Activity-guided isolation of cytotoxic constituents from the bark of Aglaia crassinervia collected in Indonesia.
Activity-guided fractionation of a CHCl(3)-soluble partition of the MeOH extract of the bark of Aglaia crassinervia collected in Indonesia led to the isolation of three new glabretal-type triterpenoids, aglaiaglabretols A-C (1-3), as well as nine known compounds, 3-epi-cabraleahydroxylactone (4), cabraleahydroxylactone (5), rocaglaol (6), 2beta,3beta-dihydroxy-5alpha-pregn-17(20)-(E)-16-one, scopoletin, and mixtures of cabraleadiol and epicotillol and of beta-sitosterol and stigmasterol. The structures of compounds 1-3 were determined on the basis of spectroscopic and chemical methods. The structure of aglaiaglabretol A (1) was confirmed by single-crystal X-ray analysis, and the absolute stereochemistry of this isolate was established by the Mosher ester method. The cytotoxic activity of all isolates and several chemical transformation products obtained in the present study was evaluated. The known cyclopenta[b]benzofuran, rocaglaol (6), was found to be significantly active and comparable in potency to the positive controls, paclitaxel and camptothecin. Aglaiaglabretol B (2) was further tested in an in vivo hollow fiber model.
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 60612, USA.
Chai
Heebyung
H
Mi
Qiuwen
Q
Riswan
Soedarsono
S
Kardono
Leonardus B S
LB
Afriastini
Johar J
JJ
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Farnsworth
Norman R
NR
Cordell
Geoffrey A
GA
Swanson
Steven M
SM
Kinghorn
A Douglas
AD
D031602:Aglaia / Q000737:chemistry*; D000818:Animals; D002478:Cells, Cultured; D006801:Humans; D007214:Indonesia; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D010936:Plant Extracts / Q000302:isolation & purification* / Q000633:toxicity*; D013237:Stereoisomerism
D010936:Plant Extracts