Abstract
A cerebroside mixture has been isolated from the marine sponge Chondrilla nucula. Acid-catalyzed methanolysis of this cerebroside mixture afforded methyl glucosides, three long-chain bases, and a mixture of alpha-hydroxy fatty acid methyl esters. The bases were identified as saturated C(17), C(18), and C(19) trihydroxy bases (1,3,4-trihydroxy-2-aminoalkanes) by gas-liquid chromatographic-mass spectrometric analysis of their corresponding trimethylsilyl derivatives. The methyl ester fraction consisted of a mixture of homologous C(16) to C(26) saturated straight-chain alpha-hydroxy esters plus a trace of saturated C(25) iso alpha-hydroxy ester.
Highlights
A cerebrosidemixturehas been isolatedfromthe marinesponge Chondrillu nucula
Cerebrosides have long been recognized as lipid constituents of vertebrates, some invertebrates, andplants
Inthe course of fractionating extracts of the marine sponge Chondrillu nuculu’ in search of a cardiovascular active component, we isolated a cerebroside mixture, and in this paper we report its structural elucidation based on degradative experiments
Summary
Alcohol-preserved sponge (5 kg, drained and air-dried) was shredded in a blender and extracted with benzene' for 30 hr in a continuous percolator-extractor [9]. Fractions 12and 13 (2.1 g) contained the crude cerebroside, which was obtained as a white solid. Examination of these fractions by TLC (silicic acid; CHC13-CH30H 80:20) revealed the presence of a single major slow-moving component with minor amounts of faster-moving impurities (visualization with 10% HzS04 spray followed by development at 110°C). Fractions 14 and 15 appeared by TLC to contain some cerebroside in addition to larger amounts of slower-moving components. The crude cerebroside (fractions 12and 13) was purified further by chromatography on a 4-cm (ID) column containing 40 g of silica gel H, Analysis: C46H9 1NOlo (avg mol wt); calculated: C, 67.52; H, 11.21; N, 1.71 found: C, 66.11; H, 10.96; N, 1.57
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