High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases
Epoxides of vegetable oils and free and methylated fatty acids are of interest for several industrial applications. In the present work, refined rapeseed, sunflower, soybean, and linseed oils, with very different profiles of mono- and poly-unsaturated fatty acids, were saponified and transesterified...
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Frontiers Media S.A.
2021-01-01
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| Series: | Frontiers in Bioengineering and Biotechnology |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fbioe.2020.605854/full |
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| author | Alejandro González-Benjumea Gisela Marques Owik M. Herold-Majumdar Jan Kiebist Katrin Scheibner José C. del Río Angel T. Martínez Ana Gutiérrez |
| author_facet | Alejandro González-Benjumea Gisela Marques Owik M. Herold-Majumdar Jan Kiebist Katrin Scheibner José C. del Río Angel T. Martínez Ana Gutiérrez |
| author_sort | Alejandro González-Benjumea |
| collection | DOAJ |
| description | Epoxides of vegetable oils and free and methylated fatty acids are of interest for several industrial applications. In the present work, refined rapeseed, sunflower, soybean, and linseed oils, with very different profiles of mono- and poly-unsaturated fatty acids, were saponified and transesterified, and the products treated with wild unspecific peroxygenases (UPOs, EC 1.11.2.1) from the ascomycete Chaetomium globosum (CglUPO) and the basidiomycete Marasmius rotula (MroUPO), as well as with recombinant UPO of the ascomycete Humicola insolens (rHinUPO), as an alternative to chemical epoxidation that is non-selective and requires strongly acidic conditions. The three enzymes were able of converting the free fatty acids and the methyl esters from the oils into epoxide derivatives, although significant differences in the oxygenation selectivities were observed between them. While CglUPO selectively produced “pure” epoxides (monoepoxides and/or diepoxides), MroUPO formed also hydroxylated derivatives of these epoxides, especially in the case of the oil hydrolyzates. Hydroxylated derivatives of non-epoxidized unsaturated fatty acids were practically absent in all cases, due to the preference of the three UPOs selected for this study to form the epoxides. Moreover, rHinUPO, in addition to forming monoepoxides and diepoxides of oleic and linoleic acid (and their methyl esters), respectively, like the other two UPOs, was capable of yielding the triepoxides of α-linolenic acid and its methyl ester. These enzymes appear as promising biocatalysts for the environmentally friendly production of reactive fatty-acid epoxides given their self-sufficient monooxygenase activity with selectivity toward epoxidation, and the ability to epoxidize, not only isolated pure fatty acids, but also complex mixtures from oil hydrolysis or transesterification containing different combinations of unsaturated (and saturated) fatty acids. |
| first_indexed | 2024-12-24T04:59:24Z |
| format | Article |
| id | doaj.art-dd62e8fcb2c944f6b4e3ff14e6493065 |
| institution | Directory Open Access Journal |
| issn | 2296-4185 |
| language | English |
| last_indexed | 2024-12-24T04:59:24Z |
| publishDate | 2021-01-01 |
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| series | Frontiers in Bioengineering and Biotechnology |
| spelling | doaj.art-dd62e8fcb2c944f6b4e3ff14e64930652022-12-21T17:14:18ZengFrontiers Media S.A.Frontiers in Bioengineering and Biotechnology2296-41852021-01-01810.3389/fbioe.2020.605854605854High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal PeroxygenasesAlejandro González-Benjumea0Gisela Marques1Owik M. Herold-Majumdar2Jan Kiebist3Katrin Scheibner4José C. del Río5Angel T. Martínez6Ana Gutiérrez7Instituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Seville, SpainInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Seville, SpainNovozymes A/S, Bagsvaerd, DenmarkJenaBios GmbH, Jena, GermanyJenaBios GmbH, Jena, GermanyInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Seville, SpainCentro de Investigaciones Biológicas Margarita Salas (CIB), CSIC, Madrid, SpainInstituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Seville, SpainEpoxides of vegetable oils and free and methylated fatty acids are of interest for several industrial applications. In the present work, refined rapeseed, sunflower, soybean, and linseed oils, with very different profiles of mono- and poly-unsaturated fatty acids, were saponified and transesterified, and the products treated with wild unspecific peroxygenases (UPOs, EC 1.11.2.1) from the ascomycete Chaetomium globosum (CglUPO) and the basidiomycete Marasmius rotula (MroUPO), as well as with recombinant UPO of the ascomycete Humicola insolens (rHinUPO), as an alternative to chemical epoxidation that is non-selective and requires strongly acidic conditions. The three enzymes were able of converting the free fatty acids and the methyl esters from the oils into epoxide derivatives, although significant differences in the oxygenation selectivities were observed between them. While CglUPO selectively produced “pure” epoxides (monoepoxides and/or diepoxides), MroUPO formed also hydroxylated derivatives of these epoxides, especially in the case of the oil hydrolyzates. Hydroxylated derivatives of non-epoxidized unsaturated fatty acids were practically absent in all cases, due to the preference of the three UPOs selected for this study to form the epoxides. Moreover, rHinUPO, in addition to forming monoepoxides and diepoxides of oleic and linoleic acid (and their methyl esters), respectively, like the other two UPOs, was capable of yielding the triepoxides of α-linolenic acid and its methyl ester. These enzymes appear as promising biocatalysts for the environmentally friendly production of reactive fatty-acid epoxides given their self-sufficient monooxygenase activity with selectivity toward epoxidation, and the ability to epoxidize, not only isolated pure fatty acids, but also complex mixtures from oil hydrolysis or transesterification containing different combinations of unsaturated (and saturated) fatty acids.https://www.frontiersin.org/articles/10.3389/fbioe.2020.605854/fullepoxidationvegetable oilsenzymesperoxygenasespolyunsaturated fatty acidsfatty acid methyl esters |
| spellingShingle | Alejandro González-Benjumea Gisela Marques Owik M. Herold-Majumdar Jan Kiebist Katrin Scheibner José C. del Río Angel T. Martínez Ana Gutiérrez High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases Frontiers in Bioengineering and Biotechnology epoxidation vegetable oils enzymes peroxygenases polyunsaturated fatty acids fatty acid methyl esters |
| title | High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases |
| title_full | High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases |
| title_fullStr | High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases |
| title_full_unstemmed | High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases |
| title_short | High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases |
| title_sort | high epoxidation yields of vegetable oil hydrolyzates and methyl esters by selected fungal peroxygenases |
| topic | epoxidation vegetable oils enzymes peroxygenases polyunsaturated fatty acids fatty acid methyl esters |
| url | https://www.frontiersin.org/articles/10.3389/fbioe.2020.605854/full |
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