沙冬青属植物的化学成分研究
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摘要
沙冬青属(Ammpiptanthus Cheng f.)隶属豆科(Leguminosae)黄华族(Thermosi- deae),是亚洲中部荒漠特有的常绿阔叶灌木,全世界仅有两种:一种是蒙古沙冬青(Ammpiptanthus mongolicus (Maxim.) Cheng f.),主要分布在内蒙古、宁夏及甘肃;另一种是新疆沙冬青(Ammpiptanthus nanus (M.Pop.) Cheng f.),主要分布于新疆西南部克孜勒苏自治州以及邻近的中亚地区。沙冬青属植物民间以其枝叶入药,能祛风、活血、止痛;外用主治冻疮、慢性风湿性关节炎等,属于民族药。据文献报道,该属植物的化学成分主要为生物碱类和黄酮类化合物,大量研究表明多数黄酮类化合物具有较好的抗糖尿病及其并发症的活性。
在抗糖尿病药物的前期活性筛选研究中发现蒙古沙冬青和新疆沙冬青的乙醇提取物具有良好的体内降血糖活性,为阐明其降血糖的有效成分,为抗糖尿病创新药物的研究与开发奠定基础,运用多种色谱技术、波谱和理化方法,对蒙古沙冬青枝的乙醇提取物和新疆沙冬青叶的乙醇提取物进行了较系统的化学成分研究。
从蒙古沙冬青枝的乙醇提取物中分离鉴定了12个化合物,包括:六个异黄酮及其苷类化合物:芒柄花素(1),芒柄花苷(2),isolupalbigenin (3),大豆苷元4′,7-二葡萄糖苷(4),沙冬青苷A(黄豆黄素4′, 7 -二葡萄糖苷,5),染料木素4′,7-二葡萄糖苷(6);1个黄酮类化合物的衍生物:(+)-maackiain (7);1个酚类化合物:短叶苏木酚(8);1个烷烃类化合物:正三十烷(9);两个甾醇及其苷类化合物:β-谷甾醇(10)、β-胡萝卜苷(11);1个环多醇类化合物:红杉醇(12);其中化合物5为新化合物,命名为沙冬青苷A(Ammopiptanoside A);化合物3、4、6、8、9、12为首次从该属植物中分离得到。从新疆沙冬青叶的乙醇提取物中分离得到13个化合物,鉴定了6个,包括3个异黄酮苷类化合物:芒柄花苷(1),大豆苷元4′,7-二葡萄糖苷(2),染料木素4′,7-二葡萄糖苷(3);1个苯甲酸苷类化合物:4-O-β-D-吡喃葡萄糖氧基苯甲酸(4);1个苯丙素类化合物:丁香苷(5);1个环多醇类化合物:红杉醇(6);这6个化合物均为首次从该种植物中分离得到。根据以上实验结果,结合TLC、LC-MS对该属两种植物的化学成分进行比较,结果显示两种植物的化学成分具有很大的相似性,叶中生物碱含量明显多于枝中。
经查阅文献,发现从该属植物中分离得到的红杉醇具有显著降血糖活性,芒柄花素降血脂功效显著,芒柄花苷具有抗氧化作用,maackiain具有较好的抗炎和抗肿瘤活性,短叶苏木酚对急慢性肝损伤有保护作用,丁香苷具有止血、抗肝毒的功效。
The genus Ammopiptanthus, a survivor of the evergreen broadleaf shrub in the central Asia desert from the Tertiary period, it belongs to the tribe Thermopsideae of the Leguminosae. Ammopiptanthus comprises two species, the one is Ammopiptanthus mongolicus (Maxim.) Cheng f., which is widely distributed in Mongolia, Ningxia and Gansu; the other is Ammopiptanthus nanus (Popov.) Cheng f., which is mainly distributed in Kizilsu Autonomous Prefecture in the southwest of Xinjiang province and neighboring central Asia.The aerial parts of Ammopiptanthus has been used as a folk medicine for the treatment of cough, congelation and chronic rheumatic arthritis, etc. Alkaloids and flavonoids are the characteristic chemical constituents of Ammopiptanthus, according to the literature.
The alcohol extracts of A. mongolicus and A. nanus showed significant hypoglycemic effect in the research of anti-diabetes drug selecting. In order to search for the hypoglycemic pricinples and to establish a foundation for researching and developing drugs that can prevent and cure diabetes, our work focused on the chemical constituents of Ammopiptanthus. Isolation and purification were carried out by various column chromatographic methods. The structures were elucidated on the basis of spectroscopic analysis and chemical methods as well.
In this thesis, 12 compounds were abtained from the twigs of A. mongolicus alcohol extracts, including 6 isoflavonoids: formononetin (1), ononin(2), isolupalb- igenin (3), daidzein 4′,7-di-O-β-D-glucoside (4), glycitein-4′, 7-di-O-β-D-glucoside (5), genistein 4′,7-di-O-β-D-glucoside(6); 1 derivate of flavonoid: (+)-maackiain (7); 1 phenols: brevifolin (8); 1 diolefine: triacontane (9); 2 sterols:β-sitosterol (10),β-dauco -sterol(11); 1 cyclitol: sequoyitol(12); Among them, compound 5 is a new compound, named as Ammopiptanoside A, and compound 3、4、6、8、9、12 were isolated from the plants of this genus for the first time. 13compounds were isolated from the leaves of A. nanus alcohol extracts and 6 were determined, including 3 isoflavonoids: ononin(1)、daidzein4′,7-di-O-β-D-glucoside(2)、genistein4′,7-di-O-β-D-glucoside (3); 1benzoic acid glycoside: 4-O-β-D-glueopy ranosyloxy-benzoic acid (4); 1 phenylprop- anoid: syringin(5);1 cyclitol: sequoyitol(6); the above 6 compounds were isolated form A. nanus for the first time. A. mongolicus and A. nanus with high similarity in chemical constituents, and the contents of alkaloids in leaves of the two species are much more than twigs, which based on the TLC、LC-MS analysis.
Some of the compounds abtained from the plants of Ammopiptanthus showed bioactivities according to the documents: sequoyitol showed significant hypoglycemic effect, formononetin have an eminent hypolipidemic effect, ononin with bioactivities of antioxidant, maackiain showed excellent anti-inflammation and anti-tumor activity, brevifolin can protect hepar from acute and chronic injury, syringin is used for stoping bleeding and hepatic detoxing.
在抗糖尿病药物的前期活性筛选研究中发现蒙古沙冬青和新疆沙冬青的乙醇提取物具有良好的体内降血糖活性,为阐明其降血糖的有效成分,为抗糖尿病创新药物的研究与开发奠定基础,运用多种色谱技术、波谱和理化方法,对蒙古沙冬青枝的乙醇提取物和新疆沙冬青叶的乙醇提取物进行了较系统的化学成分研究。
从蒙古沙冬青枝的乙醇提取物中分离鉴定了12个化合物,包括:六个异黄酮及其苷类化合物:芒柄花素(1),芒柄花苷(2),isolupalbigenin (3),大豆苷元4′,7-二葡萄糖苷(4),沙冬青苷A(黄豆黄素4′, 7 -二葡萄糖苷,5),染料木素4′,7-二葡萄糖苷(6);1个黄酮类化合物的衍生物:(+)-maackiain (7);1个酚类化合物:短叶苏木酚(8);1个烷烃类化合物:正三十烷(9);两个甾醇及其苷类化合物:β-谷甾醇(10)、β-胡萝卜苷(11);1个环多醇类化合物:红杉醇(12);其中化合物5为新化合物,命名为沙冬青苷A(Ammopiptanoside A);化合物3、4、6、8、9、12为首次从该属植物中分离得到。从新疆沙冬青叶的乙醇提取物中分离得到13个化合物,鉴定了6个,包括3个异黄酮苷类化合物:芒柄花苷(1),大豆苷元4′,7-二葡萄糖苷(2),染料木素4′,7-二葡萄糖苷(3);1个苯甲酸苷类化合物:4-O-β-D-吡喃葡萄糖氧基苯甲酸(4);1个苯丙素类化合物:丁香苷(5);1个环多醇类化合物:红杉醇(6);这6个化合物均为首次从该种植物中分离得到。根据以上实验结果,结合TLC、LC-MS对该属两种植物的化学成分进行比较,结果显示两种植物的化学成分具有很大的相似性,叶中生物碱含量明显多于枝中。
经查阅文献,发现从该属植物中分离得到的红杉醇具有显著降血糖活性,芒柄花素降血脂功效显著,芒柄花苷具有抗氧化作用,maackiain具有较好的抗炎和抗肿瘤活性,短叶苏木酚对急慢性肝损伤有保护作用,丁香苷具有止血、抗肝毒的功效。
The genus Ammopiptanthus, a survivor of the evergreen broadleaf shrub in the central Asia desert from the Tertiary period, it belongs to the tribe Thermopsideae of the Leguminosae. Ammopiptanthus comprises two species, the one is Ammopiptanthus mongolicus (Maxim.) Cheng f., which is widely distributed in Mongolia, Ningxia and Gansu; the other is Ammopiptanthus nanus (Popov.) Cheng f., which is mainly distributed in Kizilsu Autonomous Prefecture in the southwest of Xinjiang province and neighboring central Asia.The aerial parts of Ammopiptanthus has been used as a folk medicine for the treatment of cough, congelation and chronic rheumatic arthritis, etc. Alkaloids and flavonoids are the characteristic chemical constituents of Ammopiptanthus, according to the literature.
The alcohol extracts of A. mongolicus and A. nanus showed significant hypoglycemic effect in the research of anti-diabetes drug selecting. In order to search for the hypoglycemic pricinples and to establish a foundation for researching and developing drugs that can prevent and cure diabetes, our work focused on the chemical constituents of Ammopiptanthus. Isolation and purification were carried out by various column chromatographic methods. The structures were elucidated on the basis of spectroscopic analysis and chemical methods as well.
In this thesis, 12 compounds were abtained from the twigs of A. mongolicus alcohol extracts, including 6 isoflavonoids: formononetin (1), ononin(2), isolupalb- igenin (3), daidzein 4′,7-di-O-β-D-glucoside (4), glycitein-4′, 7-di-O-β-D-glucoside (5), genistein 4′,7-di-O-β-D-glucoside(6); 1 derivate of flavonoid: (+)-maackiain (7); 1 phenols: brevifolin (8); 1 diolefine: triacontane (9); 2 sterols:β-sitosterol (10),β-dauco -sterol(11); 1 cyclitol: sequoyitol(12); Among them, compound 5 is a new compound, named as Ammopiptanoside A, and compound 3、4、6、8、9、12 were isolated from the plants of this genus for the first time. 13compounds were isolated from the leaves of A. nanus alcohol extracts and 6 were determined, including 3 isoflavonoids: ononin(1)、daidzein4′,7-di-O-β-D-glucoside(2)、genistein4′,7-di-O-β-D-glucoside (3); 1benzoic acid glycoside: 4-O-β-D-glueopy ranosyloxy-benzoic acid (4); 1 phenylprop- anoid: syringin(5);1 cyclitol: sequoyitol(6); the above 6 compounds were isolated form A. nanus for the first time. A. mongolicus and A. nanus with high similarity in chemical constituents, and the contents of alkaloids in leaves of the two species are much more than twigs, which based on the TLC、LC-MS analysis.
Some of the compounds abtained from the plants of Ammopiptanthus showed bioactivities according to the documents: sequoyitol showed significant hypoglycemic effect, formononetin have an eminent hypolipidemic effect, ononin with bioactivities of antioxidant, maackiain showed excellent anti-inflammation and anti-tumor activity, brevifolin can protect hepar from acute and chronic injury, syringin is used for stoping bleeding and hepatic detoxing.
引文
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