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New eremophilenolides from Cacalia pilgeriana
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China.
Abstract:
Five new eremophilenolides and a known sesquiterpene were isolated from the methanol extract of the roots of Cacalia pilgeriana. Their structures were identified as 1 beta-hydroxy-2 beta-methyl-senecioyloxyeremophil-7(11)-en-8 beta(12)-olide (1), 1 beta-hydroxy-2 beta-methylsenecioyloxy-8 alpha-methoxyeremophil-7(11)-en- 8 beta(12)-olide, 2 beta-hydroxy-3 beta-methylsenecioyloxyeremophil-7(11)-en-8 alpha(12)-olide ( 3), 2 beta,8 beta-dihydroxy-3 beta-methylsenecioyloxyeremophil-7(11)-en-8 alpha(12)-olide and 1 beta,8 beta-dihydroxy-2 beta,3 alpha-diangeloyloxyeremophil-7(11)-en-8 alpha(12)-olide ( 5) and caryolane-1,9 beta-diol by spectroscopic methods including 2D-NMR techniques ( (1)H- (1)H COSY, HMQC, HMBC) and HR-ESI-MS. The structure and relative stereochemistry of compound 1 were unequivocally established by X-ray diffraction analysis. Bioassays showed compounds 3 and 5 to possess strong cytotoxic activity in vitro against human leukemia cells (HL-60) (IC (50) < 15 microg mL (-1)). The structure-activity relationship is discussed.
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