Harnessing the potential of halogenated natural product biosynthesis by mangrove-derived actinomycetes

Marine Drugs

Volumn 11, Issue 10, 2013, Pages 3875-3890

  Li, Xue Gong ^a,b   Tang, Xiao Min ^c   Xiao, Jing ^c   Ma, Guang Hui ^c   Xu, Li ^c   Xie, Shu Jie ^c   Xu, Min Juan ^d   Xiao, Xiang ^b   Xu, Jun ^b  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

^c Key Laboratory of Marine Genetic Resources of Fujian Province   (China)

^d Chinese National Human Genome Center at Shanghai   (China)

Author keywords

Ansamycin; Enduracidin; Genome mining; Halogenase; Mangrove derived actinomycetes

Indexed keywords

5,10 METHYLENETETRAHYDROFOLATE REDUCTASE (FADH2); ANSAMYCIN DERIVATIVE; ENRAMYCIN A; ENRAMYCIN B; HALIDE; NAPHTHOMYCIN A; NATURAL PRODUCT; NONRIBOSOMAL PEPTIDE SYNTHETASE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; XIAMENMYCIN;

ACTINOBACTERIA; ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BACTERIUM ISOLATION; CLADISTICS; CONTROLLED STUDY; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GENE DISRUPTION; HALOGENASE GENE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MANGROVE; NONHUMAN; NUCLEOTIDE SEQUENCE; PHYLOGENY; STREPTOMYCES ATROVIRENS;

ACTINOBACTERIA (CLASS); STREPTOMYCES; STREPTOMYCES ALBOGRISEOLUS;

ACTINOBACTERIA; BACTERIAL PROTEINS; BIOLOGICAL PRODUCTS; GENES, BACTERIAL; HALOGENATION; PEPTIDE SYNTHASES; PHYLOGENY; POLYKETIDE SYNTHASES; STREPTOMYCES;

EID: 84887062260     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11103875     Document Type: Article

References (45)

1. Costanza, R.; d'Arge, R.; De Groot, R.; Farber, S.; Grasso, M.; Hannon, B.; Limburg, K.; Naeem, S.; O'neill, R.V.; Paruelo, J. The value of the world's ecosystem services and natural capital. Nature 1997, 387, 253-260.
2. Kathiresan, K.; Bingham, B.L. Biology of mangroves and mangrove ecosystems. Adv. Mar. Biol. 2001, 40, 81-251. (Pubitemid 33718606)
3. Remya, M.; Vijayakumar, R. Isolation and characterization of marine antagonistic actinomycetes from west coast of India. Facta Universitatis Ser. Med. Biol. 2008, 15, 13-19.
4. Hong, K.; Gao, A.-H.; Xie, Q.-Y.; Gao, H.G.; Zhuang, L.; Lin, H.-P.; Yu, H.-P.; Li, J.; Yao, X.-S.; Goodfellow, M. Actinomycetes for marine drug discovery isolated from mangrove soils and plants in China. Mar. Drugs 2009, 7, 24-44.
5. Dias, A.C.; Andreote, F.D.; Dini-Andreote, F.; Lacava, P.T.; Sá, A.L.; Melo, I.S.; Azevedo, J.L.; Araújo, W.L. Diversity and biotechnological potential of culturable bacteria from Brazilian mangrove sediment. World J. Microbiol. Biotechnol. 2009, 25, 1305-1311.
6. Huang, H.; Lv, J.; Hu, Y.; Fang, Z.; Zhang, K.; Bao, S. Micromonospora rifamycinica sp. nov., a novel actinomycete from mangrove sediment. Int. J. Syst. Evol. Microbiol. 2008, 58, 17-20. (Pubitemid 351843531)
7. Hornung, A.; Bertazzo, M.; Dziarnowski, A.; Schneider, K.; Welzel, K.; Wohlert, S.E.; Holzenkämpfer, M.; Nicholson, G.J.; Bechthold, A.; Süssmuth, R.D. A Genomic Screening Approach to the Structure-Guided Identification of Drug Candidates from Natural Sources. Chembiochem 2007, 8, 757-766. (Pubitemid 47183632)
8. Wang, G.; Zhang, H.; Sun, G.; Wu, L.; Zhang, J.; Wang, Y. A new method for rapid identification of ansamycin compounds by inactivating KLM gene clusters in potential ansamycin-producing actinomyces. J. Appl. Microbiol. 2012, 112, 353-362.
9. Zerikly, M.; Challis, G.L. Strategies for the discovery of new natural products by genome mining. Chembiochem 2009, 10, 625-633.
10. Walsh, C.T.; Fischbach, M.A. Natural products version 2.0: Connecting genes to molecules. J. Am. Chem. Soc. 2010, 132, 2469-2493.
11. Du, L.; Lou, L. PKS and NRPS release mechanisms. Nat. Prod. Rep. 2010, 27, 255-278.
12. Olano, C.; Méndez, C.; Salas, J.A. Post-PKS tailoring steps in natural product-producing actinomycetes from the perspective of combinatorial biosynthesis. Nat. Prod. Rep. 2010, 27, 571-616.
13. Ouyang, Y.; Wu, H.; Xie, L.; Wang, G.; Dai, S.; Chen, M.; Yang, K.; Li, X. A method to type the potential angucycline producers in actinomycetes isolated from marine sponges. Antonie van Leeuwenhoek 2011, 99, 807-815.
14. Liu, T.; Cane, D.E.; Deng, Z. The enzymology of polyether biosynthesis. Methods Enzymol. 2009, 459, 187-214.
15. Jiang, C.; Wang, H.; Kang, Q.; Liu, J.; Bai, L. Cloning and Characterization of the Polyether Salinomycin Biosynthesis Gene Cluster of Streptomyces albus XM211. Appl. Environ. Microbiol. 2012, 78, 994-1003.
16. Neumann, C.S.; Fujimori, D.G.; Walsh, C.T. Halogenation strategies in natural product biosynthesis. Chem. Biol. 2008, 15, 99-109. (Pubitemid 351253619)
17. Gao, P.; Huang, Y. Detection, distribution, and organohalogen compound discovery implications of the reduced flavin adenine dinucleotide-dependent halogenase gene in major filamentous actinomycete taxonomic groups. Appl. Environ. Microbiol. 2009, 75, 4813-4820.
18. Shen, B. Polyketide biosynthesis beyond the type I, II and III polyketide synthase paradigms. Curr. Opin. Chem. Biol. 2003, 7, 285-295. (Pubitemid 36514961)
19. Schwarzer, D.; Finking, R.; Marahiel, M.A. Nonribosomal peptides: From genes to products. Nat. Prod. Rep. 2003, 20, 275-287. (Pubitemid 36770356)
20. González, I.; Ayuso-Sacido, A.; Anderson, A.; Genilloud, O. Actinomycetes isolated from lichens: Evaluation of their diversity and detection of biosynthetic gene sequences. FEMS Microbiol. Ecol. 2005, 54, 401-415. (Pubitemid 41416857)
21. Li, X.-L.; Xu, M.-J.; Zhao, Y.-L.; Xu, J. A Novel Benzo [f][1, 7] Naphthyridine Produced by Streptomyces Albogriseolus from Mangrove Sediments. Molecules 2010, 15, 9298-9307.
22. Xu, J.; Wang, Y.; Xie, S.-J.; Xu, J.; Xiao, J.; Ruan, J.-S. Streptomyces xiamenensis sp. nov., isolated from mangrove sediment. Int. J. Syst. Evol. Microbiol. 2009, 59, 472-476.
23. Xu, M.-J.; Liu, X.-J.; Zhao, Y.-L.; Liu, D.; Xu, Z.-H.; Lang, X.-M.; Ao, P.; Lin, W.-H.; Yang, S.-L.; Zhang, Z.-G. Identification and characterization of an anti-fibrotic benzopyran compound isolated from mangrove-derived Streptomyces xiamenensis. Mar. Drugs 2012, 10, 639-654.
24. Liu, X.-J.; Xu, M.-J.; Fan, S.-T.; Wu, Z.; Li, J.; Yang, X.-M.; Wang, Y.-H.; Xu, J.; Zhang, Z.-G. Xiamenmycin Attenuates Hypertrophic Scars by Suppressing Local Inflammation and the Effects of Mechanical Stress. J. Invest. Dermatol. 2013, 133, 1351-1360.
25. Zhang, X.; Sun, Y.; Bao, J.; He, F.; Xu, X.; Qi, S. Phylogenetic survey and antimicrobial activity of culturable microorganisms associated with the South China Sea black coral Antipathes dichotoma. FEMS Microbiol. Lett. 2012, 336, 122-130.
26. Yin, X.; Zabriskie, T.M. The enduracidin biosynthetic gene cluster from Streptomyces fungicidicus. Microbiology 2006, 152, 2969-2983. (Pubitemid 44542378)
27. Wu, Y.; Kang, Q.; Shen, Y.; Su, W.; Bai, L. Cloning and functional analysis of the naphthomycin biosynthetic gene cluster in Streptomyces sp. CS. Mol. Biosyst. 2011, 7, 2459-2469.
28. Marahiel, M.A.; Stachelhaus, T.; Mootz, H.D. Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 1997, 97, 2651-2674.
29. Zhao, W.; Zhong, Y.; Yuan, H.; Wang, J.; Zheng, H.; Wang, Y.; Cen, X.; Xu, F.; Bai, J.; Han, X. Complete genome sequence of the rifamycin SV-producing Amycolatopsis mediterranei U32 revealed its genetic characteristics in phylogeny and metabolism. Cell Res. 2010, 20, 1096-1108.
30. Floss, H.G.; Yu, T.-W.; Arakawa, K. The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: A review. J. Antibiot. (Tokyo) 2010, 64, 35-44.
31. Floss, H.G.; Yu, T.W. Rifamycin-mode of action, resistance, and biosynthesis. Chem. Rev. 2005, 105, 621-632.
32. Gribble, G.W. The diversity of naturally produced organohalogens. Chemosphere 2003, 52, 289-297. (Pubitemid 36612863)
33. Gribble, G.W. Naturally occurring organohalogen compounds - a comprehensive survey. Fortschr. Chem. Org. Naturst. 1996, 68, 1-423.
34. Auffinger, P.; Hays, F.A.; Westhof, E.; Ho, P.S. Halogen bonds in biological molecules. Proc. Natl. Acad. Sci. USA 2004, 101, 16789-16794. (Pubitemid 39601317)
35. Smith, D.R.; Gruschow, S.; Goss, R.J. Scope and potential of halogenases in biosynthetic applications. Curr. Opin. Chem. Biol. 2013, 17, 276-283.
36. Pistorius, D.; Muller, R. Discovery of the rhizopodin biosynthetic gene cluster in Stigmatella aurantiaca Sg a15 by genome mining. Chembiochem 2012, 13, 416-426.
37. Vaillancourt, F.H.; Vosburg, D.A.; Walsh, C.T. Dichlorination and Bromination of a Threonyl-S-Carrier Protein by the Non-heme FeII Halogenase SyrB2. Chembiochem 2006, 7, 748-752. (Pubitemid 43764182)
38. Bayer, K.; Scheuermayer, M.; Fieseler, L.; Hentschel, U. Genomic mining for novel FADH2-dependent halogenases in marine sponge-associated microbial consortia. Mar. Biotechnol. 2013, 15, 63-72.
39. Murphy, C.D. Recent developments in enzymatic chlorination. Nat. Prod. Rep. 2006, 23, 147-152.
40. Ayuso-Sacido, A.; Genilloud, O. New PCR primers for the screening of NRPS and PKS-I systems in actinomycetes: Detection and distribution of these biosynthetic gene sequences in major taxonomic groups. Microb. Ecol. 2005, 49, 10-24. (Pubitemid 40747800)
41. Schirmer, A.; Gadkari, R.; Reeves, C.D.; Ibrahim, F.; DeLong, E.F.; Hutchinson, C.R. Metagenomic analysis reveals diverse polyketide synthase gene clusters in microorganisms associated with the marine sponge Discodermia dissoluta. Appl. Environ. Microbiol. 2005, 71, 4840-4849. (Pubitemid 41129543)
42. Metsä-Ketelä, M.; Salo, V.; Halo, L.; Hautala, A.; Hakala, J.; Mäntsälä, P.; Ylihonko, K. An efficient approach for screening minimal PKS genes from Streptomyces. FEMS Microbiol. Lett. 1999, 180, 1-6. (Pubitemid 29476486)
43. Kieser, T.; Bibb, M.J.; Buttner, M.J.; Chater, K.F.; Hopwood, D.A. Practical Streptomyces Genetics; John Innes Foundation Norwich: Norwich, UK, 2000; p. 412.
44. Ishikawa, J.; Hotta, K. FramePlot: A new implementation of the frame analysis for predicting protein-coding regions in bacterial DNA with a high G + C content. FEMS Microbiol. Lett. 1999, 174, 251-253. (Pubitemid 29217014)
45. Yadav, G.; Gokhale, R.S.; Mohanty, D. SEARCHPKS: A program for detection and analysis of polyketide synthase domains. Nucleic Acids Res. 2003, 31, 3654-3658. (Pubitemid 37442216)