亚乎奴萜类和生物碱类化学成分研究

Terpenoids and alkaloids from Cissampelos pareira var. hirsuta

目的 研究亚乎奴Cissampelos pareira var. hirsuta的萜类和生物碱类化学成分。方法 采用硅胶、Sephadex LH-20、ODS、MCI等柱色谱和半制备液相色谱对其化学成分进行分离纯化,通过MS、NMR等波谱分析技术,结合理化性质分析,鉴定化合物结构。采用MTS法,测试化合物1、2、4、6~9、13、14对人急性早幼粒白血病HL-60细胞、人肺癌A549细胞、人肝癌SMMC-7721细胞、人乳腺癌MCF-7细胞、人结肠癌SW480细胞的细胞毒性。结果 从亚乎奴95%乙醇提取物中分离得到15个化合物,分别鉴定为羽扇豆醇(1)、白桦脂醇(2)、3β,14-二羟基-14β-孕甾-5-烯-20-酮(3)、3β-羟基-l7β-孕甾-5-烯-7,20-二酮(4)、假虎刺酮(5)、脱氢地芰普内酯(6)、黑麦草内酯(7)、(+)-去氢催吐萝芙木醇(8)、(3S,5R,6S,7E)-3,5,6-三羟基-7-巨豆烯-9-酮(9)、(6R,7E,9S)-9-羟基-4,7-巨豆二烯-3-酮(10)、催吐萝芙木醇(11)、8,9-二氢-8,9-二羟基巨豆三烯酮(12)、橙黄胡椒酰胺乙酸酯(13)、橙黄胡椒酰胺(14)、橙黄胡椒酰胺苯甲酸酯(15)。MTS测试结果显示,化合物2对A549细胞和SMMC-7721细胞具有一定的细胞毒活性,半数抑制浓度(median inhibition concentration,IC)值分别为23.62、27.46μmol/L。结论 所有化合物均为首次从锡生藤属植物中分离得到,包括三萜类化合物4个(1~4)、单萜类化合物8个(5~12)、生物碱类化合物3个(13~15)。羽扇豆烷型三萜可能为亚乎奴药材抗肿瘤活性的药效物质基础。

Objective To study the terpenoids and alkaloids from Cissampelos pareira var. hirsuta. Methods The compounds were isolated and purified by silica gel, Sephadex LH-20, ODS, MCI column chromatography and preparative HPLC, and their structures were identified by physicochemical properties, NMR and MS. Compounds 1, 2, 4, 6—9, 13 and 14 were tested for their cytotoxicity in human liver cancer SMMC-7721, breast cancer MCF-7, leukemia HL-60, lung cancer A549, colon cancer SW480 cell lines by MTS. Results Fifteen compounds were isolated from the 95% ethanol extract of Cissampelos pareira var.hirsuta, and their structures were identified as lupeol(1), betulin(2), 3β,14-dihydroxy-14β-pregn-5-en-20-one(3), 3β-hydroxy-l7β-pregn-5-ene-7,20-dione(4), carissone(5), dehydrololiolide(6), loliolide(7), dehydrovomifoliol(8),(3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one(9),(6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one(10), vomifoliol(11), 8,9-dihydro-8,9-dihydroxymegastigmatrienone(12), aurantiamide acetate(13), aurantiamide(14), and aurantiamide benzoate(15). Compound 2showed the most potent cytotoxic activities against the A549 and SMMC-7721 cell lines, with ICvalues of 23.62 and 27.46μmol/L, respectively. Conclusion All compounds are isolated from Cissampelos genus for the first time, including four triterpenoids(1~4), eight monoterpenoids(5~12) and three alkaloids(13~15). Lupane triterpenoids may be antitumor constituents from Cissampelos pareira var. hirsuta.