青龙衣化学成分的分离及其体外抗肿瘤活性的研究

Study on isolation of chemical constituents from green walnut husks and its antitumor activity in vitro

目的研究青龙衣(核桃楸Juglans mandshurica未成熟果实的外果皮)的化学成分及其体外抗肿瘤活性。方法应用多种色谱方法对青龙衣95%甲醇提取物进行分离纯化,利用NMR、MS等波谱技术结合理化性质进行结构鉴定;通过MTT法,以子宫颈癌细胞(HeLa)、人胃癌细胞(HGC-27)和结肠癌细胞(Ht-29)为目标细胞,检测所得到化合物的体外抗肿瘤活性。结果从青龙衣95%甲醇提取物的二氯甲烷萃取部位中分离鉴定出了12个化合物,分别为5,5′-dimethoxybiphenyl-2,2′-diol(1)、4,17-dimethoxy-2-oxatricyclo[13.2.2.13,7]eicosa-3,5,7(20),15,17,18-hexaene-10,16-diol(2)、3-羟基-1-(3-甲氧基-4-羟基-苯基)-丙基-1-酮(3)、4羟基-3,5-二甲基苯甲酸(4)、(4S)-4-羟基-1-四氢萘酮(5)、(4R)-O-methylsclerone(6)、阿魏酸(7)、(4S)-4,5,8-trihydroxy-α-tetralon(8)、5,8-二羟基-4-甲氧基-α-四氢萘酮(9)、(6R,7E)-4,7-megastigmadien-3,9-dione(10)、3,4′-dihydroxy-3′-methoxybenzenepentanoicacid(11)、vomifoliol(12)。结论其中化合物1~3、6、10~11首次从青龙衣中的得到,并且化合物2、6、8、9为青龙衣中的特有成分。化合物6、10对3种细胞均有良好的抑制作用,化合物1、3、8、9、11对3种肿瘤细胞表现出一定的体外抑制活性,其半数抑制浓度(half maximal inhibitory concentration,IC50)值为6.25~50.2μmol/L。

Objective To study the chemical constituents and their antitumor activity from green walnut husks. Methods The chemical constituents of 95% methanol extract from Green walnut husks were systematically studied by various chromatographic techniques. The chemical structures of the compounds were identified by means of spectroscopic techniques and physicochemical properties. The antitumor activity of the obtained compounds in vitro was determined by MTT assay using(Hela), human gastric cancer cells(HGC-27) and colon cancer cells(Ht-29) as target cells. Results Twelve compounds were isolated from the dichloromethane extracted of 95% methanol extracted from green walnut husks, including 5,5′-dimethoxybiphenyl-2,2′-diol(1), 4,17-dimethoxy-2-oxatricyclo[13.2.2.13,7]eicosa-3,5,7(20),15,17,18-hexaene-10,16-diol(2), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl) propan-1-one(3), 4-hydroxy-3,5-dimethoxybenzoic acid(4),(4 S)-4-hydroxy-1-tetralone(5),(4 R)-O-methylsclerone(6), ferulic acid(7),(4 S)-4,5,8-trihydroxy-α-tetralon(8), 5,8-dihydroxy-4-methoxy-α-tetralone(9),(6 R,7 E)-4,7-megastigmadien-3,9-dione(10), 3,4′-dihydroxy-3′-methoxybenzenepen tanoic acid(11), and vomifoliol(12). Conclusion Among them, compounds 1-3, 6, 10-11 are obtained from green walnut husks for the first time, and compounds 2, 6, 8, and 9 are unique to green walnut husks. The results show that compounds 6 and 10 have a good inhibitory effect on three types of cells. Compounds 1, 3, 8, 9, and 11 show a certain inhibitory activity on three kinds of tumor cells in vitro. Their IC;ranges from 6.25 to 50.2 μmol/L.