TY - JOUR
T1 - New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase β
AU - Chaturvedula, V. S.Prakash
AU - Zhou, Bing Nan
AU - Gao, Zhijie
AU - Thomas, Shannon J.
AU - Hecht, Sidney M.
AU - Kingston, David G.I.
N1 - Funding Information:
This work was supported by a National Cooperative Drug Discovery Group grant awarded to the University of Virginia by the National Cancer Institute (U19 CA 50771, Dr. Sidney M. Hecht, Principal Investigator); this support is gratefully acknowledged. The extract of S. canadensis was provided by the NCI under a collaborative agreement, and we thank Drs. David Newman and Gordon Cragg for arranging this collaboration. We also thank Mr. William Bebout and Mr. Tom Glass, Virginia Polytechnic Institute and State University, for obtaining the mass spectrometry and NMR spectroscopy data, respectively.
PY - 2004/12/1
Y1 - 2004/12/1
N2 - 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 β, 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, α-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3β-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3β-(3- ketohexadecanoyloxy)-lup-20(29)-ene (2), 3β-(3R-acetoxyhexadecanoyloxy)-29- nor-lupan-20-one (3), and 3β-(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 β.
AB - 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 β, 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, α-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3β-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3β-(3- ketohexadecanoyloxy)-lup-20(29)-ene (2), 3β-(3R-acetoxyhexadecanoyloxy)-29- nor-lupan-20-one (3), and 3β-(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 β.
KW - Bioassay
KW - DNA
KW - Solidago
KW - Triterpenoid
UR - http://www.scopus.com/inward/record.url?scp=7444231485&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=7444231485&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2004.08.048
DO - 10.1016/j.bmc.2004.08.048
M3 - Article
C2 - 15519169
AN - SCOPUS:7444231485
SN - 0968-0896
VL - 12
SP - 6271
EP - 6275
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 23
ER -