Terpenoid- and Phenyl Propanoid-Glycosides Isolated from Leaves of Hiba (Thujopsis dolabrata SEIB. et ZUCC.).

Abstract

Three terpenoid glycosides and seven phenyl propanoid glycosides were isolated from the leaves of Hiba (Thujopsis dolabrata SEIB. et ZUCC., Asunaro), and their structures were determined based on UV, MS, 1H-NMR and 13C-NMR spectroscopic data. The structures were vomifoliol 9-O-β-D-glucopyranoside (1), (6R, 7E, 9R) -9-hydroxymegastigma-4, 7-dien-3-one-9-O-β-D- glucopyranoside (2), (2E, 6R) -2, 6-dimethyl-2, 7-octadien-6-ol-1-O-β-D-glucopyranoside (3), coniferin (4), 2, 3-dihydro-2- (4'-α-L- rhamnopyranosyl-3-methoxyphenyl) -3-hydroxymethyl-7-methoxy-5-benzofuran propanol (5), 2, 3- dihydro-2- (4' -β-D-glucopyranosyl-3' -methoxyphenyl) -3-hydoxymethyl-7-methoxy-5-benzofuran propanol (6), 2, 3-dihydro-2- (4' -β-D-glucopyranosyl-3' -methoxyphenyl) -3-hydoxymethyl-7-hydroxy-5-benzofuran propanol (7), 2, 3-dihydro-2- (4' -hydroxy-3' -methoxyphenyl) -3-hydroxymethyl-7-methoxy-5- 3-O-α-rhamnopyranosylpropan benzofuran (8), 2, 3-dihydro-2- (4' -hydroxy -3' -methoxyphenyl) -3- hydroxymethyl-7-hydroxy-5- (3-O-α-rhamnopyranosylpropan) benzofuran (9), and 1- (4-hydroxy-3-methoxyphenyl) -2- {2-hydroxy-4- (3-O-α-rhamnopyranosylpropan) phenoxy} propan-1, 3-diol (10). Compounds 1 and 3 were found to have no effect on the germination of lettuce. Compounds 110 were detected in the leaves of Hiba for the first time in this study.