Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase
Linoleic acid oxidation catalyzed by lipoxygenase (lipoxidase) activity in extracts of defatted corn germ does not terminate in the product, linoleic acid hydroperoxide, unless the lipoxygenase is first partially purified. If purification is not attempted, the hydroperoxide product exists only as a...
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| Format: | Article |
| Language: | English |
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Elsevier
1970-07-01
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| Series: | Journal of Lipid Research |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520429670 |
| _version_ | 1818590563772923904 |
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| author | H.W. Gardner |
| author_facet | H.W. Gardner |
| author_sort | H.W. Gardner |
| collection | DOAJ |
| description | Linoleic acid oxidation catalyzed by lipoxygenase (lipoxidase) activity in extracts of defatted corn germ does not terminate in the product, linoleic acid hydroperoxide, unless the lipoxygenase is first partially purified. If purification is not attempted, the hydroperoxide product exists only as a barely detectable intermediate in the synthesis of three products. One of these was identified as 9-hydroxy-10-oxo-cis-12-octadecenoic acid formed from the hydroperoxide by the enzyme, linoleate hydroperoxide isomerase. Another product, 13-hydroxy-10-oxo-trans-11-octadecenoic acid, is believed to be formed by an isomerase also. The third product was the linoleate ester of one of the hydroxy-oxo-fatty acids, 9-(cis-9,cis-12-octadecadienoyl)-10-oxo-cis-12-octadecenoic acid. It is not known if the synthesis of the ester is enzyme-catalyzed.When a mixture of 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid and 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid from soybean lipoxygenase oxidation of linoleic acid was used as a substrate, 13-hydroxy-12-oxo-cis-9-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid were formed as the major products of catalysis by linoleate hydroperoxide isomerase(s) from corn. Smaller quantities of 9-hydroxy-10-oxo-cis-12-octadecenoic acid and 13-hydroxy-10-oxo-trans-11-octadecenoic acid were also formed. |
| first_indexed | 2024-12-16T09:58:32Z |
| format | Article |
| id | doaj.art-eb44db9f4de14ba48852f1c6e7a7e795 |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-16T09:58:32Z |
| publishDate | 1970-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-eb44db9f4de14ba48852f1c6e7a7e7952022-12-21T22:35:52ZengElsevierJournal of Lipid Research0022-22751970-07-01114311321Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomeraseH.W. Gardner0Northern Regional Research Laboratory, Peoria, Illinois 61604Linoleic acid oxidation catalyzed by lipoxygenase (lipoxidase) activity in extracts of defatted corn germ does not terminate in the product, linoleic acid hydroperoxide, unless the lipoxygenase is first partially purified. If purification is not attempted, the hydroperoxide product exists only as a barely detectable intermediate in the synthesis of three products. One of these was identified as 9-hydroxy-10-oxo-cis-12-octadecenoic acid formed from the hydroperoxide by the enzyme, linoleate hydroperoxide isomerase. Another product, 13-hydroxy-10-oxo-trans-11-octadecenoic acid, is believed to be formed by an isomerase also. The third product was the linoleate ester of one of the hydroxy-oxo-fatty acids, 9-(cis-9,cis-12-octadecadienoyl)-10-oxo-cis-12-octadecenoic acid. It is not known if the synthesis of the ester is enzyme-catalyzed.When a mixture of 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid and 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid from soybean lipoxygenase oxidation of linoleic acid was used as a substrate, 13-hydroxy-12-oxo-cis-9-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid were formed as the major products of catalysis by linoleate hydroperoxide isomerase(s) from corn. Smaller quantities of 9-hydroxy-10-oxo-cis-12-octadecenoic acid and 13-hydroxy-10-oxo-trans-11-octadecenoic acid were also formed.http://www.sciencedirect.com/science/article/pii/S0022227520429670linoleic acid hydroperoxide9-hydroxy-10-oxo-cis-12-octadecenoic acid13-hydroxy-12-oxo-cis-9-octadecenoic acid9-(cis-9,cis-12-octadecadienoyl)-10-oxo-cis-12-octadecenoic acid9-hydroxy-12-oxo-trans-10-octadecenoic acid13-hydroxy-10-oxo-trans-11-octadecenoic acid |
| spellingShingle | H.W. Gardner Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase Journal of Lipid Research linoleic acid hydroperoxide 9-hydroxy-10-oxo-cis-12-octadecenoic acid 13-hydroxy-12-oxo-cis-9-octadecenoic acid 9-(cis-9,cis-12-octadecadienoyl)-10-oxo-cis-12-octadecenoic acid 9-hydroxy-12-oxo-trans-10-octadecenoic acid 13-hydroxy-10-oxo-trans-11-octadecenoic acid |
| title | Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase |
| title_full | Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase |
| title_fullStr | Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase |
| title_full_unstemmed | Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase |
| title_short | Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase |
| title_sort | sequential enzymes of linoleic acid oxidation in corn germ lipoxygenase and linoleate hydroperoxide isomerase |
| topic | linoleic acid hydroperoxide 9-hydroxy-10-oxo-cis-12-octadecenoic acid 13-hydroxy-12-oxo-cis-9-octadecenoic acid 9-(cis-9,cis-12-octadecadienoyl)-10-oxo-cis-12-octadecenoic acid 9-hydroxy-12-oxo-trans-10-octadecenoic acid 13-hydroxy-10-oxo-trans-11-octadecenoic acid |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520429670 |
| work_keys_str_mv | AT hwgardner sequentialenzymesoflinoleicacidoxidationincorngermlipoxygenaseandlinoleatehydroperoxideisomerase |