ArticleBiochimica et biophysica acta2010
Omega-3 fatty acids are oxygenated at the n-7 carbon by the lipoxygenase domain of a fusion protein in the cyanobacterium Acaryochloris marina.
Article in Biochimica et biophysica acta, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 43 citations in OpenAlex.
- Bacterial lipoxygenases for fatty acid oxyfunctionalization: advances and future directions.Applied microbiology and biotechnology · 2026Review
- Altering 15-Lipoxygenases to 18-Lipoxygenases and Their Application to the Production of 5,18-Dihydroxyeicosapentaenoic Acids.Biotechnology and bioengineering · 2025Article
- The Octadecanoids: Synthesis and Bioactivity of 18-Carbon Oxygenated Fatty Acids in Mammals, Bacteria, and Fungi.Chemical reviews · 2025Review
- Intricate Evolution of Multifunctional Lipoxygenase in Red Algae.International journal of molecular sciences · 2024Article
- Discovery of α-Linolenic Acid 16(International journal of molecular sciences · 2023Article
- Stabilization and improved activity of arachidonate 11Journal of lipid research · 2018Article
- Applications of Microbial Enzymes in Food Industry.Food technology and biotechnology · 2018Review
- Biotransformation of polyunsaturated fatty acids to bioactive hepoxilins and trioxilins by microbial enzymes.Nature communications · 2018Article
- Catalase-Related Allene Oxide Synthase, on a Biosynthetic Route to Fatty Acid Cyclopentenones: Expression and Assay of the Enzyme and Preparation of the 8R-HPETE Substrate.Methods in enzymology · 2018Article
- Crystal structure of linoleate 13R-manganese lipoxygenase in complex with an adhesion protein.Journal of lipid research · 2016Article
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- Evolutionary aspects of lipoxygenases and genetic diversity of human leukotriene signaling.Progress in lipid research · 2015Review
- Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction.Journal of lipid research · 2014Article
- Chlorophyll d and Acaryochloris marina: current status.Photosynthesis research · 2013Review
- Linolenate 9R-dioxygenase and allene oxide synthase activities of Lasiodiplodia theobromae.Lipids · 2012Article
- A bisallylic mini-lipoxygenase from cyanobacterium Cyanothece sp. that has an iron as cofactor.The Journal of biological chemistry · 2010Article
- Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis.Chemistry and physics of lipidsArticle
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Lipoxygenases (LOX) are found in most organisms that contain polyunsaturated fatty acids, usually existing as individual genes although occasionally encoded as a fusion protein with a catalase-related hemoprotein. Such a fusion protein occurs in the cyanobacterium Acaryochloris marina and herein we report the novel catalytic activity of its LOX domain. The full-length protein and the C-terminal LOX domain were expressed in Escherichia coli, and the catalytic activities characterized by UV, HPLC, GC-MS, and CD. All omega-3 polyunsaturates were oxygenated by the LOX domain at the n-7 position and with R stereospecificity: alpha-linolenic and the most abundant fatty acid in A. marina, stearidonic acid (C18.4omega3), are converted to the corresponding 12R-hydroperoxides, eicosapentaenoic acid to its 14R-hydroperoxide, and docosahexaenoic acid to its 16R-hydroperoxide. Omega-6 polyunsaturates were oxygenated at the n-10 position, forming 9R-hydroperoxy-octadecadienoic acid from linoleic acid and 11R-hydroperoxy-eicosatetraenoic acid from arachidonic acid. The metabolic transformation of stearidonic acid by the full-length fusion protein entails its 12R oxygenation with subsequent conversion by the catalase-related domain to a novel allene epoxide, a likely precursor of cyclopentenone fatty acids or other signaling molecules (Gao et al, J. Biol. Chem. 284:22087-98, 2009). Although omega-3 fatty acids and lipoxygenases are of widespread occurrence, this appears to be the first description of a LOX-catalyzed oxygenation that specifically utilizes the terminal pentadiene of omega-3 fatty acids.
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