Novel oxylipins from the temperate red alga Polyneura latissima: evidence for an arachidonate 9(S)-lipoxygenase.
The oxylipin chemistry of the temperate red alga Polyneura latissima has been investigated. The structures of three novel oxylipins, 8-[1'(Z),3'(Z),6'(Z)-dodecatriene-1'-oxy]- 5(Z),7(E)-octadienoic acid, 7(S*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, 7(R*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, together with two known eicosanoids, 9(S)-hydroxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid, and 9,15-dihydroxy-5(Z),7(E),11(Z),13(E)-eicosatetraenoic acid, were elucidated by spectroscopic methods and chemical degradation. The oxygenation pattern of these oxylipins suggests that P. latissima metabolizes polyunsaturated fatty acids via a 9(S)-lipoxygenase.
Jiang
Z D
ZD
College of Pharmacy, Oregon State University, Corvallis 97331, USA.
Gerwick
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WH
D001091:Arachidonate Lipoxygenases / Q000378:metabolism*; D001095:Arachidonic Acids / Q000737:chemistry*; D015777:Eicosanoids / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000461:Rhodophyta / Q000737:chemistry* / Q000378:metabolism; D013057:Spectrum Analysis
D001095:Arachidonic Acids; D015777:Eicosanoids; D001091:Arachidonate Lipoxygenases