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The Therapeutic Potential of Naringenin: A Review of Clinical Trials

Bahare Salehi, Patrick Valere Tsouh Fokou, Mehdi Sharifi-Rad and 4 more

Pharmaceuticals · 2019 · Review · CC BY

doi:10.3390/ph12010011

Abstract

Naringenin is a flavonoid belonging to flavanones subclass. It is widely distributed in several Citrus fruits, bergamot, tomatoes and other fruits, being also found in its glycosides form (mainly naringin). Several biological activities have been ascribed to this phytochemical, among them antioxidant, antitumor, antiviral, antibacterial, anti-inflammatory, antiadipogenic and cardioprotective effects. Nonetheless, most of the data reported have been obtained from in vitro or in vivo studies. Although some clinical studies have also been performed, the main focus is on naringenin bioavailability and cardioprotective action. In addition, these studies were done in compromised patients (i.e., hypercholesterolemic and overweight), with a dosage ranging between 600 and 800 μM/day, whereas the effect on healthy volunteers is still debatable. In fact, naringenin ability to improve endothelial function has been well-established. Indeed, the currently available data are very promising, but further research on pharmacokinetic and pharmacodynamic aspects is encouraged to improve both available production and delivery methods and to achieve feasible naringenin-based clinical formulations.

Full text

From PubMed Central, U.S. National Library of Medicine, as current on Oct 17, 2026. Paragraph numbers are ours, so an answer can point at one.

1. Introduction

Naringenin is one of the most important naturally-occurring flavonoid, predominantly found in some edible fruits, like Citrus species and tomatoes, and figs belonging to smyrna-type Ficus carica. Chemically named as 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (Figure 1), naringenin shows a molecular weight of 272.26 (C15H12O5).

This widely distributed molecule is insoluble in water and soluble in organic solvents, like alcohol. Within the flavonoids class, naringenin is a flavanone that derives from naringin or narirutin (its glycone precursor) hydrolysis. In fact, naringenin occupies a central position as primary C15 intermediate in the flavonoid biosynthesis pathway. Naringenin biosynthesis has been investigated in Medicago, parsley and other plants. Overall, the metabolic pathway constitutes of a six step process, successively catalyzed by phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase and its associated cytochrome P450 reductase, para-coumarate-CoA ligase, chalcone synthase (the key enzyme for the synthesis of naringenin) and chalcone isomerase. Of note, naringenin is obtained by the condensation of para-coumaroyl-CoA with three units of malonyl-CoA. In addition, naringenin biosynthesis starter unit is para-coumaroyl-CoA, which in dicotyledonous plants derives from phenylalanine upon PAL deamination. The latter is thereafter hydroxylated at C4 by a cinnamate-4-hydroxylase and activated by a CoA-dependent ligase, through the universal phenylpropanoid pathway leading to flavonoids and stilbenes. Moreover, monocotyledonous plants may also use tyrosine as substrate, directly producing p-coumaric acid without the need of cinnamate-4-hydroxylase enzyme activity.

To overcome the limited flavonoids production, in general, and naringenin, in particular, many attempts have been made to produce naringenin from metabolic engineering of specific pathways in microbial systems, such as Escherichia coli and Saccharomyces cerevisiae. The highest naringenin titers obtained through biotransformation were reached using E. coli. In addition, S. cerevisiae engineered to produce naringenin, solely from glucose using specific naringenin biosynthesis genes from Arabidopsis thaliana, led to flux optimization towards the naringenin pathway, providing a metabolic chassis for large amounts of naringenin production and biological functions exploration. Growing evidence from both in vitro and in vivo animal studies have reinforced various naringenin pharmacological effects, including as hepatoprotective, anti-atherogenic, anti-inflammatory, anti-mutagenic, anticancer, antimicrobial agent, even suggesting its application in cardiovascular, gastrointestinal, neurological, metabolic, rheumatological, infectious and malignant diseases control and management. Based on these aspects, the present review has a specific focus on clinical trials assessing naringenin consumptions’ health benefits, whereas the reported reviews are more related to other aspects (in vitro studies, over-production approaches, or specifically on oxidative stress only).

2. Preclinical Pharmacological Activities of Naringenin

Naringenin is endowed with broad biological effects on human health (Table 1), which includes a decrease in lipid peroxidation biomarkers and protein carbonylation, promotes carbohydrate metabolism, increases antioxidant defenses, scavenges reactive oxygen species, modulates immune system activity, and also exerts anti-atherogenic and anti-inflammatory effects. It has also been reported to have a great ability to modulate signaling pathways related to fatty acids metabolism, which favors fatty acids oxidation, impairs lipid accumulation in liver and thereby prevents fatty liver, besides efficiently impairing plasma lipids and lipoproteins accumulation. In addition, naringenin potentiates intracellular signaling responses to low insulin doses by sensitizing hepatocytes to insulin, besides being able to traverse the blood–brain barrier and to exert diverse neuronal effects, through its ability to interact with protein kinase C signaling pathways.

On the other hand, anti-cancer, anti-proliferative and anticarcinogenic effects have also been ascribed to this metabolite, mostly linked to its ability to repair DNA. In fact, cells exposition to 80 mM/L naringenin, during 24 h, led to 24% DNA hydroxyl damages reduction. Moreover, antiviral effects have been reported. Naringenin shows a dose-dependent inhibitory effect against dengue virus, prevents intracellular replication of chikungunya virus, and inhibits assembly and long-term production of infectious hepatitis C virus particles in a dose-dependent manner. Unfortunately, this bioflavonoid is poorly absorbed by oral ingestion, with only 15% of ingested naringenin absorbed in the human gastrointestinal tract, which has triggered several studies on its bioavailability.

3. Bioavailability of Naringenin

Naringenin bioavailability has been properly studied in previous works, suggesting an extensive pre-systemic gut flora metabolism, leading to a wide pattern of degradation products (i.e., phenolic acids). In a recent study, ultra-fast liquid chromatography-quadrupole-time-of-flight tandem mass spectrometry (UFLC-Q-TOF-MS/MS) was used to assess the urinary excretion of flavonoids in Chinese 23–30 years old volunteers, after 250 mL orange juice consumption (containing 31 μM naringenin). An overall 22% recovery was detected in 4 to 12 h, evidencing a phase II metabolism (especially sulfation and glucuronidation) of the aglycone after intestinal hydrolysis.

Bioavailability training effect was also investigated in male endurance athletes (clinicaltrails.gov NCT02627547). In this trial, 500 mL of orange juice (containing 76 μM naringenin) was ingested before and after 7 days of physical training cessation, and the urinary excretion of phenolic metabolites analyzed. As main findings, the authors stated that the bioavailability in endurance athletes was lower when compared with less trained individuals. However, short activity cessation slightly enhanced metabolites excretion. In the same line, it was also shown that the urinary metabolites excretion does not differ after fresh oranges or pasteurized orange juice consumption, even if the latter contains about half of total flavanones amount.

Naringenin and hesperidin bioavailability were also investigated (trial NCT03032861) to deepen knowledge on orange juice prebiotic effect. In this study, a marked increase in short-chain fatty acids and commensal bacteria were stated, with a concomitant decrease in ammonium levels, even in face of a decrease in total bacteria richness values.

4. Naringenin in Clinical Trials

Although there is a huge amount of data on in vitro biological effects of naringenin, only few clinical studies have been carried out, mainly because of the reduced data on pharmacokinetic aspects, metabolic fate and chemical instability of this compound. Moreover, high isolation and purification costs further affect clinical trials feasibility.

Up to now, only 10 clinical studies were registered at clinicaltrials.gov database using “naringenin” or “naringin” (its glycoside) as keywords. Curiously, only one of these studies (NCT03582553, early phase I, still on recruiting) focused on naringenin administration isolated from Citrus sinensis extract (ranging from 150 to 900 mg). The main goal of this study was to check naringenin safety, tolerability and bioavailability, besides its effects on glucose metabolism. Data provided suggest how naringenin pharmacokinetics are still needing further investigation. Indeed, some of these studies investigated naringenin as a complex food supplement (i.e., whole orange juice), constituted by several polyphenols (including obviously naringenin), making difficult to assess the single phytochemicals contribution.

4.1. Role of Naringenin in Cardiovascular Diseases

The role of flavanones (including naringenin) on cardiovascular diseases has been well-studied, although most of the data have been collected in epidemiological and prospective studies. An inverse correlation has been stated between high flavanones consumption and cardiovascular risk, being a beneficial effect particularly related to naringenin consumption, given its great abundance in the tested samples. In fact, most of the clinical studies have been carried out using naringin (a naringenin glycoside).

In a double-blind cross-over study, 12 patients with stage I hypertension received alternatively 500 mL/day of a fruit juice containing 593 μM naringin or a juice with lower content (143 μM naringin) for 5 weeks. Systolic blood pressure decreased in both groups, but no significant differences were found, while diastolic blood pressure was more effectively reduced in high-dose naringin group.

Dyslipidemic patients treated with a commercial bergamot-derived extract (containing about 95 μM naringin/capsule) evidenced plasmatic lipids reduction, while improved lipoprotein profile after 6 months. The same glycoside was also able to decrease total plasma cholesterol levels and to enhance antioxidant defenses in hypercholesterolemic subjects. Jung and colleagues prescribed 400 mg naringin/capsule/day, and after 8 weeks they also reported a decrease in LDL-cholesterol levels and an increase in some antioxidant enzymes activity (i.e., superoxide dismutase and catalase). A somewhat similar result was obtained in 237 hyperlipemic volunteers during a 30-day program, using a bergamot extract containing several flavonoids (including naringin). This plant extract preparation was able to decrease triglycerides, total and LDL cholesterol levels. Quite surprisingly, in the study of Jung and colleagues, phytochemicals supplementation did not affect cholesterol levels in the healthy control group, but differently, in a randomized placebo-controlled trial including 194 moderately hypercholesterolemic patients, a daily dose of 1300 μM pure hesperidin or 862 μM pure naringin over 4 weeks, did not affect total or LDL cholesterol levels, this last result being in contrast to the work of Jung and collaborators. In fact, the authors suggested that the mean baseline LDL-cholesterol concentration in their study could not have contributed to the absence of LDL cholesterol effects and concluded that naringin (and hesperidin) did not have cholesterol-lowering effects when consumed as capsules. Certainly, this divergence should be further deepened; however, it appears that naringenin or naringin beneficial effects are closely related to patients with increased cardiovascular risk.

On the other hand, a clinical trial (NCT00539916) analyzed the effect of 600 mL/day orange juice consumption on 25 mild hypercholesterolemic male volunteers for 4 weeks. The authors found some improvements in antioxidant profile and a tendency towards endothelial dysfunction decrease and slight increase in plasma apolipoprotein A-1 concentration. Similar results were also stated using whole orange juice in patients under hepatitis C antiviral therapy: Increase in antioxidant defenses, and decrease in inflammation and blood serum cholesterol levels. The same research group achieved analogous effects on healthy volunteers, highlighting marked improvements in LDL-cholesterol and apolipoprotein B levels, and metabolic syndrome risk markers. Another clinical trial (NCT03527277), although still in recruiting phase, is focused on whole orange juice effects in cardiovascular diseases- and type-2 diabetes-related metabolic markers, to be compared with sugar-sweetened beverages.

4.2. Role of Naringenin in Endothelial Function

Flow-mediated dilatation (FMD) of brachial artery at 0 to 7 h was used to assess the effect of 240 mL of orange flavanone beverages (about 15 mg naringenin) in a clinical trial involving 30–65 years healthy men. Postprandial endothelial dysfunction was reduced, probably through a specific flavanone’s metabolites action on nitric oxide. Additionally, in a very interesting trial (NCT01272167), the long-term effect of 340 mL of grapefruit juice/day, containing about 480 μM naringenin glycoside, was investigated on endothelial function. From the 48 healthy menopausal women recruited, arterial stiffness beneficial effects were found 6 months after treatment (carotid-femoral pulse wave velocity was significantly reduced).

4.3. Role of Naringenin in Weight Control

A commercial polyphenolic extract from several Citrus fruits (Sinetrol-XPur), containing about 20% of naringenin, was tested in 95 healthy overweight volunteers (BMI ranging from 26 to 29.9 kg/m2). The main overweight-related endpoints were improved after 12-weeks randomized protocol (including waist and hip circumference, abdominal fat, body weight). Moreover, inflammatory and oxidative stress markers were all decreased.

Stohs and coworkers also reported the naringin use as an adjuvant (600 mg) in weight management due to the well-known thermogenic effect of Citrus aurantium (bitter orange) extract (whose main active chemical compound is protoalkaloid p-synephrine). This double-blinded, randomized, placebo-controlled clinical trial (NCT01423019), involving 10 subjects per treatment group, showed that naringin is able to synergistically increase metabolic rate, without enhancing blood pressure and heart rates.

4.4. Role of Naringenin as Anti-HCV Activity

Naringenin has also been proposed as a novel therapeutic agent for hepatitis C virus (HCV) infection treatment. Indeed, this flavanone has been described to reduce HCV secretion in infected cells by 80%, at a concentration below to the toxic value in primary human hepatocytes and in mice. Accordingly, in a phase I clinical trial already registered, 1 g naringenin supplementation (NCT01091077) was applied to examine its ability to hinder HCV infection and on very-low-density lipoproteins (vLDL) secretion lowering (usually acting as HCV carrier). Nevertheless, up to now, no published results are available. Based on the above described data, it emerges that, as no study has investigated naringenin chemopreventive potential on human cancer so far, this issue could be exploited in the near future.

However, might act by interfering with bioassays through several mechanisms and are termed Pan Assay INterference compoundS (PAINS), which may affect the obtained bioassays results’ credibility and, thus, should be carefully analyzed.

5. Conclusions

Despite the huge amount of data on naringenin in vitro biological effects, few studies are available on its use as a therapeutic molecule. However, some specific effects were established under pure compounds supplementation, as well as in several studies using complex polyphenolic mixtures containing naringenin. The most promising activity seems to be related to cardiovascular disease protection, especially in already compromised patients. Nevertheless, these few data should be urgently expanded to better understand the naringenin mechanism of action on pathological or physiological conditions. However, a scarce number of clinical studies have been conducted so far, compromising its commercial exploitation. Further clinical studies are needed to better address naringenin safety, efficacy, delivery and bioavailability in humans.

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    Not in our library10.1038/srep39735

  51. 51.

    Shan S., Zhang Y., Wu M., Yi B., Wang J., Li Q. Naringenin attenuates fibroblast activation and inflammatory response in a mechanical stretch-induced hypertrophic scar mouse model. Mol. Med. Rep. 2017;16:4643-4649.

    Not in our library10.3892/mmr.2017.7209

  52. 52.

    Jin L., Zeng W., Zhang F., Zhang C., Liang W. Naringenin ameliorates acute inflammation by regulating intracellular cytokine degradation. J. Immunol. 2017;199:3466-3477.

    Not in our library10.4049/jimmunol.1602016

  53. 53.

    Fouad A.A., Albuali W.H., Jresat I. Protective effect of naringenin against lipopolysaccharide-induced acute lung injury in rats. Pharmacology. 2016;97:224-232.

    Not in our library10.1159/000444262

  54. 54.

    Shi L.B., Tang P.F., Zhang W., Zhao Y.P., Zhang L.C., Zhang H. Naringenin inhibits spinal cord injury-induced activation of neutrophils through miR-223. Gene. 2016;592:128-133.

    Not in our library10.1016/j.gene.2016.07.037

  55. 55.

    Wang C.C., Guo L., Tian F.D., An N., Luo L., Hao R.H., Wang B., Zhou Z.H. Naringenin regulates production of matrix metalloproteinases in the knee-joint and primary cultured articular chondrocytes and alleviates pain in rat osteoarthritis model. Braz. J. Med. Biol. Res. 2017;50:e5714.

    Not in our library10.1590/1414-431x20165714

  56. 56.

    Ali R., Shahid A., Ali N., Hasan S.K., Majed F., Sultana S. Amelioration of benzo[a]pyrene-induced oxidative stress and pulmonary toxicity by naringenin in Wistar rats: A plausible role of COX-2 and NF-kappab. Hum. Exp. Toxicol. 2017;36:349-364.

    Not in our library10.1177/0960327116650009

  57. 57.
    Naringenin Inhibits Superoxide Anion-Induced Inflammatory Pain: Role of Oxidative Stress, Cytokines, Nrf-2 and the NO−cGMP−PKG−KATPChannel Signaling Pathway · 2016
    No notice
  58. 58.

    Chtourou Y., Kamoun Z., Zarrouk W., Kebieche M., Kallel C., Gdoura R., Fetoui H. Naringenin ameliorates renal and platelet purinergic signalling alterations in high-cholesterol fed rats through the suppression of ROS and NF-kappab signaling pathways. Food Funct. 2016;7:183-193.

    Not in our library10.1039/c5fo00871a

  59. 59.

    Al-Roujayee A.S. Naringenin improves the healing process of thermally-induced skin damage in rats. J. Int. Med Res. 2017;45:570-582.

    Not in our library10.1177/0300060517692483

  60. 60.

    Wang L.H., Wang M.S., Zeng X.A., Xu X.M., Brennan C.S. Membrane and genomic DNA dual-targeting of citrus flavonoid naringenin against staphylococcus aureus. Integr. Biol. 2017;9:820-829.

    Not in our library10.1039/c7ib00095b

  61. 61.

    Kozlowska J., Potaniec B., Zarowska B., Aniol M. Synthesis and biological activity of novel o-alkyl derivatives of naringenin and their oximes. Molecules. 2017;22:1485.

    Not in our library10.3390/molecules22091485

  62. 62.

    Liang J., Halipu Y., Hu F., Yakeya B., Chen W., Zhang H., Kang X. Naringenin protects keratinocytes from oxidative stress injury via inhibition of the NOD2-mediated NF-kappab pathway in pemphigus vulgaris. Biomed. Pharmacother. 2017;92:796-801.

    Not in our library10.1016/j.biopha.2017.05.112

  63. 63.

    Stylos E., Chatziathanasiadou M.V., Tsiailanis A., Kellici T.F., Tsoumani M., Kostagianni A.D., Deligianni M., Tselepis A.D., Tzakos A.G. Tailoring naringenin conjugates with amplified and triple antiplatelet activity profile: Rational design, synthesis, human plasma stability and in vitro evaluation. Biochim. Biophys. Acta Gen. Subj. 2017;1861:2609-2618.

    Not in our library10.1016/j.bbagen.2017.08.018

  64. 64.

    Wang K., Chen Z., Huang J., Huang L., Luo N., Liang X., Liang M., Xie W. Naringenin prevents ischaemic stroke damage via anti-apoptotic and anti-oxidant effects. Clin. Exp. Pharmacol. Physiol. 2017;44:862-871.

    Not in our library10.1111/1440-1681.12775

  65. 65.

    Liu Y., An W., Gao A. Protective effects of naringenin in cardiorenal syndrome. J. Surg. Res. 2016;203:416-423.

    Not in our library10.1016/j.jss.2016.03.003

  66. 66.

    Tang J.Y., Jin P., He Q., Lu L.H., Ma J.P., Gao W.L., Bai H.P., Yang J. Naringenin ameliorates hypoxia/reoxygenation-induced endoplasmic reticulum stress-mediated apoptosis in H9c2 myocardial cells: Involvement in ATF6, IRE1alpha and perk signaling activation. Mol. Cell. Biochem. 2017;424:111-122.

    Not in our library10.1007/s11010-016-2848-1

  67. 67.

    Habauzit V., Verny M.A., Milenkovic D., Barber-Chamoux N., Mazur A., Dubray C., Morand C. Flavanones protect from arterial stiffness in postmenopausal women consuming grapefruit juice for 6 mo: A randomized, controlled, crossover trial. Am. J. Clin. Nutr. 2015;102:66-74.

    Not in our library10.3945/ajcn.114.104646

  68. 68.

    Bawazeer N.A., Choudary H., Zamzami M.A., Abdulaal W.H., Zeyadi M., ALbukhari A., Middleton B., Moselhy S.S. Possible regulation of LDL-receptor by naringenin in HepG2 hepatoma cell line. Afr. J. Tradit. Complement. Altern. Med. 2017;14:278-287.

    Not in our library10.21010/ajtcam.v14i1.30

  69. 69.

    Meng X.M., Zhang Y., Huang X.R., Ren G.L., Li J., Lan H.Y. Treatment of renal fibrosis by rebalancing TGF-beta/Smad signaling with the combination of asiatic acid and naringenin. Oncotarget. 2015;6:36984-36997.

    Not in our library10.18632/oncotarget.6100

  70. 70.
    Naringenin Regulates CFTR Activation and Expression in Airway Epithelial Cells · 2017
    Not checked
  71. 71.

    Oguido A., Hohmann M.S.N., Pinho-Ribeiro F.A., Crespigio J., Domiciano T.P., Verri W.A., Casella A.M.B. Naringenin eye drops inhibit corneal neovascularization by anti-inflammatory and antioxidant mechanisms. Investig. Ophthalmol. Vis. Sci. 2017;58:5764-5776.

    Not in our library10.1167/iovs.16-19702

  72. 72.

    Adana M.Y., Akang E.N., Peter A.I., Jegede A.I., Naidu E.C.S., Tiloke C., Chuturgoon A.A., Azu O.O. Naringenin attenuates highly active antiretroviral therapy-induced sperm DNA fragmentations and testicular toxicity in sprague-dawley rats. Andrology. 2018;6:166-175.

    Not in our library10.1111/andr.12439

  73. 73.

    Maatouk M., Elgueder D., Mustapha N., Chaaban H., Bzeouich I.M., Loannou I., Kilani S., Ghoul M., Ghedira K., Chekir-Ghedira L. Effect of heated naringenin on immunomodulatory properties and cellular antioxidant activity. Cell Stress Chaperones. 2016;21:1101-1109.

    Not in our library10.1007/s12192-016-0734-0

  74. 74.

    Lin H., Zhou Z., Zhong W., Huang P., Ma N., Zhang Y., Zhou C., Lai Y., Huang S., An H., et al. Naringenin inhibits alcoholic injury by improving lipid metabolism and reducing apoptosis in zebrafish larvae. Oncol. Rep. 2017;38:2877-2884.

    Not in our library10.3892/or.2017.5965

  75. 75.

    Lin H.J., Ku K.L., Lin I.H., Yeh C.C. Naringenin attenuates hepatitis b virus x protein-induced hepatic steatosis. BMC Complement. Altern. Med. 2017;17:505.

    Not in our library10.1186/s12906-017-2019-2

  76. 76.

    Lim W., Song G. Naringenin-induced migration of embrynoic trophectoderm cells is mediated via PI3K/AKT and ERK1/2 MAPK signaling cascades. Mol. Cell. Endocrinol. 2016;428:28-37.

    Not in our library10.1016/j.mce.2016.03.018

  77. 77.

    Kumar S., Tiku A.B. Biochemical and molecular mechanisms of radioprotective effects of naringenin, a phytochemical from citrus fruits. J. Agric. Food Chem. 2016;64:1676-1685.

    Not in our library10.1021/acs.jafc.5b05067

  78. 78.

    Ke J.Y., Cole R.M., Hamad E.M., Hsiao Y.H., Cotten B.M., Powell K.A., Belury M.A. Citrus flavonoid, naringenin, increases locomotor activity and reduces diacylglycerol accumulation in skeletal muscle of obese ovariectomized mice. Mol. Nutr. Food Res. 2016;60:313-324.

    Not in our library10.1002/mnfr.201500379

  79. 79.

    Pereira-Caro G., Borges G., van der Hooft J., Clifford M.N., Del Rio D., Lean M.E., Roberts S.A., Kellerhals M.B., Crozier A. Orange juice (poly)phenols are highly bioavailable in humans. Am. J. Clin. Nutr. 2014;100:1378-1384.

    Not in our library10.3945/ajcn.114.090282

  80. 80.

    Kanaze F.I., Bounartzi M.I., Georgarakis M., Niopas I. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Eur. J. Clin. Nutr. 2007;61:472-477.

    Not in our library10.1038/sj.ejcn.1602543

  81. 81.

    Zeng X., Su W., Bai Y., Chen T., Yan Z., Wang J., Su M., Zheng Y., Peng W., Yao H. Urinary metabolite profiling of flavonoids in Chinese volunteers after consumption of orange juice by UFLC-Q-TOF-MS/MS. J. Chromatogr. B. 2017;1061–1062:79-88.

    Not in our library10.1016/j.jchromb.2017.07.015

  82. 82.

    Pereira-Caro G., Polyviou T., Ludwig I.A., Nastase A.M., Moreno-Rojas J.M., Garcia A.L., Malkova D., Crozier A. Bioavailability of orange juice (poly)phenols: The impact of short-term cessation of training by male endurance athletes. Am. J. Clin. Nutr. 2017;106:791-800.

    Not in our library10.3945/ajcn.116.149898

  83. 83.

    Aschoff J.K., Riedl K.M., Cooperstone J.L., Hogel J., Bosy-Westphal A., Schwartz S.J., Carle R., Schweiggert R.M. Urinary excretion of citrus flavanones and their major catabolites after consumption of fresh oranges and pasteurized orange juice: A randomized cross-over study. Mol. Nutr. Food Res. 2016;60:2602-2610.

    Not in our library10.1002/mnfr.201600315

  84. 84.

    Duque A.L.R.F., Monteiro M., Adorno M.A.T., Sakamoto I.K., Sivieri K. An exploratory study on the influence of orange juice on gut microbiota using a dynamic colonic model. Food Res. Int. 2016;84:160-169.

    Not in our library10.1016/j.foodres.2016.03.028

  85. 85.

    Zaidun N.H., Thent Z.C., Latiff A.A. Combating oxidative stress disorders with citrus flavonoid: Naringenin. Life Sci. 2018;208:111-122.

    Not in our library10.1016/j.lfs.2018.07.017

  86. 86.
    Cancer chemoprevention through dietary flavonoids: what’s limiting? · 2017
    Corrected
  87. 87.

    Testai L., Calderone V. Nutraceutical value of citrus flavanones and their implications in cardiovascular disease. Nutrients. 2017;9:502.

    Not in our library10.3390/nu9050502

  88. 88.

    Yamada T., Hayasaka S., Shibata Y., Ojima T., Saegusa T., Gotoh T., Ishikawa S., Nakamura Y., Kayaba K. Frequency of citrus fruit intake is associated with the incidence of cardiovascular disease: The Jichi Medical School cohort study. J. Epidemiol. 2011;21:169-175.

    Not in our library10.2188/jea.je20100084

  89. 89.

    Knekt P., Kumpulainen J., Jarvinen R., Rissanen H., Heliovaara M., Reunanen A., Hakulinen T., Aromaa A. Flavonoid intake and risk of chronic diseases. Am. J. Clin. Nutr. 2002;76:560-568.

    Not in our library10.1093/ajcn/76.3.560

  90. 90.

    Cassidy A., Rimm E.B., O’Reilly E.J., Logroscino G., Kay C., Chiuve S.E., Rexrode K.M. Dietary flavonoids and risk of stroke in women. Stroke. 2012;43:946-951.

    Not in our library10.1161/strokeaha.111.637835

  91. 91.

    Onakpoya I., O’Sullivan J., Heneghan C., Thompson M. The effect of grapefruits (Citrus paradisi) on body weight and cardiovascular risk factors: A systematic review and meta-analysis of randomized clinical trials. Crit. Rev. Food Sci. Nutr. 2017;57:602-612.

    Not in our library10.1080/10408398.2014.901292

  92. 92.

    Reshef N., Hayari Y., Goren C., Boaz M., Madar Z., Knobler H. Antihypertensive effect of sweetie fruit in patients with stage i hypertension. Am. J. Hypertens. 2005;18:1360-1363.

    Not in our library10.1016/j.amjhyper.2005.05.021

  93. 93.

    Toth P.P., Patti A.M., Nikolic D., Giglio R.V., Castellino G., Biancucci T., Geraci F., David S., Montalto G., Rizvi A., et al. Bergamot reduces plasma lipids, atherogenic small dense LDL, and subclinical atherosclerosis in subjects with moderate hypercholesterolemia: A 6 months prospective study. Front. Pharmacol. 2015;6:299.

    Not in our library10.3389/fphar.2015.00299

  94. 94.

    Jung U.J., Kim H.J., Lee J.S., Lee M.K., Kim H.O., Park E.J., Kim H.K., Jeong T.S., Choi M.S. Naringin supplementation lowers plasma lipids and enhances erythrocyte antioxidant enzyme activities in hypercholesterolemic subjects. Clin. Nutr. 2003;22:561-568.

    Not in our library10.1016/s0261-5614(03)00059-1

  95. 95.

    Mollace V., Sacco I., Janda E., Malara C., Ventrice D., Colica C., Visalli V., Muscoli S., Ragusa S., Muscoli C., et al. Hypolipemic and hypoglycaemic activity of bergamot polyphenols: From animal models to human studies. Fitoterapia. 2011;82:309-316.

    Not in our library10.1016/j.fitote.2010.10.014

  96. 96.

    Demonty I., Lin Y., Zebregs Y.E., Vermeer M.A., van der Knaap H.C., Jakel M., Trautwein E.A. The citrus flavonoids hesperidin and naringin do not affect serum cholesterol in moderately hypercholesterolemic men and women. J. Nutr. 2010;140:1615-1620.

    Not in our library10.3945/jn.110.124735

  97. 97.

    Constans J., Bennetau-Pelissero C., Martin J.F., Rock E., Mazur A., Bedel A., Morand C., Berard A.M. Marked antioxidant effect of orange juice intake and its phytomicronutrients in a preliminary randomized cross-over trial on mild hypercholesterolemic men. Clin. Nutr. 2015;34:1093-1100.

    Not in our library10.1016/j.clnu.2014.12.016

  98. 98.

    Silveira J.Q., Dourado G.K., Cesar T.B. Red-fleshed sweet orange juice improves the risk factors for metabolic syndrome. Int. J. Food Sci. Nutr. 2015;66:830-836.

    Not in our library10.3109/09637486.2015.1093610

  99. 99.

    Rendeiro C., Dong H., Saunders C., Harkness L., Blaze M., Hou Y., Belanger R.L., Corona G., Lovegrove J.A., Spencer J.P. Flavanone-rich citrus beverages counteract the transient decline in postprandial endothelial function in humans: A randomised, controlled, double-masked, cross-over intervention study. Br. J. Nutr. 2016;116:1999-2010.

    Not in our library10.1017/s0007114516004219

  100. 100.

    Dallas C., Gerbi A., Elbez Y., Caillard P., Zamaria N., Cloarec M. Clinical study to assess the efficacy and safety of a citrus polyphenolic extract of red orange, grapefruit, and orange (Sinetrol-XPur) on weight management and metabolic parameters in healthy overweight individuals. Phytother. Res. 2014;28:212-218.

    Not in our library10.1002/ptr.4981

  101. 101.

    Stohs S.J., Preuss H.G., Keith S.C., Keith P.L., Miller H., Kaats G.R. Effects of p-synephrine alone and in combination with selected bioflavonoids on resting metabolism, blood pressure, heart rate and self-reported mood changes. Int. J. Med Sci. 2011;8:295-301.

    Not in our library10.7150/ijms.8.295

  102. 102.

    Aldrich C., Bertozzi C., Georg G.I., Kiessling L., Lindsley C., Liotta D., Merz K.M., Schepartz A., Wang S. The ecstasy and agony of assay interference compounds. ACS Cent. Sci. 2017;3:143-147.

    Not in our library10.1021/acscentsci.7b00069

  103. 103.

    Baell J.B. Feeling nature’s pains: Natural products, natural product drugs, and pan assay interference compounds (pains). J. Nat. Prod. 2016;79:616-628.

    Not in our library10.1021/acs.jnatprod.5b00947

  104. 104.

    Jardim A.C.G., Shimizu J.F., Rahal P., Harris M. Plant-derived antivirals against hepatitis c virus infection. Virol. J. 2018;15:34.

    Not in our library10.1186/s12985-018-0945-3

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