title: Stereochemical determination of O-desmethylangolensin produced from daidzein.
abstract: We had isolated an O-desmethylangolensin (O-DMA)-producing bacterium, Clostridium rRNA cluster XIVa strain SY8519. According to chiral separation using HPLC, the SY8519-produced O-DMA exhibited high optical purity. To determine the absolute stereochemistry of O-DMA, we prepared 2-(4-hydroxyphenyl)propionic acid (2-HPPA) from the O-DMA using the Baeyer-Villiger reaction. From chiral analysis of the product, the major peak had the same stereochemistry to that of 2-HPPA produced from genistein by the same bacteria. As we have determined the stereochemistry of SY8519-produced 2-HPPA to have an R configuration, by the chemical synthesis of (S)-2-HPPA, the SY8519-produced O-DMA must also possess R stereochemistry at the 2-position. To study the stereoselective metabolism, we applied racemic dihydrodaidzein to SY8519. The O-DMA was isolated from the culture media and starting material was also recovered. The O-DMA produced was optically active in a similar manner to that produced from daidzein. However, the remaining dihydrodaidzein exhibited no difference between the enantiomers. These results suggested that SY8519 produces (R)-O-DMA from both enantiomers of dihydrodaidzein.
authors.affiliation: Department of Human Health and Nutrition, Shokei Gakuin University, 4-10-1, Yurigaoka, Natori, Miyagi 981-1295, Japan. Electronic address: nbononaka@hotmail.co.jp.
authors.forename: Toshio
authors.initials: T
authors.lastname: Niwa
authors.affiliation: Department of Food Technology, Industrial Technology Center, Gifu Prefectural Government, 47 Kitaoyobi, Kasamatsu-cho, Hashima-gun, Gifu 501-6064, Japan.
authors.forename: Shin-ichiro
authors.initials: S
authors.lastname: Yokoyama
authors.affiliation: Department of Human Health and Nutrition, Shokei Gakuin University, 4-10-1, Yurigaoka, Natori, Miyagi 981-1295, Japan.
authors.forename: Natsuki
authors.initials: N
authors.lastname: Matsugasaki
authors.affiliation: Department of Human Health and Nutrition, Shokei Gakuin University, 4-10-1, Yurigaoka, Natori, Miyagi 981-1295, Japan.
authors.forename: Eri
authors.initials: E
authors.lastname: Inomata
authors.affiliation: Department of Human Health and Nutrition, Shokei Gakuin University, 4-10-1, Yurigaoka, Natori, Miyagi 981-1295, Japan.
authors.forename: Asako
authors.initials: A
authors.lastname: Taira
authors.affiliation: Department of Health and Nutrition, Faculty of Psychological & Physical Science, Aichi Gakuin University, 12, Araike, Iwasaki-cho, Nisshin, Aichi 470-0195, Japan.
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Osawa
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003013:Clostridium / Q000378:metabolism*; D003470:Culture Media / Q000737:chemistry; D005260:Female; D005419:Flavonoids / Q000737:chemistry; D019833:Genistein / Q000737:chemistry; D006801:Humans; D007529:Isoflavones / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry; D012335:RNA, Ribosomal / Q000378:metabolism; D013025:Glycine max / Q000737:chemistry; D013237:Stereoisomerism; D016482:Urinalysis; D055815:Young Adult
chemical_list: C000603635:2-(4-hydroxyphenyl)propionic acid; D003470:Culture Media; D005419:Flavonoids; D007529:Isoflavones; D011422:Propionates; D012335:RNA, Ribosomal; C433163:dihydrodaidzein; C004742:daidzein; D019833:Genistein; C029658:propionic acid; C050052:O-desmethylangolensin
keywords: Human; Metabolism; O-Desmethylangolensin; Soy isoflavonoids