Four new minor taxanes from cell cultures of Taxus chinensis.

ABSTRACT

Four new minor taxanes (1-4) have been isolated from Ts-19 cell cultures of Taxus chinensis together with five known taxanes (5-9) by silica gel chromatography combined with semi-preparative HPLC chromatography. On the basis of the analyses of the chemical and spectroscopic (IR, MS, 1D, and 2D NMR) data, the structures of new compounds were elucidated as 5alpha-hydroxy-2alpha,10beta-diacetoxy-14beta-(3-hydroxy-2-methyl-butyryl)oxytaxa-4(20),11-diene (1), 2alpha,5alpha,10beta-triacetoxy-14beta-(2-hydroxy-propionyl)oxytaxa-4(20),11-diene (2), 2alpha,5alpha,10beta-triacetoxy-14beta-(2-hydroxy-3-methyl-butyryl)oxytaxa-4(20),11-diene (3), and 2alpha-benzoxy-4alpha,9alpha,10beta,13alpha-tetraacetoxytax-11-ene (4), respectively. Compounds 1-5 were pharmacologically evaluated for their cytotoxicities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) and their reversing activity towards multi-drug resistance A549/taxol tumor cell line, and the results showed that all of the tested compounds exhibited very low cytotoxicities, while compound 4 possessed twice the reversing activity as that of verapamil at 10 muM.