Conversion of dihomo-gamma-linolenic acid to mono- and dihydroxy acids by potato lipoxygenase: evidence for the formation of 8,9-leukotriene A3.
Evidence for the formation of a positional isomer of leukotriene (LT) C3 (8,9-LTC3) from dihomo-gamma-linolenic acid has been published (Hammarström, S. J. Biol. Chem. 256, 7712-7714, 1981). This report describes the conversion of dihomo-gamma-linolenic acid to a postulated intermediate in former reaction, 8,9-LTA3, by purified lipoxygenase from potato tubers. 8(S)-Hydroperoxyeicosatrienoic acid (8(S)-HPETrE) was the most abundant dioxygenation product formed followed by 11-, 15-, and 12-HPETrEs (in decreasing order of abundance). In addition, 8(S),15(S)- plus 8(S), 15(R)-dihydroperoxyeicosatetraenoic acid (DiHPE-TrE) (EZE), and 8(S),15(S)- plus 8(S),15(R)-dihydroxy-eicosatetraenoic acid (DiHETrE) (EEE) were generated. Under anaerobic conditions only the latter two isomers of 8,15-DiHETrE (EEE) were obtained from 8-HPETrE. The results suggest that 8,9-LTA3 is synthesized by the sequential action of 8- and 11-lipoxygenase activities associated with the potato enzyme.
Reddy
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CC
Department of Cell Biology, Faculty of Health Sciences, University of Linköping, Sweden.
Bertler
C
C
Hammarström
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S
D015126:8,11,14-Eicosatrienoic Acid / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D006893:Hydroxyeicosatetraenoic Acids / Q000378:metabolism; D017572:Leukotriene A4; D015289:Leukotrienes / Q000096:biosynthesis*; D008084:Lipoxygenase / Q000378:metabolism*; D010084:Oxidation-Reduction; D013189:SRS-A / Q000031:analogs & derivatives / Q000378:metabolism; D011198:Solanum tuberosum / Q000201:enzymology*; D013056:Spectrophotometry, Ultraviolet
D005231:Fatty Acids, Unsaturated; D006893:Hydroxyeicosatetraenoic Acids; D017572:Leukotriene A4; D015289:Leukotrienes; D013189:SRS-A; C028724:leukotriene C-3; D008084:Lipoxygenase; D015126:8,11,14-Eicosatrienoic Acid