Applied Microbiology and Biotechnology

, Volume 89, Issue 6, pp 1721–1727

Production of 7,10-dihydroxy-8(E)-octadecenoic acid from olive oil by Pseudomonas aeruginosa PR3

  • Min-Jung Suh
  • Ka-Yeon Baek
  • Beom-Soo Kim
  • Ching T. Hou
  • Hak-Ryul Kim
Biotechnological Products and Process Engineering
  • 244 Downloads

Abstract

Microbial modification of naturally occurring materials is one of the efficient ways to add new values to them. Hydroxylation of free unsaturated fatty acids by microorganism is a good example of those modifications. Among microbial strains studied for that purpose, a new bacterial isolate Pseudomonas aeruginosa PR3 has been well studied to produce several hydroxy fatty acids from different unsaturated fatty acids. Of those hydroxy fatty acids, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was efficiently produced from oleic acid by strain PR3. However, it was highly plausible to use vegetable oil containing oleic acid rather than free oleic acid as a substrate for DOD production by strain PR3. In this study, we firstly tried to use olive oil containing high content of oleic acid as a substrate for DOD production. DOD production from olive oil was confirmed by structural determination with GC, TLC, and GC/MS analysis. DOD production yield from olive oil was 53.5%. Several important environmental factors were also tested. Galactose and glutamine were optimal carbon and nitrogen sources, and magnesium ion was critically required for DOD production from olive oil. Results from this study demonstrated that natural vegetable oils containing oleic acid could be used as efficient substrate for the production of DOD by strain PR3.

Keywords

Hydroxy fatty acid Olive oil Bioconversion Pseudomonas aeruginosa DOD 

References

  1. Bagby MO, Calson KD (1989) Chemical and biological conversion of soybean oil for industrial products. In: Cambie RC (ed) Fats for the future. Ellis Horwood Limited Press, Chichester, pp 301–317Google Scholar
  2. Bajpai V, Shin SY, Kim MJ, Kim HR, Kang SC (2004) Antifungal activity of bioconverted oil extract of linoleic acid and fractionated dilutions against phytopathogens Rhizoctonia solani and Botrytis cinerea. Agric Chem Biotechnol 47:199–204Google Scholar
  3. Brash AR (1999) Lipoxygenases: occurrence, function, catalysis, and acquisition of substrate. J Biol Chem 274:23679–23682CrossRefGoogle Scholar
  4. Chang IA, Kim IH, Kang SC, Hou CT, Kim HR (2007) Production of 7, 10-dihydroxy-8(E)-octadecenoic acid from triolein via lipase induction by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 74:301–306CrossRefGoogle Scholar
  5. Chang IA, Bae JH, Suh MJ, Kim IH, Hou CT, Kim HR (2008) Environmental optimization for bioconversion of triolein into 7,10-dihydroxy-8(E)-octadecenoic acid by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 78:581–586CrossRefGoogle Scholar
  6. Gardner HW, Weisleder D, Kleiman R (1976) Formation of trans-12,13-epoxy-9-hydroperoxy-trans-10-octadecenoic acid from 13-l-hydroperoxy-cis-9, trans-11-octadecenoic acid catalyzed by either a soybean extract or cystein-FeCl3. Lipids 13:246–252CrossRefGoogle Scholar
  7. Hou CT, Bagby MO (1991) Production of a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid by Pseudomonas sp. PR3. J Ind Microbiol 7:123–130CrossRefGoogle Scholar
  8. Hou CT, Forman RJ (2000) Growth inhibition of plant pathogenic fungi by hydroxy fatty acids. J Ind Microbiol Biotechnol 24:275–276CrossRefGoogle Scholar
  9. Hou CT, Bagby MO, Plattner RD, Koritala S (1991) A novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid by bioconversion. J Am Oil Chem Soc 68:99–101CrossRefGoogle Scholar
  10. Kato T, Yamaguchi Y, Abe N, Uyehara T, Nakai T, Yamanaka S, Harada N (1984) Unsaturated hydroxy fatty acids, the self-defensive substances in rice plant against rice blast disease. Chem Lett 25:409–412CrossRefGoogle Scholar
  11. Kim H, Gardner HW, Hou CT (2000) Production of isomeric (9,10,13)-trihydroxy-11E(10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3. J Ind Microbiol Biotechnol 25:109–115CrossRefGoogle Scholar
  12. Kuo TM, Manthey LK, Hou CT (1998) Fatty acid bioconversion by Pseudomonas aeruginosa PR3. J Am Oil Chem Soc 75:875–879CrossRefGoogle Scholar
  13. Schilstra MJ, Veldink GA, Vliegenthart JF (1994) The dioxygenation rate in lipoxygenase catalysis is determined by the amount of iron (III) lipoxygenase in solution. Biochemistry 33:3974–3979CrossRefGoogle Scholar
  14. Shin SY, Kim HR, Kang SC (2004) Antibacterial activity of various hydroxy fatty acids bioconverted by Pseudomonas aeruginosa PR3. Agric Chem Biotechnol 47:205–208Google Scholar
  15. Wallen LL, Benedict RG, Jackson RW (1962) The microbiological production of 10-hydroxystearic acid from oleic acid. Arch Biochem Biophys 99:249–253CrossRefGoogle Scholar
  16. Yamamoto S (1991) Enzymatic lipid peroxidation: reactions of mammalian lipoxygenases. Free Radic Biol Med 10:149–159CrossRefGoogle Scholar
  17. Zhang YY, Lind B, Radmark O, Samuelsson B (1993) Iron content of human 5-lipoxygenase, effects of mutations regarding conserved histidine residues. J Biol Chem 268:2535–2541Google Scholar
  18. Zimmerman DC (1966) A new product of linoleic acid oxidation by a flaxseed enzyme. Biochem Biophys Res Commun 23:398–402CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Min-Jung Suh
    • 1
  • Ka-Yeon Baek
    • 1
  • Beom-Soo Kim
    • 2
  • Ching T. Hou
    • 3
  • Hak-Ryul Kim
    • 1
  1. 1.Department of Animal Science and BiotechnologyKyungpook National UniversityDaeguSouth Korea
  2. 2.Department of Chemical EngineeringChungbuk National UniversityCheongjuSouth Korea
  3. 3.Renewable Product Technology Research UnitNational Center for Agricultural Utilization Research, ARS, USDAPeoriaUSA

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