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Divinyl ethers and hydroxy fatty acids from three species of Laminaria (brown algae)
Author(s) -
Proteau Philip J.,
Gerwick William H.
Publication year - 1993
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/bf02536231
Subject(s) - brown algae , laminaria , polyunsaturated fatty acid , algae , saccharina , chemistry , lipoxygenase , stereochemistry , ether , fatty acid , botany , organic chemistry , biology , enzyme
Three species of brown algae, Laminaria sinclairii, L. saccharina and L. setchellii , have been investigated for the presence of oxylipins. From one, L. sinclairii , three new divinyl ether fatty acids have been characterized as methyl ester derivatives (methyl 12‐[1′ ( Z ),3′( Z )‐hexadienyloxy]‐6( Z ), 9( Z ), 11( E )‐dodecatrienoate, methyl 12‐[1′ ( Z ), 3′ ( Z )‐hexadienyloxy]‐9( Z ), 11( E )‐dodecatrienoate, and methyl 14‐[1′ ( Z ),3′ ( Z )‐hexadienyloxy]‐9( Z ),11( E )‐dodecadienoate, and methyl 14‐[1′ ( Z ),3′( Z )‐hexadienyloxy]‐5( Z ),8( Z ),11( Z ),13( E )‐tetradecatetraenoate) by a variety of spectroscopic methods. In addition, one new [13( S )‐hydroxy‐6( Z ),9( Z ),11( E ),15( Z )‐octadecatetraenoic acid] and four known monohydroxy polyunsaturated fatty acids have been isolated from all three species as their methyl ester derivatives. The occurrence of these compounds in brown algae strongly suggests that these organisms possess an active lipoxygenase(s) with ω6 specificity.