大叶匙羹藤的化学成分研究
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摘要
中草药是我国医药学的宝库,也是活性天然产物的重要来源之一。为了从中挖掘类型多样、结构新颖独特的活性化合物,以及为化学合成和创新药物提供纯导化合物,本论文对采白云南勐仑县的特有植物大叶匙羹藤茎枝采用活性指导分离的思想对其化学成分进行了系统研究；并根据其民间药用特点和同属植物成分的活性报道,在抗炎、肝保护、降血糖和抗肿瘤等药理模型上,对分离鉴定的主要成分进行了初步活性筛选。大叶匙羹藤(Gymnema tingens Spreng)为萝藦科(Asclepiadaceae)匙羹藤属(Gymnema)植物,主产于广东、广西、福建、云南和台湾等地。全株可药用,性平,味苦,有祛风止痛,生肌消肿之功效,在云南民间用于治疗肿瘤、解虐和降血糖、小儿麻痹病、肺结核、风湿痛。然而,其药用物质基础至今并不明确。迄今为止,尚未见对该匙羹藤进行系统化学成分研究的报道。
根据大叶匙羹藤的民间药用特点及相关文献报道,首先对其粗提物进行多药理模型的活性筛选。研究发现其乙酸乙酯部位有较强的抗炎作用,而正丁醇部分具有较显著的肝保护活性。因而本文重点对这两个活性部位进行化学成分研究。利用现代多种色谱学方法、波谱学技术(如NMR, IR, MS, UV, CD)和化学方法从该活性部位中分离并鉴定了80(1-80)个化合物,其中酚苷类成分14个,苯并呋喃类2个,木脂素类27个,萜类和甾体类15个,芳香族化合物12个,其他类10个。其中8个为新化合物(1*-8*),包括6个酚苷(1*-6*),2个苯并呋喃类化合物(7*-8*)。此外,13个化合物11,18,22,28,35,37,39,41,48,49,51,71,72经鉴定为新天然产物。以上所有化合物均为首次从该种中分离得到,其结构和名称见下表。
同时本文对所分得的单体化合物在多种药理模型上进行活性筛选,包括抗炎、肝保护、神经保护、降血糖、抗肿瘤等。结果表明：化合物46在10μM浓度下具有抑制小鼠腹腔巨噬细胞NO生成的活性,抑制率为81.8%;化合物1*,5*-8*,11,31,33,54,67和72在10μM浓度下具有肝保护活性,与模型组比较有显著性差异。此外,化合物15对MPP+损伤的神经细胞有保护作用,化合物12,40,41,42,45,48对LPS诱导BV2细胞NO产生有抑制作用。所有化合物均没有明显降糖和细胞毒活性。
本论文对_大叶匙羹藤进行了较系统的化学成分研究,初步阐明了其次生代谢产物的结构特征,丰富了该属植物的结构多样性及新颖性,为该属植物的化学分类学提供了一定的依据。通过对代谢产物进行多模型药理活性筛选,获得了数个具有抗炎、保肝以及神经保护作用的活性化合物,为其民间药用提供了初步的物质基础,也为研发治疗相关疾病的药物提供了一些参考。
Chinese herbal medicine, a national treasure, is one of the most important sources of bioactive natural products. Due to the large geographic diversity and the resulting diverse ecosystem, the resources of herbal plants are enormous in China. As part of our projects in searching bioactive compounds from herbal medicine, a medicinal plant Gymnema tingens Spreng was collected from Menglun country, Yunnan province. This plant was reported to have various applications in folkloric medicine, for example, as antitumor and antimalaria remedy. The current study aims to report the phytochemical investigation of G. tingens as well as the biological activities of the isolated compounds. G. tingens Spreng belongs to the genus Gymnema (Asclepiadaceae family), which is mainly distributed in Guangdong, Guangxi, FuJian, Yunnan and Taiwan Provinces. Several plants of this genus have long been used for the treatment of tumors, malaria and hyperglycemia in China. However, little is known about their bioactive substances. So far, no chemical investigation of G. tingens has been reported.
In the present study, the crude extract of G. tingens was evaluated for its biological activities on several biological targets that were selected based on the medical usage of this plant. In the preliminary assays, the EtOAc extract showed potent anti-inflammatory effect, and the BuOH extract displayed significant hepatoprotective activity. By using various chromatographic techniques,80compounds (see Figure1) were isolated from these two extracts. The structures of the isolated compounds were unambiguously determined by various spectroscopic and chemical methods including NMR, IR, MS, UV and CD. These compounds were classified according to their structural features, which include14phenolic glycosides,2benzofurans,27lignans,15triterpenoids and steroids,12benzene and its derivatives, and10other compounds. Among them,8compounds were identified as new compounds (1*-8*), including6phenolic glycosides (1*-6*), and2rare benzofuran compounds (7*-8*). In addition,13compounds (11,18,22,28,35,37,39,41,48,49,51,71,72) were determined as new natural products that had not been previously reported from natural resources. Furthermore, all compounds were isolated from this plant for the first time.
The isolated compounds were evaluated for their anti-inflammatory, hepatoprotective, neuroprotective, hypoglycemic, and cytotoxic effects. Compound46showed inhibition activity against the mouse peritoneal macrophages NO production (inhibition rate:81.8%) at a concentration of10μM. While compounds1*,5*-8*,11,31,33,54,67and72exhibited potent hepatoprotective activities at10μM, compared to the positive control. In addition, compound15displayed neuroprotective effect against MPP+injured nerve cells. Compounds12,40,41,42,45and48on LPS-induced BV2cells NO production was inhibited. However, none of them was active in the hypoglycemic and cytotoxic assays.
In summary, we have performed a systematically chemical investigation of the titled plant, which resulted in the isolation of80compounds, thus enriching the structural diversity of the genus Gymnema. The chemical profile of G. tingens is presented here for the first time, which may be valuable to the chemical taxonomy. In addition, several compounds were found to have anti-inflammatory, hepatoprotective and neuroprotective effects, which could serve as starting points for the development of drugs to treat relevant diseases.
根据大叶匙羹藤的民间药用特点及相关文献报道,首先对其粗提物进行多药理模型的活性筛选。研究发现其乙酸乙酯部位有较强的抗炎作用,而正丁醇部分具有较显著的肝保护活性。因而本文重点对这两个活性部位进行化学成分研究。利用现代多种色谱学方法、波谱学技术(如NMR, IR, MS, UV, CD)和化学方法从该活性部位中分离并鉴定了80(1-80)个化合物,其中酚苷类成分14个,苯并呋喃类2个,木脂素类27个,萜类和甾体类15个,芳香族化合物12个,其他类10个。其中8个为新化合物(1*-8*),包括6个酚苷(1*-6*),2个苯并呋喃类化合物(7*-8*)。此外,13个化合物11,18,22,28,35,37,39,41,48,49,51,71,72经鉴定为新天然产物。以上所有化合物均为首次从该种中分离得到,其结构和名称见下表。
同时本文对所分得的单体化合物在多种药理模型上进行活性筛选,包括抗炎、肝保护、神经保护、降血糖、抗肿瘤等。结果表明：化合物46在10μM浓度下具有抑制小鼠腹腔巨噬细胞NO生成的活性,抑制率为81.8%;化合物1*,5*-8*,11,31,33,54,67和72在10μM浓度下具有肝保护活性,与模型组比较有显著性差异。此外,化合物15对MPP+损伤的神经细胞有保护作用,化合物12,40,41,42,45,48对LPS诱导BV2细胞NO产生有抑制作用。所有化合物均没有明显降糖和细胞毒活性。
本论文对_大叶匙羹藤进行了较系统的化学成分研究,初步阐明了其次生代谢产物的结构特征,丰富了该属植物的结构多样性及新颖性,为该属植物的化学分类学提供了一定的依据。通过对代谢产物进行多模型药理活性筛选,获得了数个具有抗炎、保肝以及神经保护作用的活性化合物,为其民间药用提供了初步的物质基础,也为研发治疗相关疾病的药物提供了一些参考。
Chinese herbal medicine, a national treasure, is one of the most important sources of bioactive natural products. Due to the large geographic diversity and the resulting diverse ecosystem, the resources of herbal plants are enormous in China. As part of our projects in searching bioactive compounds from herbal medicine, a medicinal plant Gymnema tingens Spreng was collected from Menglun country, Yunnan province. This plant was reported to have various applications in folkloric medicine, for example, as antitumor and antimalaria remedy. The current study aims to report the phytochemical investigation of G. tingens as well as the biological activities of the isolated compounds. G. tingens Spreng belongs to the genus Gymnema (Asclepiadaceae family), which is mainly distributed in Guangdong, Guangxi, FuJian, Yunnan and Taiwan Provinces. Several plants of this genus have long been used for the treatment of tumors, malaria and hyperglycemia in China. However, little is known about their bioactive substances. So far, no chemical investigation of G. tingens has been reported.
In the present study, the crude extract of G. tingens was evaluated for its biological activities on several biological targets that were selected based on the medical usage of this plant. In the preliminary assays, the EtOAc extract showed potent anti-inflammatory effect, and the BuOH extract displayed significant hepatoprotective activity. By using various chromatographic techniques,80compounds (see Figure1) were isolated from these two extracts. The structures of the isolated compounds were unambiguously determined by various spectroscopic and chemical methods including NMR, IR, MS, UV and CD. These compounds were classified according to their structural features, which include14phenolic glycosides,2benzofurans,27lignans,15triterpenoids and steroids,12benzene and its derivatives, and10other compounds. Among them,8compounds were identified as new compounds (1*-8*), including6phenolic glycosides (1*-6*), and2rare benzofuran compounds (7*-8*). In addition,13compounds (11,18,22,28,35,37,39,41,48,49,51,71,72) were determined as new natural products that had not been previously reported from natural resources. Furthermore, all compounds were isolated from this plant for the first time.
The isolated compounds were evaluated for their anti-inflammatory, hepatoprotective, neuroprotective, hypoglycemic, and cytotoxic effects. Compound46showed inhibition activity against the mouse peritoneal macrophages NO production (inhibition rate:81.8%) at a concentration of10μM. While compounds1*,5*-8*,11,31,33,54,67and72exhibited potent hepatoprotective activities at10μM, compared to the positive control. In addition, compound15displayed neuroprotective effect against MPP+injured nerve cells. Compounds12,40,41,42,45and48on LPS-induced BV2cells NO production was inhibited. However, none of them was active in the hypoglycemic and cytotoxic assays.
In summary, we have performed a systematically chemical investigation of the titled plant, which resulted in the isolation of80compounds, thus enriching the structural diversity of the genus Gymnema. The chemical profile of G. tingens is presented here for the first time, which may be valuable to the chemical taxonomy. In addition, several compounds were found to have anti-inflammatory, hepatoprotective and neuroprotective effects, which could serve as starting points for the development of drugs to treat relevant diseases.
引文
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