千里光（Senecio scandens Buch-Ham.）化学成分的研究
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摘要
千里光(Senecio scandens Buch-Ham.)为菊目(Asterales)菊科(Compositae or Asteraceae)千里光属(Senecio)植物,主要分布于我国华东、中南及西南各地,是我国应用历史悠久的常用中药之一。该植物味苦、辛,性寒,具有清热解毒,明目退翳,杀虫止痒,散瘀消肿等功效。据文献报道该属植物的主要化学成分为吡咯里西啶类生物碱和呋喃雅槛蓝型倍半萜,此外还含有黄酮类,酚酸类,挥发油和其他一些微量元素。
本论文以四川产千里光为研究对象,对其全草的化学成分进行了系统的研究。采用水蒸气提取法提取千里光全草中的挥发油,并进行气相色谱-质谱分析。共分离鉴定了23种化合物,主要为脂肪族化合物(87.48%)和芳香族化合物(10.16%)。采用常规的正相硅胶柱层析、反相硅胶柱层析、制备型薄层层析和重结晶等实验手段对千里光地上部分的甲醇提取物进行了分离纯化,从中分离得到36个化合物,并运用现代波谱技术(1H-NMR,13C-NMR,DEPT)对纯化的化合物进行了分析测试,在与标准品对照或与文献数据比较的基础上鉴定了其中13个化合物的结构,分别是：
G-3[4-羟基-3-甲氧基苯甲醛]；G-4／G-34[2-((1R,6S)-1-羟基-6-甲氧基-4-环己羰基-2-己烯)乙酸酯]；G-5[2-(1-羟基-4-环己羰基-2-己烯)乙酸酯]；G-6[顺-((3S,8S,10R,13R)-17-((2R,5R)-5-乙基-6-甲基庚烷-2-基)-8,10,13-三甲基-2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氢-1氢-环戊烯[α]菲-3-基)11-((2S,3S)-2,3-二甲基-3-pentyloxiran-2-基)-9-oxoundec--10-己烯酸]；G-7[2-((1S,6S)-1,6-二羟基-4-环己羰基-2-己烯)乙酸酯]；G-9[3,4-二羟基苯甲醛]；G-10[β-谷甾醇]；G-17[2-((2S,6S)-1-羟基-2,6-二甲基-4-环己酮)乙酸酯]；G-23[4,4,7a-三甲基-4,5,7,7a-四氢苯并呋喃-2,6-二酮]；G-27[2-((3aR,7aS)-2,2-二甲基-6-羰基-3a,6,7,7a-四氢[d][1,3]间二氧杂环戊烯-3a-基)乙酸酯；G-28[顺-12,13-二羟基-10-二十四碳烯酸]；G-36[(3S,5R,8S,10R,13R)-17-((2R,E)-5-乙基-6-甲基-3-庚烯-2-基)-10,13-二甲基十六烷氢-1氢-环戊烯-[α]菲-3,5,8-三醇]。
此外还采用牛津杯法对千里光的水浸膏、甲醇相、水萃液、正丁醇相、三氯甲烷相、正己烷相进行了抑菌活性研究,试验结果表明各浸膏除水萃液外均对革兰氏阳性菌(金黄色葡萄球菌、巨大芽孢杆菌)显示不同程度的抑制作用；各浸膏除正己烷相外均对革兰氏阴性菌(大肠杆菌)显示不同程度的抑制作用,皆呈一定量效关系。
本论文还对千里光的化学成分、药理作用等方面的研究现状进行了文献综述,为本实验研究方案的制定和顺利进行提供了借鉴。
Senecio scandens Buch-Ham is the species of family Asterales tribe Asteraceae Class Senecio, a perennial herb widely distributed in east, south and southwestern regions. The whole plant was used in traditional and folk Chinese medicine to treat clearing heat, detoxication, cooling blood and detumescence properties, anti-inflammatory. A great deal of interest in phytochemical studies on plants of the Senecio genus has yielded various types of compounds such as pyrrolizidine alkaloids, sesquiterpenoids, diterpenoids, and flavonoids, with hepatotoxic, carcinogenic, insecticidal, antimicrobial, antitumor, antiviral, antiulcer, and immunosuppressant activities.
In this paper, chemical constituents in Senecio scandens collected at Sichuan Province in China have been comprehensively investigated. The compositions of essential oil from the S. scandens have been collected by water stream distillation method and analyzed by gas chromatography-mass spectroscopy (GC-MS).23 compounds have been identified, mainly apliphatic(87.48%) and aromatic(10.16%) In addition, the phytochemical constituents in the methanol extracts from S. scandens have been isolated by means of silica gel column chromatography, reverse phase C-18 silica gel column chromatography, preparative thin layer chromatography, and recrystallization etc. These compounds were analyzed by modern spectroscopy as 1H-NMR,13C-NMR, DEPT and so on. According to the standard sample or the comparison with the data in literature, structures of 13 compounds were identified. They were elucidated as following:G-3[4-hydroxy-3-methoxybenzaldehyde)]; G-4/ G-34 [methyl 2-((1 R,6S)-1-hydroxy-6-methoxy-4-oxocyclohex-2-enyl)acetate]; G-5 [methyl 2-(1-hydroxy-4-oxocyclohex-2-enyl)acetate]; G-6[(E)-((3S,8S,1 OR,13 R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-8,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,1 5,16,17-tetradecahydro-1 H-cyclopenta[a]phenanthren-3-yl)11-((2S,3S)-2,3-dimethyl-3-pentyIoxiran-2-yl)-9-oxoundec-10-enoate];G-7[(methyl2-((1 S,6S)-1,6-dihydroxy-4-oxocyclohex-2-enyl)acetate)]; G-9[3,4-dihydroxybenzaldehyde]; G-10[β-sitosterol]; G-17[methyl2-((2S,6S)-1-hydroxy-2,6-dimethoxy-4-oxocyclohexyl)acetate];G-23 [4, 4,7a-trimethyl-4,5,7,7a-tetrahydrobenzofuran-2,6-dione];G-27[methyl 2-((3aR,7aS)-2, 2-dimethyl-6-oxo-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxol-3a-yl)acetate];G-28[(E)- 12,13-dihydroxytetracos-10-enoicacid]; G-36[(3S,5R,8S,10R,13R)-17-((2R,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phena nthrene-3,5,8-triol].
The antibacterial activities of the extracts from S. scandens to Escherichia coli, Bacillus megaterium and Staphylococcus aureus were carried out by method of Oxford-cup tests. The results indicated the extracts by water, methanol, hextane, chloroform, butanol had the different degrees antibacterial activity. The inhibition zones diameter of each extracts from S. scandens Buch-Ham were linked with the concentration.
Chemical composition and pharmacological research on Senecio scandens Buch-Ham is also reviewed.
本论文以四川产千里光为研究对象,对其全草的化学成分进行了系统的研究。采用水蒸气提取法提取千里光全草中的挥发油,并进行气相色谱-质谱分析。共分离鉴定了23种化合物,主要为脂肪族化合物(87.48%)和芳香族化合物(10.16%)。采用常规的正相硅胶柱层析、反相硅胶柱层析、制备型薄层层析和重结晶等实验手段对千里光地上部分的甲醇提取物进行了分离纯化,从中分离得到36个化合物,并运用现代波谱技术(1H-NMR,13C-NMR,DEPT)对纯化的化合物进行了分析测试,在与标准品对照或与文献数据比较的基础上鉴定了其中13个化合物的结构,分别是：
G-3[4-羟基-3-甲氧基苯甲醛]；G-4／G-34[2-((1R,6S)-1-羟基-6-甲氧基-4-环己羰基-2-己烯)乙酸酯]；G-5[2-(1-羟基-4-环己羰基-2-己烯)乙酸酯]；G-6[顺-((3S,8S,10R,13R)-17-((2R,5R)-5-乙基-6-甲基庚烷-2-基)-8,10,13-三甲基-2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氢-1氢-环戊烯[α]菲-3-基)11-((2S,3S)-2,3-二甲基-3-pentyloxiran-2-基)-9-oxoundec--10-己烯酸]；G-7[2-((1S,6S)-1,6-二羟基-4-环己羰基-2-己烯)乙酸酯]；G-9[3,4-二羟基苯甲醛]；G-10[β-谷甾醇]；G-17[2-((2S,6S)-1-羟基-2,6-二甲基-4-环己酮)乙酸酯]；G-23[4,4,7a-三甲基-4,5,7,7a-四氢苯并呋喃-2,6-二酮]；G-27[2-((3aR,7aS)-2,2-二甲基-6-羰基-3a,6,7,7a-四氢[d][1,3]间二氧杂环戊烯-3a-基)乙酸酯；G-28[顺-12,13-二羟基-10-二十四碳烯酸]；G-36[(3S,5R,8S,10R,13R)-17-((2R,E)-5-乙基-6-甲基-3-庚烯-2-基)-10,13-二甲基十六烷氢-1氢-环戊烯-[α]菲-3,5,8-三醇]。
此外还采用牛津杯法对千里光的水浸膏、甲醇相、水萃液、正丁醇相、三氯甲烷相、正己烷相进行了抑菌活性研究,试验结果表明各浸膏除水萃液外均对革兰氏阳性菌(金黄色葡萄球菌、巨大芽孢杆菌)显示不同程度的抑制作用；各浸膏除正己烷相外均对革兰氏阴性菌(大肠杆菌)显示不同程度的抑制作用,皆呈一定量效关系。
本论文还对千里光的化学成分、药理作用等方面的研究现状进行了文献综述,为本实验研究方案的制定和顺利进行提供了借鉴。
Senecio scandens Buch-Ham is the species of family Asterales tribe Asteraceae Class Senecio, a perennial herb widely distributed in east, south and southwestern regions. The whole plant was used in traditional and folk Chinese medicine to treat clearing heat, detoxication, cooling blood and detumescence properties, anti-inflammatory. A great deal of interest in phytochemical studies on plants of the Senecio genus has yielded various types of compounds such as pyrrolizidine alkaloids, sesquiterpenoids, diterpenoids, and flavonoids, with hepatotoxic, carcinogenic, insecticidal, antimicrobial, antitumor, antiviral, antiulcer, and immunosuppressant activities.
In this paper, chemical constituents in Senecio scandens collected at Sichuan Province in China have been comprehensively investigated. The compositions of essential oil from the S. scandens have been collected by water stream distillation method and analyzed by gas chromatography-mass spectroscopy (GC-MS).23 compounds have been identified, mainly apliphatic(87.48%) and aromatic(10.16%) In addition, the phytochemical constituents in the methanol extracts from S. scandens have been isolated by means of silica gel column chromatography, reverse phase C-18 silica gel column chromatography, preparative thin layer chromatography, and recrystallization etc. These compounds were analyzed by modern spectroscopy as 1H-NMR,13C-NMR, DEPT and so on. According to the standard sample or the comparison with the data in literature, structures of 13 compounds were identified. They were elucidated as following:G-3[4-hydroxy-3-methoxybenzaldehyde)]; G-4/ G-34 [methyl 2-((1 R,6S)-1-hydroxy-6-methoxy-4-oxocyclohex-2-enyl)acetate]; G-5 [methyl 2-(1-hydroxy-4-oxocyclohex-2-enyl)acetate]; G-6[(E)-((3S,8S,1 OR,13 R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-8,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,1 5,16,17-tetradecahydro-1 H-cyclopenta[a]phenanthren-3-yl)11-((2S,3S)-2,3-dimethyl-3-pentyIoxiran-2-yl)-9-oxoundec-10-enoate];G-7[(methyl2-((1 S,6S)-1,6-dihydroxy-4-oxocyclohex-2-enyl)acetate)]; G-9[3,4-dihydroxybenzaldehyde]; G-10[β-sitosterol]; G-17[methyl2-((2S,6S)-1-hydroxy-2,6-dimethoxy-4-oxocyclohexyl)acetate];G-23 [4, 4,7a-trimethyl-4,5,7,7a-tetrahydrobenzofuran-2,6-dione];G-27[methyl 2-((3aR,7aS)-2, 2-dimethyl-6-oxo-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxol-3a-yl)acetate];G-28[(E)- 12,13-dihydroxytetracos-10-enoicacid]; G-36[(3S,5R,8S,10R,13R)-17-((2R,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phena nthrene-3,5,8-triol].
The antibacterial activities of the extracts from S. scandens to Escherichia coli, Bacillus megaterium and Staphylococcus aureus were carried out by method of Oxford-cup tests. The results indicated the extracts by water, methanol, hextane, chloroform, butanol had the different degrees antibacterial activity. The inhibition zones diameter of each extracts from S. scandens Buch-Ham were linked with the concentration.
Chemical composition and pharmacological research on Senecio scandens Buch-Ham is also reviewed.
引文
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