title: Cerebrosides from a Far-Eastern Glass Sponge Aulosaccus sp.
abstract: Nine new cerebrosides 1a-d, 2a, 2b, 3a-c were found in the extract of a Far-Eastern glass sponge Aulosaccus sp. (class Hexactinellida). These β-D-glucopyranosyl-(1 → 1)-ceramides contain sphingoid bases (2S,3S,4R,11Z)-2-aminoeicos-11-ene-1,3,4-triol (in 1a-d), (2S,3S,4R,13Z)-2-aminoeicos-13-ene-1,3,4-triol (in 2a, b) and (2S,3S,4R,13S*,14R*)-2-amino-13,14-methylene-eicosane-1,3,4-triol (in 3a-c), which are N-acylated by (2R,15Z)-2-hydroxydocos-15-enoic (in 1a, 2a, 3a), (2R,16Z)-2-hydroxytricos-16-enoic (in 1b, 2b, 3b), (2R,17Z)-2-hydroxytetracos-17-enoic (in 1d) and (2R)-2-hydroxydocosanoic (in 1c, 3c) acids. The monoenoic and cyclopropane-containing sphingoid bases of compounds 1a-d, 2a, 2b, 3a-c have not been found previously in any sphingolipids. The structures of the cerebrosides were elucidated on the basis of (1)H-, (13)C-NMR spectroscopy, mass spectrometry, optical rotation data and chemical transformations. A simplified method for the assignment of the absolute configuration of 2-hydroxy fatty acids by GC analysis of their (2R)- and (2S)-oct-2-yl esters was proposed.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Pr. 100 let Vladivostoku, 159, Vladivostok, 690022, Russia, santalova@piboc.dvo.ru.
authors.forename: Еlena А
authors.initials: ЕА
authors.lastname: Santalova
authors.forename: Vladimir А
authors.initials: VА
authors.lastname: Denisenko
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Аnatoly L
authors.initials: АL
authors.lastname: Drozdov
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D002554:Cerebrosides / Q000032:analysis*; D005227:Fatty Acids / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011161:Porifera / Q000737:chemistry*; D013107:Sphingolipids / Q000032:analysis
chemical_list: D002554:Cerebrosides; D005227:Fatty Acids; D013107:Sphingolipids