中华抱茎蓼次生代谢产物及其生物活性研究
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摘要
中药中华抱茎蓼(俗称血三七)为蓼科蓼属中华抱茎蓼(Polygonum amplexicaule D. Don var.sinense Forbes et Hemsl.)的干燥根茎,是湖北省恩施地区少数民族民间常用药材,具有清热解毒,活血化瘀的作用,用于治疗许多疾病,如促进血液循环,治疗各种骨折等,在当地被称为跌打损伤的“要药”。现临床证实其还能抗真菌、治疗脑动脉粥样硬化及妇女痛经等疾病。除药效确切外,血三七资源分布也很广泛:既有大量野生的,也有大量家种的。但到目前为止,人们对其研究仍然比较零星,尚缺乏系统性,阻碍了血三七的广泛应用。为此,本研究对血三七次生代谢产物进行了提取分离、结构鉴定和生物活性筛选,并对不同产地的血三七进行定性和定量指纹图谱分析研究,为制定该药材完善的质量标准提供了科学依据。在此基础上,利用现代药理学手段对血三七抗真菌活性、促骨折愈合作用机理及镇痛等不同药效进行了验证研究,为将来开发新药提供科学依据。本研究的主要工作及创新点如下:
(1)采用各种色谱技术,包括薄层色谱、正相硅胶柱、反向硅胶柱、葡聚糖凝胶柱、半制备高效液相柱,对血三七乙酸乙酯部位的化学成分进行了系统分离研究,获得40余个单体化合物;运用现代波谱技术(如UV、IR、1H-NMR、13C-NMR、DEPT、EI-MS)分析其结构,最终鉴定了23个化合物,其中20个化合物系首次从该植物中分离得到,更有5个是首次从蓼属中分离获得,且多数为黄酮类和蒽醌类化合物,具有较强药理活性。
(2)鉴于目前尚无血三七质量标准,在化学研究的基础上,首次采用高效液相色谱法(HPLC法)对9个不同产地的血三七进行了指纹图谱研究,结果证实不同来源血三七的特征指纹图谱具有较高相似性,其相似度均在90%以上,尚存一些细小差异。这种结果符合中药指纹图谱质量要求。因此,该方法的建立不仅为鉴别不同产地血三七提供了依据,而且为该药材质量标准制定提供了科学依据。
(3)采用体外实验对血三七抗菌活性进行了初步筛选研究。利用药敏纸片法检测了血三七粗提物的乙酸乙酯、正丁醇部位的抗真菌活性;用琼脂稀释法测定血三七抗真菌活性的最小抑菌浓度;利用平板法,考察了光照、温度、pH值对其抗菌活性的影响。结果表明血三七具有良好的抗真菌效果,且药效稳定,受外界因素干扰小,特别是极性较大的正丁醇部位,只需0.013 mg/mL就可显示出较强抑菌效果。
(4)采用体外细胞模型,对血三七总提物、石油醚部位、乙酸乙酯部位、正丁醇部位、水部位提取物及从乙酸乙酯部位分离得到的化合物Emodin-8-O-β-D-glucoside (EG)进行了促骨折愈合机理研究。以MC3T3-E1细胞系及从小鼠头盖骨分离得到的成骨细胞为模型,以CCK-8法检测成骨细胞增殖,流式细胞术检测细胞增殖周期,ELISA法检测碱性磷酸酶(ALP)活性、前列腺素E2 (PGE2)的含量。结果显示,低剂量的总提物(0.1-100μg/mL)及各提取部位(0.1-100μg/mL)和化合物(0.1-100 ng/mL)均能促进成骨细胞增殖和DNA合成:总提物和各部位作用下的S期比例从9.78%增加到27.29%,而化合物则是从16.34%增加到32.16%。这说明血三七促进成骨细胞增殖是通过促进细胞S期比例来实现的。同时,各提取物及化合物EG对成骨细胞分化均有一定作用,且呈剂量依赖关系。需特别指出的是,化合物EG不仅具有良好的细胞增殖效果,而且能显著促进成骨细胞分化,这种作用主要体现在增加成骨细胞ALP的活性和降低PGE2的含量上。上述结果表明血三七促进骨折愈合的机理是:血三七直接刺激成骨细胞的增殖和分化,化合物EG是实现这种活性的主要物质基础。
(5)采用体内实验对血三七的镇痛活性进行了验证。通过小鼠热板法和醋酸所致小鼠扭体法,对血三七总提物、石油醚部位、乙酸乙酯部位、正丁醇部位及水部位的高、中、低三个剂量组进行了实验。结果发现,三种浓度的上述血三七各提取物均可使热板所致小鼠舔足的痛阈值显著提高(p<0.05),使醋酸所致小鼠扭体次数显著减少(p<0.01),且水部位和正丁醇部位镇痛效果要好于总提物、石油醚部位及乙酸乙酯部位。
Traditional Chinese medicine Xuesanqi is the root tuber of Polygonum amplexicaule D. Don var. sinense Forb. It is the commonly used raw material for medicine among Enshi minorities in Hubei Province. It has many medical functions, such as improving blood circulation, maintaining normal menstrual flow, and curing various fractures, muscle injuries or pain from tissue swelling. Especially, Xuesanqi has been demonstrated to be an effective herb to treat rheumatism, atherosclerosis and to have antifungal activity. In addition, its distribution is very wide, there are a large number of wild and home-grown Xuesanqi in China. However, so far, there are sporadic studies about it, and lacks systematical research, which block its further applications. Therefore, the objective of the study is to isolate and identify its most effective compounds by various chromatographic techniques and to set up fingerprints of Xuesanqi from different areas in order to provide an academic basis for the scientific evaluation of the quality of Xuesanqi. On this basis, by means of modern pharmacological methods, it was tried to prove its different medical effects, including antifugal activity, mechanism of promoting the healing of bone fractures, and analgesic activity, etc, which would provide the scientific basis of developing new drug in the future.
The main work and its innovations of this research are listed below:
(1) Such chromatographic techniques, including TCL, normal-phase silica gel column, reverse-phase silica gel column, polydextran gel and semi-preparative high performance liquid colum were employed in this study. About 40 compounds were obtained by the above chromatographic techniques from EtOAc fraction of Xueshaqi. By means of modern spectroscopic methods (e.g. UV, IR, 1H-NMR, 13C-NMR, DEPT, EI-MS), 23 compounds were finally identified. Among them, 20 compounds were isolated for the first time from this plant. Moreover, 5 compounds were first obtained from Polygonaceae. A majority of these compounds belong to flavonoids and anthraquinones, which show great pharmacological activity.
(2) Since the quality standards of Xuesanqi have not been established by now, on the basis of its chemical composition analysis, the fingerprints were set up by HPLC for the flavonoids of Xuesanqi from nine different regions. A total of 11 peaks were found, and their relative retention time and relative peak area ratio of the scope were determined. The results showed that each fingerprint of P. amplexicaule exhibited 90% of similarity despite of their different origin. Thus, the results met the quality requirements of fingerprint. The establishment of this method not only can help to identify Xuesanqi from different localities, but also can provide scientific evidence to formulate the quality standards of Xuesanqi.
(3) The anti-fungal activity of secondary metabolites from Xuesanqi has been studied for the first time. Susceptibility disk assay was adopted to test the anti-fungal activity of ethyl acetate fraction and n-butanol fraction from Xuesanqi. In addition, its minimum inhibitory concentration was measured by agar dilution method and the effects of light, temperature, pH on its antifungal activity were examined by plate method. The results showed that the secondary metabolites of Xuesanqi had significant anti-fungal activity on pathogenic fungi and the deep drug-resistant strains. Its anti-fungal activity was rather stable and could not be easily interfered by the environmental factors, such as light, temperature, etc. Compared with ethyl acetate fraction, n-butanol fraction had better anti-fungal activity, even 0.013mg/ml n-butanol fraction showed strong anti-fungal effect.
(4) To investigate Xuesanqi’s pharmacological mechanism of promoting the healing of bone fractures in vitro, MC3T3-E1 cell line and osteoblasts from skull bones of mice were established to test the biological functions of the total extracts from Xuesanqi, petroleum ether fraction extracts, ethylacetate fraction extracts, n-butanol fraction extracts, water fraction and compound emodin-8-O-β-D-glucoside (EG) from ethylacetate fraction extracts. CCK-8 assay, PI staining and FACS were used to examine cell proliferation and cell cycle. The expression of alkaline phosphatase (ALP) and the content of prostaglandin E2 (PGE2) were detected by enzyme-linked immunosorbent assay (ELISA). The results of cell proliferation showed that 0.1-100μg/mL dose of total extracts, fraction extracts and compound from Xuesanqi could stimulate cell proliferation significantly (p<0.05). Total extracts and fraction extracts could increase the proportion S-phase of cells from 9.78 to 27.29%. Compound emodin-8-O-β--D-glucoside (EG) could increase the proportion S-phase of cells from 16.34% to 32.16%. Simultaneously, each extraction and compound EG had showed certain effects on the differentiation of osteoblasts, and exhibited a marked dosage dependent relationship. Especially, EG increased alkaline phosphatase (ALP) expression in MC3T3-E1 cells (0.1-100 ng/mL, p<0.01) and inhibited PGE2 production induced by TNF-αin osteoblasts (10-100 ng/mL). All the above results suggest that the mechanism of Xuesanqi to promote the healing of bone rheumatism and various fractures is that Xuesanqi directly stimulates the proliferation and differentiation of osteoblasts, and compound EG contributes most to these activities.
(5) It was for the first time to investigate the analgesic activity of Xuesanqi in vivo. Hot- plate model and the acetic acid writhing test were adopted among the low, middle and high dosage groups from ethanol extracts, petroleum ether fraction extract, ethylacetate fraction extract, n-butanol fraction extract and water fraction, respectively. The results showed that 0.4 mg/mL, 0.8 mg/mL, 1.6 mg/mL dose of all extracts could significantly increase the pain threshold of licking hot-plate in mice (p<0.05) and markedly reduced the times of writhing induced by acetic acid (p<0.01). Moreover, the analgesic activity of water fraction and n-butanol fraction were much better than ethanol extracts, petroleum ether fraction extract, ethylacetate fraction extract.
(1)采用各种色谱技术,包括薄层色谱、正相硅胶柱、反向硅胶柱、葡聚糖凝胶柱、半制备高效液相柱,对血三七乙酸乙酯部位的化学成分进行了系统分离研究,获得40余个单体化合物;运用现代波谱技术(如UV、IR、1H-NMR、13C-NMR、DEPT、EI-MS)分析其结构,最终鉴定了23个化合物,其中20个化合物系首次从该植物中分离得到,更有5个是首次从蓼属中分离获得,且多数为黄酮类和蒽醌类化合物,具有较强药理活性。
(2)鉴于目前尚无血三七质量标准,在化学研究的基础上,首次采用高效液相色谱法(HPLC法)对9个不同产地的血三七进行了指纹图谱研究,结果证实不同来源血三七的特征指纹图谱具有较高相似性,其相似度均在90%以上,尚存一些细小差异。这种结果符合中药指纹图谱质量要求。因此,该方法的建立不仅为鉴别不同产地血三七提供了依据,而且为该药材质量标准制定提供了科学依据。
(3)采用体外实验对血三七抗菌活性进行了初步筛选研究。利用药敏纸片法检测了血三七粗提物的乙酸乙酯、正丁醇部位的抗真菌活性;用琼脂稀释法测定血三七抗真菌活性的最小抑菌浓度;利用平板法,考察了光照、温度、pH值对其抗菌活性的影响。结果表明血三七具有良好的抗真菌效果,且药效稳定,受外界因素干扰小,特别是极性较大的正丁醇部位,只需0.013 mg/mL就可显示出较强抑菌效果。
(4)采用体外细胞模型,对血三七总提物、石油醚部位、乙酸乙酯部位、正丁醇部位、水部位提取物及从乙酸乙酯部位分离得到的化合物Emodin-8-O-β-D-glucoside (EG)进行了促骨折愈合机理研究。以MC3T3-E1细胞系及从小鼠头盖骨分离得到的成骨细胞为模型,以CCK-8法检测成骨细胞增殖,流式细胞术检测细胞增殖周期,ELISA法检测碱性磷酸酶(ALP)活性、前列腺素E2 (PGE2)的含量。结果显示,低剂量的总提物(0.1-100μg/mL)及各提取部位(0.1-100μg/mL)和化合物(0.1-100 ng/mL)均能促进成骨细胞增殖和DNA合成:总提物和各部位作用下的S期比例从9.78%增加到27.29%,而化合物则是从16.34%增加到32.16%。这说明血三七促进成骨细胞增殖是通过促进细胞S期比例来实现的。同时,各提取物及化合物EG对成骨细胞分化均有一定作用,且呈剂量依赖关系。需特别指出的是,化合物EG不仅具有良好的细胞增殖效果,而且能显著促进成骨细胞分化,这种作用主要体现在增加成骨细胞ALP的活性和降低PGE2的含量上。上述结果表明血三七促进骨折愈合的机理是:血三七直接刺激成骨细胞的增殖和分化,化合物EG是实现这种活性的主要物质基础。
(5)采用体内实验对血三七的镇痛活性进行了验证。通过小鼠热板法和醋酸所致小鼠扭体法,对血三七总提物、石油醚部位、乙酸乙酯部位、正丁醇部位及水部位的高、中、低三个剂量组进行了实验。结果发现,三种浓度的上述血三七各提取物均可使热板所致小鼠舔足的痛阈值显著提高(p<0.05),使醋酸所致小鼠扭体次数显著减少(p<0.01),且水部位和正丁醇部位镇痛效果要好于总提物、石油醚部位及乙酸乙酯部位。
Traditional Chinese medicine Xuesanqi is the root tuber of Polygonum amplexicaule D. Don var. sinense Forb. It is the commonly used raw material for medicine among Enshi minorities in Hubei Province. It has many medical functions, such as improving blood circulation, maintaining normal menstrual flow, and curing various fractures, muscle injuries or pain from tissue swelling. Especially, Xuesanqi has been demonstrated to be an effective herb to treat rheumatism, atherosclerosis and to have antifungal activity. In addition, its distribution is very wide, there are a large number of wild and home-grown Xuesanqi in China. However, so far, there are sporadic studies about it, and lacks systematical research, which block its further applications. Therefore, the objective of the study is to isolate and identify its most effective compounds by various chromatographic techniques and to set up fingerprints of Xuesanqi from different areas in order to provide an academic basis for the scientific evaluation of the quality of Xuesanqi. On this basis, by means of modern pharmacological methods, it was tried to prove its different medical effects, including antifugal activity, mechanism of promoting the healing of bone fractures, and analgesic activity, etc, which would provide the scientific basis of developing new drug in the future.
The main work and its innovations of this research are listed below:
(1) Such chromatographic techniques, including TCL, normal-phase silica gel column, reverse-phase silica gel column, polydextran gel and semi-preparative high performance liquid colum were employed in this study. About 40 compounds were obtained by the above chromatographic techniques from EtOAc fraction of Xueshaqi. By means of modern spectroscopic methods (e.g. UV, IR, 1H-NMR, 13C-NMR, DEPT, EI-MS), 23 compounds were finally identified. Among them, 20 compounds were isolated for the first time from this plant. Moreover, 5 compounds were first obtained from Polygonaceae. A majority of these compounds belong to flavonoids and anthraquinones, which show great pharmacological activity.
(2) Since the quality standards of Xuesanqi have not been established by now, on the basis of its chemical composition analysis, the fingerprints were set up by HPLC for the flavonoids of Xuesanqi from nine different regions. A total of 11 peaks were found, and their relative retention time and relative peak area ratio of the scope were determined. The results showed that each fingerprint of P. amplexicaule exhibited 90% of similarity despite of their different origin. Thus, the results met the quality requirements of fingerprint. The establishment of this method not only can help to identify Xuesanqi from different localities, but also can provide scientific evidence to formulate the quality standards of Xuesanqi.
(3) The anti-fungal activity of secondary metabolites from Xuesanqi has been studied for the first time. Susceptibility disk assay was adopted to test the anti-fungal activity of ethyl acetate fraction and n-butanol fraction from Xuesanqi. In addition, its minimum inhibitory concentration was measured by agar dilution method and the effects of light, temperature, pH on its antifungal activity were examined by plate method. The results showed that the secondary metabolites of Xuesanqi had significant anti-fungal activity on pathogenic fungi and the deep drug-resistant strains. Its anti-fungal activity was rather stable and could not be easily interfered by the environmental factors, such as light, temperature, etc. Compared with ethyl acetate fraction, n-butanol fraction had better anti-fungal activity, even 0.013mg/ml n-butanol fraction showed strong anti-fungal effect.
(4) To investigate Xuesanqi’s pharmacological mechanism of promoting the healing of bone fractures in vitro, MC3T3-E1 cell line and osteoblasts from skull bones of mice were established to test the biological functions of the total extracts from Xuesanqi, petroleum ether fraction extracts, ethylacetate fraction extracts, n-butanol fraction extracts, water fraction and compound emodin-8-O-β-D-glucoside (EG) from ethylacetate fraction extracts. CCK-8 assay, PI staining and FACS were used to examine cell proliferation and cell cycle. The expression of alkaline phosphatase (ALP) and the content of prostaglandin E2 (PGE2) were detected by enzyme-linked immunosorbent assay (ELISA). The results of cell proliferation showed that 0.1-100μg/mL dose of total extracts, fraction extracts and compound from Xuesanqi could stimulate cell proliferation significantly (p<0.05). Total extracts and fraction extracts could increase the proportion S-phase of cells from 9.78 to 27.29%. Compound emodin-8-O-β--D-glucoside (EG) could increase the proportion S-phase of cells from 16.34% to 32.16%. Simultaneously, each extraction and compound EG had showed certain effects on the differentiation of osteoblasts, and exhibited a marked dosage dependent relationship. Especially, EG increased alkaline phosphatase (ALP) expression in MC3T3-E1 cells (0.1-100 ng/mL, p<0.01) and inhibited PGE2 production induced by TNF-αin osteoblasts (10-100 ng/mL). All the above results suggest that the mechanism of Xuesanqi to promote the healing of bone rheumatism and various fractures is that Xuesanqi directly stimulates the proliferation and differentiation of osteoblasts, and compound EG contributes most to these activities.
(5) It was for the first time to investigate the analgesic activity of Xuesanqi in vivo. Hot- plate model and the acetic acid writhing test were adopted among the low, middle and high dosage groups from ethanol extracts, petroleum ether fraction extract, ethylacetate fraction extract, n-butanol fraction extract and water fraction, respectively. The results showed that 0.4 mg/mL, 0.8 mg/mL, 1.6 mg/mL dose of all extracts could significantly increase the pain threshold of licking hot-plate in mice (p<0.05) and markedly reduced the times of writhing induced by acetic acid (p<0.01). Moreover, the analgesic activity of water fraction and n-butanol fraction were much better than ethanol extracts, petroleum ether fraction extract, ethylacetate fraction extract.
引文
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