The C-Glucosyl Bond of Puerarin Was Cleaved Hydrolytically by a Human Intestinal Bacterium Strain PUE to Yield Its Aglycone Daidzein and an Intact Glucose
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概要
- 論文の詳細を見る
C-Glycosides are usually resistant against acidic hydrolysis and enzymatic treatments because C-1 of the sugar moiety is directly attached to the aglycone by C–C bonding. Nevertheless, a human intestinal bacterium, strain PUE, can cleave the C-glucosyl bond of puerarin to yield its aglycone daidzein. To clarify the mechanism of the cleaving reaction, we tried to identify the structure of the metabolite derived from the sugar moiety of puerarin. To detect it easily, deuterium labeled puerarin, [6″,6″-D2]puerarin, was prepared in 7 steps. Sugars contained in a metabolite mixture from [6″,6″-D2]puerarin was analyzed by an HPLC-electrospray ionization (ESI)-MS method after treatment of sugars with 1-phenyl-3-methyl-5-pyrazolone (PMP). Since deuterium labeled glucose was detected in the metabolite mixture of [6″,6″-D2]puerarin, we concluded that puerarin was metabolized to daidzein and an intact glucose by strain PUE. As C-1 of the sugar was hydroxylated instead of hydrogenating, C-glucosyl bond-cleaving reaction is not reduction but hydrolysis. This is the first report of revealing the reaction manner and the exact products of C-glucosyl bond-cleaving reaction.
著者
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MA Chao-Mei
Institute of Natural Medicine, University of Toyama
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HATTORI Masao
Institute of Natural Medicine, University of Toyama
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Nakamura Kenichi
Institute of Natural Medicine, University of Toyama
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Nishihata Tomohiro
Institute of Natural Medicine, University of Toyama
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Jin Jong-Sik
Institute of Natural Medicine, University of Toyama
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Komatsu Katsuko
Institute of Natural Medicine, University of Toyama
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Iwashima Makoto
Faculty of Pharmaceutical Sciences, Suzuka University of Medical Science
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Ma Chao-mei
Institute Of Natural Medicine University Of Toyama
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Komatsu Katsuko
Institute Of Natural Medical Toyama Medicine And Pharmaceutical University
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Nishinaka T
Osaka Univ. Pharmaceutical Sci. Osaka Jpn
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Jin Jong-sik
Institute Of Natural Medicine University Of Toyama
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Nishihara T
Department Of Oral Microbiology Kyushu Dental College
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Hattori Masao
Institute Of Natural Medicine Faculty Of Pharmaceutical Sciences
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Nishihata Tomohiro
Institute Of Natural Medicine University Of Toyama
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