Five New Triterpenoid Saponins from the Rhizomes of Panacis majoris and Their Antiplatelet Aggregation Activity.
Five new triterpenoid saponins (1-5) and four known triterpenoid saponins, ginsenoside Re5(6), majonoside R1(7), 24(R)-majonoside R1(8), and ginsenoside Rf (9), were isolated from the rhizomes ofPanacis majoris. The structures of new compounds were elucidated as (20S,24S,25R*)-6-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-dammar-20,24-epoxy-3β,6α,12β,25,26-pentaol (1), (20S,24R,25R)-6-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-dammar-20,24-epoxy-3β,6α,12β,25,26-pentaol (2), (20S)-6-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-dammar-20,25-epoxy-3β,6α,12β,24α-tetraol (3), 6-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-dammar-3β,6α,12β,20S,24R,25-hexaol (4), and 6-O-[β-D-glucop-yranosyl-(1 → 2)-β-D-glucopyranosyl]-dammar-25(26)-ene-3β,6α,12β,20S,24R-pentaol (5) on the basis of extensive spectral analysis and chemical methods. Ginsenoside Re5was isolated from the plant for the first time. The similarities of the nine compounds lie in the fact that their aglycones are conjoined with the same glucopyranose moieties, the same linkage of the glycosyl chains, and the same glycosylation sites, while they have a varied C-17 side chain. Compounds3and5exhibited moderate antiplatelet aggregation activities induced by adenosine diphosphate with IC50values of 23.24 and 18.43 µM, respectively. Compound5displayed moderate inhibition of arachidonic acid-induced platelet aggregation with an IC50value of 30.11 µM.
College of Chemistry, Jilin University, Changchun, P. R. China.
Min
M
Li
College of Basic Medical Sciences, Jilin University, Changchun, P. R. China.
Fen
F
Liu
College of Chemistry, Jilin University, Changchun, P. R. China.
Yong-Ri
YR
Jin
College of Chemistry, Jilin University, Changchun, P. R. China.
Xiao-Zhong
XZ
Wang
College of Chemistry, Jilin University, Changchun, P. R. China.
Qian
Q
Wu
College of Chemistry, Jilin University, Changchun, P. R. China.
Ying
Y
Liu
College of Chemistry, Jilin University, Changchun, P. R. China.
Xu-Wen
XW
Li
D016718:Arachidonic Acid / Q000037:antagonists & inhibitors; D027481:Araliaceae / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification; D036145:Ginsenosides / Q000737:chemistry; D006868:Hydrolysis; D020128:Inhibitory Concentration 50; D005894:Panax / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal; D010975:Platelet Aggregation Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D027343:Rhizome / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D004365:Drugs, Chinese Herbal; D036145:Ginsenosides; D010936:Plant Extracts; D010975:Platelet Aggregation Inhibitors; D012503:Saponins; D014315:Triterpenes; D016718:Arachidonic Acid; C055328:ginsenoside Rf