新型桦木醇和桦木酸与共轭亚油酸（CLA）酯的合成及其细胞毒性活性
Synthesis and cytotoxic activity of new betulin and betulinic acid esters with conjugated linoleic acid (CLA).
作者信息
Tubek Barbara, Mituła Paweł, Niezgoda Natalia, Kempińska Katarzyna, Wietrzyk Joanna, Wawrzeńczyk Czesław
机构信息
Department of Chemistry, Faculty of Food Sciences, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
出版信息
Nat Prod Commun. 2013 Apr;8(4):435-8.
The synthesis of new ester derivatives of betulin (3a-c) and betulinic acid (4) with conjugated linoleic acid isomers (CLA; in a mixture of 43.4% 9c, 11t; 49.5% 10t, 12c; 7.1% other isomers) is presented. Esterification was carried out with N,N'-dicyclohexylcarbodiimide (DCC) as the coupling agent in the presence of 4-dimethylamino-pyridine (DMAP) in dichloromethane (or pyridine). The in vitro cytotoxic effect of betulin (1), betulinic acid (2), a mixture of CLA isomers and their derivatives (3a-c, 4) was examined using the MTT assay against four cancer cell lines (P388, CEM/C2, CCRF/CEM and HL-60) and the SRB assay on the HT-29 cell line. Ester 4 was the most active among the esters synthesized against the CEM/C2 cell line with an ID50 value 16.9 +/- 6.5 microg/mL. Betulin (1), betulinic acid (2) and CLA were the most active agents against the cancer cell lines studied.
本文介绍了桦木醇（3a - c）和桦木酸（4）与共轭亚油酸异构体（CLA；其中9c，11t异构体占43.4%；10t，12c异构体占49.5%；其他异构体占7.1%）的新型酯衍生物的合成。在二氯甲烷（或吡啶）中，以N，N'-二环己基碳二亚胺（DCC）作为偶联剂，4 - 二甲氨基吡啶（DMAP）存在下进行酯化反应。使用MTT法检测桦木醇（1）、桦木酸（2）、CLA异构体混合物及其衍生物（3a - c，4）对四种癌细胞系（P388、CEM/C2、CCRF/CEM和HL - 60）的体外细胞毒性作用，并使用SRB法检测对HT - 29细胞系的作用。在合成的酯中，酯4对CEM/C2细胞系活性最高，ID50值为16.9±6.5μg/mL。桦木醇（1）、桦木酸（2）和CLA是对所研究癌细胞系活性最高的药物。
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