Syntheses of Isoflavones and Isoflavone Glycosides, and Their Inhibitory Activity against Bovine Liver β-Galactosidase.
To clarify the relationship between the structure and inhibitory action toward β-D-galactosidase (EC 3.2.1.21) of isoflavones and isoflavone glycosides, a number of polyhydroxyisoflavones, and the α-L-rhamnosides and β-L-quinovosides of daidzein and genistein were synthesized. Among the polyhydroxyisoflavones, 2',3',4',7-tetrahydroxyisoflavone showed the strongest inhibitory activity (Ki = 26 × 10(-6) M). Among the glycosides, all the L-rhamnosides were strong inhibitors, of which genistein 4',7-di-O-α-L-rhamnoside was the strongest (Ki = 4.44 × 10(-6) M), while all the isoflavone β-L-quinovosides were considerably weak or possessed no inhibition.
a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.
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Nishiyama
a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.
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Esaki
a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.
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Deguchi
a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.
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Sugiyama
a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.
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Kamiya