Dictyopterenes A, B, C, and D from Marine Algae

The review is focused on dictyopterenes A, B, C, and D found in marine algae, covering their (a) distribution; (b) methods of isolation and identification; (c) absolute configuration; and (d) biosynthesis considerations. Dictyopterenes A and B are usually present in high amounts in Dictyopteris spp. Dictyopterene A was found to be abundant in D. prolifera, D. undulata, D. latiscula, D. polypodioides, and D. membranacea. Dictyopterene B (hormosirene) was found as the major compound in D. plagiogramma, D. australis, Hormosira banksii, D. potatorum, D. willana, D. antarctica, Xiphophora chondrophylla, X. gladiata, Scytosiphon lomentaria, Colpomenia peregrina, and Haplospora globosa. Dictyopterene C (dictyotene) was a major compound in D. undulata, D. prolifera, D. membranacea, Gomphonema parvulum, Amphora veneta, Phaeodactylum tricornutum, and D. vermicularis. Dictyopterene D (ectocarpene) was present in Ectocarpus siliculosus, Analipus japonicus, D. prolifera, D. undulata, and Sargassum linifolium. The following enantiomers were found: (1S,2R)-dictyopterene A, (1R,2R)-dictyopterene B, (1S,2S)-dictyopterene B, (1S,2R)-dictyopterene B, (R)-dictyopterene C, and (S)-dictyopterene D. In marine algae, C₁₁-hydrocarbons are derived from C₂₀ polyunsaturated fatty acids by the oxidative cleavage via, e.g., 9-hydroperoxyicosa-(5Z,7E,11Z,14Z,17Z)-pentaenoic acid. An alternative biosynthetic pathway for dictyopterene A and B via the proposed intermediates (S)-dictyoprolenols was considered by oxidative cleavage of hydroperoxyicosatetraenoic acid.