Isolation and structure of glucosylceramides from the starfish Cosmasterias lurida

Abstract

From the water-insoluble lipid fraction of the methylene chloride/methanol extract of the starfish Cosmasterias lurida, two new glucosylceramides together with a known glucosylceramide, ophidiacerebroside E, were isolated by chromatographic procedures and characterized by spectroscopic (1H and 13C nuclear magnetic resonance, mass spectrometry) methods. The new compounds were identified as (2S,3R,4E,8E,10E)-1-(beta-D-glucopyranosyloxy)-3 -hydroxy-2-[(R)-2-hydroxyheptadecanoyl)amino]-9-methyl-4,8,10-o ctadecatriene (3) and (2S,3R,4E,8E,10E)-1-(beta-D-glucopyranosyloxy)-3 -hydroxy-2-[(R)-2-hydroxyoctadecanoyl)amino]-9-methyl-4,8,10-oc tadecatriene (4).

Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis

“…Glucosylceramide 1 was identified as phalluside-1, previously isolated from the ascidian Phallusia fumigata (14), whereas 2 and 3 are also known compounds previously isolated from C. lurida (20). Fraction 5 (Scheme 3) is a mixture of glucosylceramide 5a, previously isolated from Ophidiaster ophidiamus (ophidiacerebroside C) (8) and C. lurida (19) and the new 5b {(2S,3R,4E,8E,10E)-1-(β-D-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxy-15-tetracosenoyl]amino-9-methyl-4,8,10-octadecatriene}. Fraction 6 (Scheme 3) is a mixture of the known glucosylceramides ophidiacerebroside C (5a) and 6a, previously isolated from O. ophidiamus (8), and the new glucosylceramides 5b and 6b (2S,3R,4E,8E,10E)-1-(β-D-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxypentacosanoyl]amino-9-methyl-4,8,10-octadecatriene.…”

Chemical Constituents and Bioactivities of Starfish

“…Reguloside A (608) showed moderate wound-healing activity [184]. From the starfish Cosmasterias lurida collected off the Patagonian coast of Argentina, two glucosylceramides, 611 and 612, together with a known glucosylceramide, ophidiacerebroside E (607), were isolated [185]. From the Patagonian starfish Allostichaster inaequalis, two glucosylceramides, 613 and 614, were isolated [186].…”

Glycolipids from Marine Invertebrates

“…They were shown to be identical to ophidiacerebrosides C, D and E from the starfish Ophidiaster ophidiamus (Jin, Rinehart, and Jares-Erijman, 1994), while compound S-1-5 was the same as agelasphin-10 found in the sponge Agelas mauritianus (Natori et al, 1994). Two new glucosylceramides, GSL-1 and GSL-2 (see Table 5.3), together with the known ophidiacerebroside E, were isolated from the starfish Cosmasterias lurida, collected in cold waters off the Patagonian coast of Argentina (Maier, Kuriss, and Seldes, 1998). The new GSLs were b-glucopyranosylceramides with the same long-chain base and 2-hydroxylated C 17:0 and C 18:0 FA chains.…”

“…Glucosylceramides GSL-3 to -7 were methanolized and gave a single FA methyl ester by GC-MS (Table 5.3). GSL-3 was identified as phalluside-1, previously isolated from the ascidian Phallusia fumigata (Dur an et al, 1998), whereas GSL-4 and GSL-5 are also known compounds previously isolated from Cosmasterias lurida (Maier, Kuriss, and Seldes, 1998). GSL-6 was identified as ophidiacerebroside C, previously isolated from Ophidiaster ophidiamus (Jin, Rinehart, and Jares-Erijman, 1994), while GSL-7 has been isolated and characterized as a pure compound for the first time.…”

“…GSL-6 was identified as ophidiacerebroside C, previously isolated from Ophidiaster ophidiamus (Jin, Rinehart, and Jares-Erijman, 1994), while GSL-7 has been isolated and characterized as a pure compound for the first time. GSL-7 has been isolated previously as a mixture of related glucosylceramides from the Patagonian starfishes Cosmasterias lurida (Maier, Kuriss, and Seldes, 1998) and Allostichaster inaequalis (Díaz de Vivar, Seldes, and Maier, 2002). Chemical investigations of the sea star Oreaster reticulus, collected along the coasts of Grand Bahama Island, led to the isolation of nine new GLs named oreacerebrosides A-I, along with the known ophidiacerebrosides C-E (Costantino et al, 2007).…”