转筋草中极性化学成分及生物活性研究
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摘要
转筋草(Pachysandra terminalis Sieb.Zucc)为黄杨科(Buxaceae)板凳果属(Pachysandra)植物粉蕊黄杨的带根全草。黄杨科在我国有3属约35种,包括黄杨属(Buxus),板凳果属(Pachysandra)和野扇花属(Sarcococca)。转筋草为湖北省鄂西地区土家族常用民间药物,其味苦,辛,性温,具有祛风湿,舒筋活血,通经止带的功效。民间常用来治风湿发热,筋骨痛,精神病狂躁不安,闭经等症。为了阐明土家族民间药物转筋草的药效作用物质基础,我们对转筋草开展了系统的生物有效化学成份研究,以乙醇提取、不同溶剂萃取、常压柱色谱、中压柱色谱、大孔吸附树脂和凝胶柱色谱色谱分离,制备高效液相色谱纯化,从转筋草的95%乙醇提取物中共分得16个化合物,进一步利用IR、MS、1H-NMR、13C-NMR、1H-1H COSY、HMBC、HSQC、NOESY等有机波谱技术和化学方法,鉴定了其中16个化合物的结构,其中9个为未见文献报道的新化合物,分别为4-methyl-3-methylenepentane-1, 2,5-triol(1),4-methyl-3-methylenepentane-1,2,5-triol(2),3-isopropenyl-butane-1,2,4-triol(3),4-methyl-3-methylenepentane-1,2,5-triol-1-O-β-D-glucopyranoside(4),3-methylenehexane-1,2,5-triol-1-O-β-D-glucopyrano side(5),(6R,7E,9R)-9-methylamino-4,7-magastigmedien-3-one(6),(6R,7E, 9S)-9-methylamino-4,7-magastigmedien-3-one(7),Pachysandrol A(8),epipi noresinol-3-O-β-D-glucopyranoside(9).已知化合物：Boscialin-4-O-β-D-glucopyranoside(10),3-hydroxy-2-methyl-1-butene-4-O-β-D-glucopyranoside(11),2-β-D-葡萄糖苯乙醇苷(12),顺式紫丁香苷(13),松脂素-4′-O-β-D-葡萄糖苷(14),原儿茶酸(15),2,3,4-三羟基苯甲酸(16),其中化合物10～16是首次从转筋草中分离得到。多羟基烷烃类化合物为转筋草中首次分离鉴定的结构类型,为特征化学成分。
药理实验筛选中,考察了转筋草乙醇提取物的不同极性萃取物的免疫抑制作用,实验结果表明转筋草乙醇提取物以及石油醚、乙酸乙酯和正丁醇提取物具有很强的免疫抑制活性。随后对转筋草正丁醇层中提取到的单体化合物进行了抗氧化活性和免疫抑制活性筛选,发现化合物10、13～16具有较强的抗氧化活性,化合物1、2、11～14具有一定的免疫抑制活性。
Pachysandra terminalis Sieb.Zucc is the whole plant of Pachysandra terminalis (Buxaceae).It widely distributes in the southwest and northwest of the People's Republic of China. There are three genus in the Family of Buxaceae genus, they are Sarcococca, Pachysandra, Buxus. As a Chinese folk medicine, Pachysandra terminalis Sieb.Zucc has been usually used to dispel wind, activating blood, promoting menstruation.
In order to search the bioactive constituents from natural source, we began to study the chemical consitituents from Pachysandra terminalis Sieb.Zucc. By repeated column chromatography, including Silica gel, Toyopearl HW-40 and macroporous adsorption resin, and preparative HPLC,16 compounds were isolated from 95% EtOH extract of Pachysandra terminalis Sieb.Zucc. By using IR, MS, 1H-NMR,13C-NMR,1H-1H COSY, HMBC, HSQC, NOESY spectra and chemical methods, nine new compounds,4-methyl-3-methylenepentane-1,2,5-triol (1), 4-methyl-3-methylenepentane-1,2,5-triol (2),3-isopropenyl-butane-1,2, 4-triol (3),4-methyl-3-methylenepentane-1,2,5-triol-1-O-β-D-glucopyra noside (4),3-methylenehexane-1,2,5-triol-1-O-β-D-glucopyranos ide (5), (6R, 7E,9R)-9-methylamino-4,7-magastigmedien-3-one, (6R, 7E,9S)-9-methylam ino-4,7-magastigmedien-3-one (7), Pachysandrol A (8), epipinoresinol-3-O-β-D-glucopyranoside(9), along with seven known compounds were identified. Compound 1-16 were isolated from Pachysandra terminalis Sieb.Zucc for the first time. Polyhydroxy alkanes were isolated from this plant for the first time and were the characteristics constituents of Pachysandra terminalis Sieb.Zucc.
The immunosuppressive activities of different extracts and isolated compounds from Pachysandra terminalis Sieb.Zucc were also investigated. The n-BuOH extract revealed significant immunosuppressive activities. Their antioxidant activity and immunosuppressive activity had been investigated. The results showed that compound 10,13～16 had significant antioxidant activity, compound 1,2,11～14 had lower immunosuppressive activity.
药理实验筛选中,考察了转筋草乙醇提取物的不同极性萃取物的免疫抑制作用,实验结果表明转筋草乙醇提取物以及石油醚、乙酸乙酯和正丁醇提取物具有很强的免疫抑制活性。随后对转筋草正丁醇层中提取到的单体化合物进行了抗氧化活性和免疫抑制活性筛选,发现化合物10、13～16具有较强的抗氧化活性,化合物1、2、11～14具有一定的免疫抑制活性。
Pachysandra terminalis Sieb.Zucc is the whole plant of Pachysandra terminalis (Buxaceae).It widely distributes in the southwest and northwest of the People's Republic of China. There are three genus in the Family of Buxaceae genus, they are Sarcococca, Pachysandra, Buxus. As a Chinese folk medicine, Pachysandra terminalis Sieb.Zucc has been usually used to dispel wind, activating blood, promoting menstruation.
In order to search the bioactive constituents from natural source, we began to study the chemical consitituents from Pachysandra terminalis Sieb.Zucc. By repeated column chromatography, including Silica gel, Toyopearl HW-40 and macroporous adsorption resin, and preparative HPLC,16 compounds were isolated from 95% EtOH extract of Pachysandra terminalis Sieb.Zucc. By using IR, MS, 1H-NMR,13C-NMR,1H-1H COSY, HMBC, HSQC, NOESY spectra and chemical methods, nine new compounds,4-methyl-3-methylenepentane-1,2,5-triol (1), 4-methyl-3-methylenepentane-1,2,5-triol (2),3-isopropenyl-butane-1,2, 4-triol (3),4-methyl-3-methylenepentane-1,2,5-triol-1-O-β-D-glucopyra noside (4),3-methylenehexane-1,2,5-triol-1-O-β-D-glucopyranos ide (5), (6R, 7E,9R)-9-methylamino-4,7-magastigmedien-3-one, (6R, 7E,9S)-9-methylam ino-4,7-magastigmedien-3-one (7), Pachysandrol A (8), epipinoresinol-3-O-β-D-glucopyranoside(9), along with seven known compounds were identified. Compound 1-16 were isolated from Pachysandra terminalis Sieb.Zucc for the first time. Polyhydroxy alkanes were isolated from this plant for the first time and were the characteristics constituents of Pachysandra terminalis Sieb.Zucc.
The immunosuppressive activities of different extracts and isolated compounds from Pachysandra terminalis Sieb.Zucc were also investigated. The n-BuOH extract revealed significant immunosuppressive activities. Their antioxidant activity and immunosuppressive activity had been investigated. The results showed that compound 10,13～16 had significant antioxidant activity, compound 1,2,11～14 had lower immunosuppressive activity.
引文
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[3]郑勉,闵天禄.中国植物志.黄杨科(第45卷第1分册).北京：科学出版社,1980.519-592.
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[5]邱明华,李德铢.黄杨科植物化学分类初探,应用于环境生物学报,2006,8(4)：387-391.
[6]Kikuchi T,Uyeo S. Studies on the alkaloids of pachysandra terminalis sieb. et zucc. (1):Systematic separation and characterization of alkaloids. Tetrahedron letters,1965,3473-3485.
[7]Kikuchi Tohru,Uyeo Shojiro. Structure of pachysamine-A and-B. Chemical & Pharmaceutical Bulletin (1967),15(3):302-306.
[8]Kikuchi T,Uyeo S. Studies on the alkaloids of pachysandra terminalis sieb. et zucc. (2):Systematic separation and characterization of alkaloids. Chemical & Pharmaceutical Bulletin,1967,15:207-213.
[9]Kikuchi T,Uyeo S. Studies on the alkaloids of pachysandra terminalis sieb. et zucc. (3):Systematic separation and characterization of alkaloids. Tetrahedron letters,1965,3487-3490.
[10]T,Uyeo S, Nishinaga T. Systematic separation and characteriza tion of alkaloids. Chemical & Pharmaceutical Bulletin,1981,29,2531-2539.
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