Skip to main content
Log in

Production of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa KNU-2B

  • Original Research Paper
  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

Microbial production of hydroxy fatty acids (HFAs) was widely studied because of important biological properties of HFAs. Among microorganisms producing HFAs, Pseudomonas aeruginosa PR3 was well known to produce various HFAs from different unsaturated fatty acids. Recently, a new variant species of P. aeruginosa PR3 was isolated and characterized, showing improved efficiency for producing 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid. In this study, we report the production of 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD) from ricinoleic acid by the newly isolated P. aeruginosa KNU-2B. TOD was efficiently produced from ricinoleic acid by KNU-2B with the maximum conversion yield of 56.7% under the optimum reaction conditions of pH 8.0 and 48-h incubation at 27 °C, 150 rpm. Under optimized reaction conditions, maximum TOD production reached 340.3 mg/100 mL of the culture. However, requirement of nutritional factors by KNU-2B for production of TOD were considerably different from those by PR3 strain.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  • Bae JH, Suh MJ, Kim BS, Hou CT, Lee LJ, Kim LH, Kim HR (2010) Optimal production of 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa PR3. New Biotechnol 27:352–357

    Article  CAS  Google Scholar 

  • Bagby MO, Carlson KD (1989) Chemical and biological conversion of soybean oil for industrial products. In: Cambie RC (ed) Fats for the future. Ellis Horwood Limited, Chichester, pp 301–306

    Google Scholar 

  • Bajpai V, Shin SY, Kim MJ, Kim HR, Kang SC (2004) Anti-fungal activity of bioconverted oil extract of linoleic acid and fractionated dilutions against phytopathogens Rhizoctonia solani and Botrytis cinerea. Agric Chem Biotechnol 47:199–204

    CAS  Google Scholar 

  • Broun P, Somerville C (1997) Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean. Plant Physiol 113:933–942

    Article  CAS  Google Scholar 

  • 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 78:581–586

    Article  CAS  Google Scholar 

  • Ellamar JB, Kim IH, Hou CT, Park HS, Kim HR (2019) Isolation and identification of a variant strain of Pseudomonas aeruginosa PR3 with enhanced production of 7,10-dihydroxy-8(E)-octadecenoic acid. Biocatal Agric Biotechnol 18:101068

    Article  Google Scholar 

  • Estupiñán M, Diaz P, Manresa A (2014) Unveiling the genes responsible for the unique Pseudomonas aeruginosa oleate-diol synthase activity. Biochim Biophys Acta 1841:1360–1371

    Article  Google Scholar 

  • Hou CT (1994) Conversion of linoleic acid to 10-hydroxy-12(Z)-octadecenoic acid by Flavobacterium sp. (NRRL B-14859). J Am Oil Chem Soc 71:975–978

    Article  CAS  Google Scholar 

  • Hou CT (1996) 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

    Article  CAS  Google Scholar 

  • Hou CT, Bagby MO (1992) 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

    Article  CAS  Google Scholar 

  • Hou CT, Forman RJ (2000) Growth inhibition of plant pathogenic fungi by hydroxy fatty acids. J Ind Microbiol Biotechnol 24:275–276

    Article  CAS  Google Scholar 

  • 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 68:99–101

    Article  CAS  Google Scholar 

  • Kato T, Yamaguchi Y, Hirano T, Yokoyama T, Uyehara T, Namai T, Yamanaka S, Harada N (1984) Unsaturated hydroxy fatty acids, the self defensive substances in rice plant against rice blast disease. Chem Lett 13:409–412

    Article  Google Scholar 

  • Kim KR, Oh DK (2013) Production of hydroxy fatty acids by microbial fatty acid-hydroxylation enzymes. Biotechnol Adv 31:1473–1485

    Article  CAS  Google Scholar 

  • Kim H, Gardner HW, Hou CT (2000a) 10(S)-Hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. J Am Oil Chem Soc 77:95–99

    Article  CAS  Google Scholar 

  • Kim H, Gardner HW, Hou CT (2000b) Production of isomeric 9,10,13 (9,12,13)-trihydroxy-11E (10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3. J Ind Microbiol Biotechnol 25:109–115

    Article  CAS  Google Scholar 

  • Kim H, Jang YS, Hou CT (2002) Effect of metal ions on the production of isomeric 9,10,13 (9,12,13)-trihydroxy-11E (10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3. Enzyme Microb Technol 20:752–757

    Article  Google Scholar 

  • Kuo TM, Kim H, Hou CT (2001) Production of a novel compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa PR3. Curr Microbiol 43:198–203

    Article  CAS  Google Scholar 

  • Schilstra MJ, Veldink GA, Vliegenthart FG (1994) The dioxygenation rate in lipoxygenase catalysis is determined by the amount of iron(III) lipoxygenase in solution. Biochemistry 33:3974–3979

    Article  CAS  Google Scholar 

  • Smith S, Witkowski A, Joshi AK (2003) Structural and functional organization of the animal fatty acid synthase. Prog Lipid Res 42:289–317

    Article  CAS  Google Scholar 

  • Sohn HR, Back KY, Hou CT, Kim HR (2013a) Antibacterial activity of 7,10-dihydroxy-8(E)-octadecenoic acid against food-borne pathogenic bacteria. Biocatal Agric Biotechnol 2:85–87

    Article  Google Scholar 

  • Sohn HR, Bae JH, Hou CT, Kim HR (2013b) Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteria. Enzyme Microb Technol 53:152–153

    Article  CAS  Google Scholar 

  • Suh MJ, Baek KY, Kim BS, Hou CT, Kim HR (2011) Production of 7,10-dihydroxy-8(E)-octadecenoic acid from olive oil by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 89:1721–1727

    Article  CAS  Google Scholar 

  • Streckert G, Stan HJ (1975) Conversion of linoleic acid hydroperoxide by soybean lipoxygenase in the presence of guaiacol: identification of the reaction products. Lipids 10:847–854

    Article  CAS  Google Scholar 

  • Zimmerman DC (1966) A new product of linoleic acid oxidation by a flaxseed enzyme. Biochem Biophys Res Commun 23:398–402

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2018R1D1A3B07040443).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hak-Ryul Kim.

Ethics declarations

Conflict of interest

The authors declare no competing financial interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lee, YJ., Moon, JS., Kim, IH. et al. Production of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa KNU-2B. Biotechnol Lett 42, 1547–1558 (2020). https://doi.org/10.1007/s10529-020-02883-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-020-02883-4

Keywords

Navigation