以熊果酸为原料,经C-3羟基氧化、C-28羧基苄酯化保护、C-2乙酰化及水解、还原、脱保护得到2β-羟基熊果酸,6步反应的总收率为60.1%.中间体及目标化合物结构经IR、1H NMR、13C NMR和MS测试技术确证.以噻唑蓝(MTT)比色法检测2β-羟基熊果酸对人白血病细胞K562及人肺癌细胞A549肿瘤细胞的体外抑制活性,结果表明,对2种肿瘤细胞的生长均表现出一定的抑制作用.
参考文献
[1] | Okuyama E,Yamazaki M,Ishii Y,et al.Isolation and Identification of Ursolic Acid Related Compounds as the Principles of Glechoma Hederacea Having an Anti-Ulcerogenic Activity[J].Yakugaku Zasshi,1983,37:52-55. |
[2] | Wen X A,Xia J,Cheng K G,et al.Pentacyclic Triterpenes.Part 5:Synthesis and SAR Study of Corosolic Acid Derivatives as Inhibitors of Glycogen Phosphorylases[J].Bioorg Med Chem Lett,2007,17:5777-5782. |
[3] | Ukiya M,Akihisa T,Tokuda H,et al.Constituents of Compositae Plants:Ⅲ.Anti-Tumor Promoting Effects and Cytotoxic Activity Against Human Cancer Cell Lines of Triterpene Diols and Triols from Edible Chrysanthemum Flowers[J].Cancer Lett,2002,177:7-12. |
[4] | ZHAO Yu,FENG Juhong,ZHOU Changxin,etal.A Rings and C Rings Containing Multiple Oxygen Substituents of Triterpene Oleanolic Acid and Application:CN,200710194191.X[P],2008-08-06(in Chinese).赵昱,冯菊红,周长新,等.A环和C环含多个含氧取代基的齐墩果酸三萜及用途:中国,200710194191.X[P],2008-08-06. |
[5] | Xu Y F,Ge R L,Du J,et al.Corosolicacid Induces Apoptosis Through Mitochondrial Pathway and Caspases Activation in Human Cervix Adenocarcinoma HeLa Cells[J].Cancer Lett,2009,284(2):229-237. |
[6] | Ma C M,Cai S Q,Cui J R,et al.The Cytotoxic Activity of Ursolic Acid Derivatives[J].Eur J Med Chem,2005,40:582-589. |
[7] | Sun H,Fang W S,Wang W Z,et al.Structure-activity Relationships of Oleanane-and Ursanetype Triterpenoids[J].Bot Stud,2006,47:339-368. |
[8] | Begum S,Adil Q,Siddiqui B,et al.Synthesis of 2β-Hydroxyursolic Acid and Other Ursane Analogues from Ursonic Acid[J].Aust J Chem,1993,46:1067-1071. |
[9] | Wen X A,Sun H B,Liu J,et al.Naturally Occurring Pentacyclic Triterpenes as Inhibitors of Glycogen Phosphorylase:Synthesis,Structure-Activity Relationships,and X-Ray Crystallographic Studies[J].J Med Chem,2008,51:3540-3554. |
[10] | Cheng K G,Zhang P,Liu J,et al.Practical Synthesis of Bredemolic Acid,a Natural Inhibitor of Glycogen Phosphorylase[J].J Nat Prod,2008,71:1877-1880. |
[11] | CHEN Jun,LIU Jun,GONG Yanchun,et al.Synthesis and Biological Evaluation of Ursolic Acid Derivatives as Novel Inhibitors of Glycogen Phosphorylase[J].J Chinese Pharm Univ,2006,37 (5):397-402 (in Chinese).陈军,柳军,龚彦春,等:新型糖原磷酸化酶抑制剂熊果酸衍生物的合成及其生物活性[J].中国药科大学学报,2006,37(5):397-402. |
[12] | Gnoatto S C B,Klimpt A D,Nascimento S D,et al.Evaluation of Ursolic Acid Isolated from Ilex Paraguariensis and Derivatives on Aromatase Inhibition[J].Eur J Med Chem,2008,43:1865-1877. |
[13] | LIN Fengping,SHAO Jingwei,DU Huadong,et al.Synthesis,Characterization and Anti-Tumor Activity of Ursolic Acid Derivatives[J].Chinese J Appl Chem,2010,27 (8):893-898 (in Chinese).林凤屏,邵敬伟,杜华东,等.熊果酸衍生物的合成、表征及其对癌细胞的抑制活性[J].应用化学,2010,27(8):893-898. |
[14] | Hansen M B,Nielsen S E,Berg K.Re-examination and Further Development of a Precise and Rapid Dye Method for Measuring Cell Growth/Cell Kill[J].J Imnumol Method,1989,119(2):203-210. |
[15] | Takayama H,Kitajima M,Ishizuka T,et al.Process for Producing Corosolic Acid:US,7071229B2[P],2004-7. |
[16] | Hauori M,Kuo K P,Shu Y Z,et al.A Triterpene from the Fruits of Rubus Chingii[J].Phytochemistry,1988,27(12):3975-3976. |
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