Isolation and biosynthetic analysis of haliamide, a new pks-nrps hybrid metabolite from the marine myxobacterium haliangium ochraceum

Molecules

Volumn 21, Issue 1, 2016, Pages

  Sun, Yuwei ^a   Tomura, Tomohiko ^a   Sato, Junichi ^a   Iizuka, Takashi ^b   Fudou, Ryosuke ^b   Ojika, Makoto ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b AJINOMOTO CO INC   (Japan)

Author keywords

Biosynthesis; Haliamide; Haliangiumochraceum; Marine myxobacterium; Polyketide

Indexed keywords

ANTINEOPLASTIC AGENT; BACTERIAL PROTEIN; PEPTIDE; POLYKETIDE; SULFOTRANSFERASE; THIOL ESTER HYDROLASE;

AQUATIC SPECIES; CELL SURVIVAL; CHEMISTRY; DELTAPROTEOBACTERIA; DRUG EFFECTS; GENE EXPRESSION; GENETICS; HELA CELL LINE; HUMAN; IC50; ISOLATION AND PURIFICATION; METABOLISM; METABOLOME; MULTIGENE FAMILY; PROTEIN TERTIARY STRUCTURE;

ANTINEOPLASTIC AGENTS; AQUATIC ORGANISMS; BACTERIAL PROTEINS; CELL SURVIVAL; DELTAPROTEOBACTERIA; GENE EXPRESSION; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; METABOLOME; MULTIGENE FAMILY; PEPTIDES; POLYKETIDES; PROTEIN STRUCTURE, TERTIARY; SULFOTRANSFERASES; THIOLESTER HYDROLASES;

EID: 85000785565     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21010059     Document Type: Article

References (26)

1. Weissman, K.J.; Mueller, R. A brief tour of myxobacterial secondary metabolism. Bioorg. Med. Chem. 2009, 17, 2121-2136. [CrossRef] [PubMed].
2. Reichenbach, H. Myxobacteria, producers of novel bioactive substances. J. Ind. Microbiol. Biotechnol. 2001, 27, 149-156. [CrossRef] [PubMed].
3. Wenzel, S.C.; Muller, R. Myxobacteria-"Microbial factories" for the production of bioactive secondary metabolites. Mol. Biosyst. 2009, 5, 567-574. [CrossRef] [PubMed].
4. Iizuka, T.; Jojima, Y.; Fudou, R.; Tokura, M.; Hiraishi, A.; Yamanaka, S. Enhygromyxa salina gen. nov., sp nov., a slightly halophilic myxobacterium isolated from the coastal areas of Japan. Syst. Appl. Microbiol. 2003, 26, 189-196. [CrossRef] [PubMed].
5. Schaeberle, T.F.; Goralski, E.; Neu, E.; Erol, O.; Hoelzl, G.; Doermann, P.; Bierbaum, G.; Koenig, G.M. Marine Myxobacteria as a Source of Antibiotics-Comparison of Physiology, Polyketide-Type Genes and Antibiotic Production of Three New Isolates of Enhygromyxa salina. Mar. Drugs 2010, 8, 2466-2479. [CrossRef] [PubMed].
6. Iizuka, T.; Jojima, Y.; Fudou, R.; Hiraishi, A.; Ahn, J.W.; Yamanaka, S. Plesiocystis pacifica gen. nov., sp nov., a marine myxobacterium that contains dihydrogenated menaquinone, isolated from the Pacific coasts of Japan. Int. J. Syst. Evol. Microbiol. 2003, 53, 189-195. [CrossRef] [PubMed].
7. Iizuka, T.; Jojima, Y.; Hayakawa, A.; Fujii, T.; Yamanaka, S.; Fudou, R. Pseudenhygromyxa salsuginis gen. nov., sp nov., a myxobacterium isolated from an estuarine marsh. Int. J. Syst. Evol. Microbiol. 2013, 63, 1360-1369. [CrossRef] [PubMed].
8. Still, P.C.; Johnson, T.A.; Theodore, C.M.; Loveridge, S.T.; Crews, P. Scrutinizing the Scaffolds of Marine Biosynthetics from Different Source Organisms: Gram-Negative Cultured Bacterial Products Enter Center Stage. J. Nat. Prod. 2014, 77, 690-702. [CrossRef] [PubMed].
9. Komaki, H.; Fudou, R.; Iizuka, T.; Nakajima, D.; Okazaki, K.; Shibata, D.; Ojika, M.; Harayama, S. PCR Detection of Type I Polyketide Synthase Genes in Myxobacteria. Appl. Environ. Microbiol. 2008, 74, 5571-5574. [CrossRef] [PubMed].
10. Fudou, R.; Iizuka, T.; Yamanaka, S. Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium 1. Fermentation and biological characteristics. J. Antibiot. 2001, 54, 149-152. [CrossRef] [PubMed].
11. Fudou, R.; Iizuka, T.; Sato, S.; Ando, T.; Shimba, N.; Yamanaka, S. Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium 2. Isolation and structural elucidation. J. Antibiot. 2001, 54, 153-156. [CrossRef] [PubMed].
12. Kundim, B.A.; Itou, Y.; Sakagami, Y.; Fudou, R.; Iizuka, T.; Yamanaka, S.; Ojika, M. New haliangicin isomers, potent antifungalmetabolites produced by a marine myxobacterium. J. Antibiot. 2003, 56, 630-638. [CrossRef] [PubMed].
13. Ojika, M.; Inukai, Y.; Kito, Y.; Hirata, M.; Iizuka, T.; Fudou, R. Miuraenamides: Antimicrobial cyclic depsipeptides isolated from a rare and slightly halophilic myxobacterium. Chem. Asian J. 2008, 3, 126-133. [CrossRef] [PubMed].
14. Iizuka, T.; Fudou, R.; Jojima, Y.; Ogawa, S.; Yamanaka, S.; Inukai, Y.; Ojika, M. Miuraenamides A and B, novel antimicrobial cyclic depsipeptides from a new slightly halophilic myxobacterium: Taxonomy, production, and biological properties. J. Antibiot. 2006, 59, 385-391. [CrossRef] [PubMed].
15. Felder, S.; Dreisigacker, S.; Kehraus, S.; Neu, E.; Bierbaum, G.; Wright, P.R.; Menche, D.; Schaberle, T.F.; Konig, G.M. Salimabromide: Unexpected Chemistry from the Obligate Marine Myxobacterium Enhygromyxa salina. Chem. Eur. J. 2013, 19, 9319-9324. [CrossRef] [PubMed].
16. Felder, S.; Kehraus, S.; Neu, E.; Bierbaum, G.; Schaberle, T.F.; Konig, G.M. Salimyxins and Enhygrolides: Antibiotic, Sponge-Related Metabolites from the Obligate Marine Myxobacterium Enhygromyxa salina. ChemBioChem 2013, 14, 1363-1371. [CrossRef] [PubMed].
17. Ligon, J.; Hill, S.; Beck, J.; Zirkle, R.; Molnar, I.; Zawodny, J.; Money, S.; Schupp, T. Characterization of the biosynthetic gene cluster for the antifungal polyketide soraphen A from Sorangium cellulosum So ce26. Gene 2002, 285, 257-267. [CrossRef].
18. Kalaitzis, J.A.; Cheng, Q.; Meluzzi, D.; Xiang, L.K.; Izumikawa, M.; Dorrestein, P.C.; Moore, B.S. Policing starter unit selection of the enterocin type II polyketide synthase by the type II thioesterase EncL. Bioorg. Med. Chem. 2011, 19, 6633-6638. [CrossRef] [PubMed].
19. Blin, K.; Medema, M.H.; Kazempour, D.; Fischbach, M.A.; Breitling, R.; Takano, E.;Weber, T. antiSMASH 2.0-a versatile platform for genome mining of secondary metabolite producers. Nucleic Acids Res. 2013, 41, W204-W212. [CrossRef] [PubMed].
20. Keller, L.; Plaza, A.; Dubiella, C.; Groll, M.; Kaiser, M.; Muller, R. Macyranones: Structure, Biosynthesis, and Binding Mode of an Unprecedented Epoxyketone that Targets the 20S Proteasome. J. Am. Chem. Soc. 2015, 137, 8121-8130. [CrossRef] [PubMed].
21. Yadav, G.; Gokhale, R.S.; Mohanty, B. Computational approach for prediction of domain organization and substrate specificity of modular polyketide synthases. J. Mol. Biol. 2003, 328, 335-363. [CrossRef].
22. Petkovic, H.; Sandmann, A.; Challis, L.R.; Hecht, H.J.; Silakowski, B.; Low, L.; Beeston, N.; Kuscer, E.; Garcia-Bernardo, J.; Leadlay, P.F.; et al. Substrate specificity of the acyl transferase domains of EpoC from the epothilone polyketide synthase. Org. Biomol. Chem. 2008, 6, 500-506. [CrossRef] [PubMed].
23. Chang, Z.X.; Sitachitta, N.; Rossi, J.V.; Roberts, M.A.; Flatt, P.M.; Jia, J.Y.; Sherman, D.H.; Gerwick, W.H. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2004, 67, 1356-1367. [CrossRef] [PubMed].
24. Gu, L.C.;Wang, B.; Kulkarni, A.; Gehret, J.J.; Lloyd, K.R.; Gerwick, L.; Gerwick, W.H.;Wipf, P.; Hakansson, K.; Smith, J.L.; et al. Polyketide Decarboxylative Chain Termination Preceded by O-Sulfonation in Curacin A Biosynthesis. J. Am. Chem. Soc. 2009, 131, 16033-16035. [CrossRef] [PubMed].
25. Ivanova, N.; Daum, C.; Lang, E.; Abt, B.; Kopitz, M.; Saunders, E.; Lapidus, A.; Lucas, S.; del Rio, T.G.; Nolan, M.; et al. Complete genome sequence of Haliangium ochraceum type strain (SMP-2(T)). Stand. Genom. Sci. 2010, 2, 96-106. [CrossRef] [PubMed].
26. Marchler-Bauer, A.; Lu, S.N.; Anderson, J.B.; Chitsaz, F.; Derbyshire, M.K.; deWeese-Scott, C.; Fong, J.H.; Geer, L.Y.; Geer, R.C.; Gonzales, N.R.; et al. CDD: A Conserved Domain Database for the functional annotation of proteins. Nucleic Acids Res. 2011, 39, D225-D229. [CrossRef].