Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library

Journal of Antibiotics

Volumn 65, Issue 3, 2012, Pages 123-128

  Nogawa, Toshihiko ^a   Takahashi, Shunji ^a   Okano, Akiko ^a   Kawatani, Makoto ^a   Uramoto, Masakazu ^a   Saito, Tamio ^a   Osada, Hiroyuki ^a  

^a RIKEN   (Japan)

Author keywords

fraction library; microbial metabolite; spiroacetal polyketide; Streptomyces griseochromogenes; structure elucidation

Indexed keywords

ACETONITRILE; AMIDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; FUNCTIONAL GROUP; POLYKETIDE; SPIRO COMPOUND; SPIROTOAMIDE A; SPIROTOAMIDE B; UNCLASSIFIED DRUG;

ACTINOBACTERIA; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANCER CELL; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FEMALE; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MAGNAPORTHE; MAGNAPORTHE ORYZAE; MASS SPECTROMETRY; METABOLITE; MOLECULAR LIBRARY; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STAPHYLOCOCCUS AUREUS; STREPTOMYCES; STREPTOMYCES GRISEOCHROMOGENES;

ACTINOBACTERIA (CLASS); FUNGI; STREPTOMYCES GRISEOCHROMOGENES;

EID: 84859152148     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2011.121     Document Type: Article

References (26)

1. Osada, H. An overview on the diversity of actinomycete metabolites. Actinomycetol. 15, 11-14 (2001).
2. Newman, D. J. & Cragg, G. M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 70, 461-477 (2007).
3. Dobson, C. M. Chemical space and biology. Nature 432, 824-828 (2004).
4. Osada, H. Trends in bioprobe research. in Bioprobes (ed. Osada, H.) 1-14 (Springer, Berlin, 2000).
5. Osada, H. Chemical biology based on small molecule-protein interaction. Protein targeting with small molecules. in Chemical Biology Techniques and Applications (ed. Osada, H.) 1-10 (Wiley, New Jersey, 2009).
6. Nogawa,T.et al. Verticilactam, a new macrolactam isolated froma microbialmetabolite fraction library. Org. Lett. 12, 4564-4567 (2010).
7. Cheng,X. et al. A new antibiotic, tautomycin. J. Antibiot. 40, 907-909 (1987).
8. Magae, J., Watanabe, C., Osada, H., Cheng, X. C. & Isono, K. Induction of morphological change of human myeloid leukemia and activation of protein kinase C by a novel antibiotic, tautomycin. J. Antibiot. 41, 932-937 (1988).
9. Cheng, X. C., Ubukata, M. & Isono, K. The structure of tautomycin, a dialkylmaleic anhydride antibiotic. J. Antibiot. 43, 809-819 (1990).
10. Panthee, S. et al. Furaquinocins I and J: novel polyketide isoprenoid hybrid compounds from Streptomyces reveromyceticus SN-593. J. Antibiot. 64, 509-513 (2011).
11. Takahashi, S. et al. Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593. J. Bacteriol. 192, 2839-2851 (2010).
12. Osada, H., Koshino, H., Isono, K., Takahashi, H. & Kawanishi, G. Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor. J. Antibiot. 44, 259-261 (1991).
13. Bugni, T. M. et al. Marine natural product libraries for high-throughput screening and rapid drug discovery. J. Nat. Prod. 71, 1095-1098 (2008).
14. Seto, H. & Otake, N. The 13C-NMR spectra of polyether antibiotics and some empirical rules for structural studies of polyether antibiotics. Heterocycles 17, 555-580 (1982).
15. Koshino, H., Takahashi, H., Osada, H. & Isono, K. Reveromycins, new inhibitors of eukaryotic cell growth. J. Antibiot. 45, 1420-1427 (1992).
16. Höltzel, A., Kempter, C., Metzger, J. W. & Jung, G. Spirofungin, a new antifungal antibiotic from Streptomyces violaceusniger Tü 4113. J. Antibiot. 51, 699-707 (1998).
17. Igarashi, Y., Iida, T., Yoshida, R. & Furumai, T. Pteridic acids A and B, novel plant growth promoters with auxin-like activity from Streptomyces hygroscopicus TP-A0451. J. Antibiot. 55, 764-767 (2002).
18. Niggemann, J. et al. Spirangien A and B, highly cytotoxic and antifungal spiroketals from the myxobacterium Sorangium cellulosum: isolation, structure elucidation and chemical modifications. Eur. J. Org. Chem. 24, 5013-5018 (2005).
19. Li, J. et al. Virgatolides A-C, benzannulated spiroketals from the plant endophytic fungus Pestalotiopsis virgatula. Org. Lett. 13, 2670-2673 (2011).
20. Li, W., Ju, J., Rajski, S. R., Osada, H. & Shen, B. Characterization of the tautomycin biosynthetic gene cluster from Streptomyces spiroverticillatus unveiling new insights into dialkylmaleic anhydride and polyketide biosynthesis. J. Biol. Chem. 283, 28607-28617 (2008).
21. Ikeda, H., Nonomiya, T. & Omura, S. Organization of biosynthetic gene cluster for avermectin in Streptomyces avermitilis: analysis of enzymatic domains in four polyketide synthases. J. Ind. Microbiol. Biotechnol. 27, 170-176 (2001).
22. Takahashi, S. et al. Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation. Nat. Chem. Biol. 7, 461-468 (2011).
23. Cheng, X. C. et al. A new antibiotic, tautomycetin. J. Antibiot. 42, 141-144 (1989).
24. Cheng, X. C., Ubukata, M. & Isono, K. The structure of tautomycetin, a dialkylmaleic anhydride antibiotic. J. Antibiot. 43, 890-896 (1990).
25. Sambrook, J. & Russell, D. W. Molecular Cloning: A Laboratory Manual 3rd edn (Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., 2001).
26. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F. & Hopwood, D. A. Practical Streptomyces Genetics (John Innes Foundation, Norwich, UK, 2000).