Novel oxylipins from the temperate red alga polyneura latissima: Evidence for an arachidonate 9(S)‐lipoxygenase
- 1 March 1997
- Vol. 32 (3) , 231-235
- https://doi.org/10.1007/s11745-997-0029-9
Abstract
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′-oxyl-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.Keywords
This publication has 23 references indexed in Scilit:
- Structure and biosynthesis of marine algal oxylipinsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1994
- Unprecedented Oxylipins from the Marine Green Alga Acrosiphonia coalitaJournal of Natural Products, 1993
- Recent investigations into the lipoxygenase pathway of plantsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1991
- Stereospecific removal of the pro-R hydrogen at C-8 of (9S)-hydroperoxyoctadecadienoic acid in the biosynthesis of colneleic acidJournal of the Chemical Society, Perkin Transactions 1, 1990
- Total Enantiospecific Synthesis of (9S)‐ and (9R)‐9‐Hydroxyeicosatetraenoic Acid (9‐HETE) Methyl EsterAngewandte Chemie International Edition in English, 1989
- Ptilodene, a novel icosanoid inhibitor of 5-lifoxygenase and Na+/K+ ATPase from the red marine alga ptilota FilicinaJ. AgardhTetrahedron Letters, 1988
- Total synthesis of 8(S)-, 9(S)-, 11(S)-, and 12(S)-hydroxyeicosatetraenoic acids (HETE) methyl estersThe Journal of Organic Chemistry, 1986
- The occurrence of prostaglandins PGE2 and PGF2α in a plant - the red alga .Tetrahedron Letters, 1979
- Novel divinyl ether fatty acids in extracts of Solanum tuberosumChemistry and Physics of Lipids, 1973