南葶苈子各化学拆分组分化学成分的研究
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摘要
目的:研究南葶苈子各拆分组分的化学成分,诠释南葶苈子各拆分组分发挥药效的物质基础。方法:运用Diaion HP-20、Toyopearl HW-40、MCI Gel CHP-20、ODS、Silica gel等柱色谱技术结合高压制备液相等方法进行分离纯化,并根据化合物的光谱数据和理化性质鉴定结构。结果:从南葶苈子的20%和80%乙醇组分中分离并鉴定了28个化合物的结构。从20%乙醇组分中分离得到13个化合物:山柰酚-3-O-β-D-吡喃葡萄糖基-7-O-β-D-龙胆双糖苷(1),槲皮素-3-O-β-D-吡喃葡萄糖基-7-O-β-D-龙胆双糖苷(2),异鼠李素-3-O-β-D-吡喃葡萄糖基-7-O-β-D-龙胆双糖苷(3),异鼠李素-3,7-二-O-β-D-吡喃葡萄糖苷(4),槲皮素-3,7-二-O-β-D-吡喃葡萄糖苷(5),山柰酚-3,7-二-O-β-D-吡喃葡萄糖苷(6),山柰酚-3-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃葡萄糖苷(7),芥子酸甲酯(8),丁香醛(9),(S)-对羟基苯基乳酸(10),(S)-2-羟基苯丙酸(11),东莨菪内酯(12),芥子酸(13);从80%乙醇组分中分离得到15个化合物:异鼠李素-3-O-β-D-吡喃葡萄糖苷(14),槲皮素-3-O-β-D-吡喃葡萄糖苷(15),山柰酚-3-O-β-D-吡喃葡萄糖苷(16),槲皮素(17),山柰酚(18),异鼠李素(19),丁香酸(20),槲皮素-3-O-β-D-吡喃阿拉伯糖苷(21),槲皮素-3-O-β-D-吡喃木糖苷(22),6-O-[E]-Sinapoyl-(α-andβ)-D-glucopyranoside(23),dimethyl(E,E)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxylign-7,7′-dien-9,9′-dioate(24),索马榆脂酸二甲酯(25),2-羟基-3-吲哚丙酸(26),2-羟基-3-吲哚丙酸甲酯(27),4'-甲氧基二氢槲皮素(28)。结论:化合物7-11,21-28均是首次从南葶苈子中分离得到。
This article was aimed to study the chemical constituents of seeds of Descurainia Sophia (L.) Webb. ex Prantl., in order to lay the material foundation for further interpretation of seeds of D. Sophia and provide pharmacodynamic basis as well as the basis for attributing its nature and taste. The compounds were isolated and purified by Diaion HP-20, Toyopearl HW-40, MCI Gel CHP-20, ODS, Silica gel chromatography combining with Pre-HPLC. The structures were identified on the basis of spectral data and physicochemical properties. Twenty eight compounds were isolated and identified from 20% and 80% ethanol fraction. Thirteen compounds were identified from 20% ethanol fraction: kaempferol-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (1), quercetin-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (2), isorhamnetin-3-O-β-D-glucopyranosyl-7-O-β-Dgentiobioside (3), isorhamnetin-3,7-di-O-β-D-glucopyranoside (4), quercetin-3,7-di-O-β-D-glucopyranoside (5), kaempferol-3, 7-di-O-β-D-glucopyranoside (6), kaempferol-3-O-β-D-xylopyranosyl (1 → 2)-β-Dglucopyranoside (7), methyl sinapate (8), syringaldehyde (9), (S)-p- hydroxyphenyl lactate acid (10), (S)-2-hydroxyphenylpropionic acid (11), scopoletin (12), sinapic acid (13). Fifteen compounds were identified from 80% ethanol fraction: isorhamnetin-3-O-β-D-glucopyranoside (14), quercetin-3-O-β-D-glucopyranoside (15), kaempferol-3-O-β-D-glucopyranoside (16), quercetin (17), kaempferol (18), isorhamnetin (19), syringic acids (20), quercetin-3-O-β-D-arabinopyranoside (21), quercetin-3-O-β-D-xylopyranoside (22), 6-O-[E]-Sinapoyl-(α- and β)-D-glucopyranoside (23), dimethyl (E, E)-4,4'-dihydroxy-3,3',5,5'-tetramethoxylign-7,7'-dien-9,9'-dioate (24), dimethylthomasidioate (25), 2-hydroxy-3-(1H-indol-3-yl) propanoic acid (26), 2-hydroxyl-3-(1H-indol-3-yl) propanoic acid methyl ester (27), 4'-O-methyl-dihydroquercetin (28). It was concluded that compounds 7-11 and 21-28 were isolated from seeds of D. sophia (L.) Webb. ex Prantl. for the first time.
This article was aimed to study the chemical constituents of seeds of Descurainia Sophia (L.) Webb. ex Prantl., in order to lay the material foundation for further interpretation of seeds of D. Sophia and provide pharmacodynamic basis as well as the basis for attributing its nature and taste. The compounds were isolated and purified by Diaion HP-20, Toyopearl HW-40, MCI Gel CHP-20, ODS, Silica gel chromatography combining with Pre-HPLC. The structures were identified on the basis of spectral data and physicochemical properties. Twenty eight compounds were isolated and identified from 20% and 80% ethanol fraction. Thirteen compounds were identified from 20% ethanol fraction: kaempferol-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (1), quercetin-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (2), isorhamnetin-3-O-β-D-glucopyranosyl-7-O-β-Dgentiobioside (3), isorhamnetin-3,7-di-O-β-D-glucopyranoside (4), quercetin-3,7-di-O-β-D-glucopyranoside (5), kaempferol-3, 7-di-O-β-D-glucopyranoside (6), kaempferol-3-O-β-D-xylopyranosyl (1 → 2)-β-Dglucopyranoside (7), methyl sinapate (8), syringaldehyde (9), (S)-p- hydroxyphenyl lactate acid (10), (S)-2-hydroxyphenylpropionic acid (11), scopoletin (12), sinapic acid (13). Fifteen compounds were identified from 80% ethanol fraction: isorhamnetin-3-O-β-D-glucopyranoside (14), quercetin-3-O-β-D-glucopyranoside (15), kaempferol-3-O-β-D-glucopyranoside (16), quercetin (17), kaempferol (18), isorhamnetin (19), syringic acids (20), quercetin-3-O-β-D-arabinopyranoside (21), quercetin-3-O-β-D-xylopyranoside (22), 6-O-[E]-Sinapoyl-(α- and β)-D-glucopyranoside (23), dimethyl (E, E)-4,4'-dihydroxy-3,3',5,5'-tetramethoxylign-7,7'-dien-9,9'-dioate (24), dimethylthomasidioate (25), 2-hydroxy-3-(1H-indol-3-yl) propanoic acid (26), 2-hydroxyl-3-(1H-indol-3-yl) propanoic acid methyl ester (27), 4'-O-methyl-dihydroquercetin (28). It was concluded that compounds 7-11 and 21-28 were isolated from seeds of D. sophia (L.) Webb. ex Prantl. for the first time.
引文
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3 夏军,黄丽娟,韦懿馨,等.强心栓治疗充血性心力衰竭的临床观察与药理研究.中国医药学报,1992,7(2):15-17.
4 柏正平,郑兵,卜献春,等.复方葶苈子胶囊止咳袪痰作用的实验研究.湖南中医药导报,2000,6(5):41-42.
5 匡海学,王艳宏,王秋红,等.基于中药性味可拆分性和可组合性的中药性味理论研究新模式.世界科学技术-中医药现代化,2011,13(1):25-29.
6 王爱芹,王秀坤,李军林,等.南葶苈子化学成分的分离与结构鉴定.药学学报,2004,39(1):46-51.
7 Formisano C, Rigano D, Senatore F, et al. Flavonoids in subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): distribution and 13C-NMR spectral data. Chem Biodivers, 2012, 9(10):2096-2158.
8 黄胜阳,石建功,杨永春,等.长苞凹舌兰化学成分研究.药学学报,2002,37(3):199-203.
9 李兴玉,王跃虎,王鸿升,等.云南金钱槭叶子中的酚性成分.天然产物研究与开发,2010,22(1):5-10.
10 李玉美.牛心朴子草化学成分的分离与鉴定.安徽农业科学,2008,36(13):5254,5479.
11 申旭霁,格日力,王金辉.广枣的化学成分.河南大学学报(医学版),2009,28(3):196-199.
12 Suzuki Y, Kosaka M, Shindo K, et al. Identification of antioxidants produced by lactobacillus plantarum. Biosci Biotechnol Biochem, 2013, 77(6):1299-1302.
13 陈建伟,段志富,李祥,等.明党参药材水溶性活性成分的研究.天然产物研究与开发,2010,22(2):232-234,247.
14 张茂娟,刘冰,安彦峰,等.白钩藤的化学成分研究.中草药,2014,45(2):175-180.
15 赵晓宏,陈迪华,斯建勇,等.中药升麻酚酸类化学成分研究.药学学报,2002,37(7):535-538.
16 Sang S, Lapsley K, Jeoneg W S, et al. Antioxidative Phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J Agric FoodChem, 2002, 50(8):2459-2463.
17 Kazuma K, Noda N, Suzuki M. Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry, 2003, 62(2):229-237.
18 王盈盈,梁鑫,钟惠民.云贵腺药珍珠菜化学成分研究.中草药,2012,43(7):1280-1284.
19 易衍,巫鑫,王英,等.霸王花黄酮类成分研究.中药材,2011,34(5):712-716.
20 吴慧星,李晓帆,李荣,等.番石榴叶中抗氧化活性成分的研究.中草药,2010,41(10):1593-1597.
21 柳建军,刘锡葵.黄连木食用部位化学成分研究.中草药,2009,40(2):186-189.
22 Lou H X, Li X, Zhu T R, et al. Sinapic acid esters and a phenolic glycoside from Cynanchum hancockianum. Phytochemistry, 1993, 32(5):1283-1286.
23 Fang J J, Reichelt M, Kai M, et al. Metabolic profiling of lignans and other secondary metabolites from rapeseed (Brassica napus L.).J Agric Food Chem, 2012, 60(42):10523-10529.
24 赵婷婷,李晓明,李景梅,等.海洋红藻多管藻内生真菌EN-22的化学成分研究.海洋科学,2009,33(7):81-86.
25 张妮,魏孝义,林立东.罗汉果叶的化学成分研究.热带亚热带植物学报,2014,22(1):96-100.
26 冯志毅,王小兰,郑晓珂.葶苈子的本草考证.世界科学技术-中医药现代化,2014,16(9):1938-1941.
2 中国医学科学院药物研究所等.中药志(第三卷).北京:人民卫生出版社,1993:625.
3 夏军,黄丽娟,韦懿馨,等.强心栓治疗充血性心力衰竭的临床观察与药理研究.中国医药学报,1992,7(2):15-17.
4 柏正平,郑兵,卜献春,等.复方葶苈子胶囊止咳袪痰作用的实验研究.湖南中医药导报,2000,6(5):41-42.
5 匡海学,王艳宏,王秋红,等.基于中药性味可拆分性和可组合性的中药性味理论研究新模式.世界科学技术-中医药现代化,2011,13(1):25-29.
6 王爱芹,王秀坤,李军林,等.南葶苈子化学成分的分离与结构鉴定.药学学报,2004,39(1):46-51.
7 Formisano C, Rigano D, Senatore F, et al. Flavonoids in subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): distribution and 13C-NMR spectral data. Chem Biodivers, 2012, 9(10):2096-2158.
8 黄胜阳,石建功,杨永春,等.长苞凹舌兰化学成分研究.药学学报,2002,37(3):199-203.
9 李兴玉,王跃虎,王鸿升,等.云南金钱槭叶子中的酚性成分.天然产物研究与开发,2010,22(1):5-10.
10 李玉美.牛心朴子草化学成分的分离与鉴定.安徽农业科学,2008,36(13):5254,5479.
11 申旭霁,格日力,王金辉.广枣的化学成分.河南大学学报(医学版),2009,28(3):196-199.
12 Suzuki Y, Kosaka M, Shindo K, et al. Identification of antioxidants produced by lactobacillus plantarum. Biosci Biotechnol Biochem, 2013, 77(6):1299-1302.
13 陈建伟,段志富,李祥,等.明党参药材水溶性活性成分的研究.天然产物研究与开发,2010,22(2):232-234,247.
14 张茂娟,刘冰,安彦峰,等.白钩藤的化学成分研究.中草药,2014,45(2):175-180.
15 赵晓宏,陈迪华,斯建勇,等.中药升麻酚酸类化学成分研究.药学学报,2002,37(7):535-538.
16 Sang S, Lapsley K, Jeoneg W S, et al. Antioxidative Phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J Agric FoodChem, 2002, 50(8):2459-2463.
17 Kazuma K, Noda N, Suzuki M. Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry, 2003, 62(2):229-237.
18 王盈盈,梁鑫,钟惠民.云贵腺药珍珠菜化学成分研究.中草药,2012,43(7):1280-1284.
19 易衍,巫鑫,王英,等.霸王花黄酮类成分研究.中药材,2011,34(5):712-716.
20 吴慧星,李晓帆,李荣,等.番石榴叶中抗氧化活性成分的研究.中草药,2010,41(10):1593-1597.
21 柳建军,刘锡葵.黄连木食用部位化学成分研究.中草药,2009,40(2):186-189.
22 Lou H X, Li X, Zhu T R, et al. Sinapic acid esters and a phenolic glycoside from Cynanchum hancockianum. Phytochemistry, 1993, 32(5):1283-1286.
23 Fang J J, Reichelt M, Kai M, et al. Metabolic profiling of lignans and other secondary metabolites from rapeseed (Brassica napus L.).J Agric Food Chem, 2012, 60(42):10523-10529.
24 赵婷婷,李晓明,李景梅,等.海洋红藻多管藻内生真菌EN-22的化学成分研究.海洋科学,2009,33(7):81-86.
25 张妮,魏孝义,林立东.罗汉果叶的化学成分研究.热带亚热带植物学报,2014,22(1):96-100.
26 冯志毅,王小兰,郑晓珂.葶苈子的本草考证.世界科学技术-中医药现代化,2014,16(9):1938-1941.