Abstract
The optimal conditions for the production of 5,8-dihydroxy-9(Z)-octadecenoic acid (5,8-diHOME) from oleic acid by whole recombinant Escherichia coli cells expressing diol synthase from Aspergillus nidulans were 40 °C, pH 7.5, 10 % (v/v) dimethyl sulfoxide, 35 g cells l−1, and 12 g oleic acid l−1 at 250 rpm in a 250 ml baffled flask. Under these conditions, whole recombinant cells produced 5.2 g 5,8-diHOME l−1 together with 1 g l−1 of the intermediate 8-hydroperoxy-9(Z)-octadecenoic acid (8-HPOME) after 60 min. This corresponded to a conversion yield of 43 % (w/w), a volumetric productivity of 5.2 g l−1 h−1, and a specific productivity of 148 mg g cells−1 h−1. This is the first report of the biotechnological production of 5,8-diHOME from oleic acid.
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References
An JU, Oh DK (2013) Increased production of γ-lactones from hydroxyfatty acids by whole Waltomyces lipofer cells induced with oleic acid. Appl Microbiol Biotechnol 97:8265–8272
An JU, Joo YC, Oh DK (2013) New biotransformation process for production of the fragrant compound γ-dodecalactone from 10-hydroxystearate by permeabilized Waltomyces lipofer cells. Appl Environ Microbiol 79:2636–2641
Brodhun F, Gobel C, Hornung E, Feussner I (2009) Identification of PpoA from Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450. J Biol Chem 284:11792–11805
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
Hou CT (2008) New bioactive fatty acids. Asia Pac J Clin Nutr 17(1):192–195
Hou CT (2009) Biotechnology for fats and oils: new oxygenated fatty acids. New Biotechnol 26:2–10
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
Kim KR, Oh DK (2013) Production of hydroxyfatty acids by microbial fatty acid-hydroxylation enzymes. Biotechnol Adv 31:1473–1485
Kuo TM, Manthey LK, Hou CT (1998) Fatty acid bioconversions by Pseudomonas aeruginosa PR3. J Am Oil Chem Soc 75:875–879
Mazur P, Nakanishi K, El-Zayat AAE, Champe SP (1991) Structure and synthesis of sporogenic psi factors from Aspergillus nidulans. J Chem Soc, Chem Commun 20:1486–1487
Metzger JO, Bornscheuer U (2006) Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol 71:13–22
Naughton FC (1974) Production, chemistry, and commercial applications of various chemicals from castor oil. J Am Oil Chem Soc 51:65–71
Ogunniyi D (2006) Castor oil: a vital industrial raw material. Bioresour Technol 97:1086–1091
Omar MN, Moynihan H, Hamilton R (2003) Scaling-up the production of 13S-hydroxy-9Z,11E-octadecadienoic acid (13S-HODE) through chemoenzymatic technique. Bull Korean Chem Soc 24:397–399
Parra JL, Pastor J, Comelles F, Manresa MA, Bosch MP (1990) Studies of biosurfactants obtained from olive oil. Tenside Surf Det 27:302–306
Paul S, Hou CT, Kang SC (2010) α-Glucosidase inhibitory activities of 10-hydroxy-8(E)-octadecenoic acid: an intermediate of bioconversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. New Biotechnol 27:419–423
Seo MJ, Shin KC, Oh DK (2014) Production of 5,8-dihydroxy-9,12(Z,Z)-octadecadienoic acid from linoleic acid by whole recombinant Escherichia coli cells expressing diol synthase from Aspergillus nidulans. Appl Microbiol Biotechnol. doi:10.1007/s00253-014-5709-4
Sohn HR, Bae JH, Hou CT, Kim HR (2013) Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteria. Enzyme Microb Tech 53:152–153
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
Acknowledgments
This study was supported by Grants from the Bio-industry Technology Development Program, Ministry for Agriculture, Food and Rural Affairs (No. 112002-3) and the Korea Healthcare Technology R&D Project, Ministry for Health & Welfare, Republic of Korea (No. 2012-009).
Supporting information
Supplementary Fig. 1—LC–MS/MS spectrum of 8-HPOME obtained from conversion of α-linolenic acid using diol synthase from A. nidulans double-site (H1004A-C1006S) variant
Supplementary Fig. 2—Effect of temperature on the production of 5,8-diHOME from oleic acid using whole recombinant cells expressing diol synthase from A. nidulans
Supplementary Fig. 3—Effect of pH on the production of 5,8-diHOME from oleic acid using whole recombinant cells expressing diol synthase from A. nidulans
Supplementary Fig. 4—Effect of enzyme stability on the production of 5,8-diHOME from oleic acid using whole recombinant cells expressing diol synthase from A. nidulans
Supplementary Fig. 5—Effect of solvents on the production of 5,8-diHOME from oleic acid using whole recombinant cells expressing diol synthase from A. nidulans
Supplementary Fig. 6—Effect of dimethyl sulfoxide concentration on the production of 5,8-diHOME from oleic acid using whole recombinant cells expressing diol synthase from A. nidulans
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Seo, MJ., Shin, KC., Jeong, YJ. et al. Production of 5,8-dihydroxy-9(Z)-octadecenoic acid from oleic acid by whole recombinant cells of Aspergillus nidulans expressing diol synthase. Biotechnol Lett 37, 131–137 (2015). https://doi.org/10.1007/s10529-014-1650-y
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DOI: https://doi.org/10.1007/s10529-014-1650-y