Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed
Alfalfa seeds and seedlings contain an enzyme that catalyzes a reaction with the 13- and 9-hydroperoxides of linoleic acid to form 13-hydroxy-10-oxo-trans-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid, respectively. When commercial lipoxygenase is used to generate the hydroperoxi...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
1974-03-01
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| Series: | Journal of Lipid Research |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520368218 |
| _version_ | 1818671928971362304 |
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| author | Walter J. Esselman C.O. Clagett |
| author_facet | Walter J. Esselman C.O. Clagett |
| author_sort | Walter J. Esselman |
| collection | DOAJ |
| description | Alfalfa seeds and seedlings contain an enzyme that catalyzes a reaction with the 13- and 9-hydroperoxides of linoleic acid to form 13-hydroxy-10-oxo-trans-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid, respectively. When commercial lipoxygenase is used to generate the hydroperoxides, the above acids appear in about 2:1 proportions, respectively. The products of the action of the enzyme on the hydroperoxides were stabilized for analysis by reduction with H2 and LiAlH4. Trimethylsilyl derivatives of reduced products were analyzed by combined gas–liquid chromatography–mass spectrometry. Specific deuterium labeling permitted definite location of the oxo functions. 18O2 labeling experiments showed that the oxygens of both the oxo and the hydroxyl functions were derived from the hydroperoxide. Retention of both oxygens suggests that the reaction proceeds through a cyclic epiperoxide followed by a ketohydroxy-forming rearrangement. No products of hydroperoxide isomerase were found in reactions catalyzed by the crude enzyme from alfalfa seeds. |
| first_indexed | 2024-12-17T07:31:48Z |
| format | Article |
| id | doaj.art-67f1e9c6e90a45e8906bca8dbc4fefac |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-17T07:31:48Z |
| publishDate | 1974-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-67f1e9c6e90a45e8906bca8dbc4fefac2022-12-21T21:58:28ZengElsevierJournal of Lipid Research0022-22751974-03-01152173178Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seedWalter J. Esselman0C.O. Clagett1Department of Biochemistry, The Pennsylvania State University, University Park, Pennsylvania 16802Department of Biochemistry, The Pennsylvania State University, University Park, Pennsylvania 16802Alfalfa seeds and seedlings contain an enzyme that catalyzes a reaction with the 13- and 9-hydroperoxides of linoleic acid to form 13-hydroxy-10-oxo-trans-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid, respectively. When commercial lipoxygenase is used to generate the hydroperoxides, the above acids appear in about 2:1 proportions, respectively. The products of the action of the enzyme on the hydroperoxides were stabilized for analysis by reduction with H2 and LiAlH4. Trimethylsilyl derivatives of reduced products were analyzed by combined gas–liquid chromatography–mass spectrometry. Specific deuterium labeling permitted definite location of the oxo functions. 18O2 labeling experiments showed that the oxygens of both the oxo and the hydroxyl functions were derived from the hydroperoxide. Retention of both oxygens suggests that the reaction proceeds through a cyclic epiperoxide followed by a ketohydroxy-forming rearrangement. No products of hydroperoxide isomerase were found in reactions catalyzed by the crude enzyme from alfalfa seeds.http://www.sciencedirect.com/science/article/pii/S0022227520368218lipohydroperoxidaselipohydroperoxide isomeraselinoleic acid metabolismhydroperoxidesoxygenated fatty acidscombined gas–liquid chromatography–mass spectrometr |
| spellingShingle | Walter J. Esselman C.O. Clagett Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed Journal of Lipid Research lipohydroperoxidase lipohydroperoxide isomerase linoleic acid metabolism hydroperoxides oxygenated fatty acids combined gas–liquid chromatography–mass spectrometr |
| title | Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed |
| title_full | Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed |
| title_fullStr | Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed |
| title_full_unstemmed | Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed |
| title_short | Products of a linoleic hydroperoxide-decomposing enzyme of alfalfa seed |
| title_sort | products of a linoleic hydroperoxide decomposing enzyme of alfalfa seed |
| topic | lipohydroperoxidase lipohydroperoxide isomerase linoleic acid metabolism hydroperoxides oxygenated fatty acids combined gas–liquid chromatography–mass spectrometr |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520368218 |
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