Hesperetin glucuronides induce adipocyte differentiation via activation and expression of peroxisome proliferator-activated receptor-γ

References

• Garg A, Garg S, Zaneveld LJ, Singla AK. Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Phytother. Res. 2001;15:655–669.10.1002/(ISSN)1099-1573
   PubMed Web of Science ®Google Scholar
• Wilmsen PK, Spada DS, Salvador M. Antioxidant activity of the flavonoid hesperidin in chemical and biological systems. J. Agric. Food Chem. 2005;53:4757–4761.10.1021/jf0502000
   PubMed Web of Science ®Google Scholar
• Galati EM, Trovato A, Kirjavainen S, Forestieri AM, Rossitto A, Monforte MT. Biological effects of hesperidin, a Citrus flavonoid. (Note III): antihypertensive and diuretic activity in rat. Farmaco. 1996;51:219–221.
   PubMedGoogle Scholar
• Bok SH, Lee SH, Park YB, Bae KH, Son KH, Jeong TS, Choi MS. Plasma and hepatic cholesterol and hepatic activities of 3-hydroxy-3-methyl-glutaryl-CoA reductase and acyl CoA: cholesterol transferase are lower in rats fed citrus peel extract or a mixture of citrus bioflavonoids. J. Nutr. 1999;129:1182–1185.
   PubMed Web of Science ®Google Scholar
• Booth AN, Jones FT, DeEds F. Metabolic fate of hesperidin, eriodictyol, homoeridictyol, and diosmin. J. Biol. Chem. 1958;230:661–668.
   PubMed Web of Science ®Google Scholar
• Hackett AM, Marsh I, Barrow A. The bilary excretion of flavanones in the rat. Xenobiotica. 1979;9:491–501.10.3109/00498257909087263
   PubMed Web of Science ®Google Scholar
• Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA. Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation. Biochem. Biophys. Res. Commun. 1999;265:410–415.10.1006/bbrc.1999.1695
   PubMed Web of Science ®Google Scholar
• Felgines C, Texier O, Morand C, Manach C, Scalbert A, Regerat F, Remesy C. Bioavailability of the flavanone naringenin and its glycosides in rats. Am. J. Physiol. Gastrointest. Liver Physiol. 2000;279:G1148–G1154.
   PubMed Web of Science ®Google Scholar
• Flowers HM. Synthesis of two phosphate-containing “heptasaccharide” fragments of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B. Carbohydr. Res. 1971;18:211–218.10.1016/S0008-6215(00)80344-4
   Web of Science ®Google Scholar
• Koenigs W, Knorr E. Over some derivatives of grape sugar and the galactose. Ber. Deu. Chem. Ges. 1901;34:957–981.10.1002/(ISSN)1099-0682
   Google Scholar
• Nielsen SE, Breinholt V, Justesen U, Cornett C, Dragsted LO. In vitro biotransformation of flavonoids by rat liver microsomes. Xenobiotica. 1998;28:389–401.10.1080/004982598239498
   PubMed Web of Science ®Google Scholar
• Yamamoto M, Jokura H, Hashizume K, Ominami H, Shibuya Y, Suzuki A, Hase T, Shimotoyodome A. Hesperidin metabolite hesperetin-7-O-glucuronide, but not hesperetin-3′-O-glucuronide, exerts hypotensive, vasodilatory, and anti-inflammatory activities. Food Funct. 2013;4:1346–1351.10.1039/c3fo60030k
   PubMed Web of Science ®Google Scholar
• Brand W, Oosterhuis B, Krajcsi P, Barron D, Dionisi F, Bladeren PJ, Rietjens IM, Williamson G. Interaction of hesperetin glucuronide conjugates with human BCRP, MRP2 and MRP3 as detected in membrane vesicles of overexpressing baculovirus-infected Sf9 cells. Biopharm. Drug Dispos. 2011;32:530–535.10.1002/bdd.780
   PubMed Web of Science ®Google Scholar
• Chinetti G, Fruchart JC, Staels B. Peroxisome proliferator-activated receptors (PPARs): nuclear receptors at the crossroads between lipid metabolism and inflammation. Inflamm. Res. 2000;49:497–505.10.1007/s000110050622
   PubMed Web of Science ®Google Scholar
• Rosen ED, Hsu CH, Wang X, Sakai S, Freeman MW, Gonzalez FJ, Spiegelman BM. C/EBPalpha induces adipogenesis through PPARgamma: a unified pathway. Genes Dev. 2002;16:22–26.10.1101/gad.948702
   PubMed Web of Science ®Google Scholar
• Francis GA, Annicotte JS, Auwerx J. PPAR agonists in the treatment of atherosclerosis. Curr. Opin. Pharmacol. 2003;3:186–191.10.1016/S1471-4892(03)00014-6
   PubMed Web of Science ®Google Scholar
• Gurnell M, Savage DB, Chatterjee VK, O’Rahilly S. The metabolic syndrome: peroxisome proliferator-activated receptor gamma and its therapeutic modulation. J. Clin. Endocrinol. Metab. 2003;88:2412–2421.10.1210/jc.2003-030435
   PubMed Web of Science ®Google Scholar
• Matsumoto H, Ikoma Y, Sugiura M, Yano M, Hasegawa Y. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. J. Agric. Food Chem. 2004;52:6653–6659.10.1021/jf0491411
   PubMed Web of Science ®Google Scholar
• Khan MK, Rakotomanomana N, Loonis M, Dangles O. Chemical synthesis of citrus flavanone glucuronides. J. Agric. Food. Chem. 2010;58:8437–8443.
   PubMed Web of Science ®Google Scholar
• Stafslien DK, Vedvik KL, De Rosier T, Ozers MS. Analysis of ligand-dependent recruitment of coactivator peptides to RXRbeta in a time-resolved fluorescence resonance energy transfer assay. Mol. Cell. Endocrinol. 2007;264:82–89.
   PubMed Web of Science ®Google Scholar
• Yoshida H, Takamura N, Shuto T, Ogata K, Tokunaga J, Kawai K, Kai H. The citrus flavonoids hesperetin and naringenin block the lipolytic actions of TNF-alpha in mouse adipocytes. Biochem. Biophys. Res. Commun. 2010;394:728–732.
   PubMed Web of Science ®Google Scholar
• Kletzien RF, Clarke SD, Ulrich RG. Enhancement of adipocyte differentiation by an insulin-sensitizing agent. Mol. Pharmacol. 1992;41:393–398.
   PubMed Web of Science ®Google Scholar
• Huang TH, Kota BP, Razmovski V, Roufogalis BD. Herbal or natural medicines as modulators of peroxisome proliferator-activated receptors and related nuclear receptors for therapy of metabolic syndrome. Basic Clin. Pharmacol. Toxicol. 2005;96:3–14.
   PubMed Web of Science ®Google Scholar
• Puhl AC, Bernardes A, Silveira RL, Yuan J, Campos JL, Saidemberg DM, Palma MS, Cvoro A, Ayers SD, Webb P, Reinach PS, Skaf MS, Polikarpov I. Mode of peroxisome proliferator-activated receptor γ activation by luteolin. Mol. Pharmacol. 2012;81:788–799.
   PubMed Web of Science ®Google Scholar