山橙中生物碱类化学成分的研究  

Chemical constituents of alkaloids from Melodinus suaveolens

作　　者：李瑞 方忠莹 杨梓依 方磊 周洁[1,2] LI Rui;FANG Zhong-ying;YANG Zi-yi;FANG Lei;ZHOU Jie(School of Medicine,Shandong University of Traditional Chinese Medicine,Jinan 250355,China;Biological Science and Technology University of Jinan,Jinan 250022,China)

机构地区：[1]山东中医药大学药学院,山东济南250355 [2]济南大学生物科学与技术学院,山东济南250022

出　　处：《中草药》2023年第5期1362-1369,共8页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金项目(22077049);济南市《关于促进高校和科研院所协同创新和成果产业化的若干政策(试行)》项目(2020GXRC060)。

摘　　要：目的研究山橙Melodinus suaveolens茎乙醇提取物氯仿部位中的生物碱类成分。方法采用酸溶碱沉法富集,运用正相硅胶柱色谱、半制备高效液相色谱等多种色谱方法进行分离和纯化,并利用一维和二维核磁共振波谱、高分辨质谱以及圆二色谱等技术鉴定化合物的结构。结果从山橙乙醇提取物氯仿部位分离得到12个生物碱类成分,分别鉴定为美乐苏胺A(1)、柳叶水甘草碱(2)、3-羰基柳叶水甘草碱(3)、白坚木胺(4)、Δ^(14)-长春布宁(5)、Δ^(14)-vincamenine(6)、3-羰基-11-甲氧基柳叶水甘草碱(7)、alstoyunine G(8)、pachysiphine(9)、洛柯宁碱(10)、土波台文碱(11)、venalstonine(12)。初步的抗肿瘤活性评价实验表明,化合物2、8~10显示出不同程度的肿瘤细胞增殖抑制活性。结论化合物1为1个新的单萜吲哚类生物碱,化合物4、11和12首次从该植物中分离得到;化合物10对人肺癌A549、人肝癌HepG2和人前列腺癌PC-3肿瘤细胞具有显著的增殖抑制活性,半数抑制浓度(median inhibition concentration,IC_(50))分别为7.11、0.84和3.78μmol/L。Objective To study the alkaloids from the chloroform fraction of the ethanolic extract of the stems of Shancheng(Melodinus suaveolens).Methods The compounds were isolated and purified by acid extraction and alkaline precipitation method,silica gel column chromatography,semi-preparative high performance liquid chromatography,and other chromatographic methods.Their structures including absolute configurations were elucidated from a combination of NMR and HRESIMS data,as well as circular dichroism calculation.Results Twelve alkaloids were isolated and characterized from the ethanolic extract of the stems of M.suaveolens.Their structures were identified as melosuavine A(1),tabersonine(2),3-oxotabersonine(3),quebrachamine(4),Δ^(14)-vincamone(5),Δ^(14)-vincamenine(6),3-oxo-11-methoxytabersonine(7),alstoyunine G(8),pachysiphine(9),lochnerinine(10),tubotaiwine(11)and venalstonine(12).Compounds 2,8—10 showed significant cytotoxicities against all the tested tumor cell lines.Conclusions Compound 1 is a new alkaloid,and compounds 4,11 and 12 are isolated from M.suaveolens for the first time.Compound 10 displayed significant antiproliferation activity against A549,HepG2,and PC-3 cells with IC_(50) values of 7.11,0.84 and 3.78μmol/L,respectively.

关 键 词：夹竹桃科 山橙属 山橙 生物碱 美乐苏胺A 白坚木胺 土波台文碱 venalstonine 

分 类 号：R284.1[医药卫生—中药学]