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Novel Hydroxyicosatetraenoic and Hydroxyicosapentaenoic Acids and a 13‐Oxo Analog. Isolation from a Mixture of the Calcareous Red Algae Lithothamnion corallioides and Lithothamnion calcareum of Brittany Waters
Author(s) -
Guerriero Antonio,
D'Ambrosio Michele,
Pietra Francesco
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730815
Subject(s) - chemistry , algae , calcareous , stereochemistry , ethyl ester , extraction (chemistry) , red algae , chromatography , organic chemistry , botany , biology
Abstract A mixture of the red calcareous algae Lithothamnion corallioides C ROUAN and Lithothamnion calcareum (P ALLAS ) A RESCHOUGH , from Brittany waters, gives, on ethanolic extraction, the novel icosanoids ethyl 13‐hydroxy‐arachidonate (=(+)‐all‐ Z ‐ethyl 13‐hydroxyicosa‐5,8, 11,14,‐tetraenoate; (+)‐ 1 )), ethyl 13‐hydroxytimnodonate (=(+)‐(all‐ Z )‐ethyl 13‐hydroxyicosa‐5,8,11,14,17‐pentaenoate ((+)‐ 2 ), and (5 Z ,9 E ,11 E ,14 E )‐ethyl 8‐hydroxy‐13‐oxoicosa‐5,9,11,14‐tetraenoate ( 3 ). Moreover, the ethyl esters of four known icosatetraenoic acids are contained in the above algae. Structural elucidations of these metabolites are based mainly on NMR data.