title: Evaluation and evidence of natural gangliosides with two unsaturated bonds in the ceramide structure obtained by a combination of MALDI-MS and NMR spectroscopy.
abstract: Gangliosides are membrane-associated glycosphingolipids. N-Acetyl GM3 and N-glycolyl GM3 are two tumor-associated antigens expressed in cancer tissues such as melanoma and mammalian cancer. In order to use these antigens in GM3-based vaccines for patients with early stage cancer, the synthetic version is recommended to avoid the risk of animal virus transmission from the source. However, the isolation of natural gangliosides is of comparative value for the structural characterization. The structures of N-acetyl and N-glycolyl GM3 extracted from dog and horse erythrocytes were evaluated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and nuclear magnetic resonance techniques; additionally, the natural N-acetyl ganglioside was compared to a synthetic one. In addition to the main compound with C24:0 fatty acid chain, a minor component with an additional unsaturation in the ceramide chain was detected, in both the dog and the horse gangliosides. This paper shows spectroscopic evidence of the aforementioned compounds.
authors.affiliation: Center of Biomolecular Chemistry, Playa, La Habana, Cuba. raine.garrido@cqb.cu
authors.forename: Raine
authors.initials: R
authors.lastname: Garrido Arteaga
authors.forename: Roberto Carlos
authors.initials: RC
authors.lastname: Veloso Pita
authors.forename: Miguel Antonio
authors.initials: MA
authors.lastname: López López
authors.forename: José Antonio
authors.initials: JA
authors.lastname: González Labaut
authors.forename: María del Carmen
authors.initials: Mdel C
authors.lastname: Rodríguez Montero
authors.forename: Hermán
authors.initials: H
authors.lastname: Vélez Castro
authors.forename: José Alberto
authors.initials: JA
authors.lastname: Cremata Alvarez
mesh_terms: D000818:Animals; D002518:Ceramides / Q000737:chemistry; D004285:Dogs; D004912:Erythrocytes / Q000737:chemistry; D005679:G(M3) Ganglioside / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D005732:Gangliosides / Q000737:chemistry* / Q000302:isolation & purification; D006736:Horses; D009682:Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods
chemical_list: D002518:Ceramides; D005679:G(M3) Ganglioside; D005732:Gangliosides