[关键词]
[摘要]
目的 研究大蕉Musa × paradisiaca叶化学成分以及体外细胞增殖抑制活性。方法 采用硅胶、MCI gel CHP-20P、反相ODS和Sephadex LH-20柱色谱以及半制备型高效液相等色谱方法进行分离和纯化,通过核磁共振、质谱等技术手段鉴定了化合物的结构。利用CCK-8法评价了所有化合物体外细胞增殖抑制活性。结果 从大蕉叶提取物中分离得到19个化合物,分别鉴定为邻苯二甲酸二(2-乙基)己酯(1)、肉豆蔻酸(2)、正十五酸(3)、亚油酸(4)、邻苯二甲酸二丁酯(5)、4-羟基-3-甲氧基苯甲酸乙酯(6)、二氢猕猴桃内酯(7)、MF-EA-705β(8)、邻苯二甲酸丁基酯2-乙基己基酯(9)、三十四碳-(20,23)-二烯酸(10)、3-羟基豆甾-5,22-二烯-7-酮(11)、3-羟基豆甾-5-烯-7-酮(12)、luffarin X(13)、6-羟基豆甾-4,22-二烯-3-酮(14)、6-羟基豆甾-4-烯-3-酮(15)、(3S,5R,6S,7E)-5,6-环氧-3-羟基-7-巨豆烯-9-酮(16)、对羟基苯甲酸乙酯(17)、对二乙氧基苯(18)、(9Z,12Z,15Z)-十八烷基-9,12,15-三烯酸甲酯(19)。化合物2、5、7、11、13、15和17分别对人肝癌HepG2细胞、人宫颈癌Hela细胞、人乳腺癌MCF-7细胞和人皮肤恶性黑色素瘤A375细胞增殖表现出一定的抑制活性,半数抑制浓度(median inhibition concentration,IC50)值为40.26~97.75μmol/L,其中化合物7和11对A375细胞增殖有选择性抑制活性(IC50值分别为43.0、50.0 μmol/L),略低于阳性对照顺铂(IC50值40.13 μmol/L),而化合物2和15对MCF-7细胞增殖选择性抑制活性(IC50值分别为40.26、45.00 μmol/L)强于阳性对照(IC50值为48.36 μmol/L)。结论 化合物1、6~19为首次从该属植物中分离得到;化合物2~5为首次在该植物中分离得到。活性测试表明,化合物2、7、11和15对特定肿瘤细胞株表现出选择性增殖抑制活性。
[Key word]
[Abstract]
Objective To investigate the chemical constituents from the leaves of Musa × paradisiaca and their inhibitory activities on cell proliferation in vitro. Methods The compounds were isolated and purified using various chromatographic techniques, including silica gel, MCI gel CHP-20P, reversed-phase ODS, Sephadex LH-20 column chromatographies, and semi-preparative HPLC. Their structures were elucidated by spectroscopic methods such as NMR and MS. The inhibitory activities of all compounds on cell proliferation in vitro were evaluated using the CCK-8 assay. Results A total of 19 compounds were isolated from the leaves of Musa × paradisiaca and identified as di(2-ethylhexyl) phthalate (1 ), myristic acid (2 ), pentadecanoic acid (3 ), linoleic acid (4 ), dibutyl phthalate (5 ), ethyl 4-hydroxy-3-methoxybenzoate (6 ), dihydroactinidolide (7 ), MF-EA-705β (8 ), butyl 2-ethylhexyl phthalate (9 ), n-tetratriacont-20,23-dienoic acid (10 ), 3-hydroxystigmasta-5,22-dien-7-one (11 ), 3-hydroxystigmast-5-en-7-one (12 ), luffarin X (13 ), 6-hydroxystigmasta-4,22-dien-3-one (14 ), 6-hydroxystigmast-4-en-3-one(15 ), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (16 ), ethyl p-hydroxybenzoate (17 ), p-diethoxybenzene (18 ), and methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate (19 ). Among them, compounds2 , 5 ,7 ,11 ,13 ,15 , and17 exhibited certain anti-proliferative activities against human hepatocellular carcinoma HepG2, cervical cancer Hela, breast cancer MCF-7, and malignant melanoma A375 cell lines, with median inhibition concentration (IC50) values ranging from 40.26 to 97.75 μmol/L. Specifically, compounds7 and11 showed selective inhibitory activity against A375 cells (IC50 = 43.0 and 50.0 μmol/L, respectively), which was slightly weaker than that of the positive control cisplatin (IC50 = 40.13 μmol/L). In contrast, compounds2 and15 demonstrated stronger inhibitory effects against MCF-7 cells (IC50 = 40.26 and 45.00 μmol/L, respectively) compared to cisplatin (IC50 = 48.36 μmol/L). Conclusion Compounds1 and6 —19 were isolated from this genus for the first time, while compounds2 —5 were first identified from this specific plant. Furthermore, compounds2 ,7 ,11 , and15 exhibited selective inhibitory activities against specific tumor cell lines .
[中图分类号]
R284.1
[基金项目]
广东省普通高校重点领域专项(2022ZDZX2035)