Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.
Plant lignans, such as pinoresinol diglucoside, secoisolariciresinol diglucoside and arctiin, are metabolized to mammalian lignans, enterolactone or enterodiol, by human intestinal bacteria. Their metabolic processes include deglucosylation, ring cleavage, demethylation, dehydroxylation and oxidation. Here we isolated an intestinal bacterium capable of demethylating arctigenin, an aglycone of arctiin, to 2,3-bis(3,4-dihydroxybenzyl)butyrolactone (1) from human feces, and identified as an Eubacterium species (E. sp. ARC-2), which is similar to Eubacterium limosum on the basis of morphological and biochemical properties and 16S rRNA gene sequencing. By incubating with E. sp. ARC-2, arctigenin was converted to 1 through stepwise demethylation. Demethylation of arctigenin by E. sp. ARC-2 was tetrahydrofolate- and ATP-dependent, indicating that the reaction was catalyzed by methyltransferase. Moreover, E. sp. ARC-2 transformed secoisolariciresinol to 2,3-bis(3,4-dihydroxybenzyl)-1,4-butanediol by demethylation.
Jin
Jong-Sik
JS
Institute of Natural Medicine, University of Toyama, Toyama, Japan.
Zhao
Yu-Feng
YF
Nakamura
Norio
N
Akao
Teruaki
T
Kakiuchi
Nobuko
N
Hattori
Masao
M
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D000255:Adenosine Triphosphate / Q000494:pharmacology; D001711:Biotransformation; D005051:Eubacterium / Q000145:classification / Q000187:drug effects / Q000302:isolation & purification* / Q000502:physiology*; D005243:Feces / Q000382:microbiology; D005663:Furans / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; 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; D013763:Tetrahydrofolates / Q000494:pharmacology; D013997:Time Factors
D005663:Furans; D017705:Lignans; D012329:RNA, Bacterial; D012336:RNA, Ribosomal, 16S; D013763:Tetrahydrofolates; C030371:5,6,7,8-tetrahydrofolic acid; D000255:Adenosine Triphosphate; D015107:4-Butyrolactone; C071942:arctigenin; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone