Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines.

Abstract

Fractionation of an ethyl acetate-soluble extract of the stem bark of Dichapetalum gelonioides, collected in the Philippines, using the LNCaP (hormone-dependent human prostate) cell line as a monitor, led to the purification of three dichapetalin-type triterpenoids [dichapetalins A (1), I (2), and J (3)], along with two dolabrane norditerpenoids (6, 7), and the additional triterpenoids zeylanol (8), 28-hydroxyzeylanol (9), and betulinic acid. Since compounds 1-3 exhibited promising selectivity against the SW626 (human ovarian cancer) cell line, a re-collection of the plant material was carried out, to obtain more of these compounds for additional biological testing. Two further phenylpyranotriterpenoids [dichapetalins K (4) and L (5)] were isolated from the re-collected plant material. The structures of the new compounds 2-5 and 9 were determined on the basis of spectroscopic data interpretation, and the relative configuration of 6 was confirmed using X-ray crystallography. Compounds 4-6 and the methyl ester, 6a, exhibited broad cytotoxic activity when tested against a panel of human tumor cell lines. Dichapetalin A (1) was not active when evaluated in an in vivo hollow fiber assay in the dose range 1-6 mg/kg.

Cite this paper

@article{Fang2006CytotoxicCF, title={Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines.}, author={Liqiong Fang and Aiko Ito and Hee-byung Chai and Qiuwen Mi and William P. Jones and Domingo R Madulid and Mildred B Oliveros and Qi Gao and Jimmy Orjala and N. R. Farnsworth and Djaja Djendoel Soejarto and Geoffrey A. Cordell and Steven M. Swanson and John M . Pezzuto and A Douglas Kinghorn}, journal={Journal of natural products}, year={2006}, volume={69 3}, pages={332-7} }