Damicoside from Axinella damicornis: the influence of a glycosylated galactose 4-OH group on the immunostimulatory activity of alpha-galactoglycosphingolipids.
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.
Costantino
Valeria
V
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D. Montesano 49, 80131 Napoli, Italy.
D'Esposito
Monica
M
Fattorusso
Ernesto
E
Mangoni
Alfonso
A
Basilico
Nicoletta
N
Parapini
Silvia
S
Taramelli
Donatella
D
D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D047089:Axinella / Q000737:chemistry*; D049109:Cell Proliferation / Q000187:drug effects; D002518:Ceramides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006031:Glycosylation; D066298:In Vitro Techniques; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects; D051379:Mice; D008810:Mice, Inbred C57BL; D013107:Sphingolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013154:Spleen / Q000166:cytology
D000276:Adjuvants, Immunologic; D002518:Ceramides; D004187:Disaccharides; D013107:Sphingolipids; C507033:damicoside; D005690:Galactose