Abstract
The bioconversions of oleic acid, linoleic acid, and ricinoleic acid by Pseudomonas aeruginosa PR3 were investigated. The conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was improved to better than 80% yields by modifying the culture medium and reaction parameters. The microbial cultures were stable and retained the same level of DOD production capacity for up to 6 mon as examined herewith. Strain PR3 did not bioconvert linoleic acid. However, strain PR3 converted ricinoleic acid to a novel compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD), with a yield of about 35%. The product was further metabolized by strain PR3. TOD was purified by thin-layer chromatography, and its structure was determined by 1H and 13C nuclear magnetic resonance and mass spectrometry. This is the first report on the production of 7,10,12-trihydroxy unsaturated fatty acid by microbial transformation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Hou, C.T., Microbial Oxidation of Unsaturated Fatty Acids, in Advances in Applied Microbiology, edited by A.I. Laskin, Academic Press, Orlando, 1995, Vol. 41, pp. 1–23.
Wallen, L.L., R.G. Benedict, and R.W. Jackson, The Microbiological Production of 10-Hydroxystearic Acid from Oleic Acid, Arch. Biochem. Biophys. 99:249–253 (1962).
Lanser, A.C., R.D. Plattner, and M.O. Bagby, Production of 15-, 16- and 17-Hydroxy-9-Octadecenoic Acid from Oleic Acid with Bacillus pumilus, J. Am. Oil Chem. Soc. 69:363–366 (1992).
Hou, C.T., M.O. Bagby, R.D. Plattner, and S. Koritala, A Novel Compound, 7,10-Dihydroxy-8(E)-Octadecenoic Acid from Oleic Acid by Bioconversion, Ibid.:99–101 (1991).
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).
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).
Hou, C.T., L.K. Nakamura, D. Weisleder, R.E. Peterson, and M.O. Bagby, Identificatino 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).
Vick, B.A., and D.C. Zimmerman, Oxidative Systems for Modification of Fatty Acids: The Lipoxygenase Pathway, in The Biochemistry of Plants: A Comprehensive Treatise, edited by P.K. Stumpf, Academic Press, Orlando, 1987, Vol. 9, pp. 53–90.
Stodola, F.H., R.F. Vesonder, and L.J. Wickerham, 8,9,13-Trihydroxydocosanoic Acid, an Extracellular Lipid Produced by a Yeast, Biochemistry 4:1390–1394 (1965).
Graveland, A., Enzymatic Oxidations of Linoleic Acid and Glycerol-1-Monolinoleate in Doughs and Flour-Water Suspensions, J. Am. Oil Chem. Soc. 47:352–361 (1970).
Baur, C., and W. Grosch, Investigation About the Taste of Di-, Tri-and Tetrahydroxy Fatty Acids, Z. Lebensm. Unters. Forsch. 165:82–84 (1977).
Kato, T., Y. Yamaguchi, N. Abe, T. Uyehara, T. Namai, M. Kodama, and Y. Shiobara, Structure and Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids in Rice Plant Suffering from Rice Blast Disease, Tetrahedron Lett. 26:2357–2360 (1985).
Suemune, H., T. Harabe, and K. Sakai, Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids Isolated from Rice Plants Suffering from Rice Blast Disease, Chem. Pharm. Bull. 36:3632–3637 (1988).
Gosse-Kobo, B., P. Mosset, and R. Gree, Total Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids. Tetrahedron Lett. 30:4235–4236 (1989).
Kato, T., Y. Yamaguchi, S. Ohnuma, T. Uyehara, T. Namai, M. Kodama, and Y. Shiobara, Structure and Synthesis of 11,12,13-Trihydroxy-9(Z), 15(Z)-Octadecadienoic Acids from Rice Plant Suffering Rice Blast Disease, Chem. Lett. 27:577–580 (1986).
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).
DIFCO Manual, 10th edn., DIFCO Laboratories, Detroit, 1984, pp. 679–680.
Kaneshiro, T., J.K. Huang, D. Weisleder, and M.O. Bagby, 10(R)-Hydroxystearic Acid Production by a Novel Microbe, NRRL B-14797, Isolated from Compost, J. Ind. Microbiol. 13:351–355 (1994).
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).
Breslow, R., X. Zhang, and Y. Huang, Selective Catalytic Hydroxylation of a Steroid by an Artificial Cytochrome P-450 Enzyme, J. Am. Chem. Soc. 119:4535–4536 (1997).
Hou, C.T., and M.O. Bagby, 10-Hydroxy-8(Z)-Octadecenoic Acid, an Intermediate in the Bioconversion of Oleic Acid to 7,10-Dihydroxy-8(E)-Octadecenoic Acid, J. Ind. Microbiol. 9:103–107 (1992).
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Kuo, T.M., Manthey, L.K. & Hou, C.T. Fatty acid bioconversions by Pseudomonas aeruginosa PR3. J Amer Oil Chem Soc 75, 875–879 (1998). https://doi.org/10.1007/s11746-998-0240-3
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-998-0240-3