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N1376 Sigma

Naringin

≥90%, from citrus fruit

Synonym: 4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside, Naringenine-7-rhamnosidoglucoside

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Description

Biochem/physiol Actions

Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.3

General description

Naringin is a flavanone glycoside. 4

Packaging

25, 100 g in poly bottle

Application

Naringin has been used in a study to assess aldosterone production by a human adrenocortical cell line. 1 Long-term naringin consumption reverses a glucose uptake defect and can be used to improve cognitive deficits of Alzheimer′s disease. 2

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N1376.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
22-24/25
WGK Germany 
3
RTECS 
QN6340000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. The Potassium Channel, Kir3.4 Participates in Angiotensin II-Stimulated Aldosterone Production by a Human Adrenocortical Cell Line Oki, K., et al. Endocrinology, (2012)

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2. Long-term naringin consumption reverses a glucose uptake defect and improves cognitive deficits in a mouse model of Alzheimer's disease Wang, D., et al. Pharmacol. Biochem. Behav. 102, 13-20, (2012)

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3. Fruit juice inhibition of uptake transport: a new type of food-drug interaction Bailey, D.G. Br. J. Clin. Pharmacol. 70, 645-655, (2010)

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4. Evaluation of novel amylose and cellulose-based chiral stationary phases for the stereoisomer separation of flavanones by means of nano-liquid chromatography Si-Ahmed, K., et al. Anal. Chim. Acta 738, 85-94, (2012)

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Membrane transporters in drug development Giacomini, K.M., et al. Nat. Rev. Drug Discov. 9, 215-236, (2010)

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[Substrate specificity of Cryptococcus albidus and Eupenicillium erubescens alpha-L-rhamnosidases]. Hudzenko OV and Varbanets' LD Ukr. Biokhim. Zh. 85(5), 17-26, (2013)

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[Effects of naringin on proliferation, differentiation and maturation of rat calvarial osteoblasts in vitro]. Zhai YK, Niu YB, Pan YL, et al. Zhongguo Zhong Yao Za Zhi 38(1), 105-11, (2013)

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Alpha-L-rhamnosidase from Aspergillus clavato-nanicus MTCC-9611 active at alkaline pH. Yadav V, Yadav S, Yadav S, et al. Prikl. Biokhim. Mikrobiol. 48(3), 328-33, (2012)

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[Transdermal behavior of effective constituents in xuanbi gel plaster]. Liu Y, Lu Y, Du S, et al. Zhongguo Zhong Yao Za Zhi 37(9), 1202-5, (2012)

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Naringin induces death receptor and mitochondria-mediated apoptosis in human cervical cancer (SiHa) cells. Ramesh E and Alshatwi AA Food Chem. Toxicol. 51, 97-105, (2013)

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Inhibitory effects of Citrus flavonoids on starch digestion and antihyperglycemic effects in HepG2 cells. Shen W, Xu Y, and Lu YH J. Agric. Food Chem. 60(38), 9609-19, (2012)

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Inhibition of Ca(2+) entry and suicidal erythrocyte death by naringin. Shaik N, Zbidah M, and Lang F Cell Physiol. Biochem. 30(3), 678-86, (2012)

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Protein Tyrosine Phosphatase-1B Inhibitory Activity of Isoprenylated Flavonoids Isolated from Erythrina mildbraedii. MinKyun Na, et al. J. Nat. Prod. 69, 1572-1576, (2006)

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Naringin ameliorates gentamicin-induced nephrotoxicity and associated mitochondrial dysfunction, apoptosis and inflammation in rats: possible mechanism of nephroprotection. Sahu BD, Tatireddy S, Koneru M, et al. Toxicol. Appl. Pharmacol. 277(1), 8-20, (2014)

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Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells. Zhang J, Sun C, Yan Y, et al. Food Chem. 135(3), 1471-8, (2012)

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Major active components in grapefruit, orange, and apple juices responsible for OATP2B1-mediated drug interactions. Shirasaka Y, Shichiri M, Mori T, et al. J. Pharm. Sci. 102(1), 280-8, (2013)

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Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids. Dragan Ami? et al Bioorg. Med. Chem. 18, 28-35, (2010)

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Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones. H Serra et al Bioorg. Med. Chem. 16, 4009-18, (2008)

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Anti-inflammatory effects of naringin in chronic pulmonary neutrophilic inflammation in cigarette smoke-exposed rats. Nie YC, Wu H, Li PB, et al. J. Med. Food 15(10), 894-900, (2012)

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Selective inhibition of aromatase by a dihydroisocoumarin from Xyris pterygoblephara. Denise C Endringer et al J. Nat. Prod. 71, 1082-4, (2008)

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Naringin modulates oxidative stress and inflammation in 3-nitropropionic acid-induced neurodegeneration through the activation of nuclear factor-erythroid 2-related factor-2 signalling pathway. Gopinath K and Sudhandiran G Neuroscience 227, 134-43, (2012)

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In vitro effects of myricetin, morin, apigenin, (+)-taxifolin, (+)-catechin, (-)-epicatechin, naringenin and naringin on cytochrome b5 reduction by purified NADH-cytochrome b5 reductase. Çelik H, Koşar M, and Arinç E Toxicology 308, 34-40, (2013)

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Phytochemical profile and antioxidant activity of physiological drop of citrus fruits. Sun Y, Qiao L, Shen Y, et al. J. Food Sci. 78(1), C37-42, (2013)

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Emerging targets in osteoporosis disease modification. John G Allen et al J. Med. Chem. 53, 4332-53, (2010)

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Hesperidin and naringin attenuate hyperglycemia-mediated oxidative stress and proinflammatory cytokine production in high fat fed/streptozotocin-induced type 2 diabetic rats. Mahmoud AM, Ashour MB, Abdel-Moneim A, et al. J. Diabetes Complications 26(6), 483-90, (2012)

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Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials. Marlène Backleh-Sohrt et al J. Nat. Prod. 68, 1386-9, (2005)

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Mesenteric lymphatic absorption and the pharmacokinetics of naringin and naringenin in the rat. Tsai YJ and Tsai TH J. Agric. Food Chem. 60(51), 12435-42, (2012)

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Inhibiting wear particles-induced osteolysis with naringin. Yu X, Zhao X, Wu T, et al. Int. Orthop. 37(1), 137-43, (2013)

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Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques. Uckoo RM, Jayaprakasha GK, Balasubramaniam VM, et al. J. Food Sci. 77(9), C921-6, (2012)

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Memory enhancing activity of naringin in unstressed and stressed mice: possible cholinergic and nitriergic modulation. Maratha SR and Mahadevan N Neurochem. Res. 37(10), 2206-12, (2012)

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Characterization of an α-L-Rhamnosidase from Streptomyces avermitilis. Ichinose H, Fujimoto Z, and Kaneko S Biosci. Biotechnol. Biochem. 77(1), 213-6, (2013)

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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. Yin X, Gyles CL, and Gong J Int. J. Food Microbiol. 158(3), 232-8, (2012)

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Cell surface engineering of α-l-rhamnosidase for naringin hydrolysis. Liu Q, Lu L, and Xiao M Bioresour. Technol. 123, 144-9, (2012)

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Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats. Gong HL, Tang WF, Wang J, et al. Chin. J. Integr. Med. 18(9), 708-13, (2012)

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High-affinity water-soluble system for efficient naringinase immobilization in polyvinyl alcohol-dimethyl sulfoxide lens-shaped particles. Nunes MA, Fernandes PC, and Ribeiro MH J. Mol. Recognit. 25(11), 580-94, (2012)

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Novel oxime based flavanone, naringin-oxime: synthesis, characterization and screening for antioxidant activity. Ozyürek M, Akpınar D, Bener M, et al. Chem. Biol. Interact. 212, 40-6, (2014)

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Simultaneous UPLC analysis of three major flavonoids in granule decoctions of Fructus aurantii-type formulae. Huang W, Xiong ZH, Huang X, et al. Pharmazie 67(7), 586-9, (2012)

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Population pharmacokinetics of naringin in total flavonoids of Drynaria fortunei (Kunze) J. Sm. in Chinese women with primary osteoporosis. Wang JN, Jiang JJ, Xie YM, et al. Chin. J. Integr. Med. 18(12), 925-33, (2012)

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Targeting structural motifs of flavonoid diglycosides using collision-induced dissociation experiments on flavonoid/Pb2+ complexes. Ilboudo O, Tapsoba I, Bonzi-Coulibaly YL, et al. Eur. J. Mass Spectrom. (Chichester, Eng.) 18(5), 465-73, (2012)

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Merck 14,6425

Beil. 18,V,4,528

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