxyresveratrol, mulberroside F and betulinic acid) inhibited tyrosinase but the effect of DNJ on lipid glycosylation could inhibit melanin synthesis as well (N. Smit, manuscript in preparation).

Cosmetic Use of (natural) Agents for Skin Whitening

In cosmetic formulations hydroquinone (HQ) has been widely used as an effective whitening agent but it has been banned recently because of serious safety concerns: its use has been connected with mutagenicity and the increased incidence of ochronosis in African countries. Other compounds often used are kojic acid, arbutin and azelaic acid (see top of Table 2). Arbutin is a glycosylated form of HQ that is present in bearberry extracts but it can also be synthesized from HQ by glucosidation. A new derivative, deoxyarbutin was prepared by removal of all hydroxyl groups from the glucose side chain of arbutin and showed much lower cytotoxicity than arbutin. In the large variety of whitening products, nowadays commercially available the use of different natural whitening agents is noticeable. Although the information on the exact formulations for all the whitening products is not easily accessible on the internet, we made an attempt to summarize the active whitening ingredients for some of them (Table 3). The utilization of kojic acid and arbutin is still common because these agents have repeatedly been demonstrated to be effective whitening agents. The use of bearberry extracts (a natural source of β-arbutin) may strengthen the effect of α-arbutin in Meladerm and Lucederm preparations. Among the natural extracts, mulberry and licorice are popular components added to the skin whiteners. The isolation of their active components and their ffect on tyrosinase inhibition (TI) and pigment reduction (PI) has been described (see Tables 1 and 2). Also lemon extract is used in the preparations like Skin Bright, Lucederm and Meladerm as a potent skin bleaching ingredient. However, it can only be used at low concentrations because it easily causes skin irritation. In Tables 1 and 2 several studies are included describing Sophora species from which several active compounds have been isolated that act as potent inhibitors of tyrosinase and pigment production. Also in the product Synerlight from LiBiol an extract from Sophora species is present. In this case it is combined with Kiwi fruit (Actinidia Chinensis) which contains flavonoids (e.g., quercetin) that may be responsible for tyrosinase inhibition. Niacinamide, which besides inhibition of tyrosinase, interferes in melanosome transfer to keratinocytes is used in the formulations of Meladerm and Lucederm. The Revitol product Skin Brightener contains Lumiskin with some patented ingredient, diacetyl boldine, that influences tyrosinase at the expression level. The Mandresy extract of Bayer contains two compounds luteolin and verbascoside that do not only inhibit tyrosinase and pigment production but also influence the interaction between keratinocytes and melanocytes by reducing formation of dendrites. Some of the products (Meladerm and Tosseki whitening cream) contain a mixture of many extracts with the obvious tyrosinase inhibitors (Mulberry, Licorice, Sophora and Peonia) but also other extracts that may act as antioxidant or anti-inflammatory. One of the components of the Meladerm preparation is TegoCosmo which contains a guanidine compound that acts on tyrosinase activity. Another component is Gigawhite that contains various plant extracts from the Alps and that has been tested on 10 subjects of Asian origin. Its bleaching effects may partly be attributed to tyrosinase inhibition. The question arises whether the increasing amounts of potentially active whitening ingredients will cause additive effects or will reduce the effects of the most potent ingredients (by competitive inhibition).

Some companies still use single synthetic compounds. For instance Lipotec uses dimetylmethoxy chromanyl palmitate in its product Chromabright. This exhibited lightening activity in a group of 20 Asian volunteers after 30 and 60 days. Sederma company makes use of a new mechanism of action targeting the peroxisome proliferator- activated receptor (PPAR). Their active ingredient named O.D.A. White is able to reduce tyrosinase mRNA expression.

Thus, approaches for skin whitening have broadened widely in the recent years. The utilization of single agents inhibiting tyrosinase is in many cases extended to the use of complex mixtures that target different mechanism like tyrosinase expression, transfer of melanosomes, antioxidant and anti-inflammatory effects.

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    Baek YS Ryu YB Curtis-Long MJ Ha TJ Rengasamy R Yang MS Park KH Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinokiBioorg. Med. Chem2009 173541

    Not in our library10.1016/j.bmc.2008.11.022

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    Zheng ZP Cheng KW To JT Li H Wang M Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agentMol. Nutr. Food Res2008 5215301538

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    Zheng ZP Chen S Wang S Wang XC Cheng KW Wu JJ Yang D Wang M Chemical components and tyrosinase inhibitors from the twigs of Artocarpus heterophyllusJ. Agric. Food Chem2009 5766496655

    Not in our library10.1021/jf9014685

  46. 46.

    Ding HY Lin HC Chang TS Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosaJ. Cosmet. Sci2009 60347352

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    Tomita K Oda N Ohbayashi M Kamei H Miyaki T Oki T A new screening method for melanin biosynthesis inhibitors using Streptomyces bikiniensisJ. Antibiot. (Tokyo)1990 4316011605

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  48. 48.

    Briganti S Camera E Picardo M Chemical and instrumental approaches to treat hyperpigmentationPigment Cell Res2003 16101110

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  49. 49.

    Roh JS Han JY Kim JH Hwang JK Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesisBiol. Pharm. Bull2004 2719761978

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    Smit NP Kolb RM Lentjes EG Noz KC van der Meulen H Koerten HK Vermeer BJ Pavel S Variations in melanin formation by cultured melanocytes from different skin typesArch. Dermatol. Res1998 290342349

    Not in our library10.1007/s004030050315

  51. 51.

    Liu SH Chu IM Pan IH Effects of hydroxybenzyl alcohols on melanogenesis in melanocyte-keratinocyte co-culture and monolayer culture of melanocytesJ. Enzyme Inhib. Med. Chem2008 23526534

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  52. 52.

    Zhong S Wu Y Soo-Mi A Zhao J Wang K Yang S Jae-Ho Y Zhu X Depigmentation of melanocytes by the treatment of extracts from traditional Chinese herbs: A cell culture assayBiol. Pharm. Bull2006 2919471951

    Not in our library10.1248/bpb.29.1947

  53. 53.

    Greatens A Hakozaki T Koshoffer A Epstein H Schwemberger S Babcock G Bissett D Takiwaki H Arase S Wickett RR Boissy RE Effective inhibition of melanosome transfer to keratinocytes by lectins and niacinamide is reversibleExp. Dermatol2005 14498508

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  54. 54.

    Duval C Smit NP Kolb AM Regnier M Pavel S Schmidt R Keratinocytes control the pheo/eumelanin ratio in cultured normal human melanocytesPigment Cell Res2002 15440446

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    Ni-Komatsu L Leung JK Williams D Min J Khersonsky SM Chang YT Orlow SJ Triazine-based tyrosinase inhibitors identified by chemical genetic screeningPigment Cell Res2005 18447453

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  56. 56.

    Yamakoshi J Otsuka F Sano A Tokutake S Saito M Kikuchi M Kubota Y Lightening effect on ultraviolet-induced pigmentation of guinea pig skin by oral administration of a proanthocyanidin-rich extract from grape seedsPigment Cell Res2003 16629638

    Not in our library10.1046/j.1600-0749.2003.00093.x

  57. 57.

    Yoshimura M Watanabe Y Kasai K Yamakoshi J Koga T Inhibitory effect of an ellagic acid-rich pomegranate extract on tyrosinase activity and ultraviolet-induced pigmentationBiosci. Biotechnol. Biochem2005 6923682373

    Not in our library10.1271/bbb.69.2368

  58. 58.

    Choi TY Kim JH Ko DH Kim CH Hwang JS Ahn S Kim SY Kim CD Lee JH Yoon TJ Zebrafish as a new model for phenotype-based screening of melanogenic regulatory compoundsPigment Cell Res2007 20120127

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    Kim JH Baek SH Kim DH Choi TY Yoon TJ Hwang JS Kim MR Kwon HJ Lee CH Downregulation of melanin synthesis by haginin A and its application to in vivo lightening modelJ. Invest Dermatol2008 12812271235

    Not in our library10.1038/sj.jid.5701177

  60. 60.

    Tengamnuay P Pengrungruangwong K Pheansri I Likhitwitayawuid K Artocarpus lakoocha heartwood extract as a novel cosmetic ingredient: Evaluation of the in vitro anti-tyrosinase and in vivo skin whitening activitiesInt. J. Cosmet. Sci2006 28269276

    Not in our library10.1111/j.1467-2494.2006.00339.x

  61. 61.

    Francis E Wang N Parag H Halaban R Hebert DN Tyrosinase maturation and oligomerization in the endoplasmic reticulum require a melanocyte-specific factorJ. Biol. Chem2003 2782560725617

    Not in our library10.1074/jbc.m303411200

  62. 62.

    Halaban R Pomerantz SH Marshall S Lambert DT Lerner AB Regulation of tyrosinase in human melanocytes grown in cultureJ. Cell Biol1983 97480488

    Not in our library10.1083/jcb.97.2.480

  63. 63.

    Petrescu SM Petrescu AJ Titu HN Dwek RA Platt FM Inhibition of N-glycan processing in B16 melanoma cells results in inactivation of tyrosinase but does not prevent its transport to the melanosomeJ. Biol. Chem1997 2721579615803

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  64. 64.

    Lee MH Lin YP Hsu FL Zhan GR Yen KY Bioactive constituents of Spatholobus suberectus in regulating tyrosinase-related proteins and mRNA in HEMn cellsPhytochemistry2006 6712621270

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  65. 65.

    Zi SX Ma HJ Li Y Liu W Yang QQ Zhao G Lian S Oligomeric proanthocyanidins from grape seeds effectively inhibit ultraviolet-induced melanogenesis of human melanocytes in vitroInt. J. Mol. Med2009 23197204

    Not in our library

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    Sharlow ER Paine CS Babiarz L Eisinger M Shapiro S Seiberg M The protease-activated receptor-2 upregulates keratinocyte phagocytosisJ Cell Sci2000 113(Pt 17),30933101

    Not in our library10.1242/jcs.113.17.3093

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    Seiberg M Keratinocyte-melanocyte interactions during melanosome transferPigment Cell Res2001 14236242

    Not in our library10.1034/j.1600-0749.2001.140402.x

  68. 68.

    Seiberg M Paine C Sharlow E Ndrade-Gordon P Costanzo M Eisinger M Shapiro SS Inhibition of melanosome transfer results in skin lighteningJ. Invest Dermatol2000 115162167

    Not in our library10.1046/j.1523-1747.2000.00035.x

  69. 69.

    Quast T Wehner S Kirfel G Jaeger K De Luca M Herzog V sAPP as a regulator of dendrite motility and melanin release in epidermal melanocytes and melanoma cellsFASEB J2003 1717391741

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  70. 70.

    Mammone T Marenus K Muizzuddin N Maes D Evidence and utility of melanin degrading enzymesJ. Cosmet. Sci2004 55116117

    Not in our library

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    Not in our library10.1016/j.fct.2006.08.022

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    Fujiwara Y Sahashi Y Aritro M Hasegawa S Akimoto K Ninomiya S Sakaguchi Y Seyama Y Effect of simultaneous administration of vitamin C, l-cysteine and vitamin E on the melanogenesisBiofactors2004 21415418

    Not in our library10.1002/biof.552210182

  73. 73.

    Balaguer A Chisvert A Salvador A Environmentally friendly LC for the simultaneous determination of ascorbic acid and its derivatives in skin-whitening cosmeticsJ. Sep. Sci2008 31229236

    Not in our library10.1002/jssc.200700414

  74. 74.

    Silveira JE Pereda MC Eberlin S Dieamant GC Di Stasi LC Effects of Coccoloba uvifera L. on UV-stimulated melanocytesPhotodermatol. Photoimmunol. Photomed2008 24308313

    Not in our library10.1111/j.1600-0781.2008.00382.x

  75. 75.

    Nazzaro-Porro M Passi S Identification of tyrosinase inhibitors in cultures of pityrosporumJ. Invest Dermatol1978 71205208

    Not in our library10.1111/1523-1747.ep12547184

  76. 76.

    Lim JT Treatment of melasma using kojic acid in a gel containing hydroquinone and glycolic acidDermatol. Surg1999 25282284

    Not in our library10.1046/j.1524-4725.1999.08236.x

  77. 77.

    Chen JS Wei CI Marshall MR Inhibition-mechanism of kojic acid on polyphenol oxidaseJ. Agric. Food Chem1991 3918971901

    Not in our library

  78. 78.

    Maeda K Fukuda M Arbutin: Mechanism of its depigmenting action in human melanocyte cultureJ. Pharmacol. Exp. Ther1996 276765769

    Not in our library

  79. 79.

    Funayama M Arakawa H Yamamoto R Nishino T Shin T Murao S Effects of alpha-arbutin and beta-arbutin on activity of tyrosinases from mushroom and mouse melanomaBiosci. Biotechnol. Biochem1995 59143144

    Not in our library10.1271/bbb.59.143

  80. 80.

    Yagi A Kanbara T Morinobu N Inhibition of mushroom-tyrosinase by aloe extractPlanta Med1987 53515517

    Not in our library10.1055/s-2006-962798

  81. 81.

    Shimizu K Kondo R Sakai K Lee SH Sato H The inhibitory components from Artocarpus incisus on melanin biosynthesisPlanta Med1998 64408412

    Not in our library10.1055/s-2006-957470

  82. 82.

    Kim YM Yun J Lee CK Lee H Min KR Kim Y Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of actionJ. Biol. Chem2002 2771634016344

    Not in our library10.1074/jbc.m200678200

  83. 83.

    Lee SH Choi SY Kim H Hwang JS Lee BG Gao JJ Kim SY Mulberroside F isolated from the leaves of Morus alba inhibits melanin biosynthesisBiol. Pharm. Bull2002 2510451048

    Not in our library10.1248/bpb.25.1045

  84. 84.

    Sasaki K Yoshizaki F Nobiletin as a tyrosinase inhibitor from the peel of Citrus fruitBiol. Pharm. Bull2002 25806808

    Not in our library10.1248/bpb.25.806

  85. 85.

    Lee KT Lee KS Jeong JH Jo BK Heo MY Kim HP Inhibitory effects of Ramulus mori extracts on melanogenesisJ. Cosmet. Sci2003 54133142

    Not in our library

  86. 86.

    Nerya O Vaya J Musa R Izrael S Ben-Arie R Tamir S Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice rootsJ. Agric. Food Chem2003 5112011207

    Not in our library10.1021/jf020935u

  87. 87.

    Kim HJ Seo SH Lee BG Lee YS Identification of tyrosinase inhibitors from Glycyrrhiza uralensisPlanta Med2005 71785787

    Not in our library10.1055/s-2005-871232

  88. 88.

    Min KR Kim KS Ro JS Lee SH Kim JA Son JK Kim Y Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cellsPlanta Med2004 7011151118

    Not in our library10.1055/s-2004-835836

  89. 89.

    Kim KS Kim JA Eom SY Lee SH Min KR Kim Y Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expressionPigment Cell Res2006 199098

    Not in our library10.1111/j.1600-0749.2005.00281.x

  90. 90.

    Cho YH Kim JH Park SM Lee BC Pyo HB Park HD New cosmetic agents for skin whitening from Angelica dahuricaJ. Cosmet. Sci2006 571121

    Not in our library

  91. 91.

    Khan MT Choudhary MI Atta UR Mamedova RP Agzamova MA Sultankhodzhaev MN Isaev MI Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure-activity relationshipsBioorg. Med. Chem2006 1460856088

    Not in our library10.1016/j.bmc.2006.05.002

  92. 92.

    Wang KH Lin RD Hsu FL Huang YH Chang HC Huang CY Lee MH Cosmetic applications of selected traditional Chinese herbal medicinesJ. Ethnopharmacol2006 106353359

    Not in our library10.1016/j.jep.2006.01.010

  93. 93.

    Yoon JH Shim JS Cho Y Baek NI Lee CW Kim HS Hwang JK Depigmentation of melanocytes by isopanduratin A and 4-hydroxypanduratin A isolated from Kaempferia pandurata ROXBBiol. Pharm. Bull2007 3021412145

    Not in our library10.1248/bpb.30.2141

  94. 94.

    Choi SW Lee SK Kim EO Oh JH Yoon KS Parris N Hicks KB Moreau RA Antioxidant and antimelanogenic activities of polyamine conjugates from corn bran and related hydroxycinnamic acidsJ. Agric. Food Chem2007 5539203925

    Not in our library10.1021/jf0635154

  95. 95.

    Cheng KT Hsu FL Chen SH Hsieh PK Huang HS Lee CK Lee MH New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytesChem. Pharm. Bull. (Tokyo)2007 55757761

    Not in our library10.1248/cpb.55.757

  96. 96.

    Liu SH Pan IH Chu IM Inhibitory effect of p-hydroxybenzyl alcohol on tyrosinase activity and melanogenesisBiol. Pharm. Bull2007 3011351139

    Not in our library10.1248/bpb.30.1135

  97. 97.

    Hyun SK Lee WH Jeong dM Kim Y Choi JS Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesisBiol. Pharm. Bull2008 31154158

    Not in our library10.1248/bpb.31.154

  98. 98.

    Kai H Baba M Okuyama T Inhibitory effect of Cucumis sativus on melanin production in melanoma B16 cells by downregulation of tyrosinase expressionPlanta Med2008 7417851788

    Not in our library10.1055/s-0028-1088338

  99. 99.

    Sung JH Park SH Seo DH Lee JH Hong SW Hong SS Antioxidative and skin-whitening effect of an aqueous extract of Salicornia herbaceaBiosci. Biotechnol. Biochem2009 73552556

    Not in our library10.1271/bbb.80601

  100. 100.

    Chu HL Wang BS Duh PD Effects of selected organo-sulfur compounds on melanin formationJ. Agric. Food Chem2009 5770727077

    Not in our library10.1021/jf9005824

  101. 101.

    Arung ET Kusuma IW Christy EO Shimizu K Kondo R Evaluation of medicinal plants from Central Kalimantan for antimelanogenesisNat. Med. (Tokyo)2009 63473480

    Not in our library10.1007/s11418-009-0351-7

  102. 102.

    Chen LG Chang WL Lee CJ Lee LT Shih CM Wang CC Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cellsBiol. Pharm. Bull2009 3214471452

    Not in our library10.1248/bpb.32.1447

  103. 103.

    Chen YR Chiou RY-Y Lin TY Huang CP Tang WC Chen ST Lin SB Identification of an alkylhydroquinone from rhus succedanea as an inhibitor of tyrosinase and melanogenesisJ. Agric. Food Chem2009 5722002205

    Not in our library10.1021/jf802617a

  104. 104.

    Leu YL Hwang TL Hu JW Fang JY Anthraquinones from polygonum cuspidatum as tyrosinase inhibitors for dermal usePhytother. Res2008 22552556

    Not in our library10.1002/ptr.2324

  105. 105.

    Azhar UH Malik A Khan MT Anwar UH Khan SB Ahmad A Choudhary MI Tyrosinase inhibitory lignans from the methanol extract of the roots of Vitex negundo Linn. and their structure-activity relationshipPhytomedicine2006 13255260

    Not in our library10.1016/j.phymed.2004.09.001

  106. 106.

    Lu YH Chen J Wei DZ Wang ZT Tao XY Tyrosinase inhibitory effect and inhibitory mechanism of tiliroside from raspberryJ. Enzyme Inhib. Med. Chem2009 2411541160

    Not in our library10.1080/14756360802694252

  107. 107.

    Luo LH Kim HJ Nguyen DH Lee HB Lee NH Kim EK Depigmentation of melanocytes by (2Z,8Z)-matricaria acid methyl ester isolated from Erigeron breviscapusBiol. Pharm. Bull2009 3210911094

    Not in our library10.1248/bpb.32.1091

  108. 108.

    Panich U Kongtaphan K Onkoksoong T Jaemsak K Phadungrakwittaya R Thaworn A Akarasereenont P Wongkajornsilp A Modulation of antioxidant defense by Alpinia galanga and Curcuma aromatica extracts correlates with their inhibition of UVA-induced melanogenesisCell Biol Toxicol2009 doi:10.1007/s10565-009-9121-2.

    Not in our library10.1007/s10565-009-9121-2

  109. 109.

    Brenner M Hearing V Modifying skin pigmentation- approaches through intrinsic biochemistry and exogenous agentsDrug Discov. Today: Dis. Mech2008 5e189e199

    Not in our library10.1016/j.ddmec.2008.02.001

  110. 110.

    Passeron T Valencia JC Bertolotto C Hoashi T Le PE Takahashi K Ballotti R Hearing VJ SOX9 is a key player in ultraviolet B-induced melanocyte differentiation and pigmentationProc. Natl. Acad. Sci. USA2007 1041398413989

    Not in our library10.1073/pnas.0705117104

  111. 111.

    Zhang YG Hu QH Wang XZ Qi ZL Lin XX Fang JL Dai CC The regulating effect of antisense-s-oligo on TYR gene expression and melanin production of melanocytesZhonghua Zheng Xing Wai Ke Za Zhi2003 19285287(in Chinese).

    Not in our library

  112. 112.

    Akiyama T Wnt/beta-catenin signalingCytokine Growth Factor Rev2000 11273282

    Not in our library10.1016/s1359-6101(00)00011-3

  113. 113.

    Yamaguchi Y Brenner M Hearing VJ The regulation of skin pigmentationJ. Biol. Chem2007 2822755727561

    Not in our library10.1074/jbc.r700026200

  114. 114.

    Ronnstrand L Signal transduction via the stem cell factor receptor/c-KitCell Mol. Life Sci2004 6125352548

    Not in our library10.1007/s00018-004-4189-6

  115. 115.

    Na YJ Baek HS Ahn SM Shin HJ Chang IS Hwang JS [4-t-Butylphenyl]-N-(4-imidazol-1-yl phenyl)sulfonamide (ISCK03) inhibits SCF/c-kit signaling in 501mel human melanoma cells and abolishes melanin production in mice and brownish guinea pigsBiochem. Pharmacol2007 74780786

    Not in our library10.1016/j.bcp.2007.05.028

  116. 116.

    Lan WJ Wang HY Lan W Wang KY Geniposide enhances melanogenesis by stem cell factor/c-Kit signalling in norepinephrine-exposed normal human epidermal melanocyteBasic Clin. Pharmacol. Toxicol2008 1038893

    Not in our library10.1111/j.1742-7843.2008.00251.x

  117. 117.

    Park HY Lee J Gonzalez S Middelkamp-Hup MA Kapasi S Peterson S Gilchrest BA Topical application of a protein kinase C inhibitor reduces skin and hair pigmentationJ. Invest Dermatol2004 122159166

    Not in our library10.1046/j.0022-202x.2003.22134.x

  118. 118.

    Yaar M Wu C Park HY Panova I Schutz G Gilchrest BA Bone morphogenetic protein-4, a novel modulator of melanogenesisJ. Biol. Chem2006 2812530725314

    Not in our library10.1074/jbc.m600580200

  119. 119.

    Wiechers JW Rawlings AV Garcia C Chesne C Balaguer P Nicolas JC Corre S Galibert MD A new mechanism of action for skin whitening agents: Binding to the peroxisome proliferator-activated receptorInt. J. Cosmet. Sci2005 27123132

    Not in our library10.1111/j.1467-2494.2004.00256.x

  120. 120.

    Kim DS Kim SY Chung JH Kim KH Eun HC Park KC Delayed ERK activation by ceramide reduces melanin synthesis in human melanocytesCell Signal2002 14779785

    Not in our library10.1016/s0898-6568(02)00024-4

  121. 121.

    Kim DS Jeong YM Park IK Hahn HG Lee HK Kwon SB Jeong JH Yang SJ Sohn UD Park KC A new 2-imino-1,3-thiazoline derivative, KHG22394, inhibits melanin synthesis in mouse B16 melanoma cellsBiol. Pharm. Bull2007 30180183

    Not in our library10.1248/bpb.30.180

  122. 122.

    Kim DS Lee S Lee HK Park SH Ryoo IJ Yoo ID Kwon SB Baek KJ Na JI Park KC The hypopigmentary action of KI-063 (a new tyrosinase inhibitor) combined with terreinJ. Pharm. Pharmacol2008 60343348

    Not in our library10.1211/jpp.60.3.0009

  123. 123.

    Kim DS Lee HK Park SH Chae CH Park KC AVS-1357 inhibits melanogenesis via prolonged ERK activationPharmazie2009 64532537

    Not in our library

  124. 124.

    Sprong H Degroote S Claessens T van Drunen J Oorschot V Westerink BH Hirabayashi Y Klumperman J van der SP van Meer G Glycosphingolipids are required for sorting melanosomal proteins in the Golgi complexJ. Cell Biol2001 155369380

    Not in our library10.1083/jcb.200106104

  125. 125.

    Konno K Ono H Nakamura M Tateishi K Hirayama C Tamura Y Hattori M Koyama A Kohno K Mulberry latex rich in antidiabetic sugar-mimic alkaloids forces dieting on caterpillarsProc. Natl. Acad. Sci. USA2006 10313371341

    Not in our library10.1073/pnas.0506944103

  126. 126.

    Hamed SH Sriwiriyanont P de Long MA Visscher MO Wickett RR Boissy RE Comparative efficacy and safety of deoxyarbutin, a new tyrosinase-inhibiting agentJ. Cosmet. Sci2006 57291308

    Not in our library

  127. 127.

    Hu ZM Zhou Q Lei TC Ding SF Xu SZ Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: Biosafety as skin whitening agentsJ. Dermatol. Sci2009 55179184

    Not in our library10.1016/j.jdermsci.2009.06.003

  128. 128.

    Fuller BB Drake MA Spaulding DT Chaudhry F Downregulation of tyrosinase activity in human melanocyte cell cultures by yohimbineJ. Invest Dermatol2000 114268276

    Not in our library10.1046/j.1523-1747.2000.00860.x

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