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目的:合成并鉴定救必应酸酯类衍生物,并评价其体外抗肿瘤活性。方法:以救必应酸为原料,通过28位酯化、3β位和23位羟基与酸酐反应合成救必应酸酯类衍生物;采用高分辨质谱、核磁共振氢谱、核磁共振碳谱及理化性质对合成的救必应酸酯类衍生物进行结构鉴定。采用MTT法评价紫杉醇(阳性对照)、救必应酸及救必应酸酯类衍生物对人宫颈癌细胞HeLa、人恶性黑色素瘤细胞A375、人肺腺癌细胞SPC-A1、人肝癌细胞HepG2的体外抗肿瘤活性[以半数抑制浓度(IC50)为指标]。结果:共合成了6个救必应酸酯类衍生物,分别为救必应酸甲酯(化合物1)、3,23-O-双(乙酰基)救必应酸甲酯(化合物2)、3,23-O-双(丙酰基)救必应酸甲酯(化合物3)、3,23-O-双(丁酰基)救必应酸甲酯(化合物4)、3,23-O-双(邻苯二甲酰基)救必应酸甲酯(化合物5)及3,23-O-双(丁二酰基)救必应酸甲酯(化合物6)。与紫杉醇比较,化合物5和化合物6对HeLa、A375、HepG2、SPC-A1细胞的抗肿瘤活性与其相似,差异无统计学意义(P>0.05),救必应酸及其他化合物的IC50显著减小(P<0.05)。结论:本研究合成了6个救必应酸酯类衍生物,其中化合物5、6具有显著的体外抗肿瘤活性,可为后续研究提供参考。
OBJECTIVE: To synthesize and identify rotundic acid esters derivatives, and to evaluate in vitro antitumor activity. METHODS: Using rotundic acid as raw material, rotundic acid esters derivatives were synthesized by 28-esterification, 3β and 23-position hydroxyl group combined with acid anhydride. The structure of rotundic acid esters derivatives were identified by HRMS, 1H-NMR, 13C-NMR and physicochemical properties. The in vitro antitumor activities were evaluated by MTT assay against paclitaxel (positive control), rotundic acid and rotundic acid esters derivatives with human cervical cancer cells HeLa, human malignant melanoma cells A375, human lung adenocarcinoma cells SPC-A1 and human liver cancer cells HepG2 (take IC50 as an indicator). RESULTS: Totally 6 kinds of rotundic acid esters derivatives were synthesized, i.e. rotundic acid methyl ester(compound 1), 3, 23-O-di(acetyl) rotundic acid methyl ester(compound 2), 3, 23-O-di(propionyl) rotundic acid methyl ester(compound 3), 3, 23-O-di(butyryl) rotundic acid methyl ester(compound 4), 3, 23-O-di(phthaloyl) rotundic acid methyl ester(compound 5) and 3, 23-O-di(succinyl) rotundic acid methyl ester(compound 6). Compared with paclitaxel, the antitumor activity of compound 5 and compound 6 to Hela, A375, HepG2 and SPC-A1 was similar to it, and there was no significant difference between them (P>0.05); the IC50 of rotuntic acid and other compounds decreased with statistical significance (P<0.05). CONCLUSIONS: In the study, 6 kinds of rotundic acid esters derivatives are synthesized and compound 5 and compound 6 have significant antitumor activity in vitro, which can provide reference for further study.
救必应酸衍生物合成鉴定抗肿瘤活性
Rotundic acidDerivativesSynthesisIdentificationAntitumor activity
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