Withanolides of the Aerial Part of Datura stramonium Growing in Uzbekistan and Cytotoxicity of Daturametelin H

Abstract

The extract obtained from the aerial part of Datura stramonium by treatment with EtOH (90%) was fractionated with various organic solvents. Use of extraction naphtha produced 0.28% (in percentage of the raw material mass) of the extracted substances; CHCl₃, 2.24%; EtOAc, 1.19%; and n-BuOH, 12.43%. Six withanolides such as daturalactone (I), (22R)-7b,27-hydroxy-1-oxowitha-2,5,24-trienolide (II), daturataturin A (III), withastramonolide (IV), (22R)-27-hydroxy-7b-methoxy-1-oxovita-3,5,24-trienolide (V), and daturametelin H (VI) were isolated from the aerial parts of D. stramonium collected in the Fergana Region of Uzbekistan. Their structures were elucidated on the basis of vast data of IR, UV, and NMR spectroscopic studies. The presence of compounds II, III, and V in the aerial parts of D. stramonium growing in Uzbekistan was proven, while compound VI was isolated for the first time from aerial parts of D. stramonium. The cytotoxicity of chemically pure daturametelin H was studied on cancer cell lines such as cervical epithelial carcinoma HeLa, mammary adenocarcinoma HBL-100 (ATCC NTV 124), adenocarcinoma of the larynx HEp-2 (ATCC:CCL-23), and T-lymphoblastic leukemia CCRF-CEM (ATCC:CCL-19). Daturametelin H was found to exhibit pronounced cytotoxicity at a concentration of 100 mM only against T-lymphoblastic leukemia cells in vitro.