Studies on the Constituents of Zizyphi Fructus. V. Structures of Glycosides of Benzyl Alcohol, Vomifoliol and Naringenin

Abstract

New glycosides, zizybeoside I(1) and II(II), zizyvoside I(IV) and II(V), and a mixture of 6,8-di-C-glucosyl-2(S)-naringenin and 6,8-di-C-glucosyl-2(R)-naringenin (compound A), together with vomifoliol and roseoside, were isolated from the ethanol extract of Zizyphi Fructus. On the basis of spectral and chemical evidence the structures of the new glycosides were determined as benzyl β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (I), benzyl β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (II), vomifoliol 9-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (IV), vomifoliol 9-O-β-glucopyranosyl-(1→2)-β-glucopyranosyl-(1→3)]-β-glucopyranoside (V), 6,8-di-C-glucosyl-2 (S)-naringenin (VII) and 6,8-di-C-glucosyl-2(R)-naringenin (VIII). © 1981, The Pharmaceutical Society of Japan. All rights reserved.