Microsomal cytochrome p450-mediated metabolism of protopanaxatriol ginsenosides: metabolite profile, reaction phenotyping, and structure-metabolism relationship

Drug Metabolism and Disposition : the Biological Fate of Chemicals
Hai-Ping HaoGuangji Wang

Abstract

Although the biotransformation of ginsenosides in the gastrointestinal tract has been extensively studied, much less is known about hepatic cytochrome P450 (P450)-catalyzed metabolism. The major aims of this study were to clarify the metabolic pathway and P450 isoforms involved and to explore the structure-metabolism relationship of protopanaxatriol (PPT)-type ginsenosides in hepatic microsomes. Efficient depletion of ginsenoside Rh1, Rg2, Rf, and PPT was found, whereas the elimination of Re and Rg1, characterized by a glucose substitution at the C20 hydroxy group, was negligible in microsomal incubation systems. Based on high-performance liquid chromatography hybrid ion trap and time-of-flight mass spectrometry analysis, the oxygenation metabolism on the C20 aliphatic branch chain was identified as the predominant metabolic pathway of PPT ginsenosides in both human and rat hepatic microsomes. By a comparison with authentic standards, the C24-25 double bond was identified as one of the oxygenation sites to produce the metabolites of C20-24 epoxide (ocotillol-type ginsenosides). Both chemical inhibition and human recombinant P450 isoform assays indicated that CYP3A4 was the predominant isozyme responsible for the oxygenation met...Continue Reading

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Citations

Feb 22, 2014·Journal of Agricultural and Food Chemistry·Jing-Rong WangZhi-Hong Jiang
Feb 4, 2014·The Journal of Steroid Biochemistry and Molecular Biology·Subrata DebEmma S Tomlinson Guns
Jan 27, 2016·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Jing-Rong WangZhi-Hong Jiang
Nov 1, 2011·Journal of Ginseng Research·Si-Kwan Kim, Jeong Hill Park
Mar 13, 2014·Biomedical Chromatography : BMC·Xiaoying WangTianxiu Qian
Nov 29, 2014·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Wenyan WangQingguo Meng
Apr 6, 2017·Journal of Zhejiang University. Science. B·Huan-Huan PangJian-Mei Huang
May 20, 2015·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Jun ZhangHaiping Hao
Jul 16, 2011·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Zhen YangMing Hu
May 12, 2018·Biomedical Chromatography : BMC·Lei ZhangXiang-Lin Zhang
Feb 21, 2018·Phytochemical Analysis : PCA·Wei WuShuying Liu
Sep 28, 2013·Molecular Cancer Research : MCR·Jacob J JuncoThomas J Slaga
Mar 5, 2015·Journal of Agricultural and Food Chemistry·Jing-Rong WangZhi-Hong Jiang

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