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Applied and Environmental Microbiology, January 2005, p. 214-219, Vol. 71, No. 1
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.1.214-219.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Enantioselective Synthesis of S-Equol from Dihydrodaidzein by a Newly Isolated Anaerobic Human Intestinal Bacterium

Xiu-Ling Wang,1,2 Hor-Gil Hur,3* Je Hyeon Lee,4 Ki Tae Kim,4 and Su-Il Kim1

School of Agricultural Biotechnology, Seoul National University, Seoul,1 Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju,3 Research and Development Center, Takara Korea Biomedical Inc., Gyeonggi-Do, Korea,4 College of Life Science, Agricultural University of Hebei, Baoding, China2

Received 20 May 2004/ Accepted 16 August 2004

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, 1H and 13C 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.

* Corresponding author. Mailing address: Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju 500-712, Korea. Phone: 82-62-970-2437. Fax: 82-62-970-2434. E-mail: hghur{at}gist.ac.kr.

Applied and Environmental Microbiology, January 2005, p. 214-219, Vol. 71, No. 1
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.1.214-219.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



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