Three new and bioactive icosanoids from the temperate red marine alga Farlowia mollis.
Three new dihydroxyicosanoids, 12(R),13(R)-dihydroxyicosa-5(Z),8(Z),10(E),14(Z)-tetraenoic acid, 12(R),13(R)-dihydroxyicosa-5(Z),8(Z),10(E),14(Z),17(Z)-pentaeno ic acid and 10(R*),11(R*)-dihydroxyoctadeca-6(Z),8(E),12(Z)-trienoic acid, have been isolated from a previously unstudied temperate red marine alga, Farlowia mollis (Cryptonemiales, Rhodophyta). The structures of these new metabolites have been deduced from detailed nuclear magnetic resonance and mass spectrometry analyses on stabilized diacetate-methyl esters and stereochemistry deduced by 1H NMR couplings and CD analysis of a dibenzoate derivative. Collectively, these new natural products modulate fMLP-induced superoxide anion generation in human neutrophils, inhibit the conversion of arachidonic acid to lipoxygenase products by human neutrophils, and inhibit the functioning of the dog kidney Na+/K+ ATPase.
Solem
M L
ML
College of Pharmacy, Oregon State University, Corvallis 97331.
Jiang
Z D
ZD
Gerwick
W H
WH
D019377:12-Hydroxy-5,8,10,14-eicosatetraenoic Acid / Q000031:analogs & derivatives*; D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification; D006801:Humans; D006893:Hydroxyeicosatetraenoic Acids / Q000032:analysis / Q000302:isolation & purification*; D007975:Leukotriene B4 / Q000032:analysis / Q000302:isolation & purification*; D008042:Linolenic Acids / Q000032:analysis / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D009504:Neutrophils / Q000378:metabolism; D000461:Rhodophyta / Q000032:analysis*; D013481:Superoxides / Q000097:blood
D006893:Hydroxyeicosatetraenoic Acids; D008042:Linolenic Acids; D013481:Superoxides; C060289:12,13-dihydroxy-5,8,10,14-eicosatetraenoic acid; C060430:12,13-dihydroxyeicosa-5,8,10,14,17-pentaenoic acid; C060442:10,11-dihydroxyoctadeca-6,8,12-trienoic acid; D007975:Leukotriene B4; D019377:12-Hydroxy-5,8,10,14-eicosatetraenoic Acid; D015118:Eicosapentaenoic Acid