炭团木霉Trichoderma hypoxylon中一个新倍半萜
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摘要
木霉属Trichoderma真菌能够产生大量的活性次级代谢产物,是农业和工业应用的重要资源库。通过对1株炭团木霉Trichoderma hypoxylon的化学研究,从其大米发酵物中分离到6个化合物,通过核磁共振、质谱、紫外和红外等光谱手段鉴定其结构分别为:tichodermacid(1)、3-吲哚乙酸甲酯(2)、3-吲哚乙酸(3)、1-乙酰基-β-咔啉(4)、monaspilosin(5)和hydroheptelidic acid(6)。其中化合物1为新倍半萜。
Fungi of Trichoderma genus produce plenty of bioactive secondary metabolites and are very important sources for industrial and agricultural applications. Here, we conducted the chemical study of Trichoderma hypoxylon, and six compounds were isolated from the rice fermentation. Their structures were elucidated by NMR, mass spectrometry, ultraviolet and infrared spectroscopy analysis and identified as trichodermacid(1), 3-indole-methylethanoate(2), 3-indole-acetic acid(3), 1-acetyl-β-carboline(4),monaspilosin(5), and hydroheptelidic acid(6). Compound 1 is found to be a new sesquiterpenoid.
Fungi of Trichoderma genus produce plenty of bioactive secondary metabolites and are very important sources for industrial and agricultural applications. Here, we conducted the chemical study of Trichoderma hypoxylon, and six compounds were isolated from the rice fermentation. Their structures were elucidated by NMR, mass spectrometry, ultraviolet and infrared spectroscopy analysis and identified as trichodermacid(1), 3-indole-methylethanoate(2), 3-indole-acetic acid(3), 1-acetyl-β-carboline(4),monaspilosin(5), and hydroheptelidic acid(6). Compound 1 is found to be a new sesquiterpenoid.
引文
Bocchi M,Garlaschelli L,Vidari G,Mellerio G,1992.New farnesane sesquiterpenes from Hebeloma senescens.Journal of Natural Products,55(4):428-431
Chen Y,Fan CL,Wang Y,Zhang XQ,Huang XJ,Ye WC,2018.Studies on chemical constituents of radix isatidis.Chinese Journal of Chinese Materia Medica,43(10):2091-2096(in Chinese)
Cheng MJ,Wu MD,Chen IS,Yuan GF,2008.Secondary metabolites from the mycelia of the fungus Monascus pilosus BCRC 38072.Chemical and Pharmaceutical Bulletin,56(3):394-397
Contreras-Cornejo HA,Macías-Rodríguez L,del-Val E,Larsen J,2016.Ecological functions of Trichoderma spp.and their secondary metabolites in the rhizosphere:interactions with plants.FEMS Microbiology Ecology,92(4):1-17
Gamba-Invernizzi A,Garlaschelli L,Rossi A,Vidari G,Vita-Finzi P,1993.New farnesane sesquiterpenes from Lactarius porninsis.Journal of Natural Products,56(11):1948-1953
Hashimoto T,Tori M,Mizuno Y,Asakawa Y,Fukazawa Y,1989.The superoxide release inhibitors,cryptoporic acids C,D,and E;dimeric drimane sesquiterpenoid ethers of isocitric acid from the fungus Cryptoporus volvatus.Journal of the Chemical Society,Chemical Communications,1989(4):258
Hermosa R,Rubio MB,Cardoza RE,Nicolás C,Monte E,Gutiérrez S,2013.The contribution of Trichoderma to balancing the costs of plant growth and defense.International Microbiology,16:69-80
Howell CR,Stipanovic R,Lumsden R,1993.Antibiotic production by strains of Gliocladium virens and its relation to the biocontrol of cotton seedling diseases.Biocontrol Science and Technology,3(4):435-441
Lee DS,Eom SH,Jeong SY,Shin HJ,Je JY,Lee EW,Chung YH,Kim YM,Kang CK,Lee MS,2013.Anti-methicillin-resistant Staphylococcus aureus(MRSA)substance from the marine bacterium Pseudomonas sp.UJ-6.Environmental Toxicology and Pharmacology,35(2013):171-177
Lee M,Cho JY,Lee YG,Lee HJ,Lim SI,Lee SY,Nam YD,Moon JH,2016.Furan,phenolic,and heptelidic acid derivatives produced by Aspergillus oryzae.Food Science and Biotechnology,25(5):1259-1264
Liang H,Wu YL,Ji HY,Wang J,Chen J,Wu XL,2014.A survey of sesquiterpene chemical constituents in fungi.Chinese Pharmacology Conference and Fourteenth Chinese Pharmacist’s Weekly Collection in 2014.1121-1128(in Chinese)
Liu H,Wang G,Li W,Liu X,Li E,Yin WB,2018.A highly efficient genetic system for the identification of a harzianum B biosynthetic gene cluster in Trichoderma hypoxylon.Microbiology,doi:10.1099/mic.0.000649
Liu YH,Jee HJ,Zhang S,2005.Indole alkaloids from a sponge Sarcotragus species.Biochemical Systematics and Ecology,34(2006):453-456
Matarese F,Sarrocco S,Gruber S,Seidl-Seiboth V,Vannacci G,2012.Biocontrol of Fusarium head blight:interactions between Trichoderma and mycotoxigenic Fusarium.Microbiology,158:98-106
Molla AH,Fakhru’l-Razi A,Abd-Aziz S,Hanafi MM,Roychoudhury PK,Alam MZ,2002.A potential resource for bioconversion of domestic wastewater sludge.Bioresource Technology,85:263-272
Mukherjee PK,Horwitz BA,Kenerley CM,2011.Secondary metabolism in Trichoderma-a genomic perspective.Microbiology,158:35-45
Opatz T,Kolshorn H,Anke H,2008.Sterelactones:new isolactarane type sesquiterpenoids with antifungal activity from Stereum sp.IBWF 01060.The Journal of Antibiotics,61(9):563-567
Paul C,Konig WA,Wu CL,2001.Sesquiterpenoid constituents of the liverworts Lepidozia fauriana and Lepidozia vitrea.Phytochemistry,58(5):789-798
Qin WT,Chen K,Zhuang WY,2016.Five new records of Trichoderma from China and new distribution of two Trichoderma species in China.Mycosystema,35(8):994-1007(in Chinese)
Reino JL,Guerrero RF,Hernandez-Galan R,Collado IG,2008.Secondary metabolites from species of the biocontrol agent Trichoderma.Phytochemistry Reviews,7:89-123
Sun JZ,Pei YF,Li EW,Li W,Kevin DH,Yin WB,Liu XZ,2016.Anew species of Trichoderma hypoxylon harbours abundant secondary metabolites.Scientific Reports,6:37369
Vinale F,Flematti G,Sivasithamparam K,Lorito M,Marra R,Skelton BW,Ghisalberti EL,2009.Harzianic acid,an antifungal and plant growth promoting metabolite from Trichoderma harzianum.Journal of Natural Products,72:2032-2035
Wang N,Liu T,Jin YZ,Xian HQ,2018.Effects of Trichoderma on soil microbial diversity and strawberry growth and pathogenesis.Jiangsu Agricultural Sciences,46(18):108-112(in Chinese)
Zhao AH,Wei JX,1995.Advances in research on biological activity of sesquiterpenoids.Natural Product Research and Development,7(4):65-69(in Chinese)
Zhu ZX,Zhuang WY,2014.Current understanding of the genus Trichoderma(Hypocreales,Ascomycota).Mycosystema,33(6):1136-1153(in Chinese)
陈烨,范春林,王英,张晓琦,黄晓君,叶文才,2018.板蓝根的化学成分研究.中国中药杂志,43(10):2091-2096
梁虹,吴玉玲,纪红燕,汪静,陈靖,吴秀丽,2014.真菌中倍半萜化学成分研究概况.2014年中国药学大会暨第十四届中国药师周论文集,1121-1128
秦文韬,陈凯,庄文颖,2016.木霉属5个中国新记录种及2种木霉在中国的新分布.菌物学报,35(8):994-1007
王宁,刘铜,靳亚忠,咸洪泉,2018.木霉菌对土壤微生物多样性及草莓生长和发病的影响.江苏农业科学,46(18):108-112
赵爱华,魏均娴,1995.倍半萜类化合物生物活性研究进展.天然产物研究与开发,7(4):65-69
朱兆香,庄文颖,2014.木霉属研究概况.菌物学报,33(6):1136-1153
Chen Y,Fan CL,Wang Y,Zhang XQ,Huang XJ,Ye WC,2018.Studies on chemical constituents of radix isatidis.Chinese Journal of Chinese Materia Medica,43(10):2091-2096(in Chinese)
Cheng MJ,Wu MD,Chen IS,Yuan GF,2008.Secondary metabolites from the mycelia of the fungus Monascus pilosus BCRC 38072.Chemical and Pharmaceutical Bulletin,56(3):394-397
Contreras-Cornejo HA,Macías-Rodríguez L,del-Val E,Larsen J,2016.Ecological functions of Trichoderma spp.and their secondary metabolites in the rhizosphere:interactions with plants.FEMS Microbiology Ecology,92(4):1-17
Gamba-Invernizzi A,Garlaschelli L,Rossi A,Vidari G,Vita-Finzi P,1993.New farnesane sesquiterpenes from Lactarius porninsis.Journal of Natural Products,56(11):1948-1953
Hashimoto T,Tori M,Mizuno Y,Asakawa Y,Fukazawa Y,1989.The superoxide release inhibitors,cryptoporic acids C,D,and E;dimeric drimane sesquiterpenoid ethers of isocitric acid from the fungus Cryptoporus volvatus.Journal of the Chemical Society,Chemical Communications,1989(4):258
Hermosa R,Rubio MB,Cardoza RE,Nicolás C,Monte E,Gutiérrez S,2013.The contribution of Trichoderma to balancing the costs of plant growth and defense.International Microbiology,16:69-80
Howell CR,Stipanovic R,Lumsden R,1993.Antibiotic production by strains of Gliocladium virens and its relation to the biocontrol of cotton seedling diseases.Biocontrol Science and Technology,3(4):435-441
Lee DS,Eom SH,Jeong SY,Shin HJ,Je JY,Lee EW,Chung YH,Kim YM,Kang CK,Lee MS,2013.Anti-methicillin-resistant Staphylococcus aureus(MRSA)substance from the marine bacterium Pseudomonas sp.UJ-6.Environmental Toxicology and Pharmacology,35(2013):171-177
Lee M,Cho JY,Lee YG,Lee HJ,Lim SI,Lee SY,Nam YD,Moon JH,2016.Furan,phenolic,and heptelidic acid derivatives produced by Aspergillus oryzae.Food Science and Biotechnology,25(5):1259-1264
Liang H,Wu YL,Ji HY,Wang J,Chen J,Wu XL,2014.A survey of sesquiterpene chemical constituents in fungi.Chinese Pharmacology Conference and Fourteenth Chinese Pharmacist’s Weekly Collection in 2014.1121-1128(in Chinese)
Liu H,Wang G,Li W,Liu X,Li E,Yin WB,2018.A highly efficient genetic system for the identification of a harzianum B biosynthetic gene cluster in Trichoderma hypoxylon.Microbiology,doi:10.1099/mic.0.000649
Liu YH,Jee HJ,Zhang S,2005.Indole alkaloids from a sponge Sarcotragus species.Biochemical Systematics and Ecology,34(2006):453-456
Matarese F,Sarrocco S,Gruber S,Seidl-Seiboth V,Vannacci G,2012.Biocontrol of Fusarium head blight:interactions between Trichoderma and mycotoxigenic Fusarium.Microbiology,158:98-106
Molla AH,Fakhru’l-Razi A,Abd-Aziz S,Hanafi MM,Roychoudhury PK,Alam MZ,2002.A potential resource for bioconversion of domestic wastewater sludge.Bioresource Technology,85:263-272
Mukherjee PK,Horwitz BA,Kenerley CM,2011.Secondary metabolism in Trichoderma-a genomic perspective.Microbiology,158:35-45
Opatz T,Kolshorn H,Anke H,2008.Sterelactones:new isolactarane type sesquiterpenoids with antifungal activity from Stereum sp.IBWF 01060.The Journal of Antibiotics,61(9):563-567
Paul C,Konig WA,Wu CL,2001.Sesquiterpenoid constituents of the liverworts Lepidozia fauriana and Lepidozia vitrea.Phytochemistry,58(5):789-798
Qin WT,Chen K,Zhuang WY,2016.Five new records of Trichoderma from China and new distribution of two Trichoderma species in China.Mycosystema,35(8):994-1007(in Chinese)
Reino JL,Guerrero RF,Hernandez-Galan R,Collado IG,2008.Secondary metabolites from species of the biocontrol agent Trichoderma.Phytochemistry Reviews,7:89-123
Sun JZ,Pei YF,Li EW,Li W,Kevin DH,Yin WB,Liu XZ,2016.Anew species of Trichoderma hypoxylon harbours abundant secondary metabolites.Scientific Reports,6:37369
Vinale F,Flematti G,Sivasithamparam K,Lorito M,Marra R,Skelton BW,Ghisalberti EL,2009.Harzianic acid,an antifungal and plant growth promoting metabolite from Trichoderma harzianum.Journal of Natural Products,72:2032-2035
Wang N,Liu T,Jin YZ,Xian HQ,2018.Effects of Trichoderma on soil microbial diversity and strawberry growth and pathogenesis.Jiangsu Agricultural Sciences,46(18):108-112(in Chinese)
Zhao AH,Wei JX,1995.Advances in research on biological activity of sesquiterpenoids.Natural Product Research and Development,7(4):65-69(in Chinese)
Zhu ZX,Zhuang WY,2014.Current understanding of the genus Trichoderma(Hypocreales,Ascomycota).Mycosystema,33(6):1136-1153(in Chinese)
陈烨,范春林,王英,张晓琦,黄晓君,叶文才,2018.板蓝根的化学成分研究.中国中药杂志,43(10):2091-2096
梁虹,吴玉玲,纪红燕,汪静,陈靖,吴秀丽,2014.真菌中倍半萜化学成分研究概况.2014年中国药学大会暨第十四届中国药师周论文集,1121-1128
秦文韬,陈凯,庄文颖,2016.木霉属5个中国新记录种及2种木霉在中国的新分布.菌物学报,35(8):994-1007
王宁,刘铜,靳亚忠,咸洪泉,2018.木霉菌对土壤微生物多样性及草莓生长和发病的影响.江苏农业科学,46(18):108-112
赵爱华,魏均娴,1995.倍半萜类化合物生物活性研究进展.天然产物研究与开发,7(4):65-69
朱兆香,庄文颖,2014.木霉属研究概况.菌物学报,33(6):1136-1153