Pregnane glycosides and steroid saponins from Smilax bockii Warb. and their NGF-potentiating activity.
The chemical constituents of the roots of Smilax bockii Warb. were investigated and two pregnane glycosides and three steroid saponins were isolated. Their structures were established as 3beta-hydroxypregna-5,16-dien-20-one-3-O-alpha-L-rhamnopyranosyl(1 --> 4)-alpha-L-rhamnopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-glucopyranoside (1), 3beta-hydroxypregna-5,16-dien-20-one-3-O-alpha-L-rhamnopyranosyl(1 --> 2)-[alpha-L-rhamnopyranosyl(1 --> 4)]-beta-D-glucopyranoside (2), dioscin (3), methyl protodioscin (4), 26-O-beta-D-glucopyranosyl-22alpha-methoxyl-(25R)-furost-5-en-3beta, 26-diol 3-O-alpha-L-rhamnopyranosyl(1 --> 4)-alpha-L-rhamnopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-glucopyranoside (5) on the basis of spectral analysis and chemical methods. Compound 1 is a new natural product and compounds 2, 5 were first isolated from the genus Smilax. Compound 5 showed enhancing activity of nerve growth factor (NGF)-induced neurite outgrowth in PC 12D cells.
Xu
Jing
J
Department of Pharmaceutical Sciences, Nankai University, Tianjin 300071, P.R. China.
Li
Xian
X
Zhao
Chun Chao
CC
Wang
Yi
Y
D000818:Animals; D004357:Drug Synergism; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D020932:Nerve Growth Factor / Q000494:pharmacology*; D016501:Neurites / Q000187:drug effects / Q000502:physiology; D016716:PC12 Cells; D018517:Plant Roots / Q000737:chemistry; D011278:Pregnanes / Q000737:chemistry* / Q000494:pharmacology; D051381:Rats; D012503:Saponins / Q000737:chemistry / Q000494:pharmacology; D032281:Smilax / Q000737:chemistry*
C534118:3beta-hydroxypregna-5,16-dien-20-one-3-O-alpha-L-rhamnopyranosyl(1 -4)-alpha-L-rhamnopyranosyl(1-4)-(alpha-L-rhamnopyranosyl(1- 2))-beta-D-glucopyranoside; D006027:Glycosides; D011278:Pregnanes; D012503:Saponins; D020932:Nerve Growth Factor