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Monooxygenase system of Bacillus megaterium ALA2: Studies on palmitic acid oxidation products

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Journal of the American Oil Chemists' Society

Abstract

We identified many novel oxygenated FA produced from linoleic acid by microbial strain ALA2: 12,13,17-trihydroxy-9(Z)-octadecenoic acid (12,13,17-THOA); 12,13,16-trihydroxy-9(Z)-octadecenoic acid (12,13,16-THOA); 12-hydroxy-13,16-epoxy-9(Z)-octadecenoic acid; and 12,17;13,17-diepoxy-16-hydroxy-9(Z)-octadecenoic acid. 12,13,17-THOA, the main product, inhibits the growth of some plant pathogenic fungi. Recently, we reclassified strain ALA2 as Bacillus megaterium ALA2 NRRL B-21660 and opened a possible link with the well-studied catalytically self-sufficient P450 monooxygenase of Bacillus megaterium ATCC 14581 (NRRL B-3712) and B. subtilis strain 168 (NRRL B-4219). Now we have found that strain ALA2 also oxidizes palmitic acid into three oxygenated products: 13-, 14-, and 15-hydroxy palmitic acids. This indicates that strain ALA2 also possesses a monooxygenase system similar to the abovementioned well-known strains. These data facilitate studies on the oxygenase system of strain ALA2.

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References

  1. Hou, C.T., New Uses of Vegetable Oils: Novel Oxygenated Fatty Acids by Biotransformation, SIM News 53:56–61 (2003).

    Google Scholar 

  2. Wallen, L.L., R.G. Benedict, and R.W. Jackson, The Microbial Production of 10-Hydroxystearic Acid, Arch. Biochem. Biophys. 99:249–253 (1962).

    Article  CAS  Google Scholar 

  3. El-Sharkawy, S.H., W. Yang, L. Dostal, and J.P.N. Rosazza, Microbial Oxidation of Oleic Acid, Appl. Environ. Microbiol. 58:2116–2122 (1992).

    CAS  Google Scholar 

  4. De Andres, C., E. Mercade, G. Guinea, and A. Manresa, 7,10-Dihydroxy-8-(E)-octadecenoic Acid Produced by Pseudomonas 42A2: Evaluation of Different Cultural Parameters of the Fermentation, World J. Microbiol. Biotechnol. 10:106–109 (1994).

    Article  Google Scholar 

  5. Hou, C.T., Production of 10-Ketostearic Acid from Oleic Acid a New Microbiol Isolate, Flavobacterium sp. NRRL B-14859, Appl. Environ. Microbiol. 60:3760–3763 (1994).

    CAS  Google Scholar 

  6. Hou, C.T., Microbial Oxidation of Unsaturated Fatty Acids, Adv. Appl. Microbiol. 41:1–23 (1995).

    Article  CAS  Google Scholar 

  7. Hou, C.T., and M.O. Bagby, Production of a New Compound 7,10-Dihydroxy-8(E)-octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3, J. Ind. Microbiol. 7:123–130 (1991).

    Article  CAS  Google Scholar 

  8. Hou, C.T., and M.O. Bagby, 10-Hydroxy-8(Z)-octadecenoic Acid, an Intermediate in the Formation of 7,10-Dihydroxy-8(E)-octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3, 9:103–107 (1992).

    Article  CAS  Google Scholar 

  9. Hou, C.T., M.O. Bagby, R.D. Platner, and S. Koritala, A Novel Compound, 7,10-Dihydroxy-8(E)-octadecenoic Acid from Oleic Acid Bioconversion, J. Am. Oil Chem. Soc. 68:99–101 (1991).

    Article  CAS  Google Scholar 

  10. Koritala, S., L. Hosie, C.T. Hou, C.W. Hesseltine, and M.O. Bagby, Microbial Conversion of Oleic Acid to 10-Hydroxy Stearic Acid, Appl. Microbiol. Biotechnol. 32:299–304 (1989).

    Article  CAS  Google Scholar 

  11. Hou, C.T., and R.J. Forman III, Growth Inhibition of Plant Pathogenic Fungi by Hydroxy Fatty Acids, J. Ind. Microbiol. Biotechnol. 24:275–276 (2000).

    Article  CAS  Google Scholar 

  12. Kato, T., Y. Yamaguchi, N. Abe, T. Uyehara, T. Nakai, S. Yamanaka, and N. Harada, Unsaturated Hydroxy Fatty Acids, the Self-Defensive Substances in Rice Plant Against Blast Disease, Chem. Lett. 25:409–412 (1984).

    Article  Google Scholar 

  13. Masui, H., T. Kondo, and M. Kojima, An Antifungal Compound, 9,12,13-Trihydroxy-(E)-octadecenoic Acid, from Colocasia antiquorum Inoculated with Ceratocytis fimbriata, Phytochemistry 28:2613–2615 (1989).

    Article  CAS  Google Scholar 

  14. Kawagishi, H., M. Ando, T. Mizuno, H. Yokota, and S. Konishi, A Novel Fatty Acid from Mushroom Hericium erinaceum, Agric. Biol. Chem. 54:1329–1331 (1990).

    CAS  Google Scholar 

  15. Stadler, M., A. Mayer, H. Anke, and O. Sterner, Fatty Acids and Other Compounds with Nematicidal Activity from Cultures of Basidiomycetes, Planta Med. 60:128–132 (1994).

    Article  CAS  Google Scholar 

  16. Iwasaki, Y., W. Brown, and C.T. Hou, Biosynthetic Pathway of Diepoxy Bicyclic Fatty Acids from Linoleic Acid by Clavibacter sp. ALA2, J. Am. Oil Chem. Soc. 79:369–372 (2002).

    Article  CAS  Google Scholar 

  17. Hosokawa, M., C.T. Hou, D. Weisleder, and W. Brown, Biosynthesis of Tetrahydrofuranyl Fatty Acids from Linoleic Acid by Clavibacter sp. ALA2, 80:145–149 (2003).

    Article  CAS  Google Scholar 

  18. Hosokawa, M., C.T. Hou, and D. Weisleder, Production of Novel Tetrahydrofuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2, Appl. Environ. Microbiol. 69:3868–3873 (2003).

    Article  CAS  Google Scholar 

  19. Hosokawa, M., C.T. Hou, and D. Weisleder, Bioconversion of n−3 and n−6 Polyunsaturated Fatty Acids by Clavibacter sp. ALA2, J. Am. Oil Chem. Soc. 80:1085–1091 (2003).

    Article  CAS  Google Scholar 

  20. Hou, C.T., D.P. Labeda, and A. Rooney, Evaluation of Microbial Strains for Linoleic Acid Hydroxylation and Reclassification of Strain ALA2, Antonie van Leeuwenhoek 88:167–171 (2005).

    Article  CAS  Google Scholar 

  21. Narhi, L.O., and A.J. Fulco, Characterization of a Catalytically Self-Sufficient 119,000-Dalton Cytochrome P-450 Monooxygenase Induced by Barbiturates in Bacillus megaterium, J. Biol. Chem. 261:7160–7169 (1986).

    CAS  Google Scholar 

  22. Wen, L.P., and A.J. Fulco, Cloning of the Gene Encoding a Catalytically Self-Sufficient Cytochrome P-450 Fatty Acid Monooxygenase Induced by Barbiturates in Bacillus megaterium and Its Functional Expression and Regulation in Heterologous (Eschericha coli) and Homologous (Bacillus megaterium) Hosts, 262:6676–6682 (1987).

    CAS  Google Scholar 

  23. Kunst, F., N. Ogasawara, I. Moszer, A.M. Albertini, G. Alloni, V. Azevedo, M.G. Bertero, P. Bessieres, A. Bolotin, S. Borchert, et al., The Complete Genome Sequence of the Gram-Positive Bacterium Bacillus subtilis, Nature 390:249–256 (1997).

    Article  CAS  Google Scholar 

  24. Budde, M., S.C. Maureer, and R.D. Schmid, Cloning, Expression and Characterisation of CYP102A2, a Self-Sufficient P450 Monooxygenase from Bacillus subtilis, Appl. Microbiol. Biotechnol. 66:180–186 (2005).

    Article  Google Scholar 

  25. Gustafsson, M.C., C.N. Palmer, C.R. Wolf, and C. von Wachenfeldt, Fatty-Acid-Displaced Transcriptional Repressor, a Conserved Regulator of Cytochrome P450 102 Transcription in Bacillus Species, Arh. Microbiol. 176:459–464 (2001).

    Article  CAS  Google Scholar 

  26. Lentz, O., V. Urlacher, and R.D. Schmid, Substrate Specificity of Native and Mutated Cytochrome P450 (CYP102A3) from Bacillus subtilis, J. Biotechnol. 108:41–49 (2004).

    Article  CAS  Google Scholar 

  27. Hou, C.T., A Novel Compound, 12,13,17-Trihydroxy-9(Z)-octadecenoic Acid, from Linoleic Acid by a New Microbial Isolate Clavibacter sp. ALA2, J. Am. Oil Chem. Soc. 73:1359–1362 (1996).

    Article  CAS  Google Scholar 

  28. Hou, C.T., W. Brown, D.P. Labeda, T.P. Abbott, and D. Weisledel, Microbial Production of a Novel Trihydroxy Unsaturated Fatty Acid from Linoleic Acid, J. Ind. Microbiol. Biotechnol. 19:34–38 (1997).

    Article  CAS  Google Scholar 

  29. Hou, C.T., Effect of Environmental Factors on the Production of Oxygenated Unsaturated Fatty Acids from Linoleic Acids by Bacillus megaterium ALA2, Appl. Microbiol. Biotechnol., in press (2005), published online DOI: 10.1007/s00253-005-1999x.

  30. Miura, Y., and A.J. Fulco, (w−2) Hydroxylation of Fatty Acids by a Soluble System from Bacillus megaterium, J. Biol. Chem. 249:1880–1888 (1974).

    CAS  Google Scholar 

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Correspondence to Ching T. Hou.

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Hou, C.T. Monooxygenase system of Bacillus megaterium ALA2: Studies on palmitic acid oxidation products. J Am Oil Chem Soc 82, 839–843 (2005). https://doi.org/10.1007/s11746-005-1152-8

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  • DOI: https://doi.org/10.1007/s11746-005-1152-8

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