Biologically active triterpenoid saponins from Acanthopanax senticosus.
Three new triterpenoid saponins, acanthopanaxosides A (1), B (7), and C (13), were isolated from the leaves of Acanthopanax senticosus, together with 12 known saponins. The structures of these new saponins were established as 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-30-nor-olean-12,20(29)-dien-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-6-O-acetyl-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (7), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-3beta-hydroxyolean-12-ene-28,29-dioic acid (13), on the basis of spectroscopic analysis and chemical degradation. Among the known compounds, sessiloside and tauroside H1 are reported for the first time from A. senticosus. The biological activity of compounds 1-15 was examined against pancreatic lipase. Ciwujianoside C1 (6), tauroside H1 (11), 3-O-alpha-rhamnopyranosyl-(1-->2)-alpha-arabinopyranosyl mesembryanthemoidigenic acid (12), acanthopanaxoside C (13), sessiloside (14), and chiisanoside (15) inhibited pancreatic lipase activity in vitro. In turn, ciwujianosides C2 (3), D2 (5), C4 (8), and C3 (10) and hederasaponin B (9) enhanced this enzyme.
Jiang
Wenhong
W
Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.
Li
Wei
W
Han
Likun
L
Liu
Lijuan
L
Zhang
Qingbo
Q
Zhang
Shujie
S
Nikaido
Tamotsu
T
Koike
Kazuo
K
D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D028001:Eleutherococcus / Q000737:chemistry*; D008049:Lipase / Q000187:drug effects*; D015394:Molecular Structure; D010179:Pancreas / Q000201:enzymology; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D004365:Drugs, Chinese Herbal; D012503:Saponins; D014315:Triterpenes; C516614:acanthopanaxoside A; C516616:acanthopanaxoside B; C516617:acanthopanaxoside C; D008049:Lipase