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    张小丽, 吕坤, 方桂珍, 田水清, 孔维. 3--羰基--桦木酰--甘氨酸的合成与活性分析[J]. 北京林业大学学报, 2011, 33(1): 134-138.
    引用本文: 张小丽, 吕坤, 方桂珍, 田水清, 孔维. 3--羰基--桦木酰--甘氨酸的合成与活性分析[J]. 北京林业大学学报, 2011, 33(1): 134-138.
    shu
    ZHANG Xiao-Li, L Kun, FANG Gui-zhen, TIAN Shui-qing, KONG Wei. Synthesis and activity analysis of N-［3-oxo-20(29)-lupen-28-oyl］-glycine[J]. Journal of Beijing Forestry University, 2011, 33(1): 134-138.
    Citation: ZHANG Xiao-Li, L Kun, FANG Gui-zhen, TIAN Shui-qing, KONG Wei. Synthesis and activity analysis of N-［3-oxo-20(29)-lupen-28-oyl］-glycine[J]. Journal of Beijing Forestry University, 2011, 33(1): 134-138.
    shu

    3--羰基--桦木酰--甘氨酸的合成与活性分析

    Synthesis and activity analysis of N-［3-oxo-20(29)-lupen-28-oyl］-glycine

      摘要
    • 摘要: 为了增强桦木酮酸的生物活性，以桦木酮酸为原料，草酰氯为酰化剂，合成桦木酮酸酰氯，再与甘氨酸甲酯盐酸盐合成3--羰基--桦木酰--甘氨酸甲酯，水解得到3--羰基--桦木酰--甘氨酸。采用红外、核磁和质谱对产物进行化学结构分析，并用四唑盐比色试验（MTT）法对人源肺腺癌细胞(A549)、人源鼻癌细胞(CNE)、人源舌鳞癌细胞(Tca8113)细胞株的细胞毒活性进行分析。结果表明：试验合成了3--羰基--桦木酰--甘氨酸，高效液相色谱检测合成产物纯度为97.8%;3--羰基--桦木酰--甘氨酸的半抑制浓度IC50值与桦木酸的半抑制浓度IC50值相比明显降低；对Tca8113细胞，3--羰基--桦木酰--甘氨酸的IC50值约为桦木酸IC50值的1/11；对CNE细胞，3--羰基--桦木酰--甘氨酸的IC50值约为桦木酸IC50值的1/53。由此说明3--羰基--桦木酰--甘氨酸在抑制肿瘤细胞生长的活性方面明显优于桦木酸。

       

      Abstract: In order to enhance the biological activity of betulonic acid, 3-oxo-20(29)-lupen-28-oic acid chloride was synthesized with betulonic acid as raw materials and oxalyl chloride as the acylating agent. Methyl ester of  N-［3-oxo-20(29)-lupen-28-oyl］-glycine was synthesized by 3-oxo-20(29)-lupen-28-oic acid chloride and methyl ester of glycine hydrochloride. N-［3-oxo-20(29)-lupen-28-oyl］-glycine was obtained by hydrolyzing methyl ester of N-［3-oxo-20(29)-lupen-28-oyl］-glycine. The structure of the product was identified by FT-IR, 1HNMR and MS spectra. Cytotoxic activity of the target product against human lung adenocarcinoma (A549), human nose carcinoma cells (CNE) and human tongue carcinoma (Tca8113) cell lines was evaluated by MTT assay via the respective IC50. The result improved the structure of N-［3-oxo-20(29)-lupen-28-oyl］-glycine. HPLC results showed that the purity of synthetic product was 97.801%. IC50 of N-［3-oxo-20(29)-lupen-28-oyl］-glycine displayed lower values than that of betulinic acid. As regards to Tca8113 cells, N-［3-oxo-20(29)-lupen-28-oyl］-glycine showed stronger activity than betulinic acid with an IC50 ratio of about 1∶11. As regards to CNE cells, N-［3-oxo-20(29)-lupen-28-oyl］-glycine showed stronger activity than betulinic acid with an IC50 ratio of about 1∶53. The bioactive assay indicates that N-［3-oxo-20(29)-lupen-28-oyl］-glycine shows stronger activity than betulinic acid in resistance to tumor development.

       

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