华中五味子化学成分及生物活性的研究
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摘要
华中五味子(Schisandra sphenanthera )系五味子科(Schisandraceae)五味子属(Schisandra)植物,习称“南五味子”,为攀援灌木,主要分布于四川、湖北、陕西、山西、云南等地,为五味子科在全国分布最广(达12个省区)的一个种。果实功效同五味子(S. chinensis),常做五味子使用。其藤茎具有养血消瘀,理气化湿的功效,可用于治疗痨伤吐血,肢节酸痛,心胃气痛,月经不调,跌打损伤等症,根皮可用于健胃和促进消化。
国内学者对华中五味子化学成分的研究报道也较多,迄今,从华中五味子果实中分离得到6个联苯环辛烯类木脂素,5个四氢呋喃木脂素和4个萜类化合物,从华中五味子藤茎中分离得到9个结构新颖的三萜。华中五味子中联苯环辛烯类木脂素成分大多具有降低肝炎患者血清谷丙转氨酶水平、抑制胆固醇合成、抗肿瘤和抗衰老的作用,三萜成分具有一定的抗-HIV活性。由于该种植物分布较广,地域和生长环境的不同,同种植物的化学成分也会存在一定的差异,为了进一步地了解该植物生物活性的物质基础,我们对来源于湖北神农架的华中五味子的化学成分进行了系统研究。利用系统溶剂提取法、正相和反相硅胶柱色谱法、制备HLPC法进行分离和纯化,从华中五味子藤茎的乙酸乙酯提取物中得到33个化合物,采用谱学技术(NMR,MS,IR,UV等谱)和理化性质测定鉴定了31个,确定结构的化合物依次为简单芳香类化合物1、2、3;四氢呋喃类木脂素化合物4、5、6、7,联苯环辛烯类化合物8、9、10、11、12和7,8-开环-木脂素化合物13、14、15、16;萜类化合物中的单萜17,倍半萜18、19、20、21,羊毛甾烷型三萜23、24、25,环阿屯烷型三萜22、26和结构新奇的Wuweiziartane-型三萜27、28;酚苷29、30;甾体31。其中新化合物6个,分别为10、13、14、16、27、28;4个化合物4、15、19、21为首次从该属植物中分离得到;14个化合物1、2、3、6、9、11、17、19、20、22、23、24、26、29为首次从该植物中分离得到。
对华中五味子藤茎中的1、2、4、7、9、12、14、19、22、25共10个化合物进行了杀菌、杀虫和除草活性的研究。结果表明化合物2、12、22对禾生腐霉菌(Pythium graminicola)显示出微弱的杀菌活性。化合物22对棉蚜虫(Aphis gossypii)有一定的杀虫活性。化合物4、9和12对小菜蛾(Plutella xylostella)显示了较强的杀虫活性。(?)
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Schisandra sphenanthera Rehd.et Wils, is a climbing plant that is widely found in Sichuan, Hubei, Shanxi and Yunnan province. The fruits are used as antitussive and tonic agents under the name of Nan-wuweizi in traditional Chinese medicine. Modern pharmacologic researches revealed that Schisandra plants are commonly used in China as tonic, sedative, and astringent agents.
Some phytochemical studies of S. sphenanthera fruits led to the isolation of six dibenzocyclooctadiene lignans, five tetrahydrofuran lignans and four triterpenes. Nine novel schisanartane-type nortriterpenoids have been isolated from the leaves and stems of S. sphenanthera . Lignans and terpenes are bioactive constituents of S. sphenanthera, which showed various beneficial activities including antihepatitis, antitumor, anti-HIV and antilipid peroxidation effects.
In order to study on the chemical constituents from the rattan of S. sphenanthera, the compounds were isolated by the solvent extraction, silica gel, and reversed-phase silica gel column chromatography and semi-preparative HLPC. Their structures were identified by spectroscopic methods, especially 2D-NMR techniques. 33 compounds were isolated from the EtOAc - extraction. 31 of the structures were elucidated on the basis of physicochemical properities and spectra methods, including aromatic compounds 1, 2, 3; tetrahydrofuran lignans 4, 5, 6, 7; dibenzocyclooctenes 8, 9, 10, 11, 12; 7,8-seco-lignans 13, 14, 15, 16; monoterpenoid 17; sesquiterpenoids 18, 19, 20, 21; lanostane-type triterpenoids 23, 24, 25; cycloartane-type triterpenoids, 22, 26; wuweiziartane-type trierpenoids 27, 28;phenolic glycoside 29, 30; steroids 31. compounds 10, 13, 14, 16, 27, 28 were identified as new compounds;compounds 4, 15, 19, 21 were obtained for the first time from the genus;and 1, 2, 3, 6, 9, 11, 17, 19, 20, 22, 23, 24, 26, 29 were obtained from the plant for the first time.
The antifungal , insecticidal and herbicidal activities of 10 compounds: 1, 2, 4, 7, 9, 12, 14 , 19, 22, 25 from Schisandra sphenanthera was determined by using early screen method. The experimental results indicated that compounds 2, 12, 22 showed weak antifungal activities against Pythium graminicola, compound 22 showed moderate insecticidal activities against Aphis gossypii, and compounds 4, 9, 12 showed strong insecticidal activities against Plutella xylostella. (?)
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国内学者对华中五味子化学成分的研究报道也较多,迄今,从华中五味子果实中分离得到6个联苯环辛烯类木脂素,5个四氢呋喃木脂素和4个萜类化合物,从华中五味子藤茎中分离得到9个结构新颖的三萜。华中五味子中联苯环辛烯类木脂素成分大多具有降低肝炎患者血清谷丙转氨酶水平、抑制胆固醇合成、抗肿瘤和抗衰老的作用,三萜成分具有一定的抗-HIV活性。由于该种植物分布较广,地域和生长环境的不同,同种植物的化学成分也会存在一定的差异,为了进一步地了解该植物生物活性的物质基础,我们对来源于湖北神农架的华中五味子的化学成分进行了系统研究。利用系统溶剂提取法、正相和反相硅胶柱色谱法、制备HLPC法进行分离和纯化,从华中五味子藤茎的乙酸乙酯提取物中得到33个化合物,采用谱学技术(NMR,MS,IR,UV等谱)和理化性质测定鉴定了31个,确定结构的化合物依次为简单芳香类化合物1、2、3;四氢呋喃类木脂素化合物4、5、6、7,联苯环辛烯类化合物8、9、10、11、12和7,8-开环-木脂素化合物13、14、15、16;萜类化合物中的单萜17,倍半萜18、19、20、21,羊毛甾烷型三萜23、24、25,环阿屯烷型三萜22、26和结构新奇的Wuweiziartane-型三萜27、28;酚苷29、30;甾体31。其中新化合物6个,分别为10、13、14、16、27、28;4个化合物4、15、19、21为首次从该属植物中分离得到;14个化合物1、2、3、6、9、11、17、19、20、22、23、24、26、29为首次从该植物中分离得到。
对华中五味子藤茎中的1、2、4、7、9、12、14、19、22、25共10个化合物进行了杀菌、杀虫和除草活性的研究。结果表明化合物2、12、22对禾生腐霉菌(Pythium graminicola)显示出微弱的杀菌活性。化合物22对棉蚜虫(Aphis gossypii)有一定的杀虫活性。化合物4、9和12对小菜蛾(Plutella xylostella)显示了较强的杀虫活性。(?)
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Schisandra sphenanthera Rehd.et Wils, is a climbing plant that is widely found in Sichuan, Hubei, Shanxi and Yunnan province. The fruits are used as antitussive and tonic agents under the name of Nan-wuweizi in traditional Chinese medicine. Modern pharmacologic researches revealed that Schisandra plants are commonly used in China as tonic, sedative, and astringent agents.
Some phytochemical studies of S. sphenanthera fruits led to the isolation of six dibenzocyclooctadiene lignans, five tetrahydrofuran lignans and four triterpenes. Nine novel schisanartane-type nortriterpenoids have been isolated from the leaves and stems of S. sphenanthera . Lignans and terpenes are bioactive constituents of S. sphenanthera, which showed various beneficial activities including antihepatitis, antitumor, anti-HIV and antilipid peroxidation effects.
In order to study on the chemical constituents from the rattan of S. sphenanthera, the compounds were isolated by the solvent extraction, silica gel, and reversed-phase silica gel column chromatography and semi-preparative HLPC. Their structures were identified by spectroscopic methods, especially 2D-NMR techniques. 33 compounds were isolated from the EtOAc - extraction. 31 of the structures were elucidated on the basis of physicochemical properities and spectra methods, including aromatic compounds 1, 2, 3; tetrahydrofuran lignans 4, 5, 6, 7; dibenzocyclooctenes 8, 9, 10, 11, 12; 7,8-seco-lignans 13, 14, 15, 16; monoterpenoid 17; sesquiterpenoids 18, 19, 20, 21; lanostane-type triterpenoids 23, 24, 25; cycloartane-type triterpenoids, 22, 26; wuweiziartane-type trierpenoids 27, 28;phenolic glycoside 29, 30; steroids 31. compounds 10, 13, 14, 16, 27, 28 were identified as new compounds;compounds 4, 15, 19, 21 were obtained for the first time from the genus;and 1, 2, 3, 6, 9, 11, 17, 19, 20, 22, 23, 24, 26, 29 were obtained from the plant for the first time.
The antifungal , insecticidal and herbicidal activities of 10 compounds: 1, 2, 4, 7, 9, 12, 14 , 19, 22, 25 from Schisandra sphenanthera was determined by using early screen method. The experimental results indicated that compounds 2, 12, 22 showed weak antifungal activities against Pythium graminicola, compound 22 showed moderate insecticidal activities against Aphis gossypii, and compounds 4, 9, 12 showed strong insecticidal activities against Plutella xylostella. (?)
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引文
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