Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium.
A newly isolated rod-shaped, gram-negative anaerobic bacterium from human feces, named Julong 732, was found to be capable of metabolizing the isoflavone dihydrodaidzein to S-equol under anaerobic conditions. The metabolite, equol, was identified by using electron impact ionization mass spectrometry, (1)H and (13)C nuclear magnetic resonance spectroscopy, and UV spectral analyses. However, strain Julong 732 was not able to produce equol from daidzein, and tetrahydrodaidzein and dehydroequol, which are most likely intermediates in the anaerobic metabolism of dihydrodaidzein, were not detected in bacterial culture medium containing dihydrodaidzein. Chiral stationary-phase high-performance liquid chromatography eluted only one metabolite, S-equol, which was produced from a bacterial culture containing a racemic mixture of dihydrodaidzein. Strain Julong 732 did not show racemase activity to transform R-equol to S-equol and vice versa. Its full 16S rRNA gene sequence (1,429 bp) had 92.8% similarity to that of Eggerthella hongkongenis HKU10. This is the first report of a single bacterium capable of converting a racemic mixture of dihydrodaidzein to enantiomeric pure S-equol.
Wang
Xiu-Ling
XL
School of Agricultural Biotechnology, Seoul National University, Seoul, Korea.
Hur
Hor-Gil
HG
Lee
Je Hyeon
JH
Kim
Ki Tae
KT
Kim
Su-Il
SI
D004275:DNA, Ribosomal / Q000032:analysis; D060754:Equol; D020459:Genes, rRNA; D006089:Gram-Negative Anaerobic Bacteria / Q000302:isolation & purification / Q000378:metabolism*; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D007529:Isoflavones / Q000096:biosynthesis* / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D017422:Sequence Analysis, DNA; D013237:Stereoisomerism
C007610:4',7-dihydroxy-3,4-dihydroisoflavone; D004275:DNA, Ribosomal; D007529:Isoflavones; D012336:RNA, Ribosomal, 16S; D060754:Equol; C004742:daidzein