Journal of Marine Bioscience and Biotechnology (한국해양바이오학회지)

The Korean Society for Marine Biotechnology (한국해양바이오학회)
권호 표지
DOI QR코드

DOI QR Code

Whole-cell Biotransformation of Chlorella Oil Hydrolysates into Medium Chain Fatty Acids

  • Seo, Joo-Hyun (Department of Pharmaceutical Engineering & Biotechnology, Sunmoon University) ;
  • Min, Won-Ki (Department of Food Science and Industry, Kyungil University) ;
  • Lee, Jung-Hoo (Department of Food Science and Engineering, Ewha Womans University) ;
  • Lee, Sun-Mee (Department of Food and Nutrition, Daejeon University) ;
  • Lee, Choul-Gyun (National Marine Bioenergy Research Consortium & Department of Biological Engineering, Inha University) ;
  • Park, Jin-Byung (Department of Food Science and Engineering, Ewha Womans University)
  • Received : 2018.10.15
  • Accepted : 2018.11.01
  • Published : 2018.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

A synthetic pathway, which consisted of fatty acid double bond hydratase, alcohol dehydrogenase, and Baeyer-Villiger monooxygenase, was applied to Chlorella oil to produce ester fatty acids, which can be hydrolyzed into medium chain fatty acids. Since linoleic acid is a major fatty acid constituent of Chlorella oil, a fatty acid double bond hydratase from Lactobacillus acidophilus NBRC13951, which is able to convert linoleic acid into 13-hydroxyoctadec-9-enoic acid, was used. Recombinant Escherichia coli expressing the fatty acid double bond hydratase from L. acidophilus NBRC13951 successfully transformed linoleic acid in Chlorella oil hydrolysates into 13-hydroxyoctadec-9-enoic acid with approximately 60% conversion yield. 13-Hydroxyoctadec-9-enoic acid was further converted into ester fatty acids by the recombinant E. coli expressing a long chain secondary alcohol dehydrogenase and a Baeyer-Villiger monooxygenase. The resulting ester fatty acids were then hydrolyzed into medium chain fatty acids by a lipase. Overall, industrially relevant medium chain fatty acids were produced from Chlorella oil hydrolysates. Thereby, this study may contribute to biosynthesis of medium chain fatty acids from microalgae oils as well as long chain fatty acids.

Keywords

References

  1. Orsavova, J., Misurcova, L., Ambrozova, J. V., Vicha, R. and Mlcek, J. 2015. Fatty acids composition of vegetable oils and its contribution to dietary energy intake and dependence of cardiovascular mortality on dietary intake of fatty acids. Int. J. Mol. Sci. 16, 12871-12890. https://doi.org/10.3390/ijms160612871
  2. Volkman, J. K., Jeffrey, S. W., Nichols, P. D., Rogers, G. I. and Garland, C. D. 1989. Fatty acid and lipid composition of 10 species of microalgae used in mariculture. J. Exp. Mar. Biol. Ecol. 128, 219-240. https://doi.org/10.1016/0022-0981(89)90029-4
  3. Patil, V., Kallqvist, T., Olsen, E., Vogt, G. and Gislerod, H. R. 2007. Fatty acid composition of 12 microalgae for possible use in aquaculture feed. Aquacult. Int. 15, 1-9. https://doi.org/10.1007/s10499-006-9060-3
  4. Soares, A. T., da Costa, D. C., Silva, B. F., Lopes, R. G., Derner, R. B. and Antoniosi Filho, N. R. 2014. Comparative analysis of the fatty acid composition of microalgae obtained by different oil extraction methods and direct biomass transesterification. Bioenerg. Res. 7, 1035-1044. https://doi.org/10.1007/s12155-014-9446-4
  5. Jeon, E.-Y., Seo, J.-H., Kang, W.-R., Kim, M.-J., Lee, J.-H., Oh, D.-K. and Park, J.-B. 2016. Simultaneous enzyme/whole-cell biotransformation of plant oils into C9 carboxylic acids. ACS Catal. 6, 7547-7553. https://doi.org/10.1021/acscatal.6b01884
  6. Seo, E.-J., Yeon, Y. J., Seo, J.-H., Lee, J.-H., Bongol, J. P., Oh, Y., Park, J. M., Lim, S.-M., Lee, C.-G. and Park, J.-B. 2018. Enzyme/whole-cell biotransformation of plant oils, yeast derived oils, and microalgae fatty acid methyl esters into n-nonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid. Bioresour. Technol. 251, 288-294. https://doi.org/10.1016/j.biortech.2017.12.036
  7. Song, J.-W., Jeon, E.-Y., Song, D.-H., Jang, H.-Y., Bornscheuer, U. T., Oh, D.-K. and Park, J.-B. 2013. Multistep enzymatic synthesis of long-chain ${\alpha},{\omega}$-dicarboxylic and $\omega$-hydroxycarboxylic acids from renewable fatty acids and plant oils. Angew. Chem. Int. Ed. Engl. 52, 2534-2537. https://doi.org/10.1002/anie.201209187
  8. Song, J.-W., Lee, J.-H., Bornscheuer, U. T. and Park, J.-B. 2014. Microbial synthesis of medium-chain ${\alpha},{\omega}$-dicarboxylic acids and $\omega$-aminocarboxylic acids from renewable long-chain fatty acids. Adv. Synth. Catal. 356, 1782-1788. https://doi.org/10.1002/adsc.201300784
  9. Islam, M. A., Heimann, K. and Brown, R. J. 2017. Microalgae biodiesel: current status and future needs for engine performance and emissions. Renew. Sust. Energ. Rev. 79, 1160-1170. https://doi.org/10.1016/j.rser.2017.05.041
  10. Otles, S. and Pire, R. 2001. Fatty acid composition of Chlorella and Spirulina microalgae species. J. AOAC Int. 84, 1708-1714.
  11. Hong, S.-J., Park, Y. S., Han, M.-A., Kim, Z.-H., Cho, B.-K., Lee, H., Choi, H.-K. and Lee, C.-G. 2017. Enhanced production of fatty acids in three strains of microalgae using a combination of nitrogen starvation and chemical inhibitors of carbohydrate synthesis. Biotechnol. Bioprocess Eng. 22, 60-67. https://doi.org/10.1007/s12257-016-0575-9
  12. Kim, Z.-H., Park, Y.-S., Ryu, Y.-J. and Lee, C.-G. 2017. Enhancing biomass and fatty acid productivity of Tetraselmis sp. in bubble column photobioreactors by modifying light quality using light filters. Biotechnol. Bioprocess Eng. 22, 397-404. https://doi.org/10.1007/s12257-017-0200-6
  13. Kang, W.-R., Seo, M.-J., Shin, K.-C., Park, J.-B. and Oh, D.-K. 2017. Comparison of biochemical properties of the original and newly identified oleate hydratases from Stenotrophomonas maltophilia. Appl. Environ. Microbiol. 83, e03351-03316.
  14. Choi, J.-H., Seo, M.-J., Lee, K.-T. and Oh, D.-K. 2017. Biotransformation of fatty acid-rich tree oil hydrolysates to hydroxy fatty acid-rich hydrolysates by hydroxylases and their feasibility as biosurfactants. Biotechnol. Bioprocess Eng. 22, 709-716. https://doi.org/10.1007/s12257-017-0374-y
  15. Oh, H.-J., Kim, S.-U., Song, J.-W., Lee, J.-H., Kang, W.-R., Jo, Y.-S., Kim, K.-R., Bornscheuer, U. T., Oh, D.-K. and Park, J.-B. 2015. Biotransformation of linoleic acid into hydroxy fatty acids and carboxylic acids using a linoleate double bond hydratase as key enzyme. Adv. Synth. Catal. 357, 408-416. https://doi.org/10.1002/adsc.201400893
  16. Riesenberg, D. 1991. High-cell-density cultivation of Escherichia coli. Curr. Opin. Biotechnol. 2, 380-384. https://doi.org/10.1016/S0958-1669(05)80142-9
  17. Park, J. Y., Lee, S. H., Kim, K. R., Park, J. -B. and Oh, D. K. 2015. Production of 13S-hydroxy-9(Z)-octadecenoic acid from linoleic acid by whole recombinant cells expressing linoleate 13-hydratase from Lactobacillus acidophilus. J. Biotechnol. 208, 1-10. https://doi.org/10.1016/j.jbiotec.2015.05.006
  18. Cha, H.-J., Seo, E.-J., Song, J.-W., Jo, H.-J., Kumar, A. R. and Park, J.-B. 2018. Simultaneous enzyme/whole-cell biotransformation of C18 ricinoleic acid into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid. Adv. Synth. Catal. 360, 696-703. https://doi.org/10.1002/adsc.201701029
  19. Woo, J.-M., Jeon, E.-Y., Seo, E.-J., Seo, J.-H., Lee, D.-Y., Yeon, Y. J. and Park, J.-B. 2018. Improving catalytic activity of the Baeyer-Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid. Sci. Rep. 8, 10280. https://doi.org/10.1038/s41598-018-28575-8
  20. Sudheer, P. D. V. N., Yun, J., Chauhan, S., Kang, T. J. and Choi, K.-Y. 2017. Screening, expression, and characterization of Baeyer-Villiger monooxygenases for the production of 9-(nonanoyloxy)nonanoic acid from oleic acid. Biotechnol. Bioprocess Eng. 22, 717-724. https://doi.org/10.1007/s12257-017-0295-9
  21. Seo, J.-H., Kim, H.-H., Jeon, E.-Y., Song, Y.-H., Shin, C.-S. and Park, J.-B. 2016. Engineering of Baeyer-Villiger monooxygenase-based Escherichia coli biocatalyst for large scale biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid. Sci. Rep. 6, 28223. https://doi.org/10.1038/srep28223
  22. Samuelson, J. 2011. Bacterial Systems. In: Robinson, A. S. (eds), Production of membrane proteins: strategies for expression and isolation. Wiley-VCH, Weinheim, Germany, pp. 15-22.
  23. Seo, J.-H., Baek, S.-W., Lee, J. and Park, J.-B. 2017. Engineering Escherichia coli BL21 genome to improve the heptanoic acid tolerance by using CRISPR-Cas9 system. Biotechnol. Bioprocess Eng. 22, 231-238. https://doi.org/10.1007/s12257-017-0158-4