Enantioselective oxidation of enterodiol to enterolactone by human intestinal bacteria.
In the course of our experiments on the metabolic conversion of lignans to the estrogenic substances enterodiol (END) and enterolactone (ENL) by human intestinal flora, we isolated two anaerobes, Ruminococcus sp. END-1 and strain END-2, capable of oxidizing END. The former selectively converted (-)-END to (-)-ENL, while the latter selectively converted (+)-END to (+)-ENL, indicating enantioselective oxidation by intestinal bacteria.
Jin
Jong-Sik
JS
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama, Japan.
Kakiuchi
Nobuko
N
Hattori
Masao
M
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D005798:Genes, Bacterial; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D017705:Lignans / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism*; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010802:Phylogeny; D012329:RNA, Bacterial / Q000235:genetics; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D045857:Ruminococcus / Q000145:classification / Q000302:isolation & purification / Q000378:metabolism; D017423:Sequence Analysis, RNA; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013379:Substrate Specificity
D017705:Lignans; D012329:RNA, Bacterial; D012336:RNA, Ribosomal, 16S; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone