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

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

doi:10.1271/bbb.57.107

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

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

Authors

K Nishiyama¹, S Esaki¹, I Deguchi¹, N Sugiyama¹, S Kamiya¹

Affiliation

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.