Isolation and identification of three new 5-alkenyl-3,3(2H)-furanones from two Streptomyces species using a genomic screening approach

Journal of Antibiotics

Volumn 59, Issue 3, 2006, Pages 168-176

  Banskota, Arjun H ^a   McAlpine, James B ^a   Sørensen, Dan ^a   Aouidate, Mustapha ^a   Piraee, Mahmood ^a   Alarco, Anne Marie ^a   Omura, Satoshi ^b   Shiomi, Kazuro ^b   Farnet, Chris M ^a   Zazopoulos, Emmanuel ^a  

^a INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Baeyer Villiger monooxygenase; E 492; E 837; E 975; Streptomyces aculeolatus; Streptomyces sp.

Indexed keywords

3,3 (2H) FURANONE DERIVATIVE; E 492; E 837; E 975; FURANONE DERIVATIVE; OXIDOREDUCTASE; OXYGENASE; POLYKETIDE SYNTHASE; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; UNCLASSIFIED DRUG;

ARTICLE; ASCARIS SUUM; BAEYER VILLIGER REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; COW; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; ELECTRON TRANSPORT; FUNGAL GENE; FUNGAL STRAIN; GENE CLUSTER; GENE LOCUS; GENE SEQUENCE; GENOME; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PHYLOGENY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SCREENING; SPECTROSCOPY; STREPTOMYCES;

FERMENTATION; FURANS; GENOME, BACTERIAL; MAGNETIC RESONANCE SPECTROSCOPY; MULTIGENE FAMILY; PHYLOGENY; STREPTOMYCES;

ASCARIS SUUM; BOVINAE; STREPTOMYCES; STREPTOMYCES SP.;

EID: 33646348173     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2006.24     Document Type: Article

References (20)

1. Butler MS. The role of natural product chemistry in drug discovery. J Nat Prod 67: 2141-2153 (2004)
2. Zazopoulos E, Huang K, Staffa A, Liu W, Bachmann BO, Nonaka K, Ahlert J, Thorson JS, Shen B, Farnet CM. A genomics-guided approach for discovering and expressing cryptic metabolic pathways. Nat Biotechnol 21: 187-190 (2003)
3. Zazopoulos E, Farnet CM. Improving drug discovery from Microorganisms. Natural Products: Drug Discovery and Therapeutic Medicine; Eds. L. Zhang and A.L. Demain, pp. 95-106 (2005)
4. McAlpine JB, Bachmann BO, Piraee M, Tremblay S, Alarco AM, Zazopoulos E, Farnet CM. Microbial genomics as a guide to drug discovery and structural elucidation: ECO-02301, a novel antifungal agent, as an example. J Nat Prod 68: 493-496 (2005)
5. Fukuda DS, Mynderse JS, Baker PJ, Berry DM, Boeck LD, Yao RC, Mertz FP, Nakatsukasa WM, Mabe J, Ott J, Counter FT, Ensminger PW, Allen NE, Alborn WE Jr, Hobbs JN Jr. A80915, A new antibiotic complex produced by Streptomyces aculeolatus discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation. J Antibiot 43: 623-633 (1990)
6. Banskota AH, McAlpine JB, Zazopoulos E, Sørensen D, Aouidate M, Piraee M, Farnet CF. 46th Annual Meeting of American Society of Pharmacognosy: No. P-143, Corvallis (2005)
7. Brautaset T, Sekurova ON, Sletta H, Ellingsen TE, Strøm AR, Valla S, Zotchev SB. Biosynthesis of the polyene antifungal antibiotic nystatin in Streptomyces noursei ATCC 11455: analysis of the gene cluster and deduction of the biosynthetic pathway. Chem Biol 7: 395-403 (2000)
8. Ōmura S, Ikeda H, Ishikawa J, Hanamoto A, Takahashi C, Shinose M, Takahashi Y, Horikawa H, Nakazawa H, Osonoe T, Kikuchi H, Shiba T, Sakaki Y, Hattori M. Genome sequence of an industrial microorganism Streptomyces avermitilis: Deducing the ability of producing secondary metabolites. Proc Natl Acad Sci USA 98: 12215-12220 (2001)
9. Palaniappan N, Kim BS, Sekiyama Y, Osada H, Reynolds KA. Enhancement and selective production of phoslactomycin B, a protein phosphatase IIa inhibitor, through identification and engineering of the corresponding biosynthetic gene cluster. J Biol Chem 278: 35552-35557 (2003)
10. He J, Hertweck C. Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster. Chem Biol 10: 1225-1232 (2003)
11. Prado L, Fernández E, Weißbach U, Blanco G, Quirós LM, Braña AF, Méndez C, Rohr J, Salas JA. Oxidative cleavage of premithramycin B is one of the last steps in the biosynthesis of the antitumor drug mithramycin. Chem Biol 6: 19-30 (1999)
12. Liu W, Christenson CD, Standage S, Shen B. Biosynthesis of the enediyne antitumor antibiotic C-1027. Science 297: 1170-1173 (2002)
13. Reynolds WF, Enríquez RG. Choosing the best pulse sequences, acquisition parameters, post-acquisition processing strategies, and probes for natural product structure elucidation by NMR spectroscopy. J Nat Prod 65: 221-244 (2002)
14. Kuroda K, Yoshida M, Uosaki Y, Ando K, Kawamoto I, Oishi E, Onuma H, Yamada K, Matsuda Y. AS-183, a novel inhibitor of acyl-CoA: cholesterol acyltransferase produced by Scedosporium sp. SPC-15549. J Antibiot 46: 1196-1202 (1996)
15. Shiomi K, Ui H, Suzuki H, Hatano H, Nagamitsu T, Takano D, Miyadera H, Yamashita T, Kita K, Miyoshi H, Harder A, Tomoda H, Ōmura S. A γ-lactone form nafuredin, nafuredin-γ, also inhibits helminth complex I. J Antibiot 58: 50-55 (2005)
16. Kunze B, Reichenbach H, Müller R, Höfle G. Aurafuron A and B, new bioactive polyketides from Stigmatella aurantiaca and Archangium gephyra (Myxobacteria). J Antibiot 58: 244-251 (2005)
17. National Committee Clinical Laboratory Standards. Approved Standard M27-A. NCCLS Villanova PA (1997)
18. Arikan S, Yurdakul P, Hascelik G. Comparison of two methods and three end points in determination of in vitro activity of micafungin against Aspergillus spp. Antimicrob Agents Chemother 47: 2640-2643 (2003)
19. Largis EE, Wang CH, DeVries VG, Schaffer SA. CL277,082: A novel inhibitor of ACAT-catalyzed cholesterol esterification and cholesterol absorption. J Lipid Res 30: 681-689 (1989)
20. Sliskovic DR, White AD. Therapeutic potential of ACAT inhibitors as lipid lowering and antisclerotic agents. Trends Pharmacol 12: 194-199 (1991)