几株放线菌发酵液抑菌活性成分的研究
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摘要
微生物是活性先导化合物及新药最重要的来源之一。放线菌与人类的生活关系极为密切，是一类比其他微生物更为丰富的生物活性物质资源。
本文在原有工作的基础上，进一步研究了添加前体物质对放线菌Streptomycesalboflavus313菌株发酵液活性及代谢产物中各成分含量的影响，并对其发酵液中的活性成分进行了进一步的分离和结构鉴定；本文还以菌株SC11、11D2-9和GXWl作为材料，分别从菌株发酵产物的生物活性测定、主要活性代谢产物的分离纯化和结构鉴定、菌株的分类鉴定方面进行了系统的研究，主要研究结果如下：
1.研究了添加前体物质对Streptomyces alboflavus313菌株发酵液的抑菌活性及其代谢产物中各成分含量的影响，结果表明发酵液中添加0.5g/L L-谷氨酸钠时，代谢产物m/z750、723、860和743的含量分别比对照提高了10.50倍、22.48倍、16.73倍和12.59倍。
2.采用活性追踪的方法，从添加0.5g/L L-谷氨酸钠的S. alboflavus313菌株发酵液中分离得到一个抗菌活性成分，鉴定为一种新颖的环六肽化合物NW-G12。与NW-G01的区别是NW-G12的色氨酸没有被氯化。通过抗菌谱和抑菌活性的比较，发现NW-G01和NW-G12并没有明显的差异。这说明色氨酸上氯原子的有无并不是抑菌活性的决定性因素。同时，从该菌株发酵液中还分离得到了1个活性化合物F2，鉴定为沙漠霉素A。
3.研究了化合物NW-G01对番茄灰霉病菌的作用机理。100μg/mL NW-G01处理12h后，菌丝的还原糖、壳聚糖、可溶性蛋白和丙酮酸含量、几丁质酶活性均呈现降低的趋势。
4.采用活性追踪的方法，从SC11菌株发酵液中分离得到了1个活性化合物F5。室内生测结果表明，F5对革兰氏阳性菌蜡状芽孢杆菌、枯草芽孢杆菌和金黄色葡萄球菌有很强的抑菌活性，其MIC值分别为3.9μg/mL、7.8μg/mL和7.8μg/mL；而对革兰氏阴性菌大肠埃希氏菌和铜绿假单胞菌没有明显的抑菌活性，其MIC值均大于250μg/mL。对苹果炭疽病菌、茄子黄萎病菌、小麦赤霉病菌、烟草赤星病菌、西瓜枯萎病菌、油菜菌核病菌、番茄灰霉病菌等主要农作物病原真菌的菌丝生长均有一定程度的抑制作用。根据MS、1H NMR、13C NMR等波谱数据分析，将其鉴定为沙漠霉素A。
5.建立了沙漠霉素类化合物的液-质联用分析方法，可以用于抗生素筛选研究中沙漠霉素类化合物的早期识别、排重。
6.室内生测结果表明，11D2-9菌株发酵液对革兰氏阳性细菌有较好的抑制作用；对革兰氏阴性细菌无明显的抑制作用；对苹果炭疽病菌、茄子黄萎病菌、小麦赤霉病菌、烟草赤星病菌、西瓜枯萎病菌、油菜菌核病菌、番茄灰霉病菌的菌丝生长无明显的抑制作用；对小麦白粉病菌的保护和治疗效果分别为69.33%和61.93%。采用活性追踪的方法，从11D2-9发酵液中分离得到1个活性化合物F1。根据MS、1H NMR、13C NMR等波谱数据分析，将其鉴定为白利辛霉素。
7.室内生测结果表明，GXWl菌株发酵液对革兰氏阳性细菌、革兰氏阴性细菌、植物病原真菌均有一定的抑制作用。采用活性追踪的方法，从GXWl菌株发酵液中分离得到抗菌蛋白条带3-1、3-2，依赖LC-MS/MS技术，将3-1和3-2鉴定为磷酸盐结合蛋白前体。
8.采用多相分类法，通过菌株形态特征和培养特征的观察、生理生化指标的测定和16S rDNA序列分析，结果表明，SC11、11D2-9菌株与模式菌株Streptomyces alboflavusNBRC-13196T具有高度的相似性(99%)， GXWl菌株与模式菌株Streptomycesrubiginosohelvolus NBRC12912T的同源相似性也为99%。三株菌株与模式菌株的生理生化指标不完全相同，但大多数指标大体一致。因此建议将菌株SC11、11D2-9和GXWl分别命名为Streptomyces alboflavus SC11、Streptomyces alboflavus11D2-9和Streptomycesrubiginosohelvolus GXWl。
Microbial resources is a kind of potential renewable medicinal resource and one ofthe most important sources of lead compounds and new drug. Actinomycetes is veryclose to human life, and it is the resources of biological activity material that is moreabundant than other microorganisms.
This paper is about the further research work on one actinomycete strainStreptomyces alboflavus313, including the influence of the antibacterial activity andthe content of the metabolism product by feeding precursor into the fermentation brothof the strain, purification of the active compouds and structural identification. Inaddition, it is about the research work based on three strains SC11、11D2-9and GXWl,including evaluation of antimicrobial activity, purification and structural identificationof the main active metabolite, strains identification. The primary results are as follows:
1. The influence of the antibacterial activity and the content of the metabolismproduct has been studied by feeding precursor into the fermentation broth of the strainStreptomyces alboflavus313. The results showed that the content of metabolites m/z750,723,860and743was improved than the contrast by10.50times,22.48times,16.73times and12.59times respectively after feeding0.5g/L L-glutamate.
2. Guided by the results of the bioassay, an antimicrobial component, novelnon-chlorinated cyclic hexapeptide NW-G12was isolated from the fermentation of S.alboflavus313. The difference between NW-G01and NW-G12is the Trp of NW-G12was not chlorinated. Comparison of the antibacterial spectra and inhibition activities ofNW-G01and NW-G12, no obvious differences were observed. It indicated that thepresence of chlorine atom at Trp was not a decisive factor for the antibacterial activity.Also, an active compound F2was separated from the fermentation broth of S.alboflavus313. According to analysis of MS,1H NMR and13C NMR spectroscopydatas, the molecular structure of F2was identified as Desertomycin A.
3. The mechanism of action of compound NW-G01against Botrytis cinerea wasstudied. After treated with NW-G01at100μg/mL for12h, the mycelial reducing sugar,chitosan, soluble protein and pyruvate content, chitinase activity showed decliningtendency.
4. Guided by the results of the bioassay, an active compound F5was separatedfrom the fermentation broth of the strain SC11. Bioassay results in vitro showed that F5had strong antibacterial activity against gram-positive bacteria Bacillus cereus, Bacillussubtilis and Staphylococcus aureus with the MIC values of3.9μg/mL,7.8μg/mL and7.8μg/mL, but it had no obvious antibacterial activity against gram-negative bacteriaEscherichia coli and Pseudomonas aeruginosa with the MIC values of more than250μg/mL. It also exhibited inhibitory effect on mycelial growth against pathogenic fungiof main crop, such as Colletotrichum gloeosporioides, Verticillium dahliae, Gibberellazeae, Alternaria alternata, Fusarium oxysporum, Sclerotinia sclerotiorum and Botrytiscinerea. According to analysis of MS,1H NMR and13C NMR spectroscopy datas, themolecular structure of F2was identified as Desertomycin A.
5. An analytical method for the determination of Desertomycin and its analoguesin microbial fermentation broth by LC-MS was established. The method was suitablefor rapid detecting Desertomycin and its anologues in the early-stage of antibioticsscreening from the fermentation broth to avoid repeated screening.
6. Bioassay results in vitro showed that the fermentation broth of the strain11D2-9showed strong antibacterial activity against gram-positive bacteria. But had noobvious inhibitory effects against gram-negative bacteria and plant pathogenic fungi.The results of pot experiment indicated that the fermentation filtrate had69.33%protective efficacy and61.93%curative efficacy against Blumeria graminis. Guided bythe results of the bioassay, an active compound was separated from the fermentationbroth of the strain11D2-9. According to analysis of MS,1H NMR and13C NMRspectroscopy datas, the molecular structure of the compound was identified asAlborixin.
7. Bioassay results in vitro showed that the fermentation broth of the strain GXWlshowed good antibacterial activity against gram-positive bacterium, gram-negativebacterium and plant pathogenic fungi. Guided by the results of the bioassay,antimicrobial protein bands3-1and3-2were separated from the fermentation broth ofthe strain GXWl. According to technology of LC-MS/MS, the bands were identified asPhosphate-binding Protein Precursor.
8. According to the results of morphological characteristics, culture characteristics,physiological and biochemical measurement and analysis of16S rDNA sequence,strains SC11,11D2-9were highly homological (99%) with the type strain Streptomycesalboflavus NBRC-13196Tand GXWl was highly homological (99%) with the typestrain Streptomyces rubiginosohelvolus NBRC12912T. The strains were similar features in majority with the type strain. Therefore, the strain SC11,11D2-9and GXWlwere suggested to identify as Streptomyces alboflavus SC11, Streptomyces alboflavus11D2-9and Streptomyces rubiginosohelvolus GXWl, respectively.
本文在原有工作的基础上，进一步研究了添加前体物质对放线菌Streptomycesalboflavus313菌株发酵液活性及代谢产物中各成分含量的影响，并对其发酵液中的活性成分进行了进一步的分离和结构鉴定；本文还以菌株SC11、11D2-9和GXWl作为材料，分别从菌株发酵产物的生物活性测定、主要活性代谢产物的分离纯化和结构鉴定、菌株的分类鉴定方面进行了系统的研究，主要研究结果如下：
1.研究了添加前体物质对Streptomyces alboflavus313菌株发酵液的抑菌活性及其代谢产物中各成分含量的影响，结果表明发酵液中添加0.5g/L L-谷氨酸钠时，代谢产物m/z750、723、860和743的含量分别比对照提高了10.50倍、22.48倍、16.73倍和12.59倍。
2.采用活性追踪的方法，从添加0.5g/L L-谷氨酸钠的S. alboflavus313菌株发酵液中分离得到一个抗菌活性成分，鉴定为一种新颖的环六肽化合物NW-G12。与NW-G01的区别是NW-G12的色氨酸没有被氯化。通过抗菌谱和抑菌活性的比较，发现NW-G01和NW-G12并没有明显的差异。这说明色氨酸上氯原子的有无并不是抑菌活性的决定性因素。同时，从该菌株发酵液中还分离得到了1个活性化合物F2，鉴定为沙漠霉素A。
3.研究了化合物NW-G01对番茄灰霉病菌的作用机理。100μg/mL NW-G01处理12h后，菌丝的还原糖、壳聚糖、可溶性蛋白和丙酮酸含量、几丁质酶活性均呈现降低的趋势。
4.采用活性追踪的方法，从SC11菌株发酵液中分离得到了1个活性化合物F5。室内生测结果表明，F5对革兰氏阳性菌蜡状芽孢杆菌、枯草芽孢杆菌和金黄色葡萄球菌有很强的抑菌活性，其MIC值分别为3.9μg/mL、7.8μg/mL和7.8μg/mL；而对革兰氏阴性菌大肠埃希氏菌和铜绿假单胞菌没有明显的抑菌活性，其MIC值均大于250μg/mL。对苹果炭疽病菌、茄子黄萎病菌、小麦赤霉病菌、烟草赤星病菌、西瓜枯萎病菌、油菜菌核病菌、番茄灰霉病菌等主要农作物病原真菌的菌丝生长均有一定程度的抑制作用。根据MS、1H NMR、13C NMR等波谱数据分析，将其鉴定为沙漠霉素A。
5.建立了沙漠霉素类化合物的液-质联用分析方法，可以用于抗生素筛选研究中沙漠霉素类化合物的早期识别、排重。
6.室内生测结果表明，11D2-9菌株发酵液对革兰氏阳性细菌有较好的抑制作用；对革兰氏阴性细菌无明显的抑制作用；对苹果炭疽病菌、茄子黄萎病菌、小麦赤霉病菌、烟草赤星病菌、西瓜枯萎病菌、油菜菌核病菌、番茄灰霉病菌的菌丝生长无明显的抑制作用；对小麦白粉病菌的保护和治疗效果分别为69.33%和61.93%。采用活性追踪的方法，从11D2-9发酵液中分离得到1个活性化合物F1。根据MS、1H NMR、13C NMR等波谱数据分析，将其鉴定为白利辛霉素。
7.室内生测结果表明，GXWl菌株发酵液对革兰氏阳性细菌、革兰氏阴性细菌、植物病原真菌均有一定的抑制作用。采用活性追踪的方法，从GXWl菌株发酵液中分离得到抗菌蛋白条带3-1、3-2，依赖LC-MS/MS技术，将3-1和3-2鉴定为磷酸盐结合蛋白前体。
8.采用多相分类法，通过菌株形态特征和培养特征的观察、生理生化指标的测定和16S rDNA序列分析，结果表明，SC11、11D2-9菌株与模式菌株Streptomyces alboflavusNBRC-13196T具有高度的相似性(99%)， GXWl菌株与模式菌株Streptomycesrubiginosohelvolus NBRC12912T的同源相似性也为99%。三株菌株与模式菌株的生理生化指标不完全相同，但大多数指标大体一致。因此建议将菌株SC11、11D2-9和GXWl分别命名为Streptomyces alboflavus SC11、Streptomyces alboflavus11D2-9和Streptomycesrubiginosohelvolus GXWl。
Microbial resources is a kind of potential renewable medicinal resource and one ofthe most important sources of lead compounds and new drug. Actinomycetes is veryclose to human life, and it is the resources of biological activity material that is moreabundant than other microorganisms.
This paper is about the further research work on one actinomycete strainStreptomyces alboflavus313, including the influence of the antibacterial activity andthe content of the metabolism product by feeding precursor into the fermentation brothof the strain, purification of the active compouds and structural identification. Inaddition, it is about the research work based on three strains SC11、11D2-9and GXWl,including evaluation of antimicrobial activity, purification and structural identificationof the main active metabolite, strains identification. The primary results are as follows:
1. The influence of the antibacterial activity and the content of the metabolismproduct has been studied by feeding precursor into the fermentation broth of the strainStreptomyces alboflavus313. The results showed that the content of metabolites m/z750,723,860and743was improved than the contrast by10.50times,22.48times,16.73times and12.59times respectively after feeding0.5g/L L-glutamate.
2. Guided by the results of the bioassay, an antimicrobial component, novelnon-chlorinated cyclic hexapeptide NW-G12was isolated from the fermentation of S.alboflavus313. The difference between NW-G01and NW-G12is the Trp of NW-G12was not chlorinated. Comparison of the antibacterial spectra and inhibition activities ofNW-G01and NW-G12, no obvious differences were observed. It indicated that thepresence of chlorine atom at Trp was not a decisive factor for the antibacterial activity.Also, an active compound F2was separated from the fermentation broth of S.alboflavus313. According to analysis of MS,1H NMR and13C NMR spectroscopydatas, the molecular structure of F2was identified as Desertomycin A.
3. The mechanism of action of compound NW-G01against Botrytis cinerea wasstudied. After treated with NW-G01at100μg/mL for12h, the mycelial reducing sugar,chitosan, soluble protein and pyruvate content, chitinase activity showed decliningtendency.
4. Guided by the results of the bioassay, an active compound F5was separatedfrom the fermentation broth of the strain SC11. Bioassay results in vitro showed that F5had strong antibacterial activity against gram-positive bacteria Bacillus cereus, Bacillussubtilis and Staphylococcus aureus with the MIC values of3.9μg/mL,7.8μg/mL and7.8μg/mL, but it had no obvious antibacterial activity against gram-negative bacteriaEscherichia coli and Pseudomonas aeruginosa with the MIC values of more than250μg/mL. It also exhibited inhibitory effect on mycelial growth against pathogenic fungiof main crop, such as Colletotrichum gloeosporioides, Verticillium dahliae, Gibberellazeae, Alternaria alternata, Fusarium oxysporum, Sclerotinia sclerotiorum and Botrytiscinerea. According to analysis of MS,1H NMR and13C NMR spectroscopy datas, themolecular structure of F2was identified as Desertomycin A.
5. An analytical method for the determination of Desertomycin and its analoguesin microbial fermentation broth by LC-MS was established. The method was suitablefor rapid detecting Desertomycin and its anologues in the early-stage of antibioticsscreening from the fermentation broth to avoid repeated screening.
6. Bioassay results in vitro showed that the fermentation broth of the strain11D2-9showed strong antibacterial activity against gram-positive bacteria. But had noobvious inhibitory effects against gram-negative bacteria and plant pathogenic fungi.The results of pot experiment indicated that the fermentation filtrate had69.33%protective efficacy and61.93%curative efficacy against Blumeria graminis. Guided bythe results of the bioassay, an active compound was separated from the fermentationbroth of the strain11D2-9. According to analysis of MS,1H NMR and13C NMRspectroscopy datas, the molecular structure of the compound was identified asAlborixin.
7. Bioassay results in vitro showed that the fermentation broth of the strain GXWlshowed good antibacterial activity against gram-positive bacterium, gram-negativebacterium and plant pathogenic fungi. Guided by the results of the bioassay,antimicrobial protein bands3-1and3-2were separated from the fermentation broth ofthe strain GXWl. According to technology of LC-MS/MS, the bands were identified asPhosphate-binding Protein Precursor.
8. According to the results of morphological characteristics, culture characteristics,physiological and biochemical measurement and analysis of16S rDNA sequence,strains SC11,11D2-9were highly homological (99%) with the type strain Streptomycesalboflavus NBRC-13196Tand GXWl was highly homological (99%) with the typestrain Streptomyces rubiginosohelvolus NBRC12912T. The strains were similar features in majority with the type strain. Therefore, the strain SC11,11D2-9and GXWlwere suggested to identify as Streptomyces alboflavus SC11, Streptomyces alboflavus11D2-9and Streptomyces rubiginosohelvolus GXWl, respectively.
引文
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