Constituents of a fern, Diplazium subsinuatum. II. Structure elucidation of five new hopane-triterpene glycosides.
From whole fern, Diplazium subsinuatum (Wall. ex Hook. et Grev.) Tagawa, two new hopane-triterpene glycosides named diplaziosides III and IV were isolated, together with three new hopane glycosides with acetylated sugars. The structures of diplaziosides III and IV were established as (22S)-24-O-alpha-L-arabinofuranosyl-(1 --> 2)- [beta-D-glucopyranosyl-(1 --> 6)]-beta-D-glucopyranosyl-20 alpha-O-beta-D-glucopyranosyl-30-hydroxyhopan-28-oic acid (1) and (22R)-24-O-alpha-L-arabinofuranosyl-(1-->2)-[beta-D-glucopyranosyl-(1--> 6)]-beta-D-glucopyranosyl-30-carboxy-17-hydroxy-hopano-28,22-lacto ne (2), respectively, on the basis of spectral evidence. Diplazioside III (1) is novel not only in its glycoside structure, but also in its triterpene structure and moreover, 1 provides the first instance of a naturally occurring bisdesmoside with a hopane aglycone. The structures (3a, 3b, and 4a) of the acetylated glycosides were also elucidated, and this is the first report of naturally occurring acetates of hopane glycosides.
Nakanishi
T
T
Faculty of Pharmaceutical Sciences, Setsunan University, Osaka, Japan.
Inatomi
Y
Y
Nishi
M
M
Murata
H
H
Inada
A
A
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000302:isolation & purification*; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D008516:Medicine, Chinese Traditional; D008969:Molecular Sequence Data; D010946:Plants, Medicinal / Q000737:chemistry*
D006027:Glycosides