EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes


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CAS Number: 480-41-1Picture of molecule3D/inchi
Other(deleted CASRN):13308-00-4
ECHA EINECS - REACH Pre-Reg:207-550-2
Nikkaji Web:J325.849A
XlogP3-AA:2.40 (est)
Molecular Weight:272.25664000
Formula:C15 H12 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
mp: 251; Isomeric composition: R isomer 50.6% (17654-19-2); S isomer 49.4% (480-41-1)
Category:cosmetic and flavor agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
JECFA Food Flavoring:2257 (S)-naringenin
FEMA Number:4797 (S)-naringenin
FDA:No longer provide for the use of these seven synthetic flavoring substances
Physical Properties:
Appearance:Beige powder (est)
Assay: 95.00 to 100.00
Additional Assay Information:(Sum of isomers)
Food Chemicals Codex Listed: No
Melting Point: 251.00 °C. @ 760.00 mm Hg
Boiling Point: 577.50 °C. @ 760.00 mm Hg (est)
Flash Point: 436.00 °F. TCC ( 224.70 °C. ) (est)
logP (o/w): 2.520
Soluble in:
 water, 475.2 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
Alfa Biotechnology
For experimental / research use only.
Naringenin 98%
Aromiens International
Naringenin Natural
BOC Sciences
For experimental / research use only.
Layn Natural ingredients
Grapefruit Extract Naringenin
Penta International
Santa Cruz Biotechnology
For experimental / research use only.
Naringenin 98%
Shaanxi Y-Herb Biotechnology
Naringenin Monomer Powder Pomelo Peel P.E. Grapefruit Seed Extract Naringin
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
cosmetic and flavor agents
Recommendation for (S)-naringenin usage levels up to:
 not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 27
Click here to view publication 27
 average usual ppmaverage maximum ppm
baked goods: 200.00000600.00000
beverages(nonalcoholic): 100.00000300.00000
beverages(alcoholic): 100.00000300.00000
breakfast cereal: 200.00000600.00000
cheese: 1000.000001000.00000
chewing gum: 200.00000400.00000
condiments / relishes: 200.00000400.00000
confectionery froastings: 200.00000400.00000
egg products: --
fats / oils: 100.00000200.00000
fish products: --
frozen dairy: 100.00000500.00000
fruit ices: 100.00000200.00000
gelatins / puddings: 100.00000400.00000
granulated sugar: --
gravies: 100.00000500.00000
hard candy: 100.00000400.00000
imitation dairy: 100.00000500.00000
instant coffee / tea: 100.00000200.00000
jams / jellies: 100.00000400.00000
meat products: 100.00000200.00000
milk products: 100.00000500.00000
nut products: 50.00000100.00000
other grains: --
poultry: 100.00000200.00000
processed fruits: 50.00000400.00000
processed vegetables: 50.00000100.00000
reconstituted vegetables: 50.00000100.00000
seasonings / flavors: 500.000001000.00000
snack foods: 200.00000400.00000
soft candy: 100.00000400.00000
soups: 100.00000300.00000
sugar substitutes: 100.00000200.00000
sweet sauces: 100.00000400.00000
Safety References:
European Food Safety Authority (EFSA) reference(s):

Scientific Opinion of Flavouring Group Evaluation 410 (FGE.410): 4,5,7-trihydroxyflavanone from chemical group 25 (phenol derivatives containing ring-alkyl, ring-alkoxy, and side-chains with an oxygenated functional group)
View page or View pdf

EPI System: View
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :439246
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
RTECS:DJ2981530 for cas# 480-41-1
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):439246
Pubchem (sid):134974345
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C00509
HMDB (The Human Metabolome Database):HMDB02670
Export Tariff Code:2932.90.4100
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 bean mung bean plant
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 cabbage savoy cabbage
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 cashew nut
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 cherry sour cherry fruit
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 lemon pericarp
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 lippia graveolens root
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 lippia graveolens shoot
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 orange fruit
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 orange pericarp
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 oregano plant
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 oregano root
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 oregano shoot
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 parsley plant
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 parsley tissue culture
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 peach plant
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 soybean leaf
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 tarragon shoot
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 tea shoot
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 thyme plant
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 tomato fruit
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4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-
4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-


Google Patents:Flavor-improving method
PubMed:Determination of key flavonoid aglycones by means of nano-liquid chromatography for the analysis of dietary supplements and food matrices.
PubMed:Flavan hetero-dimers in the Cymbopogon citratus infusion tannin fraction and their contribution to the antioxidant activity.
PubMed:Magnetic purification of curcumin from Curcuma longa rhizome by novel naked maghemite nanoparticles.
PubMed:Enhanced action of apigenin and naringenin combination on estrogen receptor activation in non-malignant colonocytes: implications on sorghum-derived phytoestrogens.
PubMed:In vitro colonic catabolism of orange juice (poly)phenols.
PubMed:The tomato sauce making process affects the bioaccessibility and bioavailability of tomato phenolics: a pharmacokinetic study.
PubMed:Naringenin reduces cholesterol-induced hepatic inflammation in rats by modulating matrix metalloproteinases-2, 9 via inhibition of nuclear factor κB pathway.
PubMed:Electrochemical tomato (Solanum lycopersicum L.) characterisation using contact probe in situ voltammetry.
PubMed:Metabolite profile, antioxidant capacity, and inhibition of digestive enzymes in infusions of peppermint (Mentha piperita) grown under drought stress.
PubMed:Orange juice (poly)phenols are highly bioavailable in humans.
PubMed:Comparison of microwave and ultrasound-assisted extraction techniques for leaching of phenolic compounds from nettle.
PubMed:Identification of membrane proteins associated with phenylpropanoid tolerance and transport in Escherichia coli BL21.
PubMed:Fine-tuning of the fatty acid pathway by synthetic antisense RNA for enhanced (2S)-naringenin production from L-tyrosine in Escherichia coli.
PubMed:Treatment of proteins with dietary polyphenols lowers the formation of AGEs and AGE-induced toxicity.
PubMed:Phytochemical screening, anticancer and antioxidant activities of Origanum vulgare L. ssp. viride (Boiss.) Hayek, a plant of traditional usage.
PubMed:Systems metabolic engineering of microorganisms to achieve large-scale production of flavonoid scaffolds.
PubMed:Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus.
PubMed:Modular optimization of heterologous pathways for de novo synthesis of (2S)-naringenin in Escherichia coli.
PubMed:Anti-tumor effects of flavonoids from the ethnic medicine Docynia delavayi (Franch.) Schneid. and its possible mechanism.
PubMed:Effect of pre-harvest methyl jasmonate treatments on ethylene production, water-soluble phenolic compounds and fruit quality of Japanese plums.
PubMed:Bioactive compounds from culinary herbs inhibit a molecular target for type 2 diabetes management, dipeptidyl peptidase IV.
PubMed:Evaluation of bioactive components and antioxidant and anticancer properties of citrus wastes generated during bioethanol production.
PubMed:Assessment of the proliferative capacity of the flavanones 8-prenylnaringenin, 6-(1.1-dimethylallyl)naringenin and naringenin in MCF-7 cells and the rat mammary gland.
PubMed:Effects of chemopreventive natural products on non-homologous end-joining DNA double-strand break repair.
PubMed:Phenolic composition of vinegars over an accelerated aging process using different wood species (acacia, cherry, chestnut, and oak): effect of wood toasting.
PubMed:Chemical compositions by using LC-MS/MS and GC-MS and biological activities of Sedum sediforme (Jacq.) Pau.
PubMed:Encapsulation of rutin and naringenin in multilamellar vesicles for optimum antioxidant activity.
PubMed:Naringenin stimulates cholecystokinin secretion in STC-1 cells.
PubMed:Prenylation modulates the bioavailability and bioaccumulation of dietary flavonoids.
PubMed:Prunus yedoensis bark inhibits lipopolysaccharide-induced inflammatory cytokine synthesis by IκBα degradation and MAPK activation in macrophages.
PubMed:Antioxidant and hepatoprotective effects of naringenin and its β-cyclodextrin formulation in mice intoxicated with carbon tetrachloride: a comparative study.
PubMed:Sonochemical effects on 14 flavonoids common in citrus: relation to stability.
PubMed:Antioxidant and antiglycation activity of selected dietary polyphenols in a cookie model.
PubMed:Flavonoids from the pericarps of Litchi chinensis.
PubMed:The inhibitory effects of bioactive compounds of tomato juice binding to hepatic HMGCR: in vivo study and molecular modelling.
PubMed:Home processing of tomatoes (Solanum lycopersicum): effects on in vitro bioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity.
PubMed:Simultaneous kinetic spectrometric determination of three flavonoid antioxidants in fruit with the aid of chemometrics.
PubMed:Photoprotection of human dermal fibroblasts against ultraviolet light by antioxidant combinations present in tomato.
PubMed:Absorption, metabolism, and excretion of fermented orange juice (poly)phenols in rats.
PubMed:Caffeic acid, naringenin and quercetin enhance glucose-stimulated insulin secretion and glucose sensitivity in INS-1E cells.
PubMed:Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts.
PubMed:Bioactive components from flowers of Sambucus nigra L. increase glucose uptake in primary porcine myotube cultures and reduce fat accumulation in Caenorhabditis elegans.
PubMed:Flavonoid inhibitory pharmacodynamics on platelet function in physiological environments.
PubMed:BDNF signaling is necessary for the antidepressant-like effect of naringenin.
PubMed:Antioxidant and photoprotective effects of blanch water, a byproduct of the almond processing industry.
PubMed:Antioxidant activity and spectroscopic data of isoxanthohomol oxime and related compounds.
PubMed:Selenium fertilization alters the chemical composition and antioxidant constituents of tomato (Solanum lycopersicon L.).
PubMed:Development and evaluation of an HPLC method for accurate determinations of enzyme activities of naringinase complex.
PubMed:Citrus flavanones enhance carotenoid uptake by intestinal Caco-2 cells.
PubMed:Relationship analysis between flavonoids structure and subcritical water extraction (SWE).
PubMed:Suitability of antioxidant capacity, flavonoids and phenolic acids for floral authentication of honey. Impact of industrial thermal treatment.
PubMed:Impacts of selected dietary polyphenols on caramelization in model systems.
PubMed:Application of TLC method with video scanning in estimation of daily dietary intake of specific flavonoids--preliminary studies.
PubMed:Prenylation enhances quercetin uptake and reduces efflux in Caco-2 cells and enhances tissue accumulation in mice fed long-term.
PubMed:Effects of naringenin and its phase II metabolites on in vitro human macrophage gene expression.
PubMed:Naringenin enhances intestinal barrier function through the expression and cytoskeletal association of tight junction proteins in Caco-2 cells.
PubMed:Urinary phytoestrogen levels related to idiopathic male infertility in Chinese men.
PubMed:Major active components in grapefruit, orange, and apple juices responsible for OATP2B1-mediated drug interactions.
PubMed:Rapid Quantitation of Furanocoumarins and Flavonoids in Grapefruit Juice using Ultra-Performance Liquid Chromatography.
PubMed:Influence of elicitation with H₂O₂ on phenolics content, antioxidant potential and nutritional quality of Lens culinaris sprouts.
PubMed:Light gazpachos contain higher phytochemical levels than conventional gazpachos.
PubMed:Anti-inflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc.
PubMed:Antibacterial activities of almond skins on cagA-positive and-negative clinical isolates of Helicobacter pylori.
PubMed:Chemical composition of two different extracts of berries harvested in Serbia.
PubMed:Quantitative analysis of the naringenin-inducible proteome in Rhizobium leguminosarum by isobaric tagging and mass spectrometry.
PubMed:Cultivar variations in antioxidant and antihyperlipidemic properties of pomelo pulp (Citrus grandis [L.] Osbeck) in Thailand.
PubMed:Assay of phenolic compounds from four species of ber (Ziziphus mauritiana L.) fruits: comparison of three base hydrolysis procedure for quantification of total phenolic acids.
PubMed:Naturally occurring flavonoids against human norovirus surrogates.
PubMed:Antioxidant changes of leek (Allium ampeloprasum var. porrum) during spontaneous fermentation of the white shaft and green leaves.
PubMed:Phenotypic changes associated with RNA interference silencing of chalcone synthase in apple (Malus × domestica).
PubMed:Enzyme-based online monitoring and measurement of antioxidant activity using an optical oxygen sensor coupled to an HPLC system.
PubMed:Phytochemical stability in dried tomato pulp and peel as affected by moisture properties.
PubMed:Assessment of phytochemical content in human milk during different stages of lactation.
PubMed:Mesenteric lymphatic absorption and the pharmacokinetics of naringin and naringenin in the rat.
PubMed:Protective effect of naringenin against acetaminophen-induced acute liver injury in metallothionein (MT)-null mice.
PubMed:Major active components in grapefruit, orange, and apple juices responsible for OATP2B1-mediated drug interactions.
PubMed:Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins.
PubMed:Prevention of disuse muscle atrophy by dietary ingestion of 8-prenylnaringenin in denervated mice.
PubMed:Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein.
PubMed:Antioxidant profile of Trifolium pratense L.
PubMed:Interactions of different polyphenols with bovine serum albumin using fluorescence quenching and molecular docking.
PubMed:Influences of four different light-emitting diode lights on flowering and polyphenol variations in the leaves of chrysanthemum (Chrysanthemum morifolium).
PubMed:Changes in the polyphenol profile of tomato juices processed by pulsed electric fields.
PubMed:Induction of electrophile-responsive element (EpRE)-mediated gene expression by tomato extracts in vitro.
PubMed:Selected nutraceutic screening by therapeutic effects on doxorubicin-induced chronic kidney disease.
PubMed:Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry.
PubMed:Grapefruit juice and its constituents augment the effect of low pH on inhibition of survival and adherence to intestinal epithelial cells of Salmonella enterica serovar Typhimurium PT193.
PubMed:Naringenin inhibits TNF-α induced VSMC proliferation and migration via induction of HO-1.
PubMed:The naringenin-induced proapoptotic effect in breast cancer cell lines holds out against a high bisphenol a background.
PubMed:Naringenin inhibits extracellular matrix production via extracellular signal-regulated kinase pathways in nasal polyp-derived fibroblasts.
PubMed:ID-CUBE direct analysis in real time high-resolution mass spectrometry and its capabilities in the identification of phenolic components from the green leaves of Bergenia crassifolia L.
PubMed:Differential effects of flavonoids on barrier integrity in human intestinal Caco-2 cells.
PubMed:Study on the interference of rat feed to pharmacokinetics of flavonoids.
PubMed:Evaluation of flavonoids and enterolactone in overnight urine as intake biomarkers of fruits, vegetables and beverages in the Inter99 cohort study using the method of triads.
PubMed:A profile of bioactive compounds of Rumex vesicarius L.
PubMed:Phenolic acid composition and antioxidant properties of Malaysian honeys.
PubMed:Susceptibility of estrogen receptor rapid responses to xenoestrogens: Physiological outcomes.
PubMed:Inhibition of hepatic uptake transporters by flavonoids.
PubMed:Selective determination of catechin among phenolic antioxidants with the use of a novel optical fiber reflectance sensor based on indophenol dye formation on nano-sized TiO₂.
PubMed:Dietary flavonoid naringenin induces regulatory T cells via an aryl hydrocarbon receptor mediated pathway.
PubMed:Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities.
PubMed:Determination of phenolic acids and flavonoids in Taraxacum formosanum Kitam by liquid chromatography-tandem mass spectrometry coupled with a post-column derivatization technique.
PubMed:Genistein as a potential inducer of the anti-atherogenic enzyme paraoxonase-1: studies in cultured hepatocytes in vitro and in rat liver in vivo.
PubMed:Melanogenesis of murine melanoma cells induced by hesperetin, a Citrus hydrolysate-derived flavonoid.
PubMed:Assay dilution factors confound measures of total antioxidant capacity in polyphenol-rich juices.
PubMed:Isolation and structure elucidation of highly antioxidative 3,8″-linked biflavanones and flavanone-C-glycosides from Garcinia buchananii bark.
PubMed:Structural features and bioavailability of four flavonoids and their implications for lifespan-extending and antioxidant actions in C. elegans.
PubMed:Transport mechanisms of flavanone aglycones across Caco-2 cell monolayers and artificial PAMPA membranes.
PubMed:Anti-inflammatory and antifibrotic effects of naringenin in diabetic mice.
PubMed:Purple corn (Zea mays L.) phenolic compounds profile and its assessment as an agent against oxidative stress in isolated mouse organs.
PubMed:Chemical compositions and antioxidant activities of water extracts of Chinese propolis.
PubMed:Enantiomers of naringenin as pleiotropic, stereoselective inhibitors of cytochrome P450 isoforms.
PubMed:Binding of citrus flavanones and their glucuronides and chalcones to human serum albumin.
PubMed:Identification of phenolic components in dried spices and influence of irradiation.
PubMed:Removing allosteric feedback inhibition of tomato 4-coumarate:CoA ligase by directed evolution.
PubMed:A synthetic naringenin derivative, 5-hydroxy-7,4'-diacetyloxyflavanone-N-phenyl hydrazone (N101-43), induces apoptosis through up-regulation of Fas/FasL expression and inhibition of PI3K/Akt signaling pathways in non-small-cell lung cancer cells.
PubMed:Over-expression of a grape stilbene synthase gene in tomato induces parthenocarpy and causes abnormal pollen development.
PubMed:Controlling for sugar and ascorbic acid, a mixture of flavonoids matching navel oranges significantly increases human postprandial serum antioxidant capacity.
PubMed:Construction of a model to estimate the CYP3A inhibitory effect of grapefruit juice.
PubMed:Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis.
PubMed:Food-drug interactions: grapefruit juice.
PubMed:Anti-inflammatory effects and chemical study of a flavonoid-enriched fraction from adlay bran.
PubMed:NMR investigation of a novel excipient, α-glucosylhesperidin, as a suitable solubilizing agent for poorly water-soluble drugs.
PubMed:Cuban and Brazilian red propolis: botanical origin and comparative analysis by high-performance liquid chromatography-photodiode array detection/electrospray ionization tandem mass spectrometry.
PubMed:Molecular characterization of a membrane-bound prenyltransferase specific for isoflavone from Sophora flavescens.
PubMed:Flavonoids: precipitation kinetics and interaction with surfactant micelles.
PubMed:Inhibition of citral degradation by oil-in-water nanoemulsions combined with antioxidants.
PubMed:Functional expression of geraniol 10-hydroxylase reveals its dual function in the biosynthesis of terpenoid and phenylpropanoid.
PubMed:[Flavonoids--bioactive compounds in fruits juice].
PubMed:Molecular structures of citrus flavonoids determine their effects on lipid metabolism in HepG2 cells by primarily suppressing apoB secretion.
PubMed:Properties of chalconaringenin and rutin isolated from cherry tomatoes.
PubMed:Differential expression of anthocyanin biosynthetic genes and anthocyanin accumulation in tartary buckwheat cultivars 'Hokkai t8' and 'Hokkai t10'.
PubMed:Mulberry leaf polyphenols possess antiatherogenesis effect via inhibiting LDL oxidation and foam cell formation.
PubMed:Effect of flavonoids on basal and insulin-stimulated 2-deoxyglucose uptake in adipocytes.
PubMed:Citrus flavonoid represses Salmonella pathogenicity island 1 and motility in S. Typhimurium LT2.
PubMed:Five bitter compounds display different anti-inflammatory effects through modulating cytokine secretion using mouse primary splenocytes in vitro.
PubMed:Core structure of flavonoids precursor as an antihyperglycemic and antihyperlipidemic agent: an in vivo study in rats.
PubMed:(+)-methyl jasmonate-induced bioformation of myricetin, quercetin and kaempferol in red raspberries.
PubMed:Potent modification of inducible CYP1A1 expression by flavonoids.
PubMed:Identification and concentration of some flavonoid components in Malaysian young ginger (Zingiber officinale Roscoe) varieties by a high performance liquid chromatography method.
PubMed:Genetics of flavonoid, carotenoid, and chlorophyll pigments in melon fruit rinds.
PubMed:Synergistic and antagonistic interactions of phenolic compounds found in navel oranges.
PubMed:Free fruit at workplace intervention increases total fruit intake: a validation study using 24 h dietary recall and urinary flavonoid excretion.
PubMed:Sap phytochemical compositions of some bananas in Thailand.
PubMed:Phenolic acids and flavonoids in nonfermented and fermented red sorghum (Sorghum bicolor (L.) Moench).
PubMed:Naringenin up-regulates the expression of death receptor 5 and enhances TRAIL-induced apoptosis in human lung cancer A549 cells.
PubMed:Preparation and physicochemical properties of the complex of naringenin with hydroxypropyl-beta-cyclodextrin.
PubMed:Flavonoid binding to human serum albumin.
PubMed:Chemical synthesis of citrus flavanone glucuronides.
PubMed:Total phenolic compounds, flavonoids, and radical scavenging activity of 21 selected tropical plants.
PubMed:Concentration and solubility of flavanones in orange beverages affect their bioavailability in humans.
PubMed:Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
PubMed:Antioxidant properties, radical scavenging activity and biomolecule protection capacity of flavonoid naringenin and its glycoside naringin: a comparative study.
PubMed:Antioxidant activity and phenolic profile of pistachio (Pistacia vera L., variety Bronte) seeds and skins.
PubMed:Almond (Prunus dulcis (Mill.) D.A. Webb) polyphenols: from chemical characterization to targeted analysis of phenolic metabolites in humans.
PubMed:Sorption and interaction of the flavonoid naringenin on tomato fruit cuticles.
PubMed:Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.
PubMed:Identification of bioactive compounds from flowers of black elder (Sambucus nigra L.) that activate the human peroxisome proliferator-activated receptor (PPAR) gamma.
PubMed:Effects of various polyphenolics on hydrogen peroxide-induced p53 activity in NIH3T3 cells.
PubMed:Relative bioavailability of the flavonoids quercetin, hesperetin and naringenin given simultaneously through diet.
PubMed:Lipid-lowering and antioxidant effects of an ethyl acetate extract of fenugreek seeds in high-cholesterol-fed rats.
PubMed:Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from alpha-rhamnosidase-treated orange juice in human subjects.
PubMed:Anticancer effects of flavonoid derivatives isolated from Millettia reticulata Benth in SK-Hep-1 human hepatocellular carcinoma cells.
PubMed:Greater apparent absorption of flavonoids is associated with lesser human fecal flavonoid disappearance rates.
PubMed:Quercetin and naringenin transport across human intestinal Caco-2 cells.
PubMed:Profile of plasma and urine metabolites after the intake of almond [Prunus dulcis (Mill.) D.A. Webb] polyphenols in humans.
PubMed:Naringin inhibits matrix metalloproteinase-9 expression and AKT phosphorylation in tumor necrosis factor-alpha-induced vascular smooth muscle cells.
PubMed:Major phytochemical composition of 3 native Korean citrus varieties and bioactive activity on V79-4 cells induced by oxidative stress.
PubMed:Inhibitory mechanism of naringenin against carcinogenic acrylamide formation and nonenzymatic browning in Maillard model reactions.
PubMed:Identification and quantification of metabolites of orally administered naringenin chalcone in rats.
PubMed:Low-density-lipoprotein (LDL)-bound flavonoids increase the resistance of LDL to oxidation and glycation under pathophysiological concentrations of glucose in vitro.
PubMed:The citrus flavanone naringenin inhibits inflammatory signalling in glial cells and protects against neuroinflammatory injury.
PubMed:Dose-response relationship for the pharmacokinetic interaction of grapefruit juice with dextromethorphan investigated by human urinary metabolite profiles.
PubMed:Yoghurt impacts on the excretion of phenolic acids derived from colonic breakdown of orange juice flavanones in humans.
PubMed:Comparison of flavonoids and isoflavonoids as antioxidants.
PubMed:Cupric ion reducing antioxidant capacity assay for food antioxidants: vitamins, polyphenolics, and flavonoids in food extracts.
PubMed:Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.
PubMed:Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of p-glycoprotein.
PubMed:The citrus fruit flavonoid naringenin suppresses hepatic glucose production from Fao hepatoma cells.
PubMed:Bioavailability and metabolism of orange juice flavanones in humans: impact of a full-fat yogurt.
PubMed:Naringenin and hesperetin induce growth arrest, apoptosis, and cytoplasmic fat deposit in human preadipocytes.
PubMed:Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey.
PubMed:Naringenin induces apoptosis through downregulation of Akt and caspase-3 activation in human leukemia THP-1 cells.
PubMed:Assessment of the nutritional values of genetically modified wheat, corn, and tomato crops.
PubMed:Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion.
PubMed:Pharmacokinetics of anthocyanins and antioxidant effects after the consumption of anthocyanin-rich acai juice and pulp (Euterpe oleracea Mart.) in human healthy volunteers.
PubMed:Naringenin-7-O-glucoside protects against doxorubicin-induced toxicity in H9c2 cardiomyocytes by induction of endogenous antioxidant enzymes.
PubMed:Dietary flavonoid sources in Australian adults.
PubMed:Effects of adlay hull extracts on uterine contraction and Ca2+ mobilization in the rat.
PubMed:Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple.
PubMed:Accumulation of isoflavone genistin in transgenic tomato plants overexpressing a soybean isoflavone synthase gene.
PubMed:Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats.
PubMed:The potential influence of fruit polyphenols on colonic microflora and human gut health.
PubMed:LC-DAD-MS (ESI+) analysis and antioxidant capacity of crocus sativus petal extracts.
PubMed:Dietary flavonoid intake and lung cancer--a population-based case-control study.
PubMed:Interactions between iron, phenolic compounds, emulsifiers, and pH in omega-3-enriched oil-in-water emulsions.
PubMed:Distinct effects of naringenin and hesperetin on nitric oxide production from endothelial cells.
PubMed:Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers.
PubMed:Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities.
PubMed:The effects of selected dietary bioflavonoid supplementation on dental caries in young rats fed a high-sucrose diet.
PubMed:[Effects of flavonoids with different structures on proliferation of leukemia cell line HL-60].
PubMed:Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.).
PubMed:The additive effects of the active component of grapefruit juice (naringenin) and antiarrhythmic drugs on HERG inhibition.
PubMed:Antimicrobial activity of flavonoids extracted from bergamot (Citrus bergamia Risso) peel, a byproduct of the essential oil industry.
PubMed:Inhibition effect of flavonoids on monocarboxylate transporter 1 (MCT1) in Caco-2 cells.
PubMed:Antioxidant and antimutagenic activities of Mexican oregano (Lippia graveolens Kunth).
PubMed:Enzymatic acylation of flavonoids: effect of the nature of the substrate, origin of lipase, and operating conditions on conversion yield and regioselectivity.
PubMed:Effects of flavonoid mixtures on the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers: an in vitro and kinetic modeling approach to predict the combined effects on transporter inhibition.
PubMed:Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages.
PubMed:Effects of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf.) hull extracts on the secretion of progesterone and estradiol in vivo and in vitro.
PubMed:Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay.
PubMed:Identification and quantification of flavonoids of Mexican oregano (Lippia graveolens) by LC-DAD-ESI/MS analysis.
PubMed:Constitutive expression of a grapevine stilbene synthase gene in transgenic hop (Humulus lupulus L.) yields resveratrol and its derivatives in substantial quantities.
PubMed:Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography.
PubMed:Mixture effects of estrogenic compounds on proliferation and pS2 expression of MCF-7 human breast cancer cells.
PubMed:Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties.
PubMed:Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.
PubMed:Development of a food frequency questionnaire for the assessment of quercetin and naringenin intake.
PubMed:Isozyme- and gender-specific induction of glutathione S-transferases by flavonoids.
PubMed:Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake.
PubMed:(Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture.
PubMed:Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.
PubMed:Estrogenic effects of mixtures of phyto- and synthetic chemicals on uterine growth of prepubertal rats.
PubMed:Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake.
PubMed:Identification and quantification of stilbenes in fruits of transgenic tomato plants (Lycopersicon esculentum Mill.) by reversed phase HPLC with photodiode array and mass spectrometry detection.
PubMed:Absorption and pharmacokinetics of grapefruit flavanones in beagles.
PubMed:Flavanone plasma pharmacokinetics from blood orange juice in human subjects.
PubMed:Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC.
PubMed:Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
PubMed:Effect of the citrus flavanone naringenin on oxidative stress in rats.
PubMed:Attenuation of monocyte adhesion and oxidised LDL uptake in luteolin-treated human endothelial cells exposed to oxidised LDL.
PubMed:Naringin time-dependently lowers hepatic cholesterol biosynthesis and plasma cholesterol in rats fed high-fat and high-cholesterol diet.
PubMed:Hypocholesterolemic and antioxidative effects of naringenin and its two metabolites in high-cholesterol fed rats.
PubMed:Estrogenic activity of the chlorinated derivatives of estrogens and flavonoids using a GFP expression system.
PubMed:Flavonoid content of U.S. fruits, vegetables, and nuts.
PubMed:Age-related variations in flavonoid intake and sources in the Australian population.
PubMed:Gas-phase ligation of Fe+ and Cu+ ions with some flavonoids.
PubMed:The reaction of flavonoid metabolites with peroxynitrite.
PubMed:Induction of cell apoptosis in 3T3-L1 pre-adipocytes by flavonoids is associated with their antioxidant activity.
PubMed:Electromigration profiles of Cynomorium songaricum based on capillary electrophoresis with amperometric detection.
PubMed:An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers.
PubMed:Pistachio skin phenolics are destroyed by bleaching resulting in reduced antioxidative capacities.
PubMed:Quantification and stability studies on the flavonoids of Radix hedysari.
PubMed:Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods.
PubMed:Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1.
PubMed:Influence of dietary antioxidants on polyphenol intestinal absorption and metabolism in rats.
PubMed:Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida).
PubMed:Catalytic inhibition of human DNA topoisomerase by phenolic compounds in Ardisia compressa extracts and their effect on human colon cancer cells.
PubMed:Activity and mRNA levels of enzymes involved in hepatic fatty acid oxidation in mice fed citrus flavonoids.
PubMed:Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli.
PubMed:HPLC analysis of sesaminol glucosides in sesame seeds.
PubMed:Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies.
PubMed:Characterization of flavonoids and pectins from bergamot (Citrus bergamia Risso) peel, a major byproduct of essential oil extraction.
PubMed:Disposition of selected flavonoids in fruit tissues of various tomato (lycopersicon esculentum mill.) Genotypes.
PubMed:Oxidation of dietary polyphenolics by hydroperoxidase activity of lipoxygenase.
PubMed:Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).
PubMed:Bioflavonoids and glutamine in diet and the Mg, Ca, Cu, Zn concentrations in heavy metals intoxicated rats' skins.
PubMed:Content of chalconaringenin and chlorogenic acid in cherry tomatoes is strongly reduced during postharvest ripening.
PubMed:Relative ability of dietary compounds to modulate nuclear factor-kappaB activity as assessed in a cell-based reporter system.
PubMed:Inhibition of cardiac HERG channels by grapefruit flavonoid naringenin: implications for the influence of dietary compounds on cardiac repolarisation.
PubMed:Isolation and structure elucidation of phenolic antioxidants from Tamarind (Tamarindus indica L.) seeds and pericarp.
PubMed:Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols.
PubMed:Impact of high pressure and pulsed electric fields on bioactive compounds and antioxidant activity of orange juice in comparison with traditional thermal processing.
PubMed:Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT?
PubMed:Human gut microbial degradation of flavonoids: structure-function relationships.
PubMed:The effects of dietary naringenin supplementation on physiological changes in molar crestal alveolar bone-cemento-enamel junction distance in young rats.
PubMed:Seasonal variations in the level of plant constituents in greenhouse production of cherry tomatoes.
PubMed:Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices.
PubMed:Antioxidant activity of citrus limonoids, flavonoids, and coumarins.
PubMed:Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata.
PubMed:Inhibition of hydrogen peroxide-induced endothelial apoptosis by 2',4',7-trihydroxyflavanone, a flavonoid form.
PubMed:Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method.
PubMed:Effects of grapefruit juice on the multidrug transporter P-glycoprotein in the human proximal tubular cell line HK-2.
PubMed:The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids.
PubMed:Influence of organic versus conventional agricultural practice on the antioxidant microconstituent content of tomatoes and derived purees; consequences on antioxidant plasma status in humans.
PubMed:Hepatolipidemic effects of naringenin in high cornstarch- versus high coconut oil-fed rats.
PubMed:Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes.
PubMed:Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport.
PubMed:Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types.
PubMed:Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity.
PubMed:Individual and interactive effects of apigenin analogs on G2/M cell-cycle arrest in human colon carcinoma cell lines.
PubMed:Kinetic study of flavonoid reactions with stable radicals.
PubMed:Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora.
PubMed:Selective cytotoxicity of a red grape wine flavonoid fraction against MCF-7 cells.
PubMed:Effect of antioxidant flavanone, naringenin, from Citrus junoson neuroprotection.
PubMed:Inhibitory effect of some flavonoids on tumor necrosis factor-alpha production in lipopolysaccharide-stimulated mouse macrophage cell line J774.1.
PubMed:The citrus-derived flavonoid naringenin exerts uterotrophic effects in female mice at human relevant doses.
PubMed:Lethal and teratogenic effects of naringenin evaluated by means of an amphibian embryo toxicity test (AMPHITOX).
PubMed:Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
PubMed:Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.
PubMed:HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products.
PubMed:Inhibitory activity of flavonoids from Prunus davidiana and other flavonoids on total ROS and hydroxyl radical generation.
PubMed:Pro-oxidative properties of flavonoids in human lymphocytes.
PubMed:Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification.
PubMed:Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits.
PubMed:[Grapefruit juice and drugs: a hazardous combination?].
PubMed:In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice.
PubMed:Naringenin 7-O-cetyl ether as inhibitor of HMG-CoA reductase and modulator of plasma and hepatic lipids in high cholesterol-fed rats.
PubMed:Naringenin from cooked tomato paste is bioavailable in men.
PubMed:Fasting plasma concentrations of selected flavonoids as markers of their ordinary dietary intake.
PubMed:Plasma concentrations of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets, and diets high or low in fruit and vegetables.
PubMed:Effects of food processing on flavonoids and lycopene status in a Mediterranean tomato variety.
PubMed:Flavonoids in human urine as biomarkers for intake of fruits and vegetables.
PubMed:Supplementation of naringenin and its synthetic derivative alters antioxidant enzyme activities of erythrocyte and liver in high cholesterol-fed rats.
PubMed:Effects of grapefruit juice and smoking on verapamil concentrations in steady state.
PubMed:In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.
PubMed:Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch).
PubMed:Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue.
PubMed:Effect of honey and sugars on the metabolism and disposition of naringin in rabbits.
PubMed:Molecular and biochemical characterization of three aromatic polyketide synthase genes from Rubus idaeus.
PubMed:17beta-Estradiol but not the phytoestrogen naringenin attenuates aortic cholesterol accumulation in WHHL rabbits.
PubMed:Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols.
PubMed:Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes.
PubMed:Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.
PubMed:Differential estrogen receptor binding of estrogenic substances: a species comparison.
PubMed:Naringin glycosides alpha-glucosylated on ring B found in the natural food additive, enzymatically modified naringin.
PubMed:Bioavailability of the flavanone naringenin and its glycosides in rats.
PubMed:Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro.
PubMed:Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds.
PubMed:The development of methods for assessing the in vivo oestrogen-like effects of xenobiotics in CD-1 mice.
PubMed:Differential effects of dietary flavonoids on drug metabolizing and antioxidant enzymes in female rat.
PubMed:Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine.
PubMed:Antioxidant polyphenols from tart cherries (Prunus cerasus).
PubMed:Purification of cytosolic beta-glucosidase from pig liver and its reactivity towards flavonoid glycosides.
PubMed:Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats.
PubMed:Effects of food on clinical pharmacokinetics.
PubMed:Inhibition of xenobiotic-induced genotoxicity in cultured precision-cut human and rat liver slices.
PubMed:Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells.
PubMed:Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity.
PubMed:Flavonoid deactivation of ferrylmyoglobin in relation to ease of oxidation as determined by cyclic voltammetry.
PubMed:Dietary flavonoids interact with trace metals and affect metallothionein level in human intestinal cells.
PubMed:Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay.
PubMed:In vitro biotransformation of flavonoids by rat liver microsomes.
PubMed:Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance.
PubMed:Lipid peroxidation and DNA damage induced by morin and naringenin in isolated rat liver nuclei.
PubMed:Phytonutrition, phytotherapy, and phytopharmacology.
PubMed:Flavanone absorption after naringin, hesperidin, and citrus administration.
PubMed:Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols.
PubMed:Flavonoids in grapefruit juice inhibit the in vitro hepatic metabolism of 17 beta-estradiol.
PubMed:Lacking effect of grapefruit juice on theophylline pharmacokinetics.
PubMed:Inhibition of 17 beta-estradiol metabolism by grapefruit juice in ovariectomized women.
PubMed:Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes.
PubMed:Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.
PubMed:Metabolism of taxol by human hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme.
PubMed:Preparation and taste of certain glycosides of flavanones and of dihydrochalcones.
PubMed:Antimutagenic effect of plant flavonoids in the Salmonella assay system.
PubMed:Improvement of hyperglycemia and hyperlipemia in streptozotocin-diabetic rats by a methanolic extract of Prunus davidiana stems and its main component, prunin.
PubMed:Antihyperlipidemic effect of flavonoids from Prunus davidiana.
PubMed:Liquid chromatographic determination of naringin and neohesperidin as a detector of grapefruit juice in orange juice.
PubMed:Biochemical, immunological, and immunocytochemical evidence for the association of chalcone synthase with endoplasmic reticulum membranes.
a phytogenic antineoplastic agent. Most widely distributed flavanone. Citrus fruits (grapefruit, oranges and pummelos) are especially good sources. Glycosides also widely distributed Naringenin (not to be confused with naringin) is a flavanone, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulator. It is the predominant flavanone in grapefruit. (Wikipedia)
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