(2S*,5S*,6Z)-2,5-Epoxydocosan-6-en-21-ynoic Acid, New Fatty Acid from the Marine Sponge Haliclona fascigera

Abstract

Marine sponges are recognized as a rich source of new marine natural products. In this study, chemical investigation of the CH2Cl2-MeOH (1:1) extract from the marine sponge Haliclona fascigera collected in Mayotte was carried out and highlighted a new unusual acetylenic and tetrahydrofuranic fatty acid, (2S*,5S*,6Z)-2,5epoxydocosan-6-en-21-ynoic acid (1). Its planar structure was elucidated by HRESIMS data, IR, 1D and 2D NMR spectra. The relative configuration of compound 1 was deduced from density functional theory (DFT) computational calculations fitted using the recently published DP4+ probability.