Bretonin A and Isobretonin A, Unique Glycerol Derivatives Isolated from a Demosponge of Brittany Waters

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Abstract
It is shown that an unidentified marine demosponge of Brittany contains two unique lipids consisting of glycerol etherified by a C12 trienic linear alcohol and esterified by 4‐hydroxybenzoic acid. The latter is attached to the secondary position of glycerol in bretonin A (= 3‐[((4E, 6E, 8E)‐dodeca‐4,6,8‐trienyl)oxy]‐2‐(4‐hydroxy‐benzoyl)propan‐1‐ol; 1a), and to the other primary position of glycerol in isobretonin A ( = (+)‐3‐[((4E, 6E, 8E)‐dodeca‐4,6,8‐trienyl)oxy]‐1‐(4‐hydroxybenzoyl)propan‐2‐ol; (+)‐2). The structures are based on NMR and MS data, including the ones of the acetylation product (−)‐1b of 1a.