New Bioactive Lupane Triterpene Coumaroyl Esters Isolated from Buxus cochinchinensis

• Published in: Planta medica Vol. 81; no. 12-13; p. 1133
• Main Authors: Pan, Li, Muñoz Acuña, Ulyana, Chai, Heebyung, Park, Hyun-Young, Ninh, Tran Ngoc, Thanh, Bui Van, Merino, Emilio F, Cassera, Maria B, Rakotondraibe, L Harinantenaina, Carcache de Blanco, Esperanza J, Soejarto, Djaja D, Kinghorn, A Douglas
• Format: Journal Article
• Language: English
• Published: Germany 01.08.2015
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Buxus - chemistry; Esters - chemistry; Esters - isolation & purification; Esters - pharmacology; HT29 Cells; Humans; Inhibitory Concentration 50; Molecular Structure; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Plasmodium falciparum - drug effects; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; Vietnam; Vietnam
• ISSN: 1439-0221
• DOI: 10.1055/s-0035-1546118

Five new lupane triterpene coumaroyl esters (1-5), together with betulin (6) and a known Buxus alkaloid, N-3-benzoyldihydrocyclomicrophylline F (7), were isolated from a CHCl3-soluble partition of a methanol extract of Buxus cochinchinensis Pierre ex Gagnep. (Buxaceae) collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29). The structures of the new compounds (1-5) were determined on the basis of spectroscopic data interpretation. In addition to their cytotoxicity against HT-29 cells and nuclear factor-kappa B (p65) inhibitory activity in an enzyme-linked immunosorbent assay, all isolates as well as two semisynthetic compounds derived from betulin and 5, respectively, were also evaluated for their in vitro antiplasmodial activities against the drug-resistant Dd2 strain of Plasmodium falciparum and antifungal effects on the growth of the pathogenic yeast Candida albicans. The new lupane triterpene coumaroyl esters (1-5), along with a betulin derivative and the known Buxus alkaloid, were found to show significant in vitro antimalarial activities, with IC50 values ranging from 0.26 to 2.07 µM.