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Cerebrosides from a Far‐Eastern Glass Sponge Aulosaccus sp.
Author(s) -
Santalova Еlena А.,
Denisenko Vladimir А.,
Dmitrenok Pavel S.,
Drozdov Аnatoly L.,
Stonik Valentin A.
Publication year - 2015
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-014-3974-8
Subject(s) - sponge , sphingolipid , chemistry , stereochemistry , cyclopropane , triol , methylene , glycolipid , cerebroside , nuclear magnetic resonance spectroscopy , organic chemistry , diol , biology , biochemistry , botany , ring (chemistry)
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 (2 S ,3 S ,4 R ,11 Z )‐2‐aminoeicos‐11‐ene‐1,3,4‐triol (in 1a – d ), (2 S ,3 S ,4 R ,13 Z )‐2‐aminoeicos‐13‐ene‐1,3,4‐triol (in 2a , b ) and (2 S ,3 S ,4 R ,13 S *,14 R *)‐2‐amino‐13,14‐methylene‐eicosane‐1,3,4‐triol (in 3a – c ), which are N ‐acylated by (2 R ,15 Z )‐2‐hydroxydocos‐15‐enoic (in 1a , 2a , 3a ), (2 R ,16 Z )‐2‐hydroxytricos‐16‐enoic (in 1b , 2b , 3b ), (2 R ,17 Z )‐2‐hydroxytetracos‐17‐enoic (in 1d ) and (2 R )‐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 (2 R )‐ and (2 S )‐oct‐2‐yl esters was proposed.