海洋细菌041381和海洋放线菌sh6004次级代谢产物活性成分研究
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摘要
海洋微生物生存环境特殊、复杂,其次级代谢产物结构新颖、种类繁多,是新结构活性化合物的重要来源。为了寻找结构新颖的活性化合物,本论文采用活性追踪的方法开展了对海洋细菌和海洋放线菌次级代谢产物的研究工作。内容包括:活性菌株的初步评价及抗菌、抗肿瘤活性成分的追踪分离;单体化合物的结构解析;单体化合物抗肿瘤活性的初步评价;一个新化合物的合成及构型的确定。
以海洋细菌041381和海洋放线菌sh6004为研究对象,对发酵产物运用萃取,薄层层析,正相、反相硅胶柱层析,LH-20凝胶柱层析,反相高压液相等化学的分离纯化手段,采用滤纸片法进行抗菌活性追踪分离。从海洋细菌041381的次级代谢产物中分离得到14个单体化合物(1-14);从海洋放线菌sh6004的次级代谢产物中分离得到4个单体化合物(15-18)共18个化合物。
继而,利用理化性质和波谱学方法(IR,UV,MS,NMR等)结合化学反应的方法阐述了18个化合物的化学结构(化合物结构及名称参见Table 1),其中新化合物2个(1, 2)。所得的化合物主要是含氮类化合物,结构类型包括:喹唑啉酮类生物碱4个(1-4),环二肽5个(5-9),甾醇3个(10-12),苯的衍生物2个(9-13),其他生物碱4个(14-18)。
利用SRB法、滤纸片法对分离获得的单体化合物的抗肿瘤、抗菌活性分别进行了初步评价。从中筛选出了6个抗菌活性化合物(1, 2, 15-18)。新化合物1,2在浓度为10μg/mL时对白色念珠菌有强抑制作用,化合物15-18在浓度为10μg/mL时表现出较强的抗金黄色葡萄球菌和抗枯草芽孢杆菌作用。
对新化合物1进行了合成,确定了化合物1的绝对构型,同时得到两个副产物:喹唑啉酮类生物碱的对映异构体J和K。
本文对两株海洋微生物的次级代谢产物进行了系统研究,共分离鉴定了18个化合物,包括新化合物2个,分别是2-(heptan-3-yl)quinazolin-4(3H)-one和2-(heptan-3-yl)-2,3-dihy-droquinazolin-4(1H)-one;较高活性化合物6个;提供了一株能特征产生喹唑啉酮类生物碱的海洋细菌。这一研究丰富了海洋天然产物的结构类型,为抗菌药物的筛选提供了活性化合物及活性菌株。
Because of the special ecological environment, marine-derived microorganisms possess distinct and complex metabolic capabilities, resulting in wide diversity of their secondary metabolites in chemical structure and biological activity. Thus, bacterium and actinomyces become important resources of active lead compounds. This thesis describes the bioactive constituents from sponge-derived bacterium 041381 and actinomyces sh6004. The work includes screening aimed strains, fermentation studies, bioassay-guided fractionation, structural elucidation, preliminary evaluation for antibacterial activities of pure compounds, synthesizing compound 1 and determining its absolute configuration.
After choosing appropriate fermentation condition, large-scale fermentation and preparation of the active fractions were performed to obtain the active components from the bioactive strains. By means of column chromatography over silica gel, Sephadex LH-20, preparative TLC and semi-preparative HPLC, 14 and 6 compounds were isolated from marine derived bacterium 041381 and actinomyces sh6004 brothes, respectively. The separation procedure is guided by disk diffusion method. By analyzing physico-chemical properties and spectral analysis (IR, UV, MS, NMR, etc.), their structures were elucidated as 2-(heptan-3-yl)quinazolin-4(3H)-one (1), 2-(heptan-3-yl)-2,3-dihydroquinazolin-4(1H)-one (2), 2-methylquinazolin-4(3H)-one (3), 2?benzylquinazolin-4(3H)-one (4), cyclo-(Pro-Ile) (5), Cyclo-(Pro-Leu) (6), Cyclo-(Pro-Val) (7), Cyclo-(Pro-Phe) (8), Cyclo-(Tyr-Pro) (9), Campester (10), Ergosterol(11), Ergosterol peroxide(12), benzamide (13), 2-phenylacetic acid (14), bisdethiobis-(methylthio)-gliotoxin (15), actinomycin D (16), actinomycin C2a (17), actinomycin C3 (18). The identified obtained compounds include four quinazolinone alkaloids (1-4), five dicyclopeptides (5-9), three sterols (10-12), two benzene derivates (9-13) and four other alkaloids (14-18). Compounds 1 and 2 were new compounds.
Compound 1 was synthesized, and its absolute configuration was determined .Meanwhile two by-products were obtained as enantiomers.
The antibacterial activity against several bacteriums of these compounds was assayed by disk diffusion method and among them 6 compounds (1, 2, 15-18) with antibacterial activity were found. Compound 1 and 2 show high inhibition activity against Candidaalbicans. Compounds 15-18 show high inhibition activity against Staphylococcus aureus and Bacillus subtilis. In addition, our study demonstrated for the first time that the quinazolinone alkaloids show inhibitory activity again Candidaalbican .
以海洋细菌041381和海洋放线菌sh6004为研究对象,对发酵产物运用萃取,薄层层析,正相、反相硅胶柱层析,LH-20凝胶柱层析,反相高压液相等化学的分离纯化手段,采用滤纸片法进行抗菌活性追踪分离。从海洋细菌041381的次级代谢产物中分离得到14个单体化合物(1-14);从海洋放线菌sh6004的次级代谢产物中分离得到4个单体化合物(15-18)共18个化合物。
继而,利用理化性质和波谱学方法(IR,UV,MS,NMR等)结合化学反应的方法阐述了18个化合物的化学结构(化合物结构及名称参见Table 1),其中新化合物2个(1, 2)。所得的化合物主要是含氮类化合物,结构类型包括:喹唑啉酮类生物碱4个(1-4),环二肽5个(5-9),甾醇3个(10-12),苯的衍生物2个(9-13),其他生物碱4个(14-18)。
利用SRB法、滤纸片法对分离获得的单体化合物的抗肿瘤、抗菌活性分别进行了初步评价。从中筛选出了6个抗菌活性化合物(1, 2, 15-18)。新化合物1,2在浓度为10μg/mL时对白色念珠菌有强抑制作用,化合物15-18在浓度为10μg/mL时表现出较强的抗金黄色葡萄球菌和抗枯草芽孢杆菌作用。
对新化合物1进行了合成,确定了化合物1的绝对构型,同时得到两个副产物:喹唑啉酮类生物碱的对映异构体J和K。
本文对两株海洋微生物的次级代谢产物进行了系统研究,共分离鉴定了18个化合物,包括新化合物2个,分别是2-(heptan-3-yl)quinazolin-4(3H)-one和2-(heptan-3-yl)-2,3-dihy-droquinazolin-4(1H)-one;较高活性化合物6个;提供了一株能特征产生喹唑啉酮类生物碱的海洋细菌。这一研究丰富了海洋天然产物的结构类型,为抗菌药物的筛选提供了活性化合物及活性菌株。
Because of the special ecological environment, marine-derived microorganisms possess distinct and complex metabolic capabilities, resulting in wide diversity of their secondary metabolites in chemical structure and biological activity. Thus, bacterium and actinomyces become important resources of active lead compounds. This thesis describes the bioactive constituents from sponge-derived bacterium 041381 and actinomyces sh6004. The work includes screening aimed strains, fermentation studies, bioassay-guided fractionation, structural elucidation, preliminary evaluation for antibacterial activities of pure compounds, synthesizing compound 1 and determining its absolute configuration.
After choosing appropriate fermentation condition, large-scale fermentation and preparation of the active fractions were performed to obtain the active components from the bioactive strains. By means of column chromatography over silica gel, Sephadex LH-20, preparative TLC and semi-preparative HPLC, 14 and 6 compounds were isolated from marine derived bacterium 041381 and actinomyces sh6004 brothes, respectively. The separation procedure is guided by disk diffusion method. By analyzing physico-chemical properties and spectral analysis (IR, UV, MS, NMR, etc.), their structures were elucidated as 2-(heptan-3-yl)quinazolin-4(3H)-one (1), 2-(heptan-3-yl)-2,3-dihydroquinazolin-4(1H)-one (2), 2-methylquinazolin-4(3H)-one (3), 2?benzylquinazolin-4(3H)-one (4), cyclo-(Pro-Ile) (5), Cyclo-(Pro-Leu) (6), Cyclo-(Pro-Val) (7), Cyclo-(Pro-Phe) (8), Cyclo-(Tyr-Pro) (9), Campester (10), Ergosterol(11), Ergosterol peroxide(12), benzamide (13), 2-phenylacetic acid (14), bisdethiobis-(methylthio)-gliotoxin (15), actinomycin D (16), actinomycin C2a (17), actinomycin C3 (18). The identified obtained compounds include four quinazolinone alkaloids (1-4), five dicyclopeptides (5-9), three sterols (10-12), two benzene derivates (9-13) and four other alkaloids (14-18). Compounds 1 and 2 were new compounds.
Compound 1 was synthesized, and its absolute configuration was determined .Meanwhile two by-products were obtained as enantiomers.
The antibacterial activity against several bacteriums of these compounds was assayed by disk diffusion method and among them 6 compounds (1, 2, 15-18) with antibacterial activity were found. Compound 1 and 2 show high inhibition activity against Candidaalbicans. Compounds 15-18 show high inhibition activity against Staphylococcus aureus and Bacillus subtilis. In addition, our study demonstrated for the first time that the quinazolinone alkaloids show inhibitory activity again Candidaalbican .
引文
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