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Production of polyhydroxy fatty acids from linoleic acid by Clavibacter sp. ALA2

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Journal of the American Oil Chemists' Society

Abstract

Hydroxy fatty acids are important industrial materials. We isolated a microbial culture, Clavibacter sp. ALA2, which converts linoleic acid to many polyhydroxy fatty acids. Structures of the products were determined as: 12,13,17-trihydroxy-9(Z)-octadecenoic (THOA, main product), 12-[5-ethyl-2-tetrahydrofuranyl]-7,12-dihydroxy-9(Z)-dodecenoic (ETDDA), and 12-[5-ethyl-2-tetrahydrofuranyl]-12-hydroxy-9(Z)-dodecenoic (ETHDA) acid. The yield of THOA was 25% and the relative amount of the products were THOA/ETDDA/ETHDA =9:1.3:1. The structures of the hydroxy unsaturated fatty acids resemble those of plant self-defense substances.

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References

  1. 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  PubMed  CAS  Google Scholar 

  2. Litchfield, J.H., and G.E. Pierce Microbiological Synthesis of Hydroxy-Fatty Acids and Keto-Fatty Acids, U.S. Patent 4,582,804 (1986).

  3. 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 

  4. Blank, W., H. Takayanagi, T. Kido, F. Meussdoerffer, N. Esaki, and K. Soda, Transformation of Oleic Acid and Its Esters by Sarcina lutea, Agric. Biol. Chem. 55:2651–2652 (1991).

    CAS  Google Scholar 

  5. 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).

    PubMed  CAS  Google Scholar 

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

    PubMed  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. Indust. 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, J. Indust. Microbiol. 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 by Bioconversion, J. Am. Oil Chem. Soc. 68:99–101 (1991).

    CAS  Google Scholar 

  10. Hou, C.T., L.K. Nakamura, D. Weisleder, R.E. Peterson, and M.O. Bagby, Identification of NRRL Strain B-18602 (PR3) as Pseudomonas aeruginosa and Effect of Phenazine-1-Carboxylic Acid Formation on 7,10-Dihydroxy-8(E)-Octadecenoic Acid Accumulation, World J. Microbiol. Biotechnol. 9:570–573 (1993).

    Article  CAS  Google Scholar 

  11. Hou, C.T., Microbial Oxidation of Unsaturated Fatty Acids, in Advance in Applied Microbiology, edited by A.I. Laskin, Academic Press, Orlando, 1995, Vol. 41, pp. 1–23.

    Google Scholar 

  12. 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 

  13. Hamberg, M., R.P. Herman, and U. Jacobsson, Stereochemistry of Two Epoxy Alcohols from Saprolegnia parasitica, Biochim. Biophys. Acta 879:410–418 (1986).

    CAS  Google Scholar 

  14. Corey, E.J., and J.W. Suggs, Pyridinium Chlorochromate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds, Tetrahedron Lett. 2647–2650 (1975).

  15. Gardner, H.W., Analysis of Plant Lipoxygenase Metabolites, in Advances in Lipid Methodology—Four, edited by W.W. Christie, The Oily Press, Dundee, 1997, pp. 1–43.

    Google Scholar 

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

    Article  Google Scholar 

  17. Masui, H., T. Kondo, and M. Kojima, An Antifungal Compound, 9,12,13-Trihydroxy-(E)-10-Octadecenoic Acid, from Colocasia antiquorum Inoculated with Ceratocystis fimbriata, Phytochemistry 28:2613–2615 (1989).

    Article  CAS  Google Scholar 

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Correspondence to Ching T. Hou.

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Hou, C.T., Gardner, H. & Brown, W. Production of polyhydroxy fatty acids from linoleic acid by Clavibacter sp. ALA2. J Amer Oil Chem Soc 75, 1483–1487 (1998). https://doi.org/10.1007/s11746-998-0082-z

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  • DOI: https://doi.org/10.1007/s11746-998-0082-z

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