title: Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria.
abstract: During the course of experiments on the transformation of lignans to phytoestrogenic substances, such as enterodiol (END) and enterolactone (ENL), a previously isolated bacterium, Eubacterium (E.) sp. strain SDG-2, capable of phenolic p-dehydroxylation in the biotransformation of secoisolariciresinol diglucoside to END and ENL, was concluded to be Eggerthella (Eg.) lenta (Eg. sp. SDG-2) on the basis of 16S rRNA gene sequence analysis. The bacterium could transform (+)-dihydroxyenterodiol (DHEND, 3a) to (+)-END (1a), but not for (-)-DHEND (3b) to (-)-END (1b) under anaerobic conditions. By incubation of a mixture of (+)- and (-)-dihydroxyenterolactone (DHENL, 4a and 4b) with Eg. sp. SDG-2, only (-)-DHENL (4b) was converted to (-)-ENL (2b), selectively. On the other hand, we isolated a different bacterium, strain ARC-1, capable of dehydroxylating (-)-DHEND (3b) to (-)-END (1b) from human feces. Strain ARC-1 could transform not only (-)-DHEND (3b) to (-)-END (1b), but also (+)-DHENL (4a) to (+)-ENL (2b). However, the bacterium could not transform (+)-DHEND (3a) and (-)-DHENL (4b). Both bacterial strains demonstrated different enantioselective dehydroxylation.
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama, Japan.
authors.forename: Jong-Sik
authors.initials: JS
authors.lastname: Jin
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Zhao
authors.forename: Norio
authors.initials: N
authors.lastname: Nakamura
authors.forename: Teruaki
authors.initials: T
authors.lastname: Akao
authors.forename: Nobuko
authors.initials: N
authors.lastname: Kakiuchi
authors.forename: Byung-Sun
authors.initials: BS
authors.lastname: Min
authors.forename: Masao
authors.initials: M
authors.lastname: Hattori
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D001421:Bacteria, Anaerobic / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D002072:Butylene Glycols / Q000737:chemistry / Q000378:metabolism; D005051:Eubacterium / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D005243:Feces / Q000382:microbiology; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006900:Hydroxylation; D007422:Intestines / Q000382:microbiology*; D017705:Lignans / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D010802:Phylogeny; D012329:RNA, Bacterial / Q000235:genetics; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D013237:Stereoisomerism
chemical_list: D002072:Butylene Glycols; D005960:Glucosides; D017705:Lignans; D012329:RNA, Bacterial; D012336:RNA, Ribosomal, 16S; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C090142:secoisolariciresinol diglucoside; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone