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.
Costantino
Valeria
V
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D. Montesano 49, 80131 Napoli, Italy.
Fattorusso
Ernesto
E
Imperatore
Concetta
C
Mangoni
Alfonso
A
Freigang
Stefan
S
Teyton
Luc
L
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