title: Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii.
abstract: Novel structures of glycoinositolphosphorylceramide (GIPC) from the infective yeast form of Sporothrix schenckii were determined by methylation analysis, mass spectrometry and NMR spectroscopy. The lipid portion was characterized as a ceramide composed of C-18 phytosphingosine N-acylated by either 2-hydroxylignoceric acid (80%), lignoceric (15%) or 2,3-dihydroxylignoceric acids (5%). The ceramide was linked through a phosphodiester to myo-inositol (Ins) which is substituted on position O-6 by an oligomannose chain. GIPC-derived Ins oligomannosides were liberated by ammonolysis and characterized as: Manpalpha1-->6Ins; Manpalpha1-->3Manpalpha1-->6Ins; Manpalpha1-->6Manpalpha1-->3Manpalpha1-->3Manpalpha1-->6Ins; Manpalpha1-->2Manpalpha1-->6Manpalpha1-->3Manpalpha1-->3Manpalpha1-->6Ins. These structures comprise a novel family of fungal GIPC, as they contain the Manpalpha1-->6Ins substructure, which has not previously been characterized unambigously, and may be acylated with a 2,3 dihydroxylignoceric fatty acid, a feature hitherto undescribed in fungal lipids.
authors.affiliation: Departamento de Biologia Celular e Genética, UERJ, Rio de Janeiro, Brazil.
authors.forename: C V
authors.initials: CV
authors.lastname: Loureiro y Penha
authors.forename: A R
authors.initials: AR
authors.lastname: Todeschini
authors.forename: L M
authors.initials: LM
authors.lastname: Lopes-Bezerra
authors.forename: R
authors.initials: R
authors.lastname: Wait
authors.forename: C
authors.initials: C
authors.lastname: Jones
authors.forename: K A
authors.initials: KA
authors.lastname: Mattos
authors.forename: N
authors.initials: N
authors.lastname: Heise
authors.forename: L
authors.initials: L
authors.lastname: Mendonça-Previato
authors.forename: J O
authors.initials: JO
authors.lastname: Previato
mesh_terms: D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D002518:Ceramides / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D006028:Glycosphingolipids / Q000737:chemistry*; D007294:Inositol / Q000737:chemistry; D008055:Lipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry; D011487:Protein Conformation; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013110:Sphingosine / Q000031:analogs & derivatives / Q000737:chemistry; D013175:Sporothrix / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D002518:Ceramides; D005227:Fatty Acids; D006028:Glycosphingolipids; D008055:Lipids; D009844:Oligosaccharides; D011134:Polysaccharides; C068388:mannosylinositolphosphoceramide; D007294:Inositol; C012491:phytosphingosine; D013110:Sphingosine; C010210:lignoceric acid