Alkyldihydropyrones, new polyketides synthesized by a type III polyketide synthase from Streptomyces reveromyceticus

Journal of Antibiotics

Volumn 67, Issue 12, 2014, Pages 819-823

  Aizawa, Teruki ^a   Kim, Seung Young ^a   Takahashi, Shunji ^b,c   Koshita, Masahiko ^a   Tani, Mioka ^a   Futamura, Yushi ^c   Osada, Hiroyuki ^b,c   Funa, Nobutaka ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b Elements Chemistry Laboratory   (Japan)

^c RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYLDIHYDROPYRONE A; ALKYLDIHYDROPYRONE B; ALKYLDIHYDROPYRONE C; ALKYLDIHYDROPYRONE D; BETA HYDROXYL ACID THIOESTER; DIHYDROPYRONE SYNTHASE A; ISOMERASE; METHYLMALONYL COENZYME A; POLYKETIDE; POLYKETIDE SYNTHASE; THIOESTER; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; PYRONE DERIVATIVE;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HL 60 CELL LINE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; LACTONIZATION; LEUKEMIA CELL LINE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCES REVEROMYCETICUS; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; GENETICS; INFRARED SPECTROSCOPY; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PLASMID; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

STREPTOMYCES;

ANTINEOPLASTIC AGENTS; CELL SURVIVAL; HL-60 CELLS; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OPTICAL ROTATION; PLASMIDS; POLYKETIDE SYNTHASES; POLYKETIDES; PYRONES; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STREPTOMYCES;

EID: 84925284893     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2014.80     Document Type: Article

References (26)

1. Austin, M. B., Noel, J. P The chalcone synthase superfamily of type III polyketide synthases. Nat. Prod. Rep. 20, 79-110 (2003).
2. Katsuyama, Y., Kita, T., Funa, N., Horinouchi, S. Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. J. Biol. Chem. 284, 11160-11170 (2009).
3. Funa, N. et al. A new pathway for polyketide synthesis in microorganisms. Nature 400, 897-899 (1999).
4. Funa, N., Funabashi, M., Ohnishi, Y., Horinouchi, S. Biosynthesis of hexahydroxyperylenequinone melanin via oxidative aryl coupling by cytochrome P-450 in Streptomyces griseus. J. Bacteriol. 187, 8149-8155 (2005).
5. Song, L. et al. Type III polyketide synthase b-ketoacyl-ACP starter unit and ethylmalonyl-CoA extender unit selectivity discovered by Streptomyces coelicolor genome mining. J. Am. Chem. Soc. 128, 14754-14755 (2006).
6. Funabashi, M., Funa, N., Horinouchi, S. Phenolic lipids synthesized by type III polyketide synthase confer penicillin resistance on Streptomyces griseus. J. Biol. Chem. 283, 13983-13991 (2008).
7. Pfeifer, V. et al. A polyketide synthase in glycopeptide biosynthesis: the biosynthesis of the non-proteinogenic amino acid (S)-3, 5-dihydroxyphenylglycine. J. Biol. Chem. 276, 38370-38377 (2001).
8. Li, T.-L., Choroba, O. W., Hong, H., Williams, D. H., Spencer, J. B. Biosynthesis of the vancomycin group of antibiotics: characterization of a type III polyketide synthase in the pathway to (S)-3, 5-dihydroxyphenylglycine. Chem. Commun. 2001, 2156-2157 (2001).
9. Chen, H., Tseng, C. C., Hubbard, B. K., Walsh, C. T. Glycopeptide antibiotic biosynthesis: enzymatic assembly of dedicated amino acid monomer (S)-3, 5-dihydroxyphenylglycine. Proc. Natl Acad. Sci. USA 98, 14901-14906 (2001).
10. Wenzel, S. C., Bode, H. B., Kochems, I., Mü ller, R. A. Type I/type III polyketide synthase hybrid biosynthetic pathway for the structurally unique ansa compound kendomycin. Chembiochem 9, 2711-2721 (2008).
11. Tang, X. et al. A two-step sulfation in antibiotic biosynthesis requires a type III polyketide synthase. Nat. Chem. Biol. 10, 610-615 (2013).
12. Bentley, S. D. et al. Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417, 141-147 (2002).
13. Ikeda, H. et al. Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis. Nat. Biotechol. 21, 526-531 (2003).
14. 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).
15. Woo, J.-T. et al. Reveromycin A, an agent for osteoporosis, inhibits bone resorption by inducing apoptosis specifically in osteoclasts. Proc. Natl Acad. Sci. USA 103, 4729-4734 (2006).
16. Muguruma, H. et al. Reveromycin A inhibits osteolytic bone metastasis of small-cell lung cancer cells, SBC-5, through an antiosteoclastic activity. Clin. Cancer Res. 11, 8822-8828 (2005).
17. Sambrook, J., Maniatis, T., Fritsch, E. F. Molecular Cloning: A Laboratory Manual (Cold Spring Harbor, New York, NY, USA, 1989).
18. Kieser, T., Bibb, M. J., Buttner, K. F., Chater, K. F., Hopwood, D. A. Practical Streptomyces Genetics (The John Innes Foundation, Norwich, UK, 2000).
19. Takano, E., White, J., Thompson, C. J., Bibb, M. J Construction of thiostreptoninducible, high-copy-number expression vectors for use in Streptomyces spp. Gene 166, 133-137 (1995).
20. Gomez-Escribano, J. P., Bibb, M. J Engineering Streptomyces coelicolor for heterologous expression of secondary metabolite gene clusters. Microb. Biotechnol. 4, 207-215 (2011).
21. White, S. W., Zheng, J., Zhang, Y.-M., Rock, C. O. The structural biology of type II fatty acid biosynthesis. Annu. Rev. Biochem. 74, 791-831 (2005).
22. Grü schow, S., Buchholz, T. J., Seufert, W., Dordick, J. S., Sherman, D. H. Substrate profile analysis and ACP-mediated acyl transfer in Streptomyces coelicolor type III polyketide synthases. Chembiochem 8, 863-868 (2007).
23. Castonguay, R., He, W., Chen, A. Y., Khosla, C., Cane, D. E. Stereospecificity of ketoreductase domains of the 6-deoxyerythronolide B synthase. J. Am. Chem. Soc. 129, 13758-13769 (2007).
24. Itoh, T. et al. Actinorhodin biosynthesis: structural requirements for post-PKS tailoring intermediates revealed by functional analysis of ActVI-ORF1 reductase. Biochemistry 46, 8181-8188 (2007).
25. Fehr, M. J. et al. Asymmetric hydrogenation of substituted 2-pyrones. J. Org. Chem. 64, 5768-5776 (1999).
26. Denoya, C. D. et al. A second branched-chain a-keto acid dehydrogenase gene cluster (bkdFGH) from Streptomyces avermitilis: its relationship to avermectin biosynthesis and the construction of a bkdF mutant suitable for the production of novel antiparasitic avermectins. J. Bacteriol. 177, 3504-3511 (1995).