Isolation and identification of metabolites from dihydromyricetin

✍ Scribed by Yansong Zhang; Sheng Que; Xiuwei Yang; Bin Wang; Liang Qiao; Yuying Zhao

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 262 KB
• Volume: 45
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.2051

✦ Synopsis

Abstract

Dihydromyricetin (DHM) is the major bioactive constituent of Rattan Tea, which is the tender stems and leaves of Ampelopsis grossendentata. Seven metabolites (2–8) of DHM (1) were obtained by the chromatographic method. The metabolites 2–5 were obtained from the urine of rats administered orally with DHM; and metabolites 6–8 were detected in the fecal specimens of rats, which were also produced by human intestinal bacteria (HIB) in vitro, and were separated from the cultured media of HIB containing DHM. Their structures were elucidated as 5,7,3′,5′‐tetrahydroxyflavanonol (2); 5,7,3′,5′‐tetrahydroxy‐4′‐methoxyflavanonol (3); 5,7,4′,5′‐tetrahydroxy‐3′‐methoxyflavanonol (4); and dihydromyricetin‐O‐5‐β‐D‐glucuronide (5); (2__R__,3__S__)‐5,7,3′,4′,5′‐pentahydroxyflavanonol (6); 3,4,5,7,3′,4′,5′‐hepthydroxyflavan (7) and 5,7,3′,4′,5′‐pentahydroxyflavanone (8) on the basis of UV, NMR and LC‐MS/MS data. These seven metabolites were formed through familiar metabolic reactions. Dihydromyricetin‐O‐5‐β‐D‐glucuronide (5) is a new compound. The ^13^C‐NMR data of (2) and (4) are reported for the first time. Copyright © 2007 John Wiley & Sons, Ltd.