Yaoshanenolides A and B: new spirolactones from the bark of Machilus yaoshansis.
Two novel tricyclic spirolactones bearing long linear alkyl chains, yaoshanenolides A (1) and B (2), formed by Diels-Alder[4 + 2] cycloaddition of a molecule of each butenolide with β-phellandrene, were isolated from the bark of Machilus yaoshansis. Their structures and absolute configurations were determined by extensive spectroscopic methods, especially 2D NMR and ECD data analysis. The proposed biosynthetic pathway is discussed. Both compounds exhibited nonselective cytotoxic activities against several human cancer cell lines.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Mingtao
M
Liu
Sheng
S
Lin
Maoluo
M
Gan
Minghua
M
Chen
Li
L
Li
Sujuan
S
Wang
Jiachen
J
Zi
Xiaona
X
Fan
Ying
Y
Liu
Yikang
Y
Si
Yongchun
Y
Yang
Xiaoguang
X
Chen
Jiangong
J
Shi
D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D019770:Lauraceae / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
C572033:yaoshanenolide A; C572034:yaoshanenolide B; D013148:Spironolactone