Ⅰ. 覆盆子活性成分研究 Ⅱ. 金雀根中二苯乙烯类成分的稳定性研究
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摘要
覆盆子(Rubus chingii Hu),即掌叶覆盆子,系蔷薇科(Rosaceae)悬钩子属植物,以其未成熟干燥果实为药用部位,具有补肾、固精、缩尿之功效,用于肾虚遗尿、小便频数、阳痿早泄、遗精滑精等。
经生物活性筛选,我们发现覆盆子的乙酸乙酯部位具有较强的植物雌激素样作用,氯仿部位具有较强的抑制NF-κB激活作用。本课题在这两种药理活性的指导下,对覆盆子活性部位的化学成分进行了系统分离。从活性部位共分离得到22个化合物,鉴定了其中的18个化合物:对羟基苯甲酸(R1),鞣花酸(112),邻苯二甲酸二丁酯(R3),邻苯二甲酸二(2-乙基己基)酯(R4),没食子酸乙酯(R5),香橙素(R6),山奈酚(R7),槲皮素(R8),槲皮苷(R9),陆地棉苷(R10),金丝桃苷(R11),椴树苷(R12),顺式椴树苷(R13),2.羟基喹啉-4-羧酸(R14),β-谷甾醇(R15),胡萝卜苷(R16),熊果酸(R17),齐墩果酸(R18)。其中,113～R6、R9、R13和R14是首次从该植物中分离得到。
从覆盆子乙酸乙酯部位分离得到的17个化合物中,有6个化合物对MCF-7细胞具有不同程度的促增殖活性。其中,陆地绵苷(R10)、金丝桃苷(R11)和熊果酸(R17)对MCF-7细胞均表现为高浓度抑制,低浓度促进增殖的作用;鞣花酸(R2)和2-羟基喹啉-4羧酸(R14)在较高浓度表现出促增殖作用。
从覆盆子氯仿部位分离到熊果酸(R17)和齐敦果酸(R18)两个活性化合物,其抑制NF-κB激活作用的IC_(50)值分别为5.79μg/mL和6.23μg/mL。
2.羟基喹啉-4-羧酸(R14)是植物中较少报道的一个化学成分,且具有一定的植物雌激素活性。为此,我们使用毛细管电泳电化学检测(CE-ED)方法对8个不同产地的覆盆子样品中该化合物的含量进行了测定,结果显示8个样品中都含有该化合物,说明该化合物可以作为覆盆子的标识性成分,但不同产地间的含量存在一定差异。
此外,我们使用GC-MS法对覆盆子水溶性部位的有机酸类成分进行了研究,鉴定出9种有机酸成分。
覆盆子根的化学成分研究未见文献报道,我们的初步研究发现其富含三萜类化合物。从中分离得到7个化合物,鉴定了其中的5个:β-谷甾醇(R15),胡萝卜苷(R16),熊果酸(R17),蔷薇酸(R19),11α-羟基蔷薇酸(R20)。R20是首次从该植物中分离得到。
金雀根为豆科植物锦鸡儿Caragana sinica(Buc'hoz)Rehd.的根或根皮,在民间主要用于治疗虚损劳热、咳嗽、高血压、关节痛风、跌打损伤等。研究发现金雀根乙醇浸膏的乙酸乙酯部位的主要化学成分是二苯乙烯类化合物,具有多样的生物活性。其中含量最高的3个化合物是kobophenol A(1)、carasinol B(2)和(+)-α-viniferin(3)。药理实验表明这些化合物具有刺激成骨细胞增殖活性,是治疗原发性骨质疏松的有效成分。但是,金雀根原药材或金雀根浸膏在放置的过程中,包括kobophenol A(1)在内的一些二苯乙烯类成分的含量会发生变化,这对于保证药品的质量有很大影响。
为了研究二苯乙烯类低聚体的稳定性以及结构改变的可行性,本文考察了酸、碱、光、热等条件对kobophenol A(1)、carasinol B(2)和(+)-α-viniferin(3)的稳定性的影响。研究发现:3个化合物对碱和光不敏感,对酸和热较为敏感;kobophenol A(1)在加热和盐酸作用下能高比例地转化生成carasinol B(2),后者在同样条件下能转化生成carasinol D(4),延长kobophenol A(1)的反应时间,同样能生成carasinol D(4);(+)-α-viniferin(3)在盐酸作用下能较高比例地转化生成caragaphenol A(5)和一个新化合物caragaphenol B(6)。
The unripe fruits of Rubus chingii Hu(Rosaceae),referring to "Fu-pen-zi" in Chinese, have been used in China as a tonic medicine.
The pharmacological studies indicated the EtOAc soluble fraction of the crude extract of the Rubus chingii has a strong phytoestrogenic activity and chloroform soluble fraction has a strong activity in inhibiting TNF-α-induced NF-κB activation.
Thus,chromatographic separations of the two fractions of Rubus chingii were carried out under the guide of bio-assay in vitro respectively.22 pure compounds were isolated and 18 of them were determined using various modern spectroscopic analysis and chemical methods:p-hydroxybenzoic acid(R1),ellagic acid(R2),di-n-butyl phthalate (R3),di(2-ethylhexyl)phthalate(R4),ethyl gallate(R5),aromadendrin(R6),kaempferol (R7),quercetin(R8),quercitrin(R9),hirsutrin(R10),hyperin(R11),tiliroside(R12), cis-tiliroside(R13),2-hydroxyquinoline-4-carboxylic acid(R14),β-sitosterol(R15), daucosterol(R16),ursolic acid(R17),oleanolic acid(R18).Among them,R3～R6、R9、R13 and R14 were isolated from this plant for the fisrt time.
Among 17 compounds isolated from EtOAc fraction,6 compounds can stimulate the proliferation of MCF-7 cells.Hirsutrin(R10),hyperin(R11) and ursolic acid(R17) can stimulate the proliferation of cells in lower concentrations and show inhibitory activity in higher concentrations.Ellagic acid(R2) and 2-hydroxyquinoline-4-carboxylic acid(R14) can stimulate the proliferation of MCF-7 cells in higher concentrations.
From chloroform fraction,two active compounds ursolic acid(R17) and oleanolic acid(R18) were isolated.They can inhibit TNF-α-induced NF-κB activation with IC_(50) values 5.79μg/mL and 6.23μg/mL,respectively.
2-Hydroxyquinoline-4-carboxylic acid(R14),an unfrequent alkaloid in the plants, shows moderate phytoestrogenic activity in MCF-7 bio-assay.A capillary electrophoresis with electrochemical detection(CE-ED) method has been established to determine it in 8 Rubus chingii fruit samples collected from 8 different places.The result shows that R14 exists in all samples but varies in concentration.
A GC-MS method had been established to study organic acids of the water-soluble fraction of crude extract.9 organic acids were determined.
Primary study of chemical consistents of the roots of Rubus chingii Hu reveals that they are rich in triterpenoids.7 compounds were isolated and 5 of them were determined:β-sitosterol(R15),daucosterol(R16),ursolic acid(R17),euscaphic acid(R19) and 11α-euscaphic acid(R20).R20 was isolated from this plant for the fisrt time.
The roots of Caragana sinica(Buc'hoz) Rehd.(Chinese name:Jinquegen) have been used in China as a folk medicine for the treatment of asthenia syndrome,vascular hypertension,leukorrhagia,bruises and contused wounds.In our previous study,we found that the EtOAc extract of the roots contained many oligostilbenes which had multifaceted bioactivities.The major stilbenoids are kobophenol A(1),carasinol B(2) and (+)-α-viniferin(3).They can stimulate the proliferation of osteoblasts and have been developed as a type of medicine for the treatment of osteoporosis.During previous studies,the content of some stilbenoids including 1 would change in the plant materials and extracts when stored as an alcohol syrup.This instability caused great difficulties for the quality control of this traditional Chinese herb medicine.
In order to inspect the stability of oligostilbenes and feasibility of their structure modification,we studied kobophenol A(1),carasinol B(2) and(+)-α-viniferin(3) under different conditions with acid,base,light and hot,respectively.The result indicated that all 3 compounds are stable under base or light condition but unstable in acid and hot condition.Kobophenol A(1) can convert to carasinoi B(2) with a high proportion when refluxing in a hydrochloric acid solution and carasinol B(2) can convert to carasinol D(4) with a moderate proportion in the same condition.Kobophenol A also can convert to carasinol D when prolonging the reaction time.(+)-α-Viniferin(3) is also unstable when refluxing in a hydrochloric acid solution:it can convert with a high proportion to caragaphenol A(5) and a new stilbene caragaphenol B(6).
经生物活性筛选,我们发现覆盆子的乙酸乙酯部位具有较强的植物雌激素样作用,氯仿部位具有较强的抑制NF-κB激活作用。本课题在这两种药理活性的指导下,对覆盆子活性部位的化学成分进行了系统分离。从活性部位共分离得到22个化合物,鉴定了其中的18个化合物:对羟基苯甲酸(R1),鞣花酸(112),邻苯二甲酸二丁酯(R3),邻苯二甲酸二(2-乙基己基)酯(R4),没食子酸乙酯(R5),香橙素(R6),山奈酚(R7),槲皮素(R8),槲皮苷(R9),陆地棉苷(R10),金丝桃苷(R11),椴树苷(R12),顺式椴树苷(R13),2.羟基喹啉-4-羧酸(R14),β-谷甾醇(R15),胡萝卜苷(R16),熊果酸(R17),齐墩果酸(R18)。其中,113～R6、R9、R13和R14是首次从该植物中分离得到。
从覆盆子乙酸乙酯部位分离得到的17个化合物中,有6个化合物对MCF-7细胞具有不同程度的促增殖活性。其中,陆地绵苷(R10)、金丝桃苷(R11)和熊果酸(R17)对MCF-7细胞均表现为高浓度抑制,低浓度促进增殖的作用;鞣花酸(R2)和2-羟基喹啉-4羧酸(R14)在较高浓度表现出促增殖作用。
从覆盆子氯仿部位分离到熊果酸(R17)和齐敦果酸(R18)两个活性化合物,其抑制NF-κB激活作用的IC_(50)值分别为5.79μg/mL和6.23μg/mL。
2.羟基喹啉-4-羧酸(R14)是植物中较少报道的一个化学成分,且具有一定的植物雌激素活性。为此,我们使用毛细管电泳电化学检测(CE-ED)方法对8个不同产地的覆盆子样品中该化合物的含量进行了测定,结果显示8个样品中都含有该化合物,说明该化合物可以作为覆盆子的标识性成分,但不同产地间的含量存在一定差异。
此外,我们使用GC-MS法对覆盆子水溶性部位的有机酸类成分进行了研究,鉴定出9种有机酸成分。
覆盆子根的化学成分研究未见文献报道,我们的初步研究发现其富含三萜类化合物。从中分离得到7个化合物,鉴定了其中的5个:β-谷甾醇(R15),胡萝卜苷(R16),熊果酸(R17),蔷薇酸(R19),11α-羟基蔷薇酸(R20)。R20是首次从该植物中分离得到。
金雀根为豆科植物锦鸡儿Caragana sinica(Buc'hoz)Rehd.的根或根皮,在民间主要用于治疗虚损劳热、咳嗽、高血压、关节痛风、跌打损伤等。研究发现金雀根乙醇浸膏的乙酸乙酯部位的主要化学成分是二苯乙烯类化合物,具有多样的生物活性。其中含量最高的3个化合物是kobophenol A(1)、carasinol B(2)和(+)-α-viniferin(3)。药理实验表明这些化合物具有刺激成骨细胞增殖活性,是治疗原发性骨质疏松的有效成分。但是,金雀根原药材或金雀根浸膏在放置的过程中,包括kobophenol A(1)在内的一些二苯乙烯类成分的含量会发生变化,这对于保证药品的质量有很大影响。
为了研究二苯乙烯类低聚体的稳定性以及结构改变的可行性,本文考察了酸、碱、光、热等条件对kobophenol A(1)、carasinol B(2)和(+)-α-viniferin(3)的稳定性的影响。研究发现:3个化合物对碱和光不敏感,对酸和热较为敏感;kobophenol A(1)在加热和盐酸作用下能高比例地转化生成carasinol B(2),后者在同样条件下能转化生成carasinol D(4),延长kobophenol A(1)的反应时间,同样能生成carasinol D(4);(+)-α-viniferin(3)在盐酸作用下能较高比例地转化生成caragaphenol A(5)和一个新化合物caragaphenol B(6)。
The unripe fruits of Rubus chingii Hu(Rosaceae),referring to "Fu-pen-zi" in Chinese, have been used in China as a tonic medicine.
The pharmacological studies indicated the EtOAc soluble fraction of the crude extract of the Rubus chingii has a strong phytoestrogenic activity and chloroform soluble fraction has a strong activity in inhibiting TNF-α-induced NF-κB activation.
Thus,chromatographic separations of the two fractions of Rubus chingii were carried out under the guide of bio-assay in vitro respectively.22 pure compounds were isolated and 18 of them were determined using various modern spectroscopic analysis and chemical methods:p-hydroxybenzoic acid(R1),ellagic acid(R2),di-n-butyl phthalate (R3),di(2-ethylhexyl)phthalate(R4),ethyl gallate(R5),aromadendrin(R6),kaempferol (R7),quercetin(R8),quercitrin(R9),hirsutrin(R10),hyperin(R11),tiliroside(R12), cis-tiliroside(R13),2-hydroxyquinoline-4-carboxylic acid(R14),β-sitosterol(R15), daucosterol(R16),ursolic acid(R17),oleanolic acid(R18).Among them,R3～R6、R9、R13 and R14 were isolated from this plant for the fisrt time.
Among 17 compounds isolated from EtOAc fraction,6 compounds can stimulate the proliferation of MCF-7 cells.Hirsutrin(R10),hyperin(R11) and ursolic acid(R17) can stimulate the proliferation of cells in lower concentrations and show inhibitory activity in higher concentrations.Ellagic acid(R2) and 2-hydroxyquinoline-4-carboxylic acid(R14) can stimulate the proliferation of MCF-7 cells in higher concentrations.
From chloroform fraction,two active compounds ursolic acid(R17) and oleanolic acid(R18) were isolated.They can inhibit TNF-α-induced NF-κB activation with IC_(50) values 5.79μg/mL and 6.23μg/mL,respectively.
2-Hydroxyquinoline-4-carboxylic acid(R14),an unfrequent alkaloid in the plants, shows moderate phytoestrogenic activity in MCF-7 bio-assay.A capillary electrophoresis with electrochemical detection(CE-ED) method has been established to determine it in 8 Rubus chingii fruit samples collected from 8 different places.The result shows that R14 exists in all samples but varies in concentration.
A GC-MS method had been established to study organic acids of the water-soluble fraction of crude extract.9 organic acids were determined.
Primary study of chemical consistents of the roots of Rubus chingii Hu reveals that they are rich in triterpenoids.7 compounds were isolated and 5 of them were determined:β-sitosterol(R15),daucosterol(R16),ursolic acid(R17),euscaphic acid(R19) and 11α-euscaphic acid(R20).R20 was isolated from this plant for the fisrt time.
The roots of Caragana sinica(Buc'hoz) Rehd.(Chinese name:Jinquegen) have been used in China as a folk medicine for the treatment of asthenia syndrome,vascular hypertension,leukorrhagia,bruises and contused wounds.In our previous study,we found that the EtOAc extract of the roots contained many oligostilbenes which had multifaceted bioactivities.The major stilbenoids are kobophenol A(1),carasinol B(2) and (+)-α-viniferin(3).They can stimulate the proliferation of osteoblasts and have been developed as a type of medicine for the treatment of osteoporosis.During previous studies,the content of some stilbenoids including 1 would change in the plant materials and extracts when stored as an alcohol syrup.This instability caused great difficulties for the quality control of this traditional Chinese herb medicine.
In order to inspect the stability of oligostilbenes and feasibility of their structure modification,we studied kobophenol A(1),carasinol B(2) and(+)-α-viniferin(3) under different conditions with acid,base,light and hot,respectively.The result indicated that all 3 compounds are stable under base or light condition but unstable in acid and hot condition.Kobophenol A(1) can convert to carasinoi B(2) with a high proportion when refluxing in a hydrochloric acid solution and carasinol B(2) can convert to carasinol D(4) with a moderate proportion in the same condition.Kobophenol A also can convert to carasinol D when prolonging the reaction time.(+)-α-Viniferin(3) is also unstable when refluxing in a hydrochloric acid solution:it can convert with a high proportion to caragaphenol A(5) and a new stilbene caragaphenol B(6).
引文
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