Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana.
One new and eight known ceanothane- and lupane-type triterpenes were isolated from the root bark of Ziziphus cambodiana PIERRE (Rhamnaceae). Based on spectral analyses, the structure of the new compound was elucidated as 3-O-(4-hydroxy-3-methoxybenzoyl)ceanothic acid (3-O-vanillylceanothic acid) (1), while the known compounds were identified as lupeol (2), betulinaldehyde (3), betulinic acid (4), 2-O-E-p-coumaroyl alphitolic acid (5), alphitolic acid (6), zizyberanalic acid (7), zizyberenalic acid (8) and ceanothic acid (9). Compounds 1, 5 and 8 exhibited significant in vitro antiplasmodial activity against the parasite Plasmodium falciparum, with inhibitory concentration (IC50) values of 3.7, 0.9 and 3.0 microg/ml, respectively. Compounds 1 and 3-8 showed antimycobacterial activity against Mycobacterium tuberculosis with respective MIC values of 25, 25, 25, 12.5, 50, 50 and 100 microg/ml.
Suksamrarn
Sunit
S
Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, Thailand. sunit@swu.ac.th
Panseeta
Panomwan
P
Kunchanawatta
Soykam
S
Distaporn
Thanomsin
T
Ruktasing
Saovaluk
S
Suksamrarn
Apichart
A
D000818:Animals; D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology; D000962:Antimalarials / Q000302:isolation & purification / Q000494:pharmacology; D031952:Ceanothus / Q000737:chemistry; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D018517:Plant Roots / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D031957:Ziziphus / Q000737:chemistry*; D053978:Pentacyclic Triterpenes
D000900:Anti-Bacterial Agents; D000962:Antimalarials; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes