A new ursane triterpene from Monochaetum vulcanicum that inhibits DNA polymerase beta lyase.
Bioassay-directed fractionation of a butanone extract of Monochaetum vulcanicum resulted in the isolation of a new triterpene (1) and four known compounds, ursolic acid (2), 2alpha-hydroxyursolic acid (3), 3-(p-coumaroyl)ursolic acid (4), and beta-sitosteryl-beta-d-galactoside (5). The structure of the new compound 1 was established as 3beta-acetoxy-2alpha-hydroxyurs-12-en-28-oic acid on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. Compounds 1-3 and 5 exhibited polymerase beta lyase activity.
Chaturvedula
V S Prakash
VS
Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061-0212, USA.
Gao
Zhijie
Z
Jones
Shannon H
SH
Feng
Xizhi
X
Hecht
Sidney M
SM
Kingston
David G I
DG
D000107:Acetylation; D003364:Costa Rica; D019951:DNA Polymerase beta / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008190:Lyases / Q000037:antagonists & inhibitors*; D035322:Melastomataceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000097245:Ursolic Acid
D019951:DNA Polymerase beta; D004791:Enzyme Inhibitors; D008190:Lyases; D014315:Triterpenes; D000097245:Ursolic Acid; C487192:3beta-acetoxy-2alpha-hydroxyurs-12-ene-28-oic acid