[关键词]
[摘要]
目的 研究喙尾琵琶甲Blaps rhynchoptera的化学成分及其细胞毒活性。方法 采用硅胶、Sephadex LH-20凝胶、MCI柱色谱,以及制备高效液相色谱等技术进行化合物的分离纯化,通过理化性质及波谱学方法鉴定结构,运用MTT法评价化合物的细胞毒活性。结果 从喙尾琵琶甲虫体的95%乙醇提取物中分离得到了21个化合物,分别鉴定为 (3R)-6-羟基-3-甲基-3, 8-二乙基-2-吲哚酮(1)、blapindole I(2)、blapindole K(3)、尿嘧啶(4)、胸腺嘧啶(5)、胸腺嘧啶脱氧核苷(6)、对羟基苯甲酸(7)、对羟基苯乙酸(8)、对苯二酚(9)、2-甲基对苯二酚(10)、2-乙基对苯二酚(11)、原儿茶酸(12)、羟基酪醇(13)、香草醇(14)、原儿茶醛(15)、N-乙酰基多巴胺(16)、对羟基苯丙酸甲酯(17)、苯乙酸(18)、1-H-吲哚-3-羧酸(19)、12-羟基硬脂酸(20)和乌金苷(21)。化合物1、10和11对人白血病K562细胞的半数抑制浓度(median inhibition concentration,IC50)值分别为7.95、3.23和4.13 μmol/L;化合物10对人结肠癌HCT116细胞的IC50值为19.11 μmol/L。结论 化合物1为新的吲哚酮类化合物,命名为琵琶甲酮A。化合物4、5、8、14、17、18、20、21为首次从琵琶甲属中分离得到。9个化合物对K562细胞表现出抑制活性,其中化合物1、10和11显著强于顺铂(IC50=40.90 μmol/L)。化合物10对HCT116细胞具有抑制作用,与顺铂作用相当(IC50=19.80 μmol/L)。
[Key word]
[Abstract]
Objective To study the chemical constituents from Blaps rhynchoptera and their cytotoxicity. Methods By various isolation methods, such as silica gel, Sephadex LH-20 and MCI column chromatographies, together with semi-preparative HPLC, components in the ethanol extract of B. rhynchoptera were isolated, then their structures were identified by physical and chemical properties and spectroscopic methods. The cytotoxicity of the compounds on three cancer cells was tested. Results A total of 21 compounds were obtained and identified as (3R)-6-hydroxy-3-methyl-3, 8-diethyloxindole (1), blapindole I (2), blapindole K (3), uricil (4), 5-methyuricil (5), thymidine (6), 4-hydroxybenzoic acid (7), 4-hydroxyphenylacetic acid (8), hydroquinone (9), 2-methyl-1, 4-benzenediol (10), 2-ethyl-1, 4-benzenediol (11), protocatechuic acid (12), hydroxytyrosol (13), vanillic alcohol (14), protocatechnic aldehyde (15), N-acetyldopamine (16), methyl 3-(4-hydroxyphenyl) propionate (17), phenylacetic acid (18), 1-H-indole-3-carboxylic acid (19), 12-hydroxystearic acid (20), and robustaside B (21). Compounds 1, 10 and 11 showed significant cytotoxicity on K562 cells with the IC50 values of 7.95, 3.23 and 4.13 μmol/L, respectively. Compound 10 showed strong cytotoxicity on HCT-116 cells with an IC50 of 19.11 μmol/L. Conclusion Compound 1 was a new oxindole derivative and was named blapoxindole A. Compounds 4, 5, 8, 14, 17, 18, 20 and 21 were isolated from the Blap genus for the first time. Nine compounds exhibited cytotoxicity against K562 cells and compounds 1, 10 and 11 presented better efficiency than cisplatin (IC50= 40.90 μmol/L). The compound 10 showed strong cytotoxicity on HCT-116 cells, with the IC50 value roughly equal to that of cisplatin (IC50= 19.80 μmol/L).
[中图分类号]
R284.1
[基金项目]
云南省科技厅-昆明医科大学应用基础研究联合专项[2018FE001(-040)];云南省中青年学术和技术带头人后备人才项目(202205AC160073);云南省本科教育教学改革研究项目(JG2023001)