贝加尔唐松草和大叶龙胆化学成分研究
摘要
唐松草属(Thalictrum)植物系毛茛科(Ranunculaceae)一年、两年或多年生草本植物,全属约150种,分布于北温带。我国有67种,全国均有分布,主要分布于西南地区。该属植物多数在民间入药,具有清热解毒、消肿排脓、败毒抗癌等功效。贝加尔唐松草(Thalictrum baicalense Turcz.)是唐松草属中的一员,主要分布于陕西、青海、甘肃、山西、河北、河南、西藏等地。根入药具有败毒抗癌、泻火清热等功效。据报道,该属植物普遍含有生物碱、黄酮及其苷类化合物。
为了进一步挖掘唐松草属植物的活性成分,本论文对贝加尔唐松草(Thalictrumbaicalense Turcz.)化学成分进行了系统的研究。利用硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等方法分离得到40余个化合物,并且利用UV、IR、MS、~1H NMR、~(13)C NMR、DEPT、1D-NOE、2D-NMR及旋光等波谱技术,结合相关文献以及与标样对照,鉴定了38个化合物的结构,它们主要为生物碱、黄酮及其苷、苯丙素、木脂素以及三萜类化合物,其中三个木脂素(1.1-1.3)和两个生物碱(1.23-1.24)为新化合物。并且利用化学方法对化合物1.22进行了乙酰化,本论文首次报道了乙酰化产物(1.22a)的物理常数和波谱数据。
龙胆(Gentiana)是龙胆科(Gentianaceae)植物,全球约500种,广泛分布在全世界温带地区的高山地带,绝大部分为一年生或多年生的草本植物,部分为常绿品种。我国有230种以上,各地均产之,但主产地为西南部,大部分供观赏用,有些可以入药。大叶龙胆(Gentiana macrophylla Pall.)是我国重要的传统中药之一,主要用于治疗风湿关节痛、潮热骨蒸。龙胆属植物的化学成分被广泛的研究,在早期文献中,报道了单萜环烯醚、三萜和生物碱等类型化合物。近来,黄酮、香豆素和开链单萜环烯醚陆续从大叶龙胆中分离得到。
为了进一步研究大叶龙胆(Gentiana macrophylla Pall.)根部的化学成分,我们对其根部95%乙醇提取物的乙酸乙酯和正丁醇萃取部分化学成分进行了分离鉴定。利用硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段,得到12个化合物,利用IR、EI-MS、HR-ESI-MS、1D NMR(~1H NMR、~(13)C NMR、DEPT、NOE)、2D NMR(~1H-~1H COSY、HMQC、HMBC、NOESY),并结合与标准化合物对照、与相关文献比较以及适当的化学转化(乙酰化),确定了12个化合物的结构,它们分别属于单萜环烯醚、三萜、香豆素、甾体类化合物,其中化合物2.1为新化合物。
本论文最后对1995-2009年期间唐松草属植物化学成分的研究概况进行了综述。
本论文的研究丰富了天然产物数据库,有望对植物化学分类学、新药筛选和生物合成作出较大贡献。
The genus Thalictrum, belonging to Ranunculaceae family, consists of more than 150 species in the world, which are distributed in north warm area and about 67 species grow in Southwest of China. Many species have been used as folk medicines for theating infections, hepatits, dysenteric diarrhea, and enteric discords. So far, the chemical constituents, which mainly include alkaloids, flavonoids, phenols, terpenes ect., were isolated from the genus Thalictrum. Thalictrum baicalense Turcz., a member of genus Thalictrum, mainly distribute in Qinghai, Gansu、Shanxi、Hebei、Henan、Tibet ect. The roots of Thalictrum baicalense possess the efficacy of detoxfeaction and anticancer.
In order to explore much more medical potential constituents of Thalictrum, the chemical constituents of the whole plants of Thalictrum baicalense were studied. The chemical constituents were isolated by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC) and recrystallization ect., and more than 40 compounds were obtained. The structures of 38 compounds were elucidated by spectroscopic methods: UV, IR, MS, ~1H NMR, ~(13)C NMR, DEPT, 1D-NOE and 2D-NMR along with a comparison with authentic samples or the data from literature. They were identified as alkaloids, lignans and triterpenes ect., 5 of them are new compounds, including three lignans and two alkaloids.
The genus Gentiana, belonging to Gentianaceae family, consists of more than 500 species in the world, which are widely distributed in warm area and in high mountains; In China, about 230 species grow in southwest area. Gentiana macrophylla belongs to the genus Gentiana (Gentianaceae). The extract of the roots has been used as a traditional Chinese drug over 2000 years for treatment of jaundice, hepatitis, constipation, pains and rheumatism. The chemical constituents of the genus of Gentiana have been intensively investigated. Iridoids and triterpenoids as well as alkaloids have been reported as the major components of Gentiana, early reports on G. macrophylla stated the presence of gentiopicroside. Recently, flavones, coumarins and other secoiridoid glucosides were isolated from the roots of G. macrophylla.
In order to explore much more pharmacological constituents of genus Gentiana, this thesis systematically and thoroughly studied the chemical constituents of the roots of Gentiana macrophylla. The chemical constituents of EtOAc and n-Butanol extracts were respectively isolated by means of silica gel column chromatography (CC), preparative thin layer column (PTLC) and recrystallization etc, and 12 compounds were obtained; the structures of 12 compounds were elucidated on the basis of modern spectroscopic methods: IR, EI-MS, HR-ESI-MS, 1D NMR (~1H NMR, ~(13)C NMR, DEPT and NOE), 2D NMR (~1H ~1H COSY, HMQC, HMBC and NOESY), along with comparison with authentic samples or the data from literature, and proper chemical transformations (acetylation).They were identified as Iridoids and triterpenoids and coumarins. Compound 2.1 was a novel dimeric secoiridoid glucoside.
In the end of the thesis, one review was made on the systemic summarization for the chemical constituents of the genus Thalictrum reported in the past fifteen years.
The results of the investigation were expected to enrich the database of natural products, to afford the scientific basis of pharmacology, chemotaxonomy and screening of new medicines, and to help the utilization of the Chinese natural resources as well as the research of Chinese herbal modernization.
为了进一步挖掘唐松草属植物的活性成分,本论文对贝加尔唐松草(Thalictrumbaicalense Turcz.)化学成分进行了系统的研究。利用硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等方法分离得到40余个化合物,并且利用UV、IR、MS、~1H NMR、~(13)C NMR、DEPT、1D-NOE、2D-NMR及旋光等波谱技术,结合相关文献以及与标样对照,鉴定了38个化合物的结构,它们主要为生物碱、黄酮及其苷、苯丙素、木脂素以及三萜类化合物,其中三个木脂素(1.1-1.3)和两个生物碱(1.23-1.24)为新化合物。并且利用化学方法对化合物1.22进行了乙酰化,本论文首次报道了乙酰化产物(1.22a)的物理常数和波谱数据。
龙胆(Gentiana)是龙胆科(Gentianaceae)植物,全球约500种,广泛分布在全世界温带地区的高山地带,绝大部分为一年生或多年生的草本植物,部分为常绿品种。我国有230种以上,各地均产之,但主产地为西南部,大部分供观赏用,有些可以入药。大叶龙胆(Gentiana macrophylla Pall.)是我国重要的传统中药之一,主要用于治疗风湿关节痛、潮热骨蒸。龙胆属植物的化学成分被广泛的研究,在早期文献中,报道了单萜环烯醚、三萜和生物碱等类型化合物。近来,黄酮、香豆素和开链单萜环烯醚陆续从大叶龙胆中分离得到。
为了进一步研究大叶龙胆(Gentiana macrophylla Pall.)根部的化学成分,我们对其根部95%乙醇提取物的乙酸乙酯和正丁醇萃取部分化学成分进行了分离鉴定。利用硅胶柱层析(CC)、制备薄层层析(PTLC)、重结晶等手段,得到12个化合物,利用IR、EI-MS、HR-ESI-MS、1D NMR(~1H NMR、~(13)C NMR、DEPT、NOE)、2D NMR(~1H-~1H COSY、HMQC、HMBC、NOESY),并结合与标准化合物对照、与相关文献比较以及适当的化学转化(乙酰化),确定了12个化合物的结构,它们分别属于单萜环烯醚、三萜、香豆素、甾体类化合物,其中化合物2.1为新化合物。
本论文最后对1995-2009年期间唐松草属植物化学成分的研究概况进行了综述。
本论文的研究丰富了天然产物数据库,有望对植物化学分类学、新药筛选和生物合成作出较大贡献。
The genus Thalictrum, belonging to Ranunculaceae family, consists of more than 150 species in the world, which are distributed in north warm area and about 67 species grow in Southwest of China. Many species have been used as folk medicines for theating infections, hepatits, dysenteric diarrhea, and enteric discords. So far, the chemical constituents, which mainly include alkaloids, flavonoids, phenols, terpenes ect., were isolated from the genus Thalictrum. Thalictrum baicalense Turcz., a member of genus Thalictrum, mainly distribute in Qinghai, Gansu、Shanxi、Hebei、Henan、Tibet ect. The roots of Thalictrum baicalense possess the efficacy of detoxfeaction and anticancer.
In order to explore much more medical potential constituents of Thalictrum, the chemical constituents of the whole plants of Thalictrum baicalense were studied. The chemical constituents were isolated by means of silica gel column chromatography (CC), preparative thin layer chromatography (PTLC) and recrystallization ect., and more than 40 compounds were obtained. The structures of 38 compounds were elucidated by spectroscopic methods: UV, IR, MS, ~1H NMR, ~(13)C NMR, DEPT, 1D-NOE and 2D-NMR along with a comparison with authentic samples or the data from literature. They were identified as alkaloids, lignans and triterpenes ect., 5 of them are new compounds, including three lignans and two alkaloids.
The genus Gentiana, belonging to Gentianaceae family, consists of more than 500 species in the world, which are widely distributed in warm area and in high mountains; In China, about 230 species grow in southwest area. Gentiana macrophylla belongs to the genus Gentiana (Gentianaceae). The extract of the roots has been used as a traditional Chinese drug over 2000 years for treatment of jaundice, hepatitis, constipation, pains and rheumatism. The chemical constituents of the genus of Gentiana have been intensively investigated. Iridoids and triterpenoids as well as alkaloids have been reported as the major components of Gentiana, early reports on G. macrophylla stated the presence of gentiopicroside. Recently, flavones, coumarins and other secoiridoid glucosides were isolated from the roots of G. macrophylla.
In order to explore much more pharmacological constituents of genus Gentiana, this thesis systematically and thoroughly studied the chemical constituents of the roots of Gentiana macrophylla. The chemical constituents of EtOAc and n-Butanol extracts were respectively isolated by means of silica gel column chromatography (CC), preparative thin layer column (PTLC) and recrystallization etc, and 12 compounds were obtained; the structures of 12 compounds were elucidated on the basis of modern spectroscopic methods: IR, EI-MS, HR-ESI-MS, 1D NMR (~1H NMR, ~(13)C NMR, DEPT and NOE), 2D NMR (~1H ~1H COSY, HMQC, HMBC and NOESY), along with comparison with authentic samples or the data from literature, and proper chemical transformations (acetylation).They were identified as Iridoids and triterpenoids and coumarins. Compound 2.1 was a novel dimeric secoiridoid glucoside.
In the end of the thesis, one review was made on the systemic summarization for the chemical constituents of the genus Thalictrum reported in the past fifteen years.
The results of the investigation were expected to enrich the database of natural products, to afford the scientific basis of pharmacology, chemotaxonomy and screening of new medicines, and to help the utilization of the Chinese natural resources as well as the research of Chinese herbal modernization.
引文
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