α-Galactoglycosphingolipids (α-GalGSLs) are unique immunostimulatory glycosphingolipids from marine sponges. Analysis of the glycosphingolipid composition of the marine sponge Axinella damicornis revealed the presence of a new α-GalGSL, damicoside (3a), which is the first α-GalGSL with a glycosylated galactose 4-OH group. Structure elucidation of damicoside was performed using spectroscopic and chemical methods. When tested in a spleen cell proliferation assay, 3a exhibited a stimulatory activity comparable to that of agelasphin (2), showing that a free galactose 4-OH group is not essential for the immunostimulatory activity of α-GalGSLs and providing a further step toward the complete understanding of their structure-activity relationship.
Damicoside from Axinella damicornis : the influence of a glycosylated galactose 4-OH group on the immunostimulatory activity of a-galactoglycosphingolipids / V. Costantino, M. D'Esposito, E. Fattorusso, A. Mangoni, N. Basilico, S. Parapini, D. Taramelli. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - 48:23(2005), pp. 7411-7417.
Damicoside from Axinella damicornis : the influence of a glycosylated galactose 4-OH group on the immunostimulatory activity of a-galactoglycosphingolipids
N. Basilico;S. Parapini;D. Taramelli
2005
Abstract
α-Galactoglycosphingolipids (α-GalGSLs) are unique immunostimulatory glycosphingolipids from marine sponges. Analysis of the glycosphingolipid composition of the marine sponge Axinella damicornis revealed the presence of a new α-GalGSL, damicoside (3a), which is the first α-GalGSL with a glycosylated galactose 4-OH group. Structure elucidation of damicoside was performed using spectroscopic and chemical methods. When tested in a spleen cell proliferation assay, 3a exhibited a stimulatory activity comparable to that of agelasphin (2), showing that a free galactose 4-OH group is not essential for the immunostimulatory activity of α-GalGSLs and providing a further step toward the complete understanding of their structure-activity relationship.Pubblicazioni consigliate
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