Sulfation of hesperetin, naringenin and apigenin by the human cytosolic sulfotransferases: a comprehensive analysis

References

• Blanchard RL, Freimuth RR, Buck J, Weinshilboum RM, Coughtrie MW. 2004. A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily. Pharmacogenetics. 14(3):199–211.
   PubMedGoogle Scholar
• Brand W, Boersma MG, Bik H, Hoek-van den Hil EF, Vervoort J, Barron D, Meinl W, Glatt H, Williamson G, van Bladeren PJ, Rietjens IM. 2010. Phase II metabolism of hesperetin by individual UDP-glucuronosyltransferases and sulfotransferases and rat and human tissue samples. Drug Metab Dispos. 38(4):617–625.
   PubMed Web of Science ®Google Scholar
• Chen J, Lin H, Hu M. 2003. Metabolism of flavonoids via enteric recycling: role of intestinal disposition. J Pharmacol Exp Ther. 304(3):1228–1235.
   PubMed Web of Science ®Google Scholar
• Harnly JM, Doherty RF, Beecher GR, Holden JM, Haytowitz DB, Bhagwat S, Gebhardt S. 2006. Flavonoid content of U.S. fruits, vegetables, and nuts. J Agric Food Chem. 54(26):9966–9977.
   PubMed Web of Science ®Google Scholar
• Hertog MG, Feskens EJ, Hollman PC, Katan MB, Kromhout D. 1993. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet. 342(8878):1007–1011.
   PubMed Web of Science ®Google Scholar
• Hsiu SL, Huang TY, Hou YC, Chin DH, Chao PD. 2002. Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits. Life Sci. 70(13):1481–1489.
   PubMed Web of Science ®Google Scholar
• Huang C, Chen Y, Zhou T, Chen G. 2009. Sulfation of dietary flavonoids by human sulfotransferases. Xenobiotica. 39(4):312–322.
   PubMed Web of Science ®Google Scholar
• Justesen U, Knuthsen P, Leth T. 1998. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. J Chromatogr A. 799(1-2):101–110.
   PubMed Web of Science ®Google Scholar
• Lin SP, Hou YC, Tsai SY, Wang MJ, Chao PD. 2014. Tissue distribution of naringenin conjugated metabolites following repeated dosing of naringin to rats. Biomedicine (Taipei). 4:16
   PubMedGoogle Scholar
• Lipmann F. 1958. Biological sulfate activation and transfer. Science. 128(3324):575–580.
   PubMed Web of Science ®Google Scholar
• Liu Y, Hu M. 2002. Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model. Drug Metab Dispos. 30(4):370–377.
   PubMed Web of Science ®Google Scholar
• Ma H, Liu Y, Mai X, Liao Y, Zhang K, Liu B, Xie X, Du Q. 2016. Identification of the constituents and metabolites in rat plasma after oral administration of HuanglianShangqing pills by ultra high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Pharm Biomed. 125:194–204.
   PubMed Web of Science ®Google Scholar
• Meinl W, Ebert B, Glatt H, Lampen A. 2008. Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism. Drug Metab Dispos. 36(2):276–283.
   PubMed Web of Science ®Google Scholar
• Nakazawa T, Ohsawa K. 2000. Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 23(1):122–127.
   PubMed Web of Science ®Google Scholar
• Pai TG, Sugahara T, Suiko M, Sakakibara Y, Xu F, Liu MC. 2002. Differential xenoestrogen-sulfating activities of the human cytosolic sulfotransferases: molecular cloning, expression, and purification of human SULT2B1a and SULT2B1b sulfotransferases. Biochim Biophys Acta. 1573(2):165–170.
   PubMed Web of Science ®Google Scholar
• Panche AN, Diwan AD, Chandra SR. 2016. Flavonoids: an overview. J Nutr Sci. 5:e47
   PubMed Web of Science ®Google Scholar
• Patel D, Shukla S, Gupta S. 2007. Apigenin and cancer chemoprevention: progress, potential and promise (review). Int J Oncol. 30(1):233–245.
   PubMed Web of Science ®Google Scholar
• Pereira-Caro G, Borges G, van der Hooft J, Clifford MN, Del Rio D, Lean ME, Roberts SA, Kellerhals MB, Crozier A. 2014. Orange juice (poly)phenols are highly bioavailable in humans. Am J Clin Nutr. 100(5):1378–1384.
   PubMed Web of Science ®Google Scholar
• Riches Z, Stanley EL, Bloomer JC, Coughtrie MW. 2009. Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT "pie". Drug Metab Dispos. 37(11):2255–2261.
   PubMed Web of Science ®Google Scholar
• Sakakibara Y, Suiko M, Pai TG, Nakayama T, Takami Y, Katafuchi J, Liu MC. 2002. Highly conserved mouse and human brain sulfotransferases: molecular cloning, expression, and functional characterization. Gene. 285(1-2):39–47.
   PubMed Web of Science ®Google Scholar
• Sakakibara Y, Takami Y, Nakayama T, Suiko M, Liu MC. 1998. Localization and functional analysis of the substrate specificity/catalytic domains of human M-form and P-form phenol sulfotransferases. J Biol Chem. 273(11):6242–6247.
   PubMed Web of Science ®Google Scholar
• Suiko M, Kurogi K, Hashiguchi T, Sakakibara Y, Liu MC. 2017. Updated perspectives on the cytosolic sulfotransferases (SULTs) and SULT-mediated sulfation. Biosci Biotechnol Biochem. 81(1):63–72.
   PubMed Web of Science ®Google Scholar
• Suiko M, Sakakibara Y, Liu MC. 2002. Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases. Biochem. Biophys. Res. Commun. 267(1):80–84.
   Web of Science ®Google Scholar
• Teubner W, Meinl W, Florian S, Kretzschmar M, Glatt H. 2007. Identification and localization of soluble sulfotransferases in the human gastrointestinal tract. Biochem J. 404(2):207–215.
   PubMed Web of Science ®Google Scholar
• Tomas-Barberan FA, Clifford MN. 2000. Flavanones, chalcones and dihydrochalcones –nature, occurrence and dietary burden. J Sci Food Agric. 80(7):1073–1080.
   Web of Science ®Google Scholar
• Walle T, Hsieh F, DeLegge MH, Oatis JE, Jr, Walle UK. 2003. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos. 32(12):1377–1382.
   Web of Science ®Google Scholar
• Westerink WM, Schoonen WG. 2007. Phase II enzyme levels in HepG2 cells and cryopreserved primary human hepatocytes and their induction in HepG2 cells. Toxicol in Vitro. 21(8):1592–1602.
   PubMed Web of Science ®Google Scholar
• Xiao J, Högger P. 2013. Metabolism of dietary flavonoids in liver microsomes. Curr Drug Metab. 14(4):381–391.
   PubMed Web of Science ®Google Scholar
• Yanagisawa K, Sakakibara Y, Suiko M, Takami Y, Nakayama T, Nakajima H, Takayanagi K, Natori Y, Liu MC. 1998. cDNA cloning, expression, and characterization of the human bifunctional ATP sulfurylase/adenosine 5’-phosphosulfate kinase enzyme. Biosci. Biotech. Biochem. 62(5):1037–1040.
   PubMed Web of Science ®Google Scholar
• Zeng X, Su W, Bai Y, Chen T, Yan Z, Wang J, Su M, Zheng Y, Peng W, Yao H. 2017. Urinary metabolite profiling of flavonoids in Chinese volunteers after consumption of orange juice by UFLC-Q-TOF-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 1061-1062:79–88.
   PubMed Web of Science ®Google Scholar