• Title/Summary/Keyword: 2-HPPA

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C-Ring Cleavage of Isoflavones Daidzein and Genistein by a Newly-Isolated Human Intestinal Bacterium Eubacterium ramulus Julong 601

  • Wang, Xiu-Ling;Kim, Ki-Tae;Lee, Je-Hyeon;Hur, Hor-Gil;Kim, Su-Il
    • Journal of Microbiology and Biotechnology
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    • v.14 no.4
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    • pp.766-771
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    • 2004

  • Julong 601, a Gram-positive anaerobic bacterium strain capable of cleaving the C-ring of isoflavones daidzein and genistein, was isolated from human feces. BLAST search revealed that its complete 16S rDNA gene sequence has 99% similarity to Eubacterium ramulus. Metabolites of daidzein and genistein were determined as O-desmethylangolensin (O-Dma) and 2-(4-hydroxyphenyl) propionic acid (2-HPPA), respectively, based on UV, EI-MS, and $^1H$ and ^{13}C$ NMR spectral analyses. Enantiomers of O-Dma and 2-HPPA were isolated by chiral stationary-phase HPLC (CSP HPLC). Cleavage of the C-ring of daidzein and genistein by strain Julong 601 was highly enantioselective. Specific rotation ([$\alpha]_D$) and circular dichroism (CD) spectra of the enantiomers are reported here for the first time. Biotransformation kinetics of daidzein and genistein indicated that the C-ring of genistein has a higher susceptibility to bacterial degradation than that of daidzein.

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