[The structure and absolute configuration of isorupestonic acid from Artemisia rupestris L].
A new sesquiterpene compound named isorupestonic acid was isolated from Artemisia rupestris and its absolute stereostructure was elucidated as 3B by spectral and X-ray crystallographic methods. Interestingly, the isorupestonic acid is based upon an unusual 6, 7 membered ring skeleton differing from the 5, 7 membered ring rupestonic acid although both have the same absolute configuration at C-1. The biogenesis of isorupestonic acid most likely involves breaking the C4-C5 bond of rupestonic skeleton and forming the C5-C14 bond. The absolute configuration of rupestonic acid was also determined as 4C by X-ray analysis and CD data.
Xu
G S
GS
Xinjiang Institute of Materia Medica, Urumuqi.
Zhao
W
W
Wu
D
D
Yu
D Q
DQ
He
C H
CH
Yang
J J
JJ
Sun
F
F
D052176:Azulenes; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification
D052176:Azulenes; D004365:Drugs, Chinese Herbal; D012717:Sesquiterpenes; C057488:rupestonic acid; C073949:isorupestonic acid