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In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats
Wu W.; Hu N.; Zhang Q.; Li Y.; Li P.; Yan R.; Wang Y.
2014
Source PublicationChemico-Biological Interactions
Volume219Pages:18
Abstract

Anthraquinones naturally distribute in many plants including rhubarb and have widespread applications throughout industry and medicine. Recent studies provided new insights in potential applications of these traditional laxative constituents. Glucuronidation was the main metabolic pathway of rhubarb anthraquinones in vivo. This study examined the activity and regioselectivity of glucuronidation of rhubarb anthraquinones (aloe-emodin, emodin, chrysophanol, physcion, rhein) in liver and intestinal microsomes from rats and humans, by comparing with the core structure danthron. All anthraquinones formed mono-glucuronides and, except for rhein, the conjugation sites of the main metabolites were unambiguously identified. Two minor glucuronides of emodin were first reported together with the dominant emodin-3-O-β-d-glucuronide. The substitution on the anthraquinone ring was crucial to the activity and regioselectivity of glucuronidation. In general, the activity was decreased greatly with a β-COOH (rhein), while enhanced dramatically with a β-OH (emodin). Glucuronidation showed an absolute preference towards β-OH, followed by α-OH and β-alcoholic OH. The glucuronidation activity and regioselectivity also varied slightly with organs and species. All glucuronides of aloe-emodin, emodin, chrysophanol and physcion were formed by multiple human UGT isoforms with 1A9 being the most prominent in most cases. The UGT2B subfamily (2B7 and 2B15) only showed high activity towards a β-OH. In conclusion, the substitution at the anthraquinone ring was crucial to the rate and preference of glucuronidation. The high glucuronidation activity of UGT1A9 towards anthraquinones highlighted potential drug interactions. © 2014 Published by Elsevier Ireland Ltd.

KeywordAnthraquinones Glucuronidation Regioselectivity Rhubarb Ugts
DOI10.1016/j.cbi.2014.05.006
URLView the original
Indexed BySCI
Language英语
WOS Research AreaBiochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Toxicology
WOS SubjectBiochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Toxicology
WOS IDWOS:000345637600004
The Source to ArticleScopus
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Cited Times [WOS]:34   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Affiliation1.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Av. Padre Tomás Pereira, Taipa, Macau
2.School of Chinese Meteria Medica, Beijing University of Chinese Medicine, Beijing, China
Recommended Citation
GB/T 7714
Wu W.,Hu N.,Zhang Q.,et al. In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats[J]. Chemico-Biological Interactions,2014,219:18.
APA Wu W..,Hu N..,Zhang Q..,Li Y..,Li P..,...&Wang Y..(2014).In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats.Chemico-Biological Interactions,219,18.
MLA Wu W.,et al."In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats".Chemico-Biological Interactions 219(2014):18.
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