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Three new and bioactive icosanoids from the temperate red marine alga Farlowia mollis
Author(s) -
Solem Michele L.,
Jiang Zhi D.,
Gerwick William H.
Publication year - 1989
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535159
Subject(s) - temperate climate , lipidology , botany , biology , clinical chemistry , biochemistry
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),10(Z),17(Z)‐pentaenoic 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 1 H 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.