Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis

An Erratum to this article was published on 02 June 2012

Abstract

A recombinant enzyme from Lysinibacillus fusiformis was expressed, purified, and identified as an oleate hydratase because the hydration activity of the enzyme was the highest for oleic acid (with a k cat of 850 min−1 and a K m of 540 μM), followed by palmitoleic acid, γ-linolenic acid, linoleic acid, myristoleic acid, and α-linolenic acid. The optimal reaction conditions for the enzymatic production of 10-hydroxystearic acid were pH 6.5, 35 °C, 4% (v/v) ethanol, 2,500 U ml−1 (8.3 mg ml−1) of enzyme, and 40 g l−1 oleic acid. Under these conditions, 40 g l−1 (142 mM) oleic acid was converted into 40 g l−1 (133 mM) 10-hydroxystearic acid for 150 min, with a molar yield of 94% and a productivity of 16 g l−1 h−1, and olive oil hydrolyzate containing 40 g l−1 oleic acid was converted into 40 g l−1 10-hydroxystearic acid for 300 min, with a productivity of 8 g l−1 h−1.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

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, Chichester, pp 301–317

    Google Scholar 

  2. Bevers LE, Pinkse MW, Verhaert PD, Hagen WR (2009) Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond. J Bacteriol 191:5010–5012

    Article  CAS  Google Scholar 

  3. Chen TC, Ju YH (2001) An improved fractional crystallization method for the enrichment of gamma-linolenic acid in borage oil fatty acid. Ind Eng Chem Res 40:3781–3784

    Article  CAS  Google Scholar 

  4. el-Sharkawy SH, Yang W, Dostal L, Rosazza JP (1992) Microbial oxidation of oleic acid. Appl Environ Microbiol 58:2116–2122

    CAS  Google Scholar 

  5. Garcia EE, Belin JM, Wache Y (2007) Use of a Doehlert factorial design to investigate the effects of pH and aeration on the accumulation of lactones by Yarrowia lipolytica. J Appl Microbiol 103:1508–1515

    Article  CAS  Google Scholar 

  6. Heo SH, Kim BS (2009) Production and recovery of oxygenated fatty acids from oleic acid by Flavobacterium sp. strain DS5. Korean Chem Eng Res 47:620–623

    CAS  Google Scholar 

  7. Hou CT (1994a) 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 

  8. Hou CT (1994b) Production of 10-ketostearic acid from oleic acid by Flavobacterium sp. strain DS5 (NRRL B-14859). Appl Environ Microbiol 60:3760–3763

    CAS  Google Scholar 

  9. Hou CT (1995a) Is strain DS5 hydratase a C-10 positional specific enzyme? Identification of bioconversion products from α- and γ-linolenic acids by Flavibacterium sp. DS5. J Ind Microbiol 14:31–34

    Article  Google Scholar 

  10. Hou CT (1995b) Production of hydroxy fatty acids from unsaturated fatty acids by Flavobacterium sp. DS5 hydratase, a C-10 positional- and cis unsaturation-specific enzyme. J Am Oil Chem Soc 72:1265–1270

    Article  CAS  Google Scholar 

  11. Hudson JA, MacKenzie CA, Joblin KN (1995) Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Appl Microbiol Biotechnol 44:1–6

    Article  CAS  Google Scholar 

  12. Kim BN, Yeom SJ, Oh DK (2011) Conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens. Biotechnol Lett 33:993–997

    Article  CAS  Google Scholar 

  13. Koritala S, Hosie L, Hou CT, Hesseltine CW, Bagby MO (1989) Microbial conversion of oleic acid to 10-hydroxystearic acid. Appl Microbiol Biotechnol 32:299–304

    Article  CAS  Google Scholar 

  14. Kuo TM, Lanser AC, Nakamura LK, Hou CT (2000) Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure. Curr Microbiol 40:105–109

    Article  CAS  Google Scholar 

  15. Latrasse A, Paitier S, Lachot B, Bonnarme P, Feron G, Durand A, Le Quere JL (1997) Conversion of oleic acid to 10-hydroxystearic acid by Nocardia paraffinae. Biotechnol Lett 19:715–718

    Article  CAS  Google Scholar 

  16. Morvan B, Joblin KN (1999) Hydration of oleic acid by Enterococcus gallinarum, Pediococcus acidilactici and Lactobacillus sp. isolated from the rumen. Anaerobe 5:605–611

    Article  CAS  Google Scholar 

  17. Naughton FC (1974) Production, chemistry and commercial applications of various chemicals from castor oil. J Am Oil Chem Soc 51:65–71

    Article  CAS  Google Scholar 

  18. Niehaus WG Jr, Torkelson A, Kisic A, Bednarczyk DJ, Schroepfer GJ Jr (1970) Stereospecific hydration of the delta-9 double bond of oleic acid. J Biol Chem 245:3790–3797

    CAS  Google Scholar 

  19. Rosberg-Cody E, Liavonchanka A, Gobel C, Ross RP, O’Sullivan O, Fitzgerald GF, Feussner I, Stanton C (2011) Myosin-cross-reactive antigen (MCRA) protein from Bifidobacterium breve is a FAD-dependent fatty acid hydratase which has a function in stress protection. BMC Biochem 12:9–20

    Article  CAS  Google Scholar 

  20. Turner NJ (2009) Directed evolution drives the next generation of biocatalysts. Nat Chem Biol 5:567–573

    Article  CAS  Google Scholar 

  21. Volkov A, Liavonchanka A, Kamneva O, Fiedler T, Goebel C, Kreikemeyer B, Feussner I (2010) Myosin cross-reactive antigen of Streptococcus pyogenes M49 encodes a fatty acid double bond hydratase that plays a role in oleic acid detoxification and bacterial virulence. J Biol Chem 285:10353–10361

    Article  CAS  Google Scholar 

  22. Wache Y, Aguedo M, Choquet A, Gatfield IL, Nicaud JM, Belin JM (2001) Role of beta-oxidation enzymes in gamma-decalactone production by the yeast Yarrowia lipolytica. Appl Environ Microbiol 67:5700–5704

    Article  CAS  Google Scholar 

  23. Yang W, Dostal L, Rosazza JP (1993) Stereospecificity of microbial hydrations of oleic acid to 10-hydroxystearic acid. Appl Environ Microbiol 59:281–284

    CAS  Google Scholar 

Download references

Acknowledgment

This study was supported by a grant (Code#000407980110) from Small and Medium Business Administration, Republic of Korea.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Deok-Kun Oh.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Kim, BN., Joo, YC., Kim, YS. et al. Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis . Appl Microbiol Biotechnol 95, 929–937 (2012). https://doi.org/10.1007/s00253-011-3805-2

Download citation

Keywords

  • Lysinibacillus fusiformis
  • Oleic acid
  • 10-Hydroxystearic acid production
  • Oleate hydratase
  • Olive oil hydrolyzate