Corrugoside, a new immunostimulatory alpha-galactoglycosphingolipid from the marine sponge Axinella corrugata.
Corrugoside (1a), a new immunostimulatory triglycosilated alpha-galactoglycosphingolipid, was isolated from the marine sponge Axinella corrugata, and its structure determined by spectral analysis and chemical degradation. Compound 1a activated murine NKT cells in vitro, with a potency of about 2 logs lower than that of alphaGalCer. Four stereoisomeric glycosphingolipids (2a-2d) were also obtained, beta-glucosylceramides bearing unusual endoperoxide and allylic hydroperoxide functionalities on the sphinganine chain. They were shown to be photooxidation artifacts of the known glycosphingolipids 3, also present in the sponge. A possible role of compound 3 as a singlet oxygen scavenger to protect the organism from oxidative damage is proposed.
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D. Montesano 49, 80131 Napoli, Italy.
Valeria
V
Costantino
Ernesto
E
Fattorusso
Concetta
C
Imperatore
Alfonso
A
Mangoni
Stefan
S
Freigang
Luc
L
Teyton
D000818:Animals; D047089:Axinella / Q000737:chemistry*; D002478:Cells, Cultured; D016166:Free Radical Scavengers / Q000302:isolation & purification; D006028:Glycosphingolipids; D007155:Immunologic Factors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007694:Killer Cells, Natural / Q000187:drug effects*; D051379:Mice; D015394:Molecular Structure; D026082:Singlet Oxygen; D014281:Trihexosylceramides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
D016166:Free Radical Scavengers; D006028:Glycosphingolipids; D007155:Immunologic Factors; D014281:Trihexosylceramides; C529247:corrugoside; D026082:Singlet Oxygen