Chaturvedula V S Prakash, Zhou Bing-Nan, Gao Zhijie, Thomas Shannon J, Hecht Sidney M, Kingston David G I
Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061-0212, USA.
Bioorg Med Chem. 2004 Dec 1;12(23):6271-5. doi: 10.1016/j.bmc.2004.08.048.
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.
以检测DNA聚合酶β裂解酶活性的分析方法，对加拿大一枝黄花（菊科）的甲乙酮提取物进行生物测定导向的分级分离，从中分离出4种新的羽扇烷三萜类化合物1 - 4以及7种已知化合物羽扇豆醇、羽扇豆醇乙酸酯、熊果酸、环阿屯醇、环阿屯醇棕榈酸酯、α-香树脂醇乙酸酯和豆甾醇。通过广泛的一维和二维核磁共振光谱解析及化学修饰研究，确定新化合物的结构分别为3β-(3R-乙酰氧基十六烷酰氧基)-羽扇-20(29)-烯（1）、3β-(3-氧代十六烷酰氧基)-羽扇-20(29)-烯（2）、3β-(3R-乙酰氧基十六烷酰氧基)-29-降羽扇-20-酮（3）和3β-(3-己酰氧基)-29-降羽扇-20-酮（4）。所有11种化合物均对DNA聚合酶β的裂解酶活性有抑制作用。
