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H5254 Sigma

Hesperidin

≥80%

Synonym: Hesperetin 7-rhamnoglucoside, Hesperitin-7-rutinoside

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Description

Biochem/physiol Actions

Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2

Application

Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H5254.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

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Safety & Documentation

Safety Information

WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Hesperidin and hesperetin membrane interaction: understanding the role of 7-O-glycoside moiety in flavonoids Londoño-Londoño, J. et al. Arch. Biochem. Biophys. 499, 6-16, (2010)

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2. Acid-catalyzed hydrolysis of hesperidin at elevated temperatures. Carbohydr. Res. 328, 141-146, (2000)

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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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[Prevention of osteoporosis by foods and dietary supplements. Hesperidin and bone metabolism]. Uehara M Clin. Calcium 16(10), 1669-76, (2006)

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[Pharmacological action of hesperidin]. Ou S Zhong Yao Cai 25(7), 531-3, (2002)

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[Hemorrhoids and conservative treatment. Review of the literature on the use of diosmin and micronized hesperidin]. La Torre F, Nicolai AP, and Otti M Minerva Chir. 54(12), 909-16, (1999)

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Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Garg A, Garg S, Zaneveld LJ, et al. Phytother Res. 15(8), 655-69, (2001)

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Citrus flavonoids and lipid metabolism. Assini JM, Mulvihill EE, and Huff MW Curr. Opin. Lipidol. 24(1), 34-40, (2013)

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Evidence for the involvement of the serotonergic 5-HT(1A) receptors in the antidepressant-like effect caused by hesperidin in mice. Souza LC, de Gomes MG, Goes AT, et al. Prog. Neuropsychopharmacol. Biol. Psychiatry 40, 103-9, (2013)

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Hesperetin ameliorates hyperglycemia induced retinal vasculopathy via anti-angiogenic effects in experimental diabetic rats. Kumar B, Gupta SK, Srinivasan BP, et al. Vascul. Pharmacol. 57(5-6), 201-7, (2012)

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Interaction of antitumor flavonoids with dsDNA in the absence and presence of Cu(II). Temerk YM, Ibrahim MS, Kotb M, et al. Anal. Bioanal. Chem 405(11), 3839-46, (2013)

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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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Cancer chemoprevention by citrus pulp and juices containing high amounts of β-cryptoxanthin and hesperidin. Tanaka T, Tanaka T, Tanaka M, et al. J. Biomed. Biotechnol. 2012, 516981, (2012)

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Hesperetin: an inhibitor of the transforming growth factor-β (TGF-β) signaling pathway. Yang Y, Wolfram J, Shen H, et al. Eur. J. Med. Chem. 58, 390-5, (2012)

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Kappa-opioid receptors mediate the antidepressant-like activity of hesperidin in the mouse forced swimming test. Filho CB, Del Fabbro L, de Gomes MG, et al. Eur. J. Pharmacol. 698(1-3), 286-91, (2013)

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Assessment of phytochemical content in human milk during different stages of lactation. Song BJ, Jouni ZE, and Ferruzzi MG Nutrition 29(1), 195-202, (2013)

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Effect of increasing levels of bioflavonoids in broiler feed on plasma anti-oxidative potential, lipid metabolites, and fatty acid composition of meat. Kamboh AA and Zhu WY Poult. Sci. 92(2), 454-61, (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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Hesperidin prevents retinal and plasma abnormalities in streptozotocin-induced diabetic rats. Shi X, Liao S, Mi H, et al. Molecules 17(11), 12868-81, (2012)

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Neohesperidin dihydrochalcone: presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector. Kashani-Amin E, Larijani B, and Ebrahim-Habibi A FEBS Lett. 587(6), 652-8, (2013)

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A comparison study on the binding of hesperetin and luteolin to bovine serum albumin by spectroscopy. Tang L and Jia W Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 103, 114-9, (2013)

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Neohesperidin attenuates cerebral ischemia-reperfusion injury via inhibiting the apoptotic pathway and activating the Akt/Nrf2/HO-1 pathway. Wang JJ and Cui P J. Asian Nat. Prod. Res. 15(9), 1023-37, (2013)

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Quantification of hesperidin in citrus-based foods using a fungal diglycosidase. Mazzaferro LS and Breccia JD Food Chem. 134(4), 2338-44, (2012)

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Enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reductase, and growth of Helicobacter pylori. Lee YS, Huh JY, Nam SH, et al. Food Chem. 135(4), 2253-9, (2012)

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Individual and combined effects of genistein and hesperidin supplementation on meat quality in meat-type broiler chickens. Kamboh AA and Zhu WY J. Sci. Food Agric. 93(13), 3362-7, (2013)

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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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Effects of genistein and hesperidin on biomarkers of heat stress in broilers under persistent summer stress. Kamboh AA, Hang SQ, Bakhetgul M, et al. Poult. Sci. 92(9), 2411-8, (2013)

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Synthesis and anti-hyperglycemic activity of hesperidin derivatives. Zhang B, Chen T, Chen Z, et al. Bioorg. Med. Chem. Lett. 22(23), 7194-7, (2012)

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Hesperidin alleviates oxidative stress and downregulates the expressions of proliferative and inflammatory markers in azoxymethane-induced experimental colon carcinogenesis in mice. Saiprasad G, Chitra P, Manikandan R, et al. Inflamm. Res. 62(4), 425-40, (2013)

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Molecular spectroscopic on interaction between Methyl hesperidin and Buman serum albumin. Li J and Wang S Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 102, 200-4, (2013)

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Antimicrobial and immunomodulating activities of hesperidin and ellagic acid against diarrheic Aeromonas hydrophila in a murine model. Abuelsaad AS, Mohamed I, Allam G, et al. Life Sci. 93(20), 714-22, (2013)

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7,3'-dimethoxy hesperetin inhibits inflammation by inducing synovial apoptosis in rats with adjuvant-induced arthritis. Li R, Cai L, Xie XF, et al. Immunopharmacol. Immunotoxicol. 35(1), 139-46, (2013)

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Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro. Hu L, Li L, Xu D, et al. Chem. Biol. Interact. 213, 51-9, (2014)

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Neohesperidin induces cellular apoptosis in human breast adenocarcinoma MDA-MB-231 cells via activating the Bcl-2/Bax-mediated signaling pathway. Xu F, Zang J, Chen D, et al. Nat. Prod. Commun. 7(11), 1475-8, (2012)

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Evaluation of first-pass cytochrome P4503A (CYP3A) and P-glycoprotein activities using felodipine and hesperetin in combination in Wistar rats and everted rat gut sacs in vitro. Sridhar V, Surya Sandeep M, Ravindra Babu P, et al. Phytother Res. 28(5), 699-705, (2014)

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Effects of long-term feeding of α-glucosylhesperidin on the mechanical properties of rabbit femoral arteries. Naiki T, Kurose Y, Hayashi K, et al. Biorheology 49(5-6), 353-63, (2012)

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Hesperidinase encapsulation towards hesperitin production targeting improved bioavailability. Furtado AF, Nunes MA, and Ribeiro MH J. Mol. Recognit. 25(11), 595-603, (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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Effects of diosmine-hesperidine on experimental colonic anastomosis. Cengiz A, Tabak S, Kuru S, et al. Bratisl. Lek. Listy 113(12), 692-7, (2012)

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Evaluating the bioactive effects of flavonoid hesperidin--a new literature data survey. Kuntić V, Brborić J, Holclajtner-Antunović I, et al. Vojnosanit. Pregl. 71(1), 60-5, (2014)

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Merck 14,4671

Beil. 18,V,5,218

FT-IR 2 (2), 2503:D / RegBook 1 (2), 1695:K / Sax 6, 1504 / Structure Index 1, 270:C:3

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