Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids

Authors

Tanud Tanachatchairatana, Ramkhamhaeng University
John B. Bremner, University of WollongongFollow
Ratchanaporn Chokchaisiri, Ramkhamhaeng University
Apichart Suksamrarn, Ramkhamhaeng University

RIS ID

26499

Publication Details

Tanachatchairatana, T., Bremner, J. B., Chokchaisiri, R. & Suksamrarn, A. (2008). Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. Chemical and Pharmaceutical Bulletin, 56 (2), 194-198.

Abstract

Betulinic acid, oleanolic acid and ursolic acid have been modified at the C-3 position to cinnamate-based esters and in vitro antimycobacterial activity against Mycobacterium tuberculosis H₃₇Ra has been determined. The results indicated that modification of the parent structures of betulinic acid, oleanolic acid and ursolic acid to the p-coumarate and, in the case of the latter two triterpenes, the ferulate ester analogues resulted in high antimycobacterial activity. Structure–activity relationships within the lupane, oleanane and ursane analogues and between these triterpenes are discussed.