摘要
目的分离、鉴定海州常山茎正丁醇部位的化学成分,并考察其体外抗肿瘤活性。方法使用85%乙醇回流提取海州常山的干燥茎得到其乙醇提取物。将所得乙醇提取物用水分散后,依次用石油醚、乙酸乙酯和正丁醇萃取,减压浓缩后分别得到各萃取部位浸膏。采用D101大孔树脂柱层析以及包括硅胶、羟丙基葡聚糖凝胶和ToyopearlHW-40F大孔树脂等在内的各种色谱技术对海州常山茎正丁醇部位进行分离纯化,并结合化合物的物理、化学性质以及质谱、核磁共振谱等波谱技术确定其结构。采用MTT法检测所得化合物对4种人源肿瘤细胞K562、MCF-7、A549和HepG2的增殖抑制活性。结果从海州常山茎85%乙醇提取物的正丁醇部位共分离鉴定出14个化合物,分别鉴定为teuvincenone B(1)、钩大青酮(2)、villosin C(3)、丁香脂素(4)、丁香脂素-4′-O-β-葡萄糖(5)、3,12-O-β-D-二吡喃葡萄糖基-11,16-二羟基松香醇-8,11,13-三烯(6)、五叶山小橘苷C(7)、角胡麻苷(8)、异地黄苷(9)、2-(4-hydroxyphenyl)ethanol-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranoside(10)、3,4-二甲氧基苯基-1-O-β-D-呋喃芹糖基-(1→2)-β-D-葡萄糖苷(11)、2,6-二甲氧基-4-羟苯基-1-O-β-D-吡喃葡萄糖苷(12)、腺苷(13)和肉苁蓉苷F(14)。体外抗肿瘤活性研究表明,化合物1~3具有一定的抗肿瘤活性,其中化合物2对MCF-7、A549和HepG2细胞的增殖抑制活性最强,半数抑制浓度(IC_(50))分别为25.00、22.34、12.50μmol/L;化合物3对K562细胞的增殖抑制活性较强,IC_(50)为28.41μmol/L。结论化合物10~13为首次从该属植物中分离得到,化合物4、5、14为首次从该植物中分离得到;松香烷型二萜类化合物(化合物1~3)对上述4种肿瘤细胞株的增殖抑制活性较好。
OBJECTIVE To separate and identify the chemical constituents of the n-butanol fraction from the stems of Clerodendrum trichotomum,and to investigate their antitumor activities in vitro.METHODS The ethanol extracts were obtained with 85%ethanol from dried stems of C.trichotomum.After dispersed with water,ethanol extracts were distributed by petroleum ether,ethyl acetate and n-butanol in turn,then concentrated under reduced pressure to obtain the fractions of each extraction part.The n-butanol fraction from the stems of C.trichotomum was isolated and purified by macroporous resin D101 column chromatography and various chromatographic techniques including silica gel,hydroxypropyl glucan gel and Toyopearl HW-40F macroporous resin and so on.The structures of them were identified by physical and chemical properties,MS and NMR.All these compounds were evaluated for cytotoxic activities against 4 kinds of human tumor cells such as cultured K562,MCF-7,A549 and HepG2,using the MTT assay.RESULTS Fourteen chemical constituents were isolated and identified as teuvincenone B(1),uncinatone(2),villosin C(3),syringaresinol(4),syringaresinol-4'-O-β-glucopyranoside(5),3,12-O-β-D-diglucopyranosyl-11,16-dihydroxyabieta-8,11,13-triene(6),glypentoside C(7),martynoside(8),isomartynoside(9),2-(4-hydroxyphenyl)ethanol-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranoside(10),3,4-dimethoxyphenyl-1-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside(11),2,6-dimethoxy-4-hydroxy-1-O-β-D-glucopyranoside(12),adenosine(13)and cistanoside F(14).In vitro anti-tumor activity studies showed that compounds 1-3 showed certain inhibitory activities against tumor cell proliferation,among which compound 2 displayed the strongest inhibitory activity against MCF-7,A549 and HepG2 cells,and their IC_(50) values were 25.00,22.34 and 12.50μmol/L respectively;only compound 3 showed stronger inhibitory activity against K562 cell with IC_(50) of 28.41μmol/L.CONCLUSIONS Among them,compounds 10 to 13 are isolated from genus Clerodendrum for the first time,compounds 4,5,14 were isolated from C.trichotomum for the first time.The abietane diterpenoids(compounds 1-3)have better inhibitory activities against above four tumor cell lines.
作者
李林珍
张宇
陈亮
岑银芝
涂杨丽
杨小生
李勇军
LI Linzhen;ZHANG Yu;CHEN Liang;CEN Yinzhi;TU Yangli;YANG Xiaosheng;LI Yongjun(School of Pharmacy,Guizhou Medical University,Guiyang 550025,China;State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University,Guiyang 550004,China;Engineering Research Center for the Development and Application of Ethnic Medicine and TCM(Ministry of Education),Guizhou Medical University,Guiyang 550004,China)
出处
《中国药房》
CAS
北大核心
2022年第21期2578-2583,2589,共7页
China Pharmacy
基金
国家自然科学基金资助项目(No.81860689)
贵州省科技合作计划项目(No.黔科合LH字〔2015〕7359)。
关键词
海州常山
茎
正丁醇部位
化学成分
结构鉴定
抗肿瘤活性
Clerodendrum trichotomum
stem
n-butanol fraction
chemical constituents
structural identification
antitumor activities
