Analysis of Metabolites of Anthraquinones by Human Fecal Bacteria Using UPLC-Q-TOF-HRMS/MS
2016
Fan, Min | Peng, Chongsheng | Peng, Ying | Zhang, Min | Li, Xiaobo
This study aimed to investigate the metabolism of anthraquinones, including chrysophanol (1), rhein (2), aloe-emodin (3), emodin (4), sennoside A (5) and sennoside B (6), by mixed human fecal bacteria to clarify the relationship between their chemical structural characteristics and intestinal metabolism. Six parent compounds were incubated with mixed human fecal bacteria in vitro to study the metabolic process. A highly sensitive and specific ultra-performance liquid chromatography-quadrupole time-of-flight high-resolution tandem mass spectrometry (UPLC-Q-TOF-HRMS/MS) with MSᴱ technology and MetaboLynx software has been developed to analyze the metabolites of anthraquinones. With this method, a total of ten metabolites were identified, including 1,4,8-trihydroxy-3-hydroxymethylanthraquinone (M1), 2-methylrhein (M2), 7-methylrhein (M3), methyl-esterificated rhein (M4), 1,8-dihydroxy-3-hydroxymethyl-4-methylanthraquinone (M5), physcion (M6), sennidin A (M7), rhein (M8), sennidin B (M9) and rhein (M10), six (M1–M6) of which were first detected on the basis of the exact mass by mixed human fecal bacteria in this work. The metabolism of anthraquinones occurred via hydroxylation, oxidation, methylation, deglycosylation and esterification. In particular, the methyl-esterificated rhein (M4) was first identified as one of the metabolites of rhein, whose metabolic pathway (esterification) is also reported for the first time. The presence of human fecal bacteria played a vital role in the metabolism of anthraquinones and the substitutional groups determined the different metabolic reactions for anthraquinones, which will be useful for the investigation of the study of anthraquinones in vivo.
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