中药野菊花和款冬花及草药烟管头草中倍半萜和其它成分研究
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摘要
清热解毒中药是中医临床上用于治疗温病热毒症的物质基础。现代药理研究表明清热解毒中药具有抗病原微生物、抗内毒素、抗炎、提高机体免疫能力及清除热毒等功效,对治疗流感、恶性肿瘤、糖尿病、冠心病、关节炎和心血管疾病等疾病都要显著疗效。恶性肿瘤是威胁人类生命的头号杀手,目前对恶性肿瘤的治疗主要以手术、放疗和化疗为主,结合一定的药物辅助治疗,因此寻找新的抗肿瘤药物一直是研究热点。中医中清热解毒法是治疗恶性肿瘤的重要法则之一,清热解毒中药对恶性肿瘤的预防和治疗扮演着不可替代的作用。本论文概述了2010版《中华人民共和国药典》中载录的72味清热解毒中药的抗肿瘤作用研究情况,将为中药中抗肿瘤活性成分的筛选作出一定的参考。
在课题组研究菊科(Asteraceae)植物中多样性倍半萜结构的思路指引下,本论文对两种清热解毒中药野菊花和草药烟管头草,及润肺止咳中药款冬花中的倍半萜以及其它化学成分进行了系统的研究。其中中药野菊花是菊科菊属植物野菊(Chrysanthemum indicum L.)的干燥头状花序,收录于《中华人民共和国药典》2010版,功效为清热解毒,治疗疔疮痈肿、目赤肿痛、头痛眩晕等症状,临床上用于治疗前列腺炎、慢性盘腔炎、外感发炎及上呼吸道感染等疾病：中药款冬花是菊科款冬属植物款冬(Tussilago farfara L.)的干燥花蕾,收录于《中华人民共和国药典》2010版,功效为润肺下气、止咳化痰,临床上用于治疗新久咳嗽、喘咳痰多、劳嗽咯血等症状,疗效显著；草药烟管头草是菊科天名精属植物烟管头草(Carpesium cernuum L.)的干燥全草,民间常与中药金挖耳混用,功效为清热解毒,用于治疗疟疾和喉炎等等。
在提取、分离和结构鉴定过程中,主要采用由硅胶、ODS反相硅胶、Sephadex LH-20葡聚糖凝胶等填料填充的各种常压色谱以及高效液相色谱等分离手段进行分离,结合IR, UV、MS、CD、1D/2D NMR等各种现代光谱和波谱技术鉴定分离化合物的结构。共有129个化合物被鉴定,29个化合物为新结构,其中包括一种聚乙炔类新骨架。新化合物以及倍半萜的编号、名称及骨架类型见表1。从中药野菊花中分离鉴定了60个化合物,其结构类型涉及倍半萜、黄酮、聚乙炔、三萜、甾体,其中倍半萜类化合物有34个涉及9种骨架,17个为新化合物,主要包括17个桉烷(包括11个新化合物)、6个吉玛烷(包括4个新化合物)、5个愈创木(包括1个新化合物)和1个新的Iphionane骨架化合物；除了倍半萜,从野菊花中还分离鉴定了10个聚乙炔类化合物(包括4个新化合物)。从中药款冬花中分离鉴定了25个化合物,其结构类型涉及倍半萜、2,2-二甲基色原酮、三萜、甾体、生物碱、含糖类、糠醛,其中倍半萜类化合物11个涉及5种骨架,主要包括4个Oplopanane骨架结构(包括1个新化合物)、3个按烷(包括1个新化合物)和1个新的没药烷,用CD实验确定了这些新倍半萜结构的绝对构型；从款冬花中还有三个连接有乙氧基的新工作产物：(4R*)-6-(1-Ethoxyethyl)-2,2-dimethylchroman-4-ol,5-Ethoxymethyl-1H-pyrrole-2-carbaldehyde和3-Hydroxy-7-ethoxy-24-ethyl-cholest-5-ene被分离鉴定。从草药烟管头草中分离鉴定了44个化合物,其结构类型涉及倍半萜、黄酮、苯酚、甾体、木脂素、三萜、吲哚、香豆素及黑麦草内酯,主要包括24个倍半萜类化合物涉及8种骨架,其结构多数为倍半萜内酯,主要包括9个桉烷内酯,5个愈创木内酯(包括1个新化合物)和1个新艾里莫酚内酯。
本论文分离鉴定了69个倍半萜,表明三种菊科植物的主要成分为倍半萜类。本论文研究成果能够为这些中药和草药的植物化学分类学、活性成分筛选以及治病原理提供一定的科学依据,为这些中药和草药的有效组分提取提供可靠的质量控制标准,同时在某种程度上为中药新剂型的开发提供参考。
The traditional Chinese medicines (TCMs) with functions of Heat-clearing and toxin-resolving have been used to treat febrile disease due to heat-toxin syndrome in clinical. And modern pharmacological studies indicated these herbal medicines were used to treat influenza, cancer, diabetes, coronary heart disease, arthritis and cardiovascular disease because of possess anti-pathogenic microorganism, antiendotoxin, anti-inflammatory, and enhancing immunologic effects. Cancer is the leading death cause worldwide. At present, the main cancer therapies are surgery, radiotherapy and chemotherapy, and combined with adjuvant treatment with certain anticancer drugs, so search for new anticancer drugs are a rearch hot spot all the time. TCMs play an irreplaceable role in the prevention and treatment of cancer, and herein we gave an overview of antitumor activities of 72 TCMs being recorded in Chinese Pharmacopoeia,2010 version.
In the course of our group continuing research on sesquiterpenoids from the Asteraceae plants, we have made systematic studies on chemical constituents from Ye-Ju-Hua and Yan-Guan-Tou-Cao and Kuan-Dong-Hua. Ye-Ju-Hua, as TCM, is the dried flowers of C. indicum of the Asteraceae, recorded in Chinese Pharmacopoeia, which is used to treat furunculosis, swelling and pain of eye, headache and dizziness and all kinds of inflammations, such as prostatitis, chronic pelvic inflammation, etc.; and Kuan-Dong-Hua is the dries flower buds of T. farfara of the Asteraceae, also recorded in Chinese Pharmacopoeia, being used for treatment of cough, bronchitis and asthmatic disorders; Yan-Guan-Tou-Cao, as a herbal medicine, is the whole plant of C. cernuum of the Asteraceae, being used in folk medicine to instead of C. divaricatum for treatment of anti-malarial and laryngitis, and more.
Various chromatographic techniques, i.e. Silica gel, C18 reversed-phase Silica gel and Sephadex LH-20 for column chromatography and HPLC were used in the process of extraction, isolation and structural elucidation. And 129 compouds, including 29 new structures and two of them beared a rare polyacetylene skeleton, were elucidated on the basis of comprehensive spectroscopic methods, such as IR, UV, MS, CD and 1D/2D NMR, etc. The structure names, sketelon types and sources of these new compounds and sesquiterpeniods were showen in Table 1.60 compounds determined as sesquiterpenoids, flavonoids, polyacetylenes and triterpenoids, were isolated from the flowers of C. indicum; and 34 of them bearing 9 skeletons were elucidated as sesquiterpenoids, including 17 eudesmanes (11 of them as new ones),6 germacranes (4 of them as new ones),5 guaianes (including one new compound) and one new iphionane compoud; additionally,10 polyacetylenes, including 4 new ones were also isolated from the flowers of C. indicum. From the flower buds of T. farfara,25 compounds appearing as sesquiterpenoids, 2,2-dimethylchromans,5-hydroxymethylfurfural derivatives, alkaloids, fructofuranoside, steroids and triterpenoids were isolated; among these compounds,11 of them with 5 frameworks were elucidated as sesquiterpenoids, including 4 oplopananes (including one new compound),3 eudesmanes (including one new compound) and one new bisabolane, and 3 new artifact products with EtO groups were elucidated as (4R*)-6-(1-ethoxyethyl)-2,2-dimethylchroman-4-ol,5-ethoxymethyl-lH-pyrrole-2-carbaldehyde and 3-hydroxy-7-ethoxy-24-ethyl-cholest-5-ene; the absolute configurations of these new compounds were assigned by CD experiments.44 compounds including sesquiterpenoids, flavonoids, phenols, steroids, lignans and triterpenoids were isolated from the whole plant of C. cernuum; among these compounds,24 of them were elucidated as sesquiterpenoids bearing 8 frameworks, and more of them as sesquiterpene lactones, including 9 eudesmanolides,5 guaianolides (including one new compound) and one new eremophilenolide.
In the dissertation,69 sesquiterpenoids with various skeletons were obtained, indicating that the sesquiterpenoids were their main components. The results can provide several scientific evidences for these herbs in chemotaxonomy, active components screening and treatment principles. And credible quality control standards can be afforded from the results to the effective components. While our results can offer some references for new dosage form development.
在课题组研究菊科(Asteraceae)植物中多样性倍半萜结构的思路指引下,本论文对两种清热解毒中药野菊花和草药烟管头草,及润肺止咳中药款冬花中的倍半萜以及其它化学成分进行了系统的研究。其中中药野菊花是菊科菊属植物野菊(Chrysanthemum indicum L.)的干燥头状花序,收录于《中华人民共和国药典》2010版,功效为清热解毒,治疗疔疮痈肿、目赤肿痛、头痛眩晕等症状,临床上用于治疗前列腺炎、慢性盘腔炎、外感发炎及上呼吸道感染等疾病：中药款冬花是菊科款冬属植物款冬(Tussilago farfara L.)的干燥花蕾,收录于《中华人民共和国药典》2010版,功效为润肺下气、止咳化痰,临床上用于治疗新久咳嗽、喘咳痰多、劳嗽咯血等症状,疗效显著；草药烟管头草是菊科天名精属植物烟管头草(Carpesium cernuum L.)的干燥全草,民间常与中药金挖耳混用,功效为清热解毒,用于治疗疟疾和喉炎等等。
在提取、分离和结构鉴定过程中,主要采用由硅胶、ODS反相硅胶、Sephadex LH-20葡聚糖凝胶等填料填充的各种常压色谱以及高效液相色谱等分离手段进行分离,结合IR, UV、MS、CD、1D/2D NMR等各种现代光谱和波谱技术鉴定分离化合物的结构。共有129个化合物被鉴定,29个化合物为新结构,其中包括一种聚乙炔类新骨架。新化合物以及倍半萜的编号、名称及骨架类型见表1。从中药野菊花中分离鉴定了60个化合物,其结构类型涉及倍半萜、黄酮、聚乙炔、三萜、甾体,其中倍半萜类化合物有34个涉及9种骨架,17个为新化合物,主要包括17个桉烷(包括11个新化合物)、6个吉玛烷(包括4个新化合物)、5个愈创木(包括1个新化合物)和1个新的Iphionane骨架化合物；除了倍半萜,从野菊花中还分离鉴定了10个聚乙炔类化合物(包括4个新化合物)。从中药款冬花中分离鉴定了25个化合物,其结构类型涉及倍半萜、2,2-二甲基色原酮、三萜、甾体、生物碱、含糖类、糠醛,其中倍半萜类化合物11个涉及5种骨架,主要包括4个Oplopanane骨架结构(包括1个新化合物)、3个按烷(包括1个新化合物)和1个新的没药烷,用CD实验确定了这些新倍半萜结构的绝对构型；从款冬花中还有三个连接有乙氧基的新工作产物：(4R*)-6-(1-Ethoxyethyl)-2,2-dimethylchroman-4-ol,5-Ethoxymethyl-1H-pyrrole-2-carbaldehyde和3-Hydroxy-7-ethoxy-24-ethyl-cholest-5-ene被分离鉴定。从草药烟管头草中分离鉴定了44个化合物,其结构类型涉及倍半萜、黄酮、苯酚、甾体、木脂素、三萜、吲哚、香豆素及黑麦草内酯,主要包括24个倍半萜类化合物涉及8种骨架,其结构多数为倍半萜内酯,主要包括9个桉烷内酯,5个愈创木内酯(包括1个新化合物)和1个新艾里莫酚内酯。
本论文分离鉴定了69个倍半萜,表明三种菊科植物的主要成分为倍半萜类。本论文研究成果能够为这些中药和草药的植物化学分类学、活性成分筛选以及治病原理提供一定的科学依据,为这些中药和草药的有效组分提取提供可靠的质量控制标准,同时在某种程度上为中药新剂型的开发提供参考。
The traditional Chinese medicines (TCMs) with functions of Heat-clearing and toxin-resolving have been used to treat febrile disease due to heat-toxin syndrome in clinical. And modern pharmacological studies indicated these herbal medicines were used to treat influenza, cancer, diabetes, coronary heart disease, arthritis and cardiovascular disease because of possess anti-pathogenic microorganism, antiendotoxin, anti-inflammatory, and enhancing immunologic effects. Cancer is the leading death cause worldwide. At present, the main cancer therapies are surgery, radiotherapy and chemotherapy, and combined with adjuvant treatment with certain anticancer drugs, so search for new anticancer drugs are a rearch hot spot all the time. TCMs play an irreplaceable role in the prevention and treatment of cancer, and herein we gave an overview of antitumor activities of 72 TCMs being recorded in Chinese Pharmacopoeia,2010 version.
In the course of our group continuing research on sesquiterpenoids from the Asteraceae plants, we have made systematic studies on chemical constituents from Ye-Ju-Hua and Yan-Guan-Tou-Cao and Kuan-Dong-Hua. Ye-Ju-Hua, as TCM, is the dried flowers of C. indicum of the Asteraceae, recorded in Chinese Pharmacopoeia, which is used to treat furunculosis, swelling and pain of eye, headache and dizziness and all kinds of inflammations, such as prostatitis, chronic pelvic inflammation, etc.; and Kuan-Dong-Hua is the dries flower buds of T. farfara of the Asteraceae, also recorded in Chinese Pharmacopoeia, being used for treatment of cough, bronchitis and asthmatic disorders; Yan-Guan-Tou-Cao, as a herbal medicine, is the whole plant of C. cernuum of the Asteraceae, being used in folk medicine to instead of C. divaricatum for treatment of anti-malarial and laryngitis, and more.
Various chromatographic techniques, i.e. Silica gel, C18 reversed-phase Silica gel and Sephadex LH-20 for column chromatography and HPLC were used in the process of extraction, isolation and structural elucidation. And 129 compouds, including 29 new structures and two of them beared a rare polyacetylene skeleton, were elucidated on the basis of comprehensive spectroscopic methods, such as IR, UV, MS, CD and 1D/2D NMR, etc. The structure names, sketelon types and sources of these new compounds and sesquiterpeniods were showen in Table 1.60 compounds determined as sesquiterpenoids, flavonoids, polyacetylenes and triterpenoids, were isolated from the flowers of C. indicum; and 34 of them bearing 9 skeletons were elucidated as sesquiterpenoids, including 17 eudesmanes (11 of them as new ones),6 germacranes (4 of them as new ones),5 guaianes (including one new compound) and one new iphionane compoud; additionally,10 polyacetylenes, including 4 new ones were also isolated from the flowers of C. indicum. From the flower buds of T. farfara,25 compounds appearing as sesquiterpenoids, 2,2-dimethylchromans,5-hydroxymethylfurfural derivatives, alkaloids, fructofuranoside, steroids and triterpenoids were isolated; among these compounds,11 of them with 5 frameworks were elucidated as sesquiterpenoids, including 4 oplopananes (including one new compound),3 eudesmanes (including one new compound) and one new bisabolane, and 3 new artifact products with EtO groups were elucidated as (4R*)-6-(1-ethoxyethyl)-2,2-dimethylchroman-4-ol,5-ethoxymethyl-lH-pyrrole-2-carbaldehyde and 3-hydroxy-7-ethoxy-24-ethyl-cholest-5-ene; the absolute configurations of these new compounds were assigned by CD experiments.44 compounds including sesquiterpenoids, flavonoids, phenols, steroids, lignans and triterpenoids were isolated from the whole plant of C. cernuum; among these compounds,24 of them were elucidated as sesquiterpenoids bearing 8 frameworks, and more of them as sesquiterpene lactones, including 9 eudesmanolides,5 guaianolides (including one new compound) and one new eremophilenolide.
In the dissertation,69 sesquiterpenoids with various skeletons were obtained, indicating that the sesquiterpenoids were their main components. The results can provide several scientific evidences for these herbs in chemotaxonomy, active components screening and treatment principles. And credible quality control standards can be afforded from the results to the effective components. While our results can offer some references for new dosage form development.
引文
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