• 대한화학회지
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• 제58권6호
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• pp.569-574
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• 2014

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-${\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

• Journal of Microbiology and Biotechnology
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• 제14권4호
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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.