楹树的活性成分研究仪花中真菌053的代谢产物研究
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摘要
本论文包括楹树的活性成分研究和豆科植物仪花中真菌053的代谢产物研究两个部分。
楹树Albizia chinensis(Osb.)Merr.为豆科合欢属植物。《全国中草药汇编》(下册)记载其药用树皮,有固涩止泻、收敛生肌之功效。主治肠炎、腹泻、痢疾。分布于福建、湖南、广东、广西、云南。其茎皮和叶有毒。茎皮中主要有毒成分是三萜酸苷—合欢催产素(albitocin)。但其化学成分结构尚未见报道。而其叶的化学成分和生物活性也未见报道。对楹树茎皮乙醇提取物及其乙酸乙酯、正丁醇部位和水部位的活性筛选结果表明,发现正丁醇部位具有明显的细胞毒活性,我们利用活性跟踪从正丁醇部位分离得到6个化合物。通过理化性质、波谱学方法和化学方法鉴定了它们的结构:Albizoside A～E(1-5),Julibroside J_8(6)。其中化合物1-5为新化合物。对楹树叶95%乙醇提取物及其乙酸乙酯、正丁醇和水部位的活性筛选结果表明,发现乙酸乙酯部位和正丁醇部位具有抗氧化活性,从中分离得到15个化合物。通过理化性质和波谱学方法,确定了它们的结构,分别为:kaempferol(7),quercetin(8),kaempferol 3-O-α-L-arabinofuranoside(9),kaempferol3-O-α-L-rhamnopyranoside(10),quercetin 3-O-α-L-rhamnopyranoside(11),quercetin3-O-β-D-glucopyranoside(12),quercetin 3′-O-β-D-glucopyranosyl-3-O-rutinoside(13),kaempferol 3,7-di-O-β-D-glucopyranoside(14),quercetin 7-O-rutinoside(15),rutin(16),D-pinitol(17),luteolin 7-O-β-D-glucopyranoside(18),(+)-lyoniresinol3α-O-β-D-glucopyranoside(19),(-)-lyoniresinol 3a-O-β-D-glucopyranoside(20),syringin(21)。
本课题组前期从豆科植物仪花Lysidicie rhodostegia Hance根中分离得到44个化合物,其中包括一些结构新颖的间苯三酚类型的衍生物。部分新化合物有较强的生物活性,如扩张血管活性,抗氧化活性。为了进一步寻找新颖结构的活性化合物,同时解决药用资源问题,本论文作者利用PDA培养基发酵仪花中真菌053,从发酵液乙酸乙酯萃取部位分离得到13个化合物。通过理化常数测定、波谱数据分析鉴定了它们的结构:(p-hydroxyphenyl)ethanol(1),2-(2-hydroxy-propionylamino)-benzamide(2),2-Acetyl-3H-quinazolin-4-one(3),Hydroxypestalopyrone(4),Rhodostegone A(5),Nectriapyrone A(6),Nectriapyrone(7),RhodostegoneB(8),Rhodostegone C(9),Rhodostegone D(10),Rhodostegone E(11),cis-Hydroxyscytalone(12),(+)-Scytalone(13)。其中新化合物5个。这些化合物包括6个α-吡喃酮类型化合物、2个环己烯酮衍生物、2个二氢萘型化合物和3个其它结构类型化合物。
活性筛选结果表明,楹树茎皮中分离得到的5个新三萜皂苷(1.5)具有较强的细胞毒活性,IC_(50)值为0.01-7.69μM(除化合物5对HCT-8无活性外)。体内试验中,总皂苷静脉注射ICR小鼠,LD_(50)值为5 mg/kg。
仪花中真菌053的发酵液乙酸乙酯萃取部位具有一定的细胞毒活性,IC_(50)值为17.07-48.87μM。
The thesis included two parts of studies on bioactivity constituents from Albizia chinensis(Osb.) Merr.and metabolites from the 053 fungus of Lysidicie rhodostegia Hance.
Albizia chinensis(Osb.) Merr.,belonging to the family Leguminosae,is widely distributed in Fujian,Hunan,Guangdong,Guangxi and Yunnan Provinces,in China.Its stem barks have been used in Chinese folk medicine for the treatment of diarrhea and wounds.It is reported that the leaves and stem barks were toxic,and triterpene acid glycosides-albitocin is the main toxic components of stem barks.In our investigation, the BuOH extract of dried stem barks of A.chinensis.showed cytotoxicity against five cultured human tumor cell lines.Chromatographic fractionation led to the isolation of six compounds(1-6).The structures of five new triterpenoid saponins,named albizoside A～E(1 - 5),were established on the basis of extensive 1D and 2D NMR experiments and confirmed by chemical hydrolysis,while one known compound was identified as Julibroside J_8(6).The five new triterpenoid saponins showed significant cytotoxicity with IC_(50) values of 0.01-7.69μM against five tumor cell lines(except compound 5 showed no activity against HCT-8).In vivo experiments,intravenous injection of total saponins of ICR mice with LD_(50) value of 5 mg/kg.Pharmacological activity screening showed that the EtOAc and BuOH extracts of the leaves of this plant exhibited anti-oxidant activities,from which 15 compounds were isolated.On the basis of physicochemical properties and spectroscopic methods,these compounds were elucidated as kaempferol(7),quercetin(8),kaempferol 3-O-α-L-arabinofuranoside(9), kaempferol 3-O-α-L-rhamnopyranoside(10),quercetin 3-O-α-L-rhamnopyranoside(11), quercetin 3-O-β-D-glucopyranoside(12),quercetin 3'-O-β-D-glucopyranosyl-3-O-rutinoside (13),kaempferol 3,7-di-O-β-D-glucopyranoside(14),quercetin7-O-rutinoside (15),rutin(16),D-pinitol(17),luteolin 7-O-β-D-glucopyranoside(18),(+)-lyoniresinol 3a-O-β-D-glucopyranoside(19),(-) -lyoniresinol 3α-O-β-D-glucopyranoside(20), syringin(21).
The previous research by our group isolated 44 compounds from the roots of Lysidicie rhodostegia Hance,including some novel compounds of phloroglucinol derivatives.Many compounds exhibited strong biological activity,such as the expansion of vascular activity,antioxidant activity.To further search for new active compounds,while addressing the issue of medicinal resources,the author make use of PDA medium fermentation of fungus 053 of Lysidicie rhodostegia Hance.From the fermentation broth,13 compounds were isolated from the part of ethyl acetate extraction.Based on physicochemical properties and spectroscopic methods,their structures were elucidated as(p-hydroxyphenyl) ethanol(1),2-(2-hydroxy-propionyl amino)-benzamide(2),2-Acetyl-3H-quinazolin-4-one(3),Hydroxypestalopyrone(4), Rhodostegone A(5),Nectriapyrone A(6),Nectriapyrone(7),Rhodostegone B(8), Rhodostegone C(9),Rhodostegone D(10),Rhodostegone E(11),cis-Hydroxyscytalone (12),(+)-Scytalone(13).Among them,five were new compounds.These compounds including sixα-pyrone type compounds,two cyclohexenone type derivatives,two dihydronaphthalene type derivatives and three other type structures.The ethyl acetate extraction showed weak cytotoxicity with IC_(50) of 17.07-48.87μM.
楹树Albizia chinensis(Osb.)Merr.为豆科合欢属植物。《全国中草药汇编》(下册)记载其药用树皮,有固涩止泻、收敛生肌之功效。主治肠炎、腹泻、痢疾。分布于福建、湖南、广东、广西、云南。其茎皮和叶有毒。茎皮中主要有毒成分是三萜酸苷—合欢催产素(albitocin)。但其化学成分结构尚未见报道。而其叶的化学成分和生物活性也未见报道。对楹树茎皮乙醇提取物及其乙酸乙酯、正丁醇部位和水部位的活性筛选结果表明,发现正丁醇部位具有明显的细胞毒活性,我们利用活性跟踪从正丁醇部位分离得到6个化合物。通过理化性质、波谱学方法和化学方法鉴定了它们的结构:Albizoside A～E(1-5),Julibroside J_8(6)。其中化合物1-5为新化合物。对楹树叶95%乙醇提取物及其乙酸乙酯、正丁醇和水部位的活性筛选结果表明,发现乙酸乙酯部位和正丁醇部位具有抗氧化活性,从中分离得到15个化合物。通过理化性质和波谱学方法,确定了它们的结构,分别为:kaempferol(7),quercetin(8),kaempferol 3-O-α-L-arabinofuranoside(9),kaempferol3-O-α-L-rhamnopyranoside(10),quercetin 3-O-α-L-rhamnopyranoside(11),quercetin3-O-β-D-glucopyranoside(12),quercetin 3′-O-β-D-glucopyranosyl-3-O-rutinoside(13),kaempferol 3,7-di-O-β-D-glucopyranoside(14),quercetin 7-O-rutinoside(15),rutin(16),D-pinitol(17),luteolin 7-O-β-D-glucopyranoside(18),(+)-lyoniresinol3α-O-β-D-glucopyranoside(19),(-)-lyoniresinol 3a-O-β-D-glucopyranoside(20),syringin(21)。
本课题组前期从豆科植物仪花Lysidicie rhodostegia Hance根中分离得到44个化合物,其中包括一些结构新颖的间苯三酚类型的衍生物。部分新化合物有较强的生物活性,如扩张血管活性,抗氧化活性。为了进一步寻找新颖结构的活性化合物,同时解决药用资源问题,本论文作者利用PDA培养基发酵仪花中真菌053,从发酵液乙酸乙酯萃取部位分离得到13个化合物。通过理化常数测定、波谱数据分析鉴定了它们的结构:(p-hydroxyphenyl)ethanol(1),2-(2-hydroxy-propionylamino)-benzamide(2),2-Acetyl-3H-quinazolin-4-one(3),Hydroxypestalopyrone(4),Rhodostegone A(5),Nectriapyrone A(6),Nectriapyrone(7),RhodostegoneB(8),Rhodostegone C(9),Rhodostegone D(10),Rhodostegone E(11),cis-Hydroxyscytalone(12),(+)-Scytalone(13)。其中新化合物5个。这些化合物包括6个α-吡喃酮类型化合物、2个环己烯酮衍生物、2个二氢萘型化合物和3个其它结构类型化合物。
活性筛选结果表明,楹树茎皮中分离得到的5个新三萜皂苷(1.5)具有较强的细胞毒活性,IC_(50)值为0.01-7.69μM(除化合物5对HCT-8无活性外)。体内试验中,总皂苷静脉注射ICR小鼠,LD_(50)值为5 mg/kg。
仪花中真菌053的发酵液乙酸乙酯萃取部位具有一定的细胞毒活性,IC_(50)值为17.07-48.87μM。
The thesis included two parts of studies on bioactivity constituents from Albizia chinensis(Osb.) Merr.and metabolites from the 053 fungus of Lysidicie rhodostegia Hance.
Albizia chinensis(Osb.) Merr.,belonging to the family Leguminosae,is widely distributed in Fujian,Hunan,Guangdong,Guangxi and Yunnan Provinces,in China.Its stem barks have been used in Chinese folk medicine for the treatment of diarrhea and wounds.It is reported that the leaves and stem barks were toxic,and triterpene acid glycosides-albitocin is the main toxic components of stem barks.In our investigation, the BuOH extract of dried stem barks of A.chinensis.showed cytotoxicity against five cultured human tumor cell lines.Chromatographic fractionation led to the isolation of six compounds(1-6).The structures of five new triterpenoid saponins,named albizoside A～E(1 - 5),were established on the basis of extensive 1D and 2D NMR experiments and confirmed by chemical hydrolysis,while one known compound was identified as Julibroside J_8(6).The five new triterpenoid saponins showed significant cytotoxicity with IC_(50) values of 0.01-7.69μM against five tumor cell lines(except compound 5 showed no activity against HCT-8).In vivo experiments,intravenous injection of total saponins of ICR mice with LD_(50) value of 5 mg/kg.Pharmacological activity screening showed that the EtOAc and BuOH extracts of the leaves of this plant exhibited anti-oxidant activities,from which 15 compounds were isolated.On the basis of physicochemical properties and spectroscopic methods,these compounds were elucidated as kaempferol(7),quercetin(8),kaempferol 3-O-α-L-arabinofuranoside(9), kaempferol 3-O-α-L-rhamnopyranoside(10),quercetin 3-O-α-L-rhamnopyranoside(11), quercetin 3-O-β-D-glucopyranoside(12),quercetin 3'-O-β-D-glucopyranosyl-3-O-rutinoside (13),kaempferol 3,7-di-O-β-D-glucopyranoside(14),quercetin7-O-rutinoside (15),rutin(16),D-pinitol(17),luteolin 7-O-β-D-glucopyranoside(18),(+)-lyoniresinol 3a-O-β-D-glucopyranoside(19),(-) -lyoniresinol 3α-O-β-D-glucopyranoside(20), syringin(21).
The previous research by our group isolated 44 compounds from the roots of Lysidicie rhodostegia Hance,including some novel compounds of phloroglucinol derivatives.Many compounds exhibited strong biological activity,such as the expansion of vascular activity,antioxidant activity.To further search for new active compounds,while addressing the issue of medicinal resources,the author make use of PDA medium fermentation of fungus 053 of Lysidicie rhodostegia Hance.From the fermentation broth,13 compounds were isolated from the part of ethyl acetate extraction.Based on physicochemical properties and spectroscopic methods,their structures were elucidated as(p-hydroxyphenyl) ethanol(1),2-(2-hydroxy-propionyl amino)-benzamide(2),2-Acetyl-3H-quinazolin-4-one(3),Hydroxypestalopyrone(4), Rhodostegone A(5),Nectriapyrone A(6),Nectriapyrone(7),Rhodostegone B(8), Rhodostegone C(9),Rhodostegone D(10),Rhodostegone E(11),cis-Hydroxyscytalone (12),(+)-Scytalone(13).Among them,five were new compounds.These compounds including sixα-pyrone type compounds,two cyclohexenone type derivatives,two dihydronaphthalene type derivatives and three other type structures.The ethyl acetate extraction showed weak cytotoxicity with IC_(50) of 17.07-48.87μM.
引文
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