Dereplication of pentacyclic triterpenoids in plants by GC-EI/MS

• Published in: Phytochemical analysis Vol. 17; no. 2; pp. 102 - 106
• Main Authors: Gu, J.Q, Wang, Y, Franzblau, S.G, Montenegro, G, Timmermann, B.N
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.03.2006
• Subjects: anti-tubercular activity; antibacterial properties; antimicrobial agents; Antitubercular Agents - chemistry; Asteraceae; Betulinic Acid; chemical constituents of plants; chemical structure; Chromatography, Gas; cultured cells; cytotoxicity; dereplication; esters; gas chromatography; GC-EI/MS; isomers; Lamiaceae; Lavandula; Lavandula - chemistry; Lavandula dentata; mass spectrometry; methylation; Molecular Structure; Mycobacterium tuberculosis; oleanolic acid; Oleanolic Acid - chemistry; Pentacyclic Triterpenes; pentacyclic triterpenoids; phytochemicals; plant extracts; Spectrometry, Mass, Electrospray Ionization; structure-activity relationships; Tanacetum parthenium; Tanacetum parthenium - chemistry; Triterpenes - chemistry; triterpenoids; tuberculosis; Ursolic Acid; Valerian - chemistry; Valeriana; Valeriana laxiflora; Valerianaceae; Chile
• ISSN: 0958-0344; 1099-1565
• DOI: 10.1002/pca.892

Three common plant-derived pentacyclic triterpenoids, oleanolic acid (1), betulinic acid (2) and ursolic acid (3), have been found to exhibit moderate anti-tubercular activity in a microplate alamar blue assay. In order to facilitate the discovery of novel anti-tubercular leads with diverse chemical structures, a new and rapid GC-EI/MS method was developed simultaneously and unambiguously to dereplicate 1-3 as their methyl esters with limits of detection of 25.6, 26.9 and 26.8 ng, respectively.