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The structural elucidation of primary and secondary peroxidation products, formed from complex lipids, is a challenge in lipid analysis. In the present study, rare minor oxidized cerebrosides, isolated from the extract of a far eastern deep-sea glass sponge, Aulosaccus sp., were analyzed as constituents of a multi-component RP-HPLC (high-performance liquid chromatography on reversed-phase column) fraction using NMR (nuclear magnetic resonance) spectroscopy, mass spectrometry, GC (gas chromatography), and chemical transformations (including hydrogenation or derivatization with dimethyl disulfide before hydrolysis). Eighteen previously unknown β-D-glucopyranosyl-(1→1)-ceramides ( 1a - a //  , 1b - b //  , 2a - a //  , 2b - b //  , 3c - c //  , 3d - d //  ) were shown to contain phytosphingosine-type backbones (2 S ,3 S ,4 R ,11 Z )-2-aminoeicos-11-ene-1,3,4-triol (in 1 ), (2 S ,3 S ,4 R ,13 Z )-2-aminoeicos-13-ene-1,3,4-triol (in 2 ), and (13 S *,14 R *)-2-amino-13,14-methylene-eicosane-1,3,4-triol (in 3 ). These backbones were N -acylated with straight-chain monoenoic (2 R )-2-hydroxy acids that had allylic hydroperoxy/hydroxy/keto groups on C-17  /  in the 15  /   E -23:1 chain ( a - a //  ), C-16  /  in the 17  /   E -23:1 ( b - b //  ) and 14  /   E -22:1 ( c - c //  ) chains, and C-15  /  in the 16  /   E -22:1 chain ( d - d //  ). Utilizing complementary instrumental and chemical methods allowed for the first detailed structural analysis of a complex mixture of glycosphingolipids, containing allylically oxygenated monoenoic acyl chains.

molecules/molecules online/molecules annual

Structural Analysis of Oxidized Cerebrosides from the Extract of Deep-Sea Sponge Aulosaccus sp.: Occurrence of Amide-Linked Allylically Oxygenated Fatty Acids