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3-羰基-桦木酰-甘氨酸的合成与活性分析 被引量：1

Synthesis and activity analysis of N-[3-oxo-20(29)-lupen-28-oyl]-glycine
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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。 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 ceils, 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 ceils, 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-oy1] -glycine shows stronger activity than betulinic acid in resistance to tumor development.
作者 张小丽 吕坤 方桂珍 田水清 孔维
机构地区 东北林业大学材料科学与工程学院 吉林大学生命科学学院
出处 《北京林业大学学报》 CAS CSCD 北大核心 2011年第1期134-138,共5页 Journal of Beijing Forestry University
基金 黑龙江省重大攻关项目(GB05B601)
关键词 桦木酮酸 3-羰基-桦木酰-甘氨酸 肿瘤细胞 生物活性 betulonic acid N- [ 3 -oxo-20 （ 29 ） -lupen-28-oyl ] -glycine tumor cells biological activity
分类号 TQ351 [化学工程]
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参考文献9

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共引文献23

同被引文献15

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北京林业大学学报
2011年 第1期

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