An Efficient and Scalable Method for the Isolation of Costatolide, A Naturally-Occurring Anti-HIV Agent, from the Latex of Calophyllum teysmannii var. inophylloide

Abstract

An efficient and scalable method is reported for the isolation of costatolide (2), a naturally-occurring and HIV-1-specific non-nucleoside reverse transcriptase inhibitor, from the latex of Calophyllum teysmannii Miq. var. inophylloide (King.) P. F. Stevens (Clusiaceae). An overall yield of 10.6% of costatolide (2), with a purity of 96%, was obtained by repetitive recrystallization of the latex from a single organic solvent, subsequent to the pre-treatment of latex with hexane and dichloromethane to remove undesirable oily material. A second major component of the latex, soulattrolide (3), another HIV-1 non-nucleoside reverse transcriptase inhibitor, was also isolated. Both compounds were characterized by spectroscopic and chromatographic analyses and their in vitro anti-HIV activities were also confirmed. The results suggest that sufficient quantities of costatolide for preclinical and clinical development can be obtained in a relatively low-cost manner from the natural source.