Transformation of 15-hydroperoxide of eicosapentaenoic acid to lipoxins and trihydroxyeicosatetraenoic acids by 5-lipoxygenase partially purified from potato tubers.
Incubation of 15-hydroperoxide of 5,8,11,14,17-eicosapentaenoic acid (15-HPEPE) with 5-lipoxygenase enzyme, partially purified from potato tubers, resulted in the generation of 6 isomers of lipoxin A5. These compounds were identified by GC/MS analysis of their methyl ester and trimethylsilyl ether derivatives with C-values: 23.3, 24.5, 24.6, 24.9, 25 and 25.2 respectively. The major products of the enzymatic reaction on 15-HPEPE are 5,15-DiHEPE and 13,14,15-trihydroxy eicosatetraenoic acid as identified by RP-HPLC and GC/MS analysis. There are also two new trihydroxyl compounds of eicosapentaenoic acid identified as 11,12,15-trihydroxy and 11,14,15-trihydroxy eicosatetraenoic acid respectively. The transformation of these two trihydroxyl compounds may be due to non-enzymatic rearrangement of 15-HPEPE.
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Laboratory of Eicosanoid and Lipid Mediator Research, Institute of Biomedical Sciences, Academic Sinica, Nankang, Taiwan, R.O.C.
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D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006893:Hydroxyeicosatetraenoic Acids / Q000378:metabolism*; D015289:Leukotrienes / Q000378:metabolism*; D008054:Lipid Peroxides / Q000378:metabolism*; D044045:Lipoxins; D013058:Mass Spectrometry; D015394:Molecular Structure; D010944:Plants / Q000201:enzymology*; D011198:Solanum tuberosum
D006893:Hydroxyeicosatetraenoic Acids; D015289:Leukotrienes; D008054:Lipid Peroxides; D044045:Lipoxins; C025086:15-hydroperoxy-5,8,11,13-eicosatetraenoic acid; C051283:11,14,15-trihydroxyeicosa-5,8,12-trienoic acid; C066049:11,12,15-trihydroxyeicosatrienoic acid; C044354:lipoxin A5; D015118:Eicosapentaenoic Acid; D001094:Arachidonate 5-Lipoxygenase; D015126:8,11,14-Eicosatrienoic Acid