Metabolism of Paeoniflorin and Related Compounds by Human Intestinal Bacteria. II. Structures of 7S-and 7R-Paeonimetabolines I and II Formed by Bacteroides fragilis and Lactobacillus brevis

YUE-ZHONG SHU; MASAO HATTORI; TERUAKI AKAO; KYOICHI KOBASHI; KATSUMI KAGEI; KEIICHI FUKUYAMA; TOMITAKE TSUKIHARA; TSUNEO NAMBA

doi:10.1248/cpb.35.3726

Metabolism of Paeoniflorin and Related Compounds by Human Intestinal Bacteria. II. Structures of 7S-and 7R-Paeonimetabolines I and II Formed by Bacteroides fragilis and Lactobacillus brevis

YUE-ZHONG SHU, MASAO HATTORI, TERUAKI AKAO, KYOICHI KOBASHI, KATSUMI KAGEI, KEIICHI FUKUYAMA, TOMITAKE TSUKIHARA, TSUNEO NAMBA

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Keywords: Bacteroides fragilis, biotransformation, 5-hydroxy-3, 6-dimethyl-2, 3-dihydrobenzofuran, intestinal bacteria, Lactobacillus brevis, Paeonia albiflora, paeoniflorin, paeonimetaboline I, paeonimetaboline II, X-ray analysis

JOURNAL FREE ACCESS

1987 Volume 35 Issue 9 Pages 3726-3733

DOI https://doi.org/10.1248/cpb.35.3726

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Abstract

Paeoniflorin from peony roots was incubated with a cell suspension of Bacteroides fragilis or Lactobacillus brevis isolated from human intestinal flora. Paeoniflorin was converted into the 7S and 7R isomers of paeonimetaboline I as major metabolites, along with the 7R and 7S isomers of paeonimetaboline II as minor metabolites in the case of the former strain. The structures were elucidated by various spectroscopic methods, and the structure of 7R-paeonimetaboline I was confirmed by X-ray analysis.

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