粘细菌的筛选及其产生的新型抗肿瘤抗生素
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摘要
粘细菌(myxobacteria)是一类近年来引起广泛关注,但却研究尚少的重要药源微生物类群。根据细胞形态学,粘细菌分为12个属,约40个种。本课题在粘细菌传统筛选方法的基础上,采用高通量的试管培养方法,对分离的粘细菌进行了较大规模的筛选和初步鉴定,得到了376株粘细菌,并对其中的67株菌初步归到属。以埃坡霉素(Epothilones)的特征为筛选依据,筛选出在紫外区间扫描具有较强吸收的样品312个。
以B16、SGC7901肿瘤细胞系为筛选模型,对上述菌株经高通量定向筛选得到了45株产生高抑瘤活性物质的粘细菌菌株,复筛得到了六株菌,结合多种显微技术对它们进行了鉴定与分类,WXNXJ-A为多囊菌属(Polyangium sp.),WXNXJ-B为标桩菌属(Stigmatella sp.),WXNXJ-C为堆囊菌属(Sorangium sp.),WXNXJ-D、WXNXJ-E为粘球菌属(Myxococcus sp.),WXNXJ-F为囊孢杆菌属(Cystobacter sp.)。
对六株粘细菌产物复筛的结果显示,粘细菌菌株WXNXJ-A和WXNXJ-C代谢产生的物质不仅对小鼠黑色素瘤B16(IC_(50)值,0.2715/0.0082μg/mL)、人胃腺癌SGC7901细胞株(IC_(50)值,4.192/0.0362μg/mL)具有很高的抑制活性,而且对人肝癌Bel7402、人非小细胞肺癌H446、人乳腺癌MCF-7等细胞株也具有较高的抑制活性。
通过HPLC分析和LC/MS分析验证了菌株WXNXJ-C发酵产物在HPLC分析的图谱中保留时间t_R=32.6 min(flow:0.50 mL/min)的物质是epothilone B。
由优化实验研究了WXNXJ-C菌株最佳生长规律,确定细胞最佳生长时间为3d,发酵产生epothilone B的最佳时间为6 d,并确定了最佳发酵培养基组成以及氨基酸和微量元素的最佳添加量。培养基优化后摇瓶发酵得到epothilone B最高产量31.95 mg/L。
WXNXJ-C菌株发酵产物中有7个具有较高抗癌活性和较宽的抗肿瘤谱的物质。经C-18层析柱、15rpc柱、C-18制备柱等多次分离、纯化,采用LC/MS、MALDI-TOF、MS/MS、IR、NMR等分析技术对7F组分进行结构分析,得到分子量为424 Da的C_(22)H_(32)O_8,系统名称为[1R,7R,8R,10S,11S,12S,13S]-1,7,12,13-tetrahydroxy-14-methoxy-8,10-dimethyl-6-phenyl-5,15-dioxa-bicyclo[9.3.1]pentadecan-4-one;1,7,12,13-四羟基-14-甲氧基-8,10-二甲基-6-苯基-5,15-二氧-双环[9.3.1]十五烷-4-酮),起名Phoxalone。查新确证Phoxalone是粘细菌WXNXJ-C产生的一种新型的含有15元环的大环内酯化合物。根据LC/MS、MALDI-TOF MS/MS分析结果,对Phoxalone的离子碎片进行了解析,构建了其分子离子结构,并对其可能产生的途径及机理进行了初步研究。
通过对Phoxalone、Soraphen、epothilones和Paclitaxel的构象进行比较分析,发现Phoxalone有7个手性C原子,2个手性对称中心,结构更加简单,有利于合成和修饰;与epothilone空间结构比较推测出二者在诱导细胞凋亡方面可能有相似的作用机制。
以B16、Bel7402、MCF-7、H446、SGC7901、L02等细胞系为筛选模型,对Phoxalone进行的体外抑制肿瘤细胞实验表明:Phoxalone不仅有较高的抗肿瘤活性和较广的抗肿瘤谱,而且对人正常肝细胞的毒性也比较小。以人非小细胞肺癌H446细胞系为模型,经Phoxalone处理后,通过光学显微镜、扫描电镜和荧光显微镜观察发现Phoxalone对H446细胞系具有较强的抑制作用。
对细胞凋亡周期的研究解释了Phoxalone的作用机制,细胞经Phoxalone作用48 h后在G2/M期被阻滞,能有效地诱导肿瘤细胞凋亡,且呈现量效关系。以荧光染料PI和膜联蛋白(annexin)V双重染色作用的细胞,流式分析的结果表明,Phoxalone可能在不影响细胞膜完整性的情况下,诱导H446细胞线粒体ΔΨ_m下降,同样证实了阻止细胞分裂在G2/M期。
通过对H446细胞系凋亡相关基因蛋白的表达分析表明,作用48 h后Phoxalone通过上调H446细胞中促凋亡因子Bax、下调抑凋亡因子Bcl-2,以及上调线粒体依赖的Caspase-3,激活凋亡信号通路,诱导细胞凋亡,从而起到了抗肿瘤的作用。
Myxobacteria,a class of microorganisms including 12 genuses and about 40 species, have attracted much more interest as drug sources but seldom been studied yet.Based on the traditional screening methodology for myxobacteria,a high-throughout method with tubes culturing was used in the research for large scale screening and 376 myxobacteria strains were isolated.Among which 67 strains were identified to genuse by their distinct morphological characters.As epothilone has character UV absorption,312 samples with strong absorption peaks at UV area were screened out.
Based on bioactivity evaluation,45 high tumor inhibiting active samples were directly screened via B16 and SGC7901 cell lines models.With extended tumor screening models in re-screening,6 strains which produced higher bioactive metabolites were obtained and confirmed as myxobacteria gunes by various microscope technologies.They were WXNXJ-A(Polyangium sp.),WXNXJ-B(Stigmatella sp.),WXNXJ-C(Polyangium sp.),WXNXJ-D & WXNXJ-E(Myxococcus) and WXNXJ-F(Cystobacter sp.).
The results on the re-screening showed that the metabolites of myxobacteria WXNXJ-A and WXNXJ-C had not only high bioactivity to B16 cell line(IC_(50) 0.2715/0.0082μg/mL) and SGC7901 cell line(IC_(50) 4.192/0.0362μg/mL),but also high bioactivity to Bel7402,H446 and MCF-7 cell lines.
By HPLC and LC/MS analyzing the component of WXNXJ-C metabolite with t_R= 32.6min(flow:0.50 mL/min) in the spectrum of HPLC was confirmed as epothilone B.
The growth curve of WXNXJ-C showed optimal cell growth at 3 clays and good fermentation condition at 6 days,respectively.The optimal fermentation medium with additive of amino acids and microelement components were confirmed and the highest yield of epothilone B was 31.95 mg/L in 250 mL Erlenmeyer flasks.
There are 7 components with higher and broad-spectrum antitumor bioactivity in the WXNXJ-C fermentation elution.By using C-18 column chromatography,15RPC column and C-18 chromatography column,a component(named 7F) with molecular weight 424 Da was obtained.The structure of 7F component was analyzed with LC/MS,MALDI-TOF, MS/MS,IR and NMR.The molecular formula of 7F was calculated as C_(22)H_(32)O_8.The traditional name and systemic name of compound C_(22)H_(32)O_8 were Phoxalone and [1R,7R,8R,10S,11S,12S,13S]-1,7,12,13-tetrahydroxy-14-methoxy-8,10-dimethyl-6-phenyl-5, 15-dioxa-bicyclo[9.3.1]pentadecan-4-one,respectively.Via confirming with investigating by L08 Station of Science and Technology,Minister of Education it was confirmed as a novel 15-number ring macrolide containing an oxygen-bridge.According to the results of LC/MS,MALDI-TOF MS/MS analysis,the fragment ions had been analyzed and the synthetic path or mechanisms were studied preliminarily.
Further research on the structure of Phoxalone,comparing with the dimensional structure of Soraphen,epothilones and Paclitaxel,revealed that 7 chiral carbon atoms and 2 chiral centers in Phoxalone molecular gave a simplest,easiest synthesized,and modified structure.It also showed that 15-memmber ring of Phoxalone was inosculating to 16-memmber ring of epothilone B in their 3D structure,and was in a similar manner in the inducing cell apoptosis mechanism.
Research results of bioactive evaluation indicated that Phoxalone not only did have higher and broad-spectrum antitumor bioactivity to tumor cell lines,such as B16,Bel7402, MCF-7,H446,SGC7901,but also did have less cytotoxicity to L02 cell line in vitro. Taking H446 cell line as model,the cytotoxic bioactivity was well studied by using microscope,phase-contrast microscope,and scanning electron microscope,and the result showed that Phoxalone had stronger inhibiting action on H446 cell line.
Flow cytometric analysis explained that the H446 cell cycle was arrested at the G2/M phase with Phoxalone treatment for 48h,sum apoptotic cells showed positive correlations with the quantity of samples and culture time.The results of dyeing with fluorescent dyestuffs PI and Annexin V indicated that Phoxalone induced the potential voltage(ΔΨ_m) of mitochondria decreasing without destroying the integrality of cell membrane.It also revealed that the cell cycle was arrested at the G2/M phase.
More investigation results showed that the apoptotic machinery of H446 induced by Phoxalone was associated with a decrease in BCL-2/Bax ratio,dropping in mitochondrial trans-membrane potential voltage,and upgrading the protein expression of caspase-3 by immunocytochemical staining.
以B16、SGC7901肿瘤细胞系为筛选模型,对上述菌株经高通量定向筛选得到了45株产生高抑瘤活性物质的粘细菌菌株,复筛得到了六株菌,结合多种显微技术对它们进行了鉴定与分类,WXNXJ-A为多囊菌属(Polyangium sp.),WXNXJ-B为标桩菌属(Stigmatella sp.),WXNXJ-C为堆囊菌属(Sorangium sp.),WXNXJ-D、WXNXJ-E为粘球菌属(Myxococcus sp.),WXNXJ-F为囊孢杆菌属(Cystobacter sp.)。
对六株粘细菌产物复筛的结果显示,粘细菌菌株WXNXJ-A和WXNXJ-C代谢产生的物质不仅对小鼠黑色素瘤B16(IC_(50)值,0.2715/0.0082μg/mL)、人胃腺癌SGC7901细胞株(IC_(50)值,4.192/0.0362μg/mL)具有很高的抑制活性,而且对人肝癌Bel7402、人非小细胞肺癌H446、人乳腺癌MCF-7等细胞株也具有较高的抑制活性。
通过HPLC分析和LC/MS分析验证了菌株WXNXJ-C发酵产物在HPLC分析的图谱中保留时间t_R=32.6 min(flow:0.50 mL/min)的物质是epothilone B。
由优化实验研究了WXNXJ-C菌株最佳生长规律,确定细胞最佳生长时间为3d,发酵产生epothilone B的最佳时间为6 d,并确定了最佳发酵培养基组成以及氨基酸和微量元素的最佳添加量。培养基优化后摇瓶发酵得到epothilone B最高产量31.95 mg/L。
WXNXJ-C菌株发酵产物中有7个具有较高抗癌活性和较宽的抗肿瘤谱的物质。经C-18层析柱、15rpc柱、C-18制备柱等多次分离、纯化,采用LC/MS、MALDI-TOF、MS/MS、IR、NMR等分析技术对7F组分进行结构分析,得到分子量为424 Da的C_(22)H_(32)O_8,系统名称为[1R,7R,8R,10S,11S,12S,13S]-1,7,12,13-tetrahydroxy-14-methoxy-8,10-dimethyl-6-phenyl-5,15-dioxa-bicyclo[9.3.1]pentadecan-4-one;1,7,12,13-四羟基-14-甲氧基-8,10-二甲基-6-苯基-5,15-二氧-双环[9.3.1]十五烷-4-酮),起名Phoxalone。查新确证Phoxalone是粘细菌WXNXJ-C产生的一种新型的含有15元环的大环内酯化合物。根据LC/MS、MALDI-TOF MS/MS分析结果,对Phoxalone的离子碎片进行了解析,构建了其分子离子结构,并对其可能产生的途径及机理进行了初步研究。
通过对Phoxalone、Soraphen、epothilones和Paclitaxel的构象进行比较分析,发现Phoxalone有7个手性C原子,2个手性对称中心,结构更加简单,有利于合成和修饰;与epothilone空间结构比较推测出二者在诱导细胞凋亡方面可能有相似的作用机制。
以B16、Bel7402、MCF-7、H446、SGC7901、L02等细胞系为筛选模型,对Phoxalone进行的体外抑制肿瘤细胞实验表明:Phoxalone不仅有较高的抗肿瘤活性和较广的抗肿瘤谱,而且对人正常肝细胞的毒性也比较小。以人非小细胞肺癌H446细胞系为模型,经Phoxalone处理后,通过光学显微镜、扫描电镜和荧光显微镜观察发现Phoxalone对H446细胞系具有较强的抑制作用。
对细胞凋亡周期的研究解释了Phoxalone的作用机制,细胞经Phoxalone作用48 h后在G2/M期被阻滞,能有效地诱导肿瘤细胞凋亡,且呈现量效关系。以荧光染料PI和膜联蛋白(annexin)V双重染色作用的细胞,流式分析的结果表明,Phoxalone可能在不影响细胞膜完整性的情况下,诱导H446细胞线粒体ΔΨ_m下降,同样证实了阻止细胞分裂在G2/M期。
通过对H446细胞系凋亡相关基因蛋白的表达分析表明,作用48 h后Phoxalone通过上调H446细胞中促凋亡因子Bax、下调抑凋亡因子Bcl-2,以及上调线粒体依赖的Caspase-3,激活凋亡信号通路,诱导细胞凋亡,从而起到了抗肿瘤的作用。
Myxobacteria,a class of microorganisms including 12 genuses and about 40 species, have attracted much more interest as drug sources but seldom been studied yet.Based on the traditional screening methodology for myxobacteria,a high-throughout method with tubes culturing was used in the research for large scale screening and 376 myxobacteria strains were isolated.Among which 67 strains were identified to genuse by their distinct morphological characters.As epothilone has character UV absorption,312 samples with strong absorption peaks at UV area were screened out.
Based on bioactivity evaluation,45 high tumor inhibiting active samples were directly screened via B16 and SGC7901 cell lines models.With extended tumor screening models in re-screening,6 strains which produced higher bioactive metabolites were obtained and confirmed as myxobacteria gunes by various microscope technologies.They were WXNXJ-A(Polyangium sp.),WXNXJ-B(Stigmatella sp.),WXNXJ-C(Polyangium sp.),WXNXJ-D & WXNXJ-E(Myxococcus) and WXNXJ-F(Cystobacter sp.).
The results on the re-screening showed that the metabolites of myxobacteria WXNXJ-A and WXNXJ-C had not only high bioactivity to B16 cell line(IC_(50) 0.2715/0.0082μg/mL) and SGC7901 cell line(IC_(50) 4.192/0.0362μg/mL),but also high bioactivity to Bel7402,H446 and MCF-7 cell lines.
By HPLC and LC/MS analyzing the component of WXNXJ-C metabolite with t_R= 32.6min(flow:0.50 mL/min) in the spectrum of HPLC was confirmed as epothilone B.
The growth curve of WXNXJ-C showed optimal cell growth at 3 clays and good fermentation condition at 6 days,respectively.The optimal fermentation medium with additive of amino acids and microelement components were confirmed and the highest yield of epothilone B was 31.95 mg/L in 250 mL Erlenmeyer flasks.
There are 7 components with higher and broad-spectrum antitumor bioactivity in the WXNXJ-C fermentation elution.By using C-18 column chromatography,15RPC column and C-18 chromatography column,a component(named 7F) with molecular weight 424 Da was obtained.The structure of 7F component was analyzed with LC/MS,MALDI-TOF, MS/MS,IR and NMR.The molecular formula of 7F was calculated as C_(22)H_(32)O_8.The traditional name and systemic name of compound C_(22)H_(32)O_8 were Phoxalone and [1R,7R,8R,10S,11S,12S,13S]-1,7,12,13-tetrahydroxy-14-methoxy-8,10-dimethyl-6-phenyl-5, 15-dioxa-bicyclo[9.3.1]pentadecan-4-one,respectively.Via confirming with investigating by L08 Station of Science and Technology,Minister of Education it was confirmed as a novel 15-number ring macrolide containing an oxygen-bridge.According to the results of LC/MS,MALDI-TOF MS/MS analysis,the fragment ions had been analyzed and the synthetic path or mechanisms were studied preliminarily.
Further research on the structure of Phoxalone,comparing with the dimensional structure of Soraphen,epothilones and Paclitaxel,revealed that 7 chiral carbon atoms and 2 chiral centers in Phoxalone molecular gave a simplest,easiest synthesized,and modified structure.It also showed that 15-memmber ring of Phoxalone was inosculating to 16-memmber ring of epothilone B in their 3D structure,and was in a similar manner in the inducing cell apoptosis mechanism.
Research results of bioactive evaluation indicated that Phoxalone not only did have higher and broad-spectrum antitumor bioactivity to tumor cell lines,such as B16,Bel7402, MCF-7,H446,SGC7901,but also did have less cytotoxicity to L02 cell line in vitro. Taking H446 cell line as model,the cytotoxic bioactivity was well studied by using microscope,phase-contrast microscope,and scanning electron microscope,and the result showed that Phoxalone had stronger inhibiting action on H446 cell line.
Flow cytometric analysis explained that the H446 cell cycle was arrested at the G2/M phase with Phoxalone treatment for 48h,sum apoptotic cells showed positive correlations with the quantity of samples and culture time.The results of dyeing with fluorescent dyestuffs PI and Annexin V indicated that Phoxalone induced the potential voltage(ΔΨ_m) of mitochondria decreasing without destroying the integrality of cell membrane.It also revealed that the cell cycle was arrested at the G2/M phase.
More investigation results showed that the apoptotic machinery of H446 induced by Phoxalone was associated with a decrease in BCL-2/Bax ratio,dropping in mitochondrial trans-membrane potential voltage,and upgrading the protein expression of caspase-3 by immunocytochemical staining.
引文
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