Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria.
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.
Jin
Jong-Sik
JS
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama, Japan.
Zhao
Yu-Feng
YF
Nakamura
Norio
N
Akao
Teruaki
T
Kakiuchi
Nobuko
N
Min
Byung-Sun
BS
Hattori
Masao
M
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
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