三株放线菌次生代谢产物的化学研究
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摘要
本论文为三年攻读硕士学位期间的研究工作,共由三部分组成。第一部分综述了微生物次级代谢产物中环肽类化合物的研究概况(第一章);第二部分阐述了放线菌次级代谢产物的化学筛选(第二章);第三部分详述了三株放线菌次级代谢产物化学成分的研究(第三、四、五章)。
第一部分微生物次级代谢产物中环肽的研究进展
环肽是指一类主要由常见氨基酸和一些不常见氨基酸以肽键形成的环状化化合物。环肽类化合物由于其具有抗肿瘤、抗菌、抗真菌等生物活性,已成为20世纪乃至是21世纪科学研究的一个热门领域。本文在查阅文献的基础上,主要对2005-2009年微生物代谢产物中发现的环肽就来源和生物活性进行了综述。
第二部分放线菌次生代谢产物的化学筛选
化学筛选法已被用来评价微生物的发酵产物。在活性筛选的基础上,对活性较好的6株菌在八种不同的发酵培养基中进行培养发酵,通过对其发酵物进行TLC及HPLC检测分析,确定了各株菌的最佳发酵培养基。EA培养基作为YIM63342菌株的发酵培养基;HKI培养基作为菌株YIM56130的发酵培养基;SF培养基做为菌株YIM65408的发酵培养基;61#培养基作为菌株YIM61470的发酵培养基;GL培养基作为菌株YIM61297的发酵培养基;HKI培养基作为菌株YIM48924的发酵培养基。
第三部分三株放线菌次级代谢产物化学成分的研究
微生物次级代谢产物多样,很多具有药物活性,已成为天然产物研究开发的一个重要资源。而在微生物中,放线菌是微生物代谢产物研究最重要的类群,它们存在于不同自然生态环境中,可以产生多种不同的天然产物。
我们对三株放线菌发酵液的化学成分进行了研究,运用硅胶柱层析、凝胶柱层析等方法进行分离纯化。从其发酵液提取物中共分离得到32个化合物,经IR,ESI-MS,NMR等光谱数据鉴定及与文献对照,确定了27个化合物,其中有7个在不同的放线菌中重复分离得到。化合物类型包括环二肽、核苷、糖苷、多元醇、异黄酮、甾体、脂类等。其中有6个化合物为新的天然产物,其他化合物均首次从该属放线菌发酵液中分离得到。
从菌株YIM48782的发酵液中分离得到了10个化合物,鉴定了其中的8个化合物,分别为O6-乙基-β-D-呋喃果糖苷(1)、环(脯-天冬酰胺)(2)、环(脯-丝)(3)、环(脯-丙)(4)、环(脯-苏)(5)、尿嘧啶(6)、对羟基苯甲醛(7)、β-胡萝卜甙(8)。化合物1、2首次从天然物中分离得到,化合物3～8均首次从该放线菌的发酵物中分离得到。
从菌株YIM48789的发酵液中分离得到了9个化合物,根据光谱数据鉴定为:1-O-乙酰基-D-甘露醇(1)、环(脯-丝)(2)、尿嘧啶核苷(3)、2’-脱氧尿嘧啶核苷(4)、腺嘌呤核苷(5)、甘露醇(6)、4’,7-二羟基异黄酮(7)、2,3-丁二醇(8)、β-胡萝卜甙(9)。化合物1首次从天然物中分离得到,化合物2～9均首次从该放线菌的发酵物中分离得到。
从菌株YIM30006的发酵液中分离得到了13个化合物,鉴定了其中的10个化合物:环二(δ-N-乙酰基-L-鸟氨酸)肽(1)、环(脯-丝)(2)、环(脯-苏)(3)、己二酸二甲酯(4)、O6-n-丁基-D-甘露糖苷(5)、尿嘧啶(6)、尿嘧啶核苷(7)、4’,5,7-三羟基异黄酮(8)、尿素(9)、D-吡喃葡萄糖基-(1→6)-D-吡喃葡萄糖基(4→1)-D-吡喃葡萄糖苷(10)。其中化合物1、4和5为新的天然产物,其余化合物均首次从该放线菌的发酵物中分离得到。
This dissertation consists of three parts altogether. In the first part, the cyclopeptides isolated from the secondary metabolites of microorganism were reviewed(the first chapter). In the second part, we discussed the use of chemical screening in the fermentation broths of actinomycetes(the second chapter). The third part described the isolation and identification of chemical constituents from the secondary metabolites of three actinomycetes, including the last three chapters.
Part 1. Summarization on the Cyclopeptides from the Secondary Metabolites of Microorganism
Cyclopeptides are important compounds which were formed by the usual or unusual amino acid. Cyclopeptides have attracted much attention in the last 30 years, because of their antitumor and antifungal activities. In this paper, the cyclopeptides isolated from the secondary metabolites of microorganism published between 2005 and 2009 were reviewed.
Part 2. The Use of Chemical Screening in the Fermentation Broths of Actinomycetes
Chemical screening apprach has been used for evaluating the culture broths of microorganism. we descibed the chemical screening of six strains in eight different the culture broths. As a result of TLC and HPLC analysis on the different fermentation broths of actinomycetes, EA、HKI、SF、61#、HK and GL culture broths were used as the fermentation broths of strain YIM63342、YIM56130、YIM65408、YIM61470、YIM61297 and YIM48924, respectively.
Part 3. Study on Chemical Constituents from the Secondary Metabolites of Three Actinomycetes
Many secondary metabolites of microorganism have biological activities, they are the important resources to find natural active products. Actinomycetes is the most important group to the studies of secondary metabolites from microbiology., which exist in different ecological environments, and the compounds from them is also diversity. The actinomycetes in the special environmental of yunnan province might produce more compounds with novel chemical structure and strong activity.
We study on the chemical constituents from the fermentation broth of three actinomycetes. Thirty-two compounds were isolated and purified by silica chromatography、gel filtration chromatography and high-performance liquid chromatography.The structures of twenty-seven compounds were elucidated by NMR、IR and MS technologies. Seven of them were isolated twice from different sources. The types of structures include cyclic depeptides、nucleotides、glycosides、polyols、isoflavones、steroids、lipids and so on . Six Compounds were firstly isolated from natural sources.
Ten compounds were obtained from fermentation broth of actinomycete YIM48782 and night of them were determined as O6-ethyl-β-D-fructofuranosides(1)、cyclo(Pro-Asn)(2)、cyclo(Pro-Ser)(3)、cyclo(Pro-Ala)(4)、cyclo(Pro-Thr)(5)、Uarcil(6)、p-hydroxybenzaldehyde(7)、β-daucosterol(8). Compound 1 and 2 were firstly isolated from natural sources, compounds 3-8 were isolated from this actinomycete for the first time.
Nine compounds were obtained from fermentation broth of actinomycete YIM48789 and were determined as 1-O-acetyl-D-mannitol(1)、cyclo(Pro-Ser)(2)、uridine(3),2’-deoxyu-ridine(4),adenosine(5)、4’,7-dihydroxy- isoflavone(6)、2,3-butandio(l7)、mannito(l8)、β-daucostero(l9). Compound 1 was firstly isolated from natural sources, compounds 3-9 were isolated from this actinomycete for the first time.
Thirteen compounds were obtained from fermentation broth of actinomycete YIM30006 and ten of them were determined as Cyclo-di(δ-N-acety-L-ornithin)(1)、cyclo(Pro-Ser)(2)、cyclo(Pro-Thr)(3)、octanedioic acid dimethyl ester(4)、O6- n-Butyl–D-mannoside(5)、uarcil(6)、uridine(7)、4’,5,7-trihydroxy- isoflavone(8)、urea(9)、D-Glu(1→6)-D-Glu(4→1)D-Glu(10). Compound 1、4 and 5 were firstly isolated from natural sources, the others were isolated from this actinomycete for the first time.
第一部分微生物次级代谢产物中环肽的研究进展
环肽是指一类主要由常见氨基酸和一些不常见氨基酸以肽键形成的环状化化合物。环肽类化合物由于其具有抗肿瘤、抗菌、抗真菌等生物活性,已成为20世纪乃至是21世纪科学研究的一个热门领域。本文在查阅文献的基础上,主要对2005-2009年微生物代谢产物中发现的环肽就来源和生物活性进行了综述。
第二部分放线菌次生代谢产物的化学筛选
化学筛选法已被用来评价微生物的发酵产物。在活性筛选的基础上,对活性较好的6株菌在八种不同的发酵培养基中进行培养发酵,通过对其发酵物进行TLC及HPLC检测分析,确定了各株菌的最佳发酵培养基。EA培养基作为YIM63342菌株的发酵培养基;HKI培养基作为菌株YIM56130的发酵培养基;SF培养基做为菌株YIM65408的发酵培养基;61#培养基作为菌株YIM61470的发酵培养基;GL培养基作为菌株YIM61297的发酵培养基;HKI培养基作为菌株YIM48924的发酵培养基。
第三部分三株放线菌次级代谢产物化学成分的研究
微生物次级代谢产物多样,很多具有药物活性,已成为天然产物研究开发的一个重要资源。而在微生物中,放线菌是微生物代谢产物研究最重要的类群,它们存在于不同自然生态环境中,可以产生多种不同的天然产物。
我们对三株放线菌发酵液的化学成分进行了研究,运用硅胶柱层析、凝胶柱层析等方法进行分离纯化。从其发酵液提取物中共分离得到32个化合物,经IR,ESI-MS,NMR等光谱数据鉴定及与文献对照,确定了27个化合物,其中有7个在不同的放线菌中重复分离得到。化合物类型包括环二肽、核苷、糖苷、多元醇、异黄酮、甾体、脂类等。其中有6个化合物为新的天然产物,其他化合物均首次从该属放线菌发酵液中分离得到。
从菌株YIM48782的发酵液中分离得到了10个化合物,鉴定了其中的8个化合物,分别为O6-乙基-β-D-呋喃果糖苷(1)、环(脯-天冬酰胺)(2)、环(脯-丝)(3)、环(脯-丙)(4)、环(脯-苏)(5)、尿嘧啶(6)、对羟基苯甲醛(7)、β-胡萝卜甙(8)。化合物1、2首次从天然物中分离得到,化合物3～8均首次从该放线菌的发酵物中分离得到。
从菌株YIM48789的发酵液中分离得到了9个化合物,根据光谱数据鉴定为:1-O-乙酰基-D-甘露醇(1)、环(脯-丝)(2)、尿嘧啶核苷(3)、2’-脱氧尿嘧啶核苷(4)、腺嘌呤核苷(5)、甘露醇(6)、4’,7-二羟基异黄酮(7)、2,3-丁二醇(8)、β-胡萝卜甙(9)。化合物1首次从天然物中分离得到,化合物2～9均首次从该放线菌的发酵物中分离得到。
从菌株YIM30006的发酵液中分离得到了13个化合物,鉴定了其中的10个化合物:环二(δ-N-乙酰基-L-鸟氨酸)肽(1)、环(脯-丝)(2)、环(脯-苏)(3)、己二酸二甲酯(4)、O6-n-丁基-D-甘露糖苷(5)、尿嘧啶(6)、尿嘧啶核苷(7)、4’,5,7-三羟基异黄酮(8)、尿素(9)、D-吡喃葡萄糖基-(1→6)-D-吡喃葡萄糖基(4→1)-D-吡喃葡萄糖苷(10)。其中化合物1、4和5为新的天然产物,其余化合物均首次从该放线菌的发酵物中分离得到。
This dissertation consists of three parts altogether. In the first part, the cyclopeptides isolated from the secondary metabolites of microorganism were reviewed(the first chapter). In the second part, we discussed the use of chemical screening in the fermentation broths of actinomycetes(the second chapter). The third part described the isolation and identification of chemical constituents from the secondary metabolites of three actinomycetes, including the last three chapters.
Part 1. Summarization on the Cyclopeptides from the Secondary Metabolites of Microorganism
Cyclopeptides are important compounds which were formed by the usual or unusual amino acid. Cyclopeptides have attracted much attention in the last 30 years, because of their antitumor and antifungal activities. In this paper, the cyclopeptides isolated from the secondary metabolites of microorganism published between 2005 and 2009 were reviewed.
Part 2. The Use of Chemical Screening in the Fermentation Broths of Actinomycetes
Chemical screening apprach has been used for evaluating the culture broths of microorganism. we descibed the chemical screening of six strains in eight different the culture broths. As a result of TLC and HPLC analysis on the different fermentation broths of actinomycetes, EA、HKI、SF、61#、HK and GL culture broths were used as the fermentation broths of strain YIM63342、YIM56130、YIM65408、YIM61470、YIM61297 and YIM48924, respectively.
Part 3. Study on Chemical Constituents from the Secondary Metabolites of Three Actinomycetes
Many secondary metabolites of microorganism have biological activities, they are the important resources to find natural active products. Actinomycetes is the most important group to the studies of secondary metabolites from microbiology., which exist in different ecological environments, and the compounds from them is also diversity. The actinomycetes in the special environmental of yunnan province might produce more compounds with novel chemical structure and strong activity.
We study on the chemical constituents from the fermentation broth of three actinomycetes. Thirty-two compounds were isolated and purified by silica chromatography、gel filtration chromatography and high-performance liquid chromatography.The structures of twenty-seven compounds were elucidated by NMR、IR and MS technologies. Seven of them were isolated twice from different sources. The types of structures include cyclic depeptides、nucleotides、glycosides、polyols、isoflavones、steroids、lipids and so on . Six Compounds were firstly isolated from natural sources.
Ten compounds were obtained from fermentation broth of actinomycete YIM48782 and night of them were determined as O6-ethyl-β-D-fructofuranosides(1)、cyclo(Pro-Asn)(2)、cyclo(Pro-Ser)(3)、cyclo(Pro-Ala)(4)、cyclo(Pro-Thr)(5)、Uarcil(6)、p-hydroxybenzaldehyde(7)、β-daucosterol(8). Compound 1 and 2 were firstly isolated from natural sources, compounds 3-8 were isolated from this actinomycete for the first time.
Nine compounds were obtained from fermentation broth of actinomycete YIM48789 and were determined as 1-O-acetyl-D-mannitol(1)、cyclo(Pro-Ser)(2)、uridine(3),2’-deoxyu-ridine(4),adenosine(5)、4’,7-dihydroxy- isoflavone(6)、2,3-butandio(l7)、mannito(l8)、β-daucostero(l9). Compound 1 was firstly isolated from natural sources, compounds 3-9 were isolated from this actinomycete for the first time.
Thirteen compounds were obtained from fermentation broth of actinomycete YIM30006 and ten of them were determined as Cyclo-di(δ-N-acety-L-ornithin)(1)、cyclo(Pro-Ser)(2)、cyclo(Pro-Thr)(3)、octanedioic acid dimethyl ester(4)、O6- n-Butyl–D-mannoside(5)、uarcil(6)、uridine(7)、4’,5,7-trihydroxy- isoflavone(8)、urea(9)、D-Glu(1→6)-D-Glu(4→1)D-Glu(10). Compound 1、4 and 5 were firstly isolated from natural sources, the others were isolated from this actinomycete for the first time.
引文
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