新疆紫草化学成分研究  

Chemical constituents from Arnebia euchroma

作　　者：王乐 王淑慧 王琪琪 王喻淇 屠鹏飞[2] WANG Le;WANG Shuhui;WANG Qiqi;WANG Yuqi;TU Pengfei(School of Pharmacy,Minzu University of China,Beijing 100081,China;State Key Laboratory of Natural and Biomimetic Drugs,School of Pharmaceutical Sciences,Peking University,Beijing 100191,China)

机构地区：[1]中央民族大学药学院,北京100081 [2]北京大学天然药物及仿生药物国家重点实验室,北京大学药学院,北京100191

出　　处：《中草药》2024年第7期2131-2141,共11页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金青年基金项目(82304690)。

摘　　要：目的研究新疆紫草Arnebia euchroma的化学成分。方法采用硅胶、ODS、凝胶柱色谱等多种柱色谱分离技术进行分离纯化,通过质谱、核磁共振波谱、圆二色谱等技术并结合文献报道的数据,对化合物进行结构鉴定。采用CCK8法,研究化合物对体外培养的人乳腺癌MCF-7细胞增殖的影响。结果从新疆紫草石油醚部位中共分离得到24个化合物,分别鉴定为(S)-1-(6-异丙基-2,3-二氢-1H-茚-4-基)乙-1-酮(1)、(Z)-2-(2-(2,5-二羟基苯基)-2-氧亚乙基)-6-甲基庚-5-烯酸乙酯(2)、2-(2Z)-(3-羟基-3,7-二甲基-2,6-辛二烯基)-1,4-苯二醇(3)、新藏紫草酚(4)、(+)-(R)-脱氧碘化叶黄素(5)、3-(4-甲基-3-戊烯-1-基)-6-羟基-9-甲氧基-2H-1-苯并氧杂环庚烯-5-酮(6)、对羟基苯甲醛(7)、香草醛(8)、乙酰香草酮(9)、2-羟基-4-甲氧基肉桂醛(10)、guttaquinol B(11)、岩大戟内酯E(12)、3-乙酰氧基齐墩果酸(13)、羟基何帕酮(14)、β-谷甾醇(15)、豆甾-4-烯-3,6-二酮(16)、麦角甾-4,6,8(14),22-四烯-3-酮(17)、柠黄醇(18)、euchroquinol B(19)、docosanyl ferulate(20)、arnebin-7(21)、阿卡宁(22)、β,β-二甲基丙烯酰阿卡宁(23)、异丁酰阿卡宁(24)。化合物21、22对MCF-7细胞的增殖具有抑制作用,其半数抑制浓度(median inhibition concentration,IC_(50))值分别为(16.58±0.02)μmol/L和(9.19±0.02)μmol/L。结论化合物1和2为新化合物,分别命名为新疆紫草酮(euchromone)和新疆紫草酚(euchromol)。化合物7~11、16、18为首次从软紫草属中分离得到,化合物3和12为首次从新疆紫草中分离得到。化合物21、22具有良好的抑制MCF-7细胞增殖活性。Objective To investigate the chemical constituents of Xinjiangzicao(Arnebia euchroma).Methods Multiple chromatographic separation techniques including silica gel,ODS,Sephadex LH-20 column chromatography were employed to isolate and purify the compounds.Their structures were identified by means of the MS,NMR and ECD data analysis,combined with the data reported in the literatures.The inhibitory effect of compounds on cancer cell line MCF-7 was investigated through CCK8 assay.Results Twenty four compounds were isolated and identified as(S)-1-(6-isopropyl-2,3-dihydro-1H-inden-4-yl)ethan-1-one(1),ethyl(Z)-2-(2-(2,5-dihydroxyphenyl)-2-oxoethylidene)-6-methylhept-5-enoate(2),2-(2Z)-(3-hydroxy-3,7-dimethylocta-2,6-dienyl)-1,4-benzenediol(3),arnebinol(4),(+)-(R)-de-O-methyllasiodiplodin(5),3-(4-methyl-3-penten-1-yl)-6-hydroxy-9-methoxy-2H-1-benzoxepin-5-one(6),p-hydroxy-benzaldehyde(7),vanillin(8),acetovanillone(9),2-hydroxy-4-methoxyl-cinnamaldehyde(10),guttaquinol B(11),jolkinolide E(12),3β-acetoxyolean-12-en-28-oic acid(13),22-hydroxyhopan-3-one(14),β-sitosterol(15),stigmast-4-en-3,6-dione(16),ergosta-4,6,8(14),22-tetraen-3-one(17),citrostadienol(18),euchroquinol B(19),docosanyl ferulate(20),arnebin-7(21),alkannin(22),β,β-dimethylacrylalkannin(23)and isobutyrylalkannin(24).Compounds 21 and 22 had inhibitory effects on MCF-7 cells,with IC_(50) values of(16.58±0.02)μmol/L and(9.19±0.02)μmol/L,respectively.Conclusion Compounds 1 and 2 were identified as two new compounds,named euchromone and euchromol,respectively.Compounds 7—11,16 and 18 were isolated from Arnebia genus for the first time,and compounds 3 and 12 were isolated from the roots of A.euchroma for the first time.Compounds 21 and 22 had the inhibitory effects on MCF-7 cells.

关 键 词：新疆紫草 新疆紫草酮 新疆紫草酚 阿卡宁 豆甾-4-烯-3 6-二酮 柠黄醇 细胞毒活性 

分 类 号：R284.1[医药卫生—中药学]