Damicoside from Axinella damicornis:  The Influence of a Glycosylated Galactose 4-OH Group on the Immunostimulatory Activity of α-Galactoglycosphingolipids

• Published in: Journal of medicinal chemistry Vol. 48; no. 23; pp. 7411 - 7417
• Main Authors: COSTANTINO, Valeria, D'ESPOSITO, Monica, FATTORUSSO, Ernesto, MANGONI, Alfonso, BASILICO, Nicoletta, PARAPINI, Silvia, TARAMELLI, Donatella
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 17-11-2005
• Subjects: Adjuvants, Immunologic - chemistry; Adjuvants, Immunologic - isolation & purification; Adjuvants, Immunologic - pharmacology; Animals; Axinella - chemistry; Biological and medical sciences; Cell Proliferation - drug effects; Ceramides - chemistry; Ceramides - isolation & purification; Ceramides - pharmacology; Disaccharides - chemistry; Disaccharides - isolation & purification; Disaccharides - pharmacology; Galactose - analogs & derivatives; Galactose - chemistry; Galactose - isolation & purification; Galactose - pharmacology; General pharmacology; Glycosylation; In Vitro Techniques; Lymphocytes - cytology; Lymphocytes - drug effects; Medical sciences; Mice; Mice, Inbred C57BL; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Sphingolipids - chemistry; Sphingolipids - isolation & purification; Sphingolipids - pharmacology; Spleen - cytology; Mediterranean Sea; Aldose; Pharmacognosy; Animal origin; Sphingolipid; Lipids; Glycosylation; In vitro; Biological activity; Disaccharide; Glycolipid; Immunomodulator; Marine environment; Immunostimulant agent; Porifera; Aminoglycoside; Sphingoglycolipid; Isolation; Glycoside; Invertebrata; Galactose; Structural analysis
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm050506y

Alpha-galactoglycosphingolipids (alpha-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 alpha-GalGSL, damicoside (3a), which is the first alpha-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 alpha-GalGSLs and providing a further step toward the complete understanding of their structure-activity relationship.