New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta.
Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.
Chaturvedula
V S Prakash
VS
Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061-0212, USA.
Zhou
Bing-Nan
BN
Gao
Zhijie
Z
Thomas
Shannon J
SJ
Hecht
Sidney M
SM
Kingston
David G I
DG
D019951:DNA Polymerase beta / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008190:Lyases / Q000037:antagonists & inhibitors; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts; D036624:Solidago / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D010936:Plant Extracts; D014315:Triterpenes; D019951:DNA Polymerase beta; D008190:Lyases