喙尾琵琶甲化学成分的研究  

Chemical constitutions from Blaps rhynchoptera

作　　者：张兴平 周轶平 缪晶茜 李碧桃[3] 文政琦[3] 王扣 ZHANG Xingping;ZHOU Yiping;MIU Jingqian;LI Bitao;WEN Zhengqi;WANG Kou(Yunnan Key Laboratory of Pharmacology of Natural Products,School of Pharmaceutical Science,Kunming Medical University,Kunming 650500,China;Yunnan College of Modern Biomedical Industry,Kunming 650500,China;Department of Oncology,First Affiliated Hospital of Kunming Medical University,Kunming 650032,China)

机构地区：[1]昆明医科大学药学院暨云南省天然药物药理重点实验室,云南昆明650500 [2]云南省现代生物医药产业学院,云南昆明650500 [3]昆明医科大学第一附属医院肿瘤科,云南昆明650032

出　　处：《中草药》2025年第4期1130-1137,共8页Chinese Traditional and Herbal Drugs

基　　金：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)。

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,IC_(50))值分别为7.95、3.23和4.13μmol/L;化合物10对人结肠癌HCT116细胞的IC_(50)值为19.11μmol/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(IC_(50)=40.90μmol/L)。化合物10对HCT116细胞具有抑制作用,与顺铂作用相当(IC_(50)=19.80μmol/L)。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 IC_(50)values of 7.95,3.23 and 4.13μmol/L,respectively.Compound 10 showed strong cytotoxicity on HCT-116 cells with an IC_(50)of 19.11μmol/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(IC_(50)=40.90μmol/L).The compound 10 showed strong cytotoxicity on HCT-116 cells,with the IC_(50)value roughly equal to that of cisplatin(IC_(50)=19.80μmol/L).

关 键 词：喙尾琵琶甲 吲哚酮类 琵琶甲酮A 2-甲基对苯二酚 2-乙基对苯二酚 细胞毒活性 

分 类 号：R284.1[医药卫生—中药学]