Formation of 6,13-dihydroxyoctadecatrienoic acid isomers from gamma-linolenic acid

Incubation of gamma-linolenic acid with soybean lipoxygenase initially at pH 9.3 and subsequently at pH 7.9 gave rise to the conjugated triene dioxygenation product (lambda max = 267 nm, greater than 50% yield), which was reduced to form 9-cis isomer of 6,13-dihydroxyoctadecatrienoic acid (6,13-diHOT) accompanied by minor isomers. Meanwhile, hemoglobin converted 13-hydroperoxyoctadecatrienoic acid into two major 9-trans isomers of 6,13-diHOT and two 9-cis isomers as minor products. The four isomers of 6,13-diHOT methyl ester were separated from each other on SP-HPLC, and characterized by chromatographic, spectrometric and cis----trans isomerization analyses.