Structure-activity relationship of triterpenoids isolated from Mitragyna stipulosa on cytotoxicity.
Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid 3-O-beta-D-glucopyranoside (3, quinovin glycoside C), quinovic acid 3-O-[(2-O-sulfo)-beta-D-quinovopyranoside] (4, zygophyloside D) and quinovic acid 3-O-beta-D-quinovopyranosyl-27-O-beta-D-glucopyranosyl ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.
Tapondjou
Leon Azefack
LA
Department of Chemistry, Faculty of Science, University of Dschang, Cameroon.
Lontsi
David
D
Sondengam
Beiham Luc
BL
Choudhary
Muhammad Iqbal
MI
Park
Hee-Juhn
HJ
Choi
Jongwon
J
Lee
Kyung-Tae
KT
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004396:Coloring Agents; D004354:Drug Screening Assays, Antitumor; D007723:Korea; D009682:Magnetic Resonance Spectroscopy; D032065:Mitragyna / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013778:Tetrazolium Salts; D013844:Thiazoles; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D004396:Coloring Agents; D010936:Plant Extracts; D013778:Tetrazolium Salts; D013844:Thiazoles; D014315:Triterpenes; C022616:thiazolyl blue