Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids.
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 H(37)Ra 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.
Tanachatchairatana
Tanud
T
Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkapi, Bangkok, Thailand.
Bremner
John Barnard
JB
Chokchaisiri
Ratchanaporn
R
Suksamrarn
Apichart
A
D000107:Acetylation; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002934:Cinnamates / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D053978:Pentacyclic Triterpenes; D016339:Spectrometry, Mass, Fast Atom Bombardment; D017550:Spectroscopy, Fourier Transform Infrared; D014315:Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000094062:Betulinic Acid; D000097245:Ursolic Acid
D000995:Antitubercular Agents; D002934:Cinnamates; D007202:Indicators and Reagents; D009828:Oleanolic Acid; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid; D000097245:Ursolic Acid