小单胞菌属次级代谢产物及其生物活性研究进展
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摘要
小单胞菌属(Micromonospora)为稀有放线菌,广泛分布在土壤、海洋和动植物中,其所产代谢产物不仅具有抗菌、抗肿瘤、抗HIV等多种生物活性,而且化学结构新颖多样。本文从化学结构分类、生物活性等方面对近几年已报道的小单胞菌属来源的重要天然产物做了简要综述,以期为小单胞菌天然产物的开发和应用奠定基础。
Micromonospora was a rare actinomycete and widely distributed in the soil,sea,animals and plants.Its metabolites not only had anti-microbial,anti-tumor,anti-HIV and other biological activities,but also had novel and diverse chemical structures.Herein,we briefly reviewed the chemical structure and biological activity of natural products from the genus Micromonospora within the recent years,by which to lay a foundation for future development and application of natural products from Micromonospora.
Micromonospora was a rare actinomycete and widely distributed in the soil,sea,animals and plants.Its metabolites not only had anti-microbial,anti-tumor,anti-HIV and other biological activities,but also had novel and diverse chemical structures.Herein,we briefly reviewed the chemical structure and biological activity of natural products from the genus Micromonospora within the recent years,by which to lay a foundation for future development and application of natural products from Micromonospora.
引文
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2 Tiwari K,et al.Rare actinomycetes:A potential storehouse for novel antibiotics[J].Crit Rev Biotechnol,2012,32:108-132.
3 Zhang XW,et al.Taxonomy and application of Micromonospora[J].Microbiology China (微生物学通报),2006,33:117-121.
4 Gaertner A,et al.Diversity of Micromonospora strains from the deep mediterranean sea and their potential to produce bioactive compounds[J].Aims Microbiology,2016,2:205-221.
5 Peng F,et al.A new 20-membered macrolide produced by a marine-derived Micromonospora strain[J].Nat Prod Res,2013,27:1366-1371.
6 Ni X,et al.Assembly of a novel biosynthetic pathway for gentamicin B production in Micromonospora echinospora[J].Microb Cell Fact,2016,15(1):1-9.
7 Gao Q,et al.The biosynthetic genes encoding for the production of the dynemicin enediyne core in Micromonospora chersina ATCC53710[J].Fems Microbiol Lett,2008,282:105-114.
8 Maretina I A,et al.Enediyne antibiotics and their models:new prospects of acetylene chemistry[J].Uspekhi Khimii,2006,75:913-935.
9 Guo J,et al.Specificity and promiscuity at the branch point in Gentamicin biosynthesis[J].Chemistry & Biology,2014,21:608-618.
10 Krezel A,et al.Acid-base versus structural properties of an aminoglycoside antibiotic-sisomicin:NMR and potentiometric approach[J].Bioorgan Med Chem,2004,12:4075-4080.
11 Wagman GH,et al.A new Micromonospora-produced macrolide antibiotic,rosamicin[J].J Antibiot,1972,25:641-646.
12 Cheng YR,et al.Micromonospora spp.and their secondary bioactive metabolites[J].Chinese Journal of Antibiotics(中国抗生素杂志),2006,31:321-327.
13 Zhang XM,et al.Research progress on the Micromonsporaceae family[J].J Northwest A & F Univ:Nat Sci(西北农林科技大学学报:自科版),2013,41:175-185.
14 Boumehira AZ,et al.Recent progress on the development of antibiotics from the genus Micromonospora[J].Biotechnol Bioproc E,2016,21:199-223.
15 Jiang HL,et al.Gene screening of macrolide-producing strain and its metabolites[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:1895-1899.
16 Li ZY,et al.Progress in studies of macrolide antibotics[J].World Notes on Antibiotics,2013,1:6-15.
17 Gui C,et al.Antimicrobial spirotetronate metabolites from marine-derived Micromonospora harpali SCSIO GJ089[J].J Nat Prod,2017,80:1594-1603.
18 Gong T,et al.Tetrocarcin Q,a new spirotetronate with a unique glycosyl group from a marine-derived actinomycete Micromonospora carbonacea LS276[J].Mar Drugs,2018,16(2):74.
19 Daduang R,et al.29-Deoxymaklamicin,a new maklamicin analogue produced by a genetically engineered strain of Micromonospora sp.NBRC 110955[J].J Biosci Bioeng,2015,120:608-613.
20 Ochoa JL,et al.Marine mammal microbiota yields novel antibiotic with potent activity against Clostridium difficile[J].ACS Infect Dis,2018,4(1):59-67.
21 Perez-Bonilla M,et al.Phocoenamicins B and C,new antibacterial spirotetronates isolated from a marine Micromonospora sp.[J].Mar Drugs,2018,16(3):95.
22 Schulze CJ,et al.Genome-directed lead discovery:biosynthesis,structure elucidation,and biological evaluation of two families of polyene macrolactams against Trypanosoma brucei[J].ACS Chem Biol,2015,10:2373-2381.
23 Hoshino S,et al.Mycolic Acid containing bacterium stimulates tandem cyclization of Polyene macrolactam in a lake sediment derived rare actinomycete[J].Org Lett,2017,19:4992-4995.
24 Nie Y,et al.Structure elucidation and antitumour activity of a new macrolactam produced by marine-derived actinomycete Micromonospora sp.FIM05328.[J].Nat Prod Res,2017:32:2133-2138.
25 Williams DE,et al.Aminorifannycins and Sporalactams produced in culture by a Micromonospora sp.isolated from a Northeastern-Pacific marine sediment are potent antibiotics[J].Org Lett,2017,19:766-769.
26 Mullowney MW,et al.A pimarane diterpene and cytotoxic angucyclines from a marine-derived Micromonospora sp.in Vietnam's East Sea[J].Mar Drugs,2015,13:5815-5827.
27 Jiang X,et al.Isolation,structure elucidation and biosynthesis of benzo[α]fluorene nenestatin A from deep-sea derived Micromonospora echinospora SCSIO 04089[J].Tetrahedron,2017,73:3585-3590.
28 Yan X,et al.Genome mining of Micromonospora yangpuensis DSM 45577 as a producer of an anthraquinone-fused enediyne[J].Org Lett,2017,19:6192-6195.
29 Adnani N,et al.Coculture of marine invertebrate-associated bacteria and interdisciplinary technologies enable biosynthesis and discovery of a new antibiotic,Keyicin[J].ACS Chem Biol,2017,12:3093-3102.
30 Chen L,et al.Purification and identification of anti-tumor antibiotic from Micromonospora FIM060152[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:400-403.
31 Yang ZZ,et al.Research status of enediyne antitumor antibiotics and their targeted drugs[J].Progress in Pharmaceutical Sciences (药学进展),2014,38:747-753.
32 Miao YH,et al.Review on the syntheses and biological activity of 1,3-diyne natural products[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:1608-1616.
33 Ogasawara Y,et al.Exploring peptide ligase orthologs in actinobacteria-discovery of pseudopeptide natural products,ketomemicins[J].ACS Chem Biol,2016,11:1686-1692.
34 Pang X,et al.Surfactin derivatives from Micromonospora sp.CPCC 202787 and their anti-HIV activities[J].J Antibiot,2017,70:105-108.
35 Guo NY,et al.Review on alkaloids from marine-derived actinomycetes[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:159-171.
36 Boonsnongcheep P,et al.Diversity of endophytic actinomycetes isolated from roots and root nodules of Pueraria candollei Grah.ex Benth.and the analyses of their secondary metabolites[J].Chiang Mai J Sci,2017,44(1):1-14.
37 Talukdar M,et al.Structure elucidation and biological activity of antibacterial compound from Micromonospora auratinigra,a soil Actinomycetes[J].J Appl Microbiol,2016,121:973-987.
38 Dashti Y,et al.Actinomycete metabolome induction/suppression with N-acetylglucosamine[J].J Nat Prod,2017,80:828-836.
39 Sarmiento-Vizcaino A,et al.Paulomycin G,a new natural product with cytotoxic activity against tumor Cell lines produced by deep-sea sediment derived Micromonospora matsumotoense M-412 from the aviles canyon in the cantabrian sea[J].Mar Drugs,2017,15:2719.
40 Zhang W,et al.Pyrazolofluostatins A-C,pyrazole-fused Benzo[α]fluorenes from south china sea-derived Micromonospora rosaria SCSIO N160[J].Org Lett,2017,19:592-595.
41 Li ZK,et al.Review on activity of terpenoids from mushroom[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:357-369.
42 Zhang Y,et al.Micromonohalimanes A and B:Antibacterial halimane-type diterpenoids from a marine Micromonospora Species[J].J Nat Prod,2016,79:2968-2972.
43 Gao M,et al.A new naphthalenepropanoic acid analog from the marine-derived actinomycetes Micromonospora sp.HS-HM-036[J].J Asian Nat Prod Res,2017,19:930-934.
44 Iniyan AM,et al.Anti-MRSA potential of phenolic compound isolated from a marine derived actinomycete Micromonospora sp.ICN36[J].Indian J Geo-Mar Sci,2016,45:1279-1287.
45 Montes Vidal D,et al.Long-chain alkyl cyanides:unprecedented volatile compounds released by Pseudomonas and Micromonospora bacteria[J].Angew Chem Int Edit,2017,56:4342-4346.
46 Igarashi Y,et al.Maklamicin,an antibacterial polyketide from an endophytic Micromonospora sp.[J].J Nat Prod,2011,74:670-674.
2 Tiwari K,et al.Rare actinomycetes:A potential storehouse for novel antibiotics[J].Crit Rev Biotechnol,2012,32:108-132.
3 Zhang XW,et al.Taxonomy and application of Micromonospora[J].Microbiology China (微生物学通报),2006,33:117-121.
4 Gaertner A,et al.Diversity of Micromonospora strains from the deep mediterranean sea and their potential to produce bioactive compounds[J].Aims Microbiology,2016,2:205-221.
5 Peng F,et al.A new 20-membered macrolide produced by a marine-derived Micromonospora strain[J].Nat Prod Res,2013,27:1366-1371.
6 Ni X,et al.Assembly of a novel biosynthetic pathway for gentamicin B production in Micromonospora echinospora[J].Microb Cell Fact,2016,15(1):1-9.
7 Gao Q,et al.The biosynthetic genes encoding for the production of the dynemicin enediyne core in Micromonospora chersina ATCC53710[J].Fems Microbiol Lett,2008,282:105-114.
8 Maretina I A,et al.Enediyne antibiotics and their models:new prospects of acetylene chemistry[J].Uspekhi Khimii,2006,75:913-935.
9 Guo J,et al.Specificity and promiscuity at the branch point in Gentamicin biosynthesis[J].Chemistry & Biology,2014,21:608-618.
10 Krezel A,et al.Acid-base versus structural properties of an aminoglycoside antibiotic-sisomicin:NMR and potentiometric approach[J].Bioorgan Med Chem,2004,12:4075-4080.
11 Wagman GH,et al.A new Micromonospora-produced macrolide antibiotic,rosamicin[J].J Antibiot,1972,25:641-646.
12 Cheng YR,et al.Micromonospora spp.and their secondary bioactive metabolites[J].Chinese Journal of Antibiotics(中国抗生素杂志),2006,31:321-327.
13 Zhang XM,et al.Research progress on the Micromonsporaceae family[J].J Northwest A & F Univ:Nat Sci(西北农林科技大学学报:自科版),2013,41:175-185.
14 Boumehira AZ,et al.Recent progress on the development of antibiotics from the genus Micromonospora[J].Biotechnol Bioproc E,2016,21:199-223.
15 Jiang HL,et al.Gene screening of macrolide-producing strain and its metabolites[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:1895-1899.
16 Li ZY,et al.Progress in studies of macrolide antibotics[J].World Notes on Antibiotics,2013,1:6-15.
17 Gui C,et al.Antimicrobial spirotetronate metabolites from marine-derived Micromonospora harpali SCSIO GJ089[J].J Nat Prod,2017,80:1594-1603.
18 Gong T,et al.Tetrocarcin Q,a new spirotetronate with a unique glycosyl group from a marine-derived actinomycete Micromonospora carbonacea LS276[J].Mar Drugs,2018,16(2):74.
19 Daduang R,et al.29-Deoxymaklamicin,a new maklamicin analogue produced by a genetically engineered strain of Micromonospora sp.NBRC 110955[J].J Biosci Bioeng,2015,120:608-613.
20 Ochoa JL,et al.Marine mammal microbiota yields novel antibiotic with potent activity against Clostridium difficile[J].ACS Infect Dis,2018,4(1):59-67.
21 Perez-Bonilla M,et al.Phocoenamicins B and C,new antibacterial spirotetronates isolated from a marine Micromonospora sp.[J].Mar Drugs,2018,16(3):95.
22 Schulze CJ,et al.Genome-directed lead discovery:biosynthesis,structure elucidation,and biological evaluation of two families of polyene macrolactams against Trypanosoma brucei[J].ACS Chem Biol,2015,10:2373-2381.
23 Hoshino S,et al.Mycolic Acid containing bacterium stimulates tandem cyclization of Polyene macrolactam in a lake sediment derived rare actinomycete[J].Org Lett,2017,19:4992-4995.
24 Nie Y,et al.Structure elucidation and antitumour activity of a new macrolactam produced by marine-derived actinomycete Micromonospora sp.FIM05328.[J].Nat Prod Res,2017:32:2133-2138.
25 Williams DE,et al.Aminorifannycins and Sporalactams produced in culture by a Micromonospora sp.isolated from a Northeastern-Pacific marine sediment are potent antibiotics[J].Org Lett,2017,19:766-769.
26 Mullowney MW,et al.A pimarane diterpene and cytotoxic angucyclines from a marine-derived Micromonospora sp.in Vietnam's East Sea[J].Mar Drugs,2015,13:5815-5827.
27 Jiang X,et al.Isolation,structure elucidation and biosynthesis of benzo[α]fluorene nenestatin A from deep-sea derived Micromonospora echinospora SCSIO 04089[J].Tetrahedron,2017,73:3585-3590.
28 Yan X,et al.Genome mining of Micromonospora yangpuensis DSM 45577 as a producer of an anthraquinone-fused enediyne[J].Org Lett,2017,19:6192-6195.
29 Adnani N,et al.Coculture of marine invertebrate-associated bacteria and interdisciplinary technologies enable biosynthesis and discovery of a new antibiotic,Keyicin[J].ACS Chem Biol,2017,12:3093-3102.
30 Chen L,et al.Purification and identification of anti-tumor antibiotic from Micromonospora FIM060152[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:400-403.
31 Yang ZZ,et al.Research status of enediyne antitumor antibiotics and their targeted drugs[J].Progress in Pharmaceutical Sciences (药学进展),2014,38:747-753.
32 Miao YH,et al.Review on the syntheses and biological activity of 1,3-diyne natural products[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:1608-1616.
33 Ogasawara Y,et al.Exploring peptide ligase orthologs in actinobacteria-discovery of pseudopeptide natural products,ketomemicins[J].ACS Chem Biol,2016,11:1686-1692.
34 Pang X,et al.Surfactin derivatives from Micromonospora sp.CPCC 202787 and their anti-HIV activities[J].J Antibiot,2017,70:105-108.
35 Guo NY,et al.Review on alkaloids from marine-derived actinomycetes[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:159-171.
36 Boonsnongcheep P,et al.Diversity of endophytic actinomycetes isolated from roots and root nodules of Pueraria candollei Grah.ex Benth.and the analyses of their secondary metabolites[J].Chiang Mai J Sci,2017,44(1):1-14.
37 Talukdar M,et al.Structure elucidation and biological activity of antibacterial compound from Micromonospora auratinigra,a soil Actinomycetes[J].J Appl Microbiol,2016,121:973-987.
38 Dashti Y,et al.Actinomycete metabolome induction/suppression with N-acetylglucosamine[J].J Nat Prod,2017,80:828-836.
39 Sarmiento-Vizcaino A,et al.Paulomycin G,a new natural product with cytotoxic activity against tumor Cell lines produced by deep-sea sediment derived Micromonospora matsumotoense M-412 from the aviles canyon in the cantabrian sea[J].Mar Drugs,2017,15:2719.
40 Zhang W,et al.Pyrazolofluostatins A-C,pyrazole-fused Benzo[α]fluorenes from south china sea-derived Micromonospora rosaria SCSIO N160[J].Org Lett,2017,19:592-595.
41 Li ZK,et al.Review on activity of terpenoids from mushroom[J].Nat Prod Res Dev (天然产物研究与开发),2017,29:357-369.
42 Zhang Y,et al.Micromonohalimanes A and B:Antibacterial halimane-type diterpenoids from a marine Micromonospora Species[J].J Nat Prod,2016,79:2968-2972.
43 Gao M,et al.A new naphthalenepropanoic acid analog from the marine-derived actinomycetes Micromonospora sp.HS-HM-036[J].J Asian Nat Prod Res,2017,19:930-934.
44 Iniyan AM,et al.Anti-MRSA potential of phenolic compound isolated from a marine derived actinomycete Micromonospora sp.ICN36[J].Indian J Geo-Mar Sci,2016,45:1279-1287.
45 Montes Vidal D,et al.Long-chain alkyl cyanides:unprecedented volatile compounds released by Pseudomonas and Micromonospora bacteria[J].Angew Chem Int Edit,2017,56:4342-4346.
46 Igarashi Y,et al.Maklamicin,an antibacterial polyketide from an endophytic Micromonospora sp.[J].J Nat Prod,2011,74:670-674.