Antimycobacterial Activity of Cinnamate-Based Esters of the Triterpenes Betulinic, Oleanolic and Ursolic Acids

• Published in: Chemical & Pharmaceutical Bulletin Vol. 56; no. 2; pp. 194 - 198
• Main Authors: Tanachatchairatana, Tanud, Bremner, John Barnard, Chokchaisiri, Ratchanaporn, Suksamrarn, Apichart
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.02.2008; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Acetylation; antimycobacterial activity; Antitubercular Agents - chemical synthesis; Antitubercular Agents - pharmacology; Betulinic Acid; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Cinnamates - chemical synthesis; Cinnamates - pharmacology; Indicators and Reagents; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Methylation; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; oleanolic acid; Oleanolic Acid - analogs & derivatives; Oleanolic Acid - chemical synthesis; Oleanolic Acid - pharmacology; Pentacyclic Triterpenes; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Spectrometry, Mass, Fast Atom Bombardment; Spectroscopy, Fourier Transform Infrared; structure–activity relationship; triterpene ester; Triterpenes - chemical synthesis; Triterpenes - pharmacology; Ursolic Acid; MYCOBACTERIUM-TUBERCULOSIS; antimycobacterial activity; oleanolic acid; GROWTH; AGENTS; betulinic acid; structure-activity relationship; DERIVATIVES; triterpene ester; ursolic acid
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.56.194

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.