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Biosci Biotechnol Biochem. 1993 Jan;57(1):107-14. doi: 10.1271/bbb.57.107.

Syntheses of Isoflavones and Isoflavone Glycosides, and Their Inhibitory Activity against Bovine Liver β-Galactosidase.

Bioscience, biotechnology, and biochemistry

K Nishiyama, S Esaki, I Deguchi, N Sugiyama, S Kamiya

Affiliations

  1. a Laboratory of Organic and Food Chemistry, School of Food and Nutritional Sciences, University of Shizuoka , Shizuoka 422 , Japan.

PMID: 27316881 DOI: 10.1271/bbb.57.107

Abstract

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.

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