Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis.
A phytochemical study of secondary metabolites produced by Schisandra chinensis has led to the isolation of six novel highly oxygenated nortriterpenoids, wuweizidilactones A-F (1-6). Compounds 3-6 possess an unprecedented 3,4-seco-18(13-->14)-abeo-artane skeleton. Interestingly, structures 3-6 have a beta-oriented methyl group at the C-14 position. This structural feature corroborates the biogenetic pathway proposed for the formation of 18-norschiartane-type compounds 1 and 2. The structures of these novel metabolites were established on the basis of their detailed spectroscopic analysis. The structure of 1 was also confirmed by single-crystal X-ray diffraction analysis. For the first time, the absolute configuration of these nortriterpenoids was determined by using a modified Mosher method.
Huang
Sheng-Xiong
SX
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650204, Yunnan, China.
Yang
Li-Bin
LB
Xiao
Wei-Lie
WL
Lei
Chun
C
Liu
Jing-Pin
JP
Lu
Yang
Y
Weng
Zhi-Ying
ZY
Li
Li-Mei
LM
Li
Rong-Tao
RT
Yu
Jun-Lin
JL
Zheng
Qi-Tai
QT
Sun
Han-Dong
HD
D018360:Crystallography, X-Ray; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D032141:Schisandra / Q000378:metabolism*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
D007783:Lactones; D014315:Triterpenes; D010100:Oxygen