Cimicifugadine from Cimicifuga foetida, a new class of triterpene alklaoids with novel reactivity.
[structure: see text] An unprecedented triterpene alkaloid glycoside, designated cimicifugadine (1), with a pyridine ring incorporated to a cycloartane triterpenoid nucleus, was isolated from the roots of Cimicifuga foetida. Its structure was established on the basis of extensive spectroscopic measurements and chemical transformation with the absolute configuration at C-24 determined to be S by a modified Mosher method. It demonstrated a novel reactivity in mild acidic media whereby the cyclopropane ring is opened followed by the formation of two isomeric conjugated trienes.
Dan
Chun
C
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.
Zhou
Yan
Y
Ye
Deng
D
Peng
Shulin
S
Ding
Lisheng
L
Gross
Michael L
ML
Qiu
Samuel X
SX
D000107:Acetylation; D000143:Acids / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry* / Q000145:classification*; D031885:Cimicifuga / Q000737:chemistry* / Q000378:metabolism; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D014315:Triterpenes / Q000737:chemistry*
D000143:Acids; D000470:Alkaloids; D014315:Triterpenes; C520153:cimicifugadine