Occurrence of novel antigenic phosphoinositol-containing sphingolipids in the pathogenic yeast Histoplasma capsulatum

Five alkali-stable lipids from the yeast phase of Histoplasma capsulatum have been purified and analyzed. Each compound has equimolar amounts of hydroxysphinganine (phytosphingosine) and a hydroxy or nonhydroxy 24:0 fatty acid. All yield inositol phosphate after acid hydrolysis, and several are novel in that they also yield dimannosylinositol (compound V) and isomeric galactosyldimannosylinositols (compounds VI and VIII) after strong ammonolysis. The foregoing as well as other data suggest that compound V is a dimannosylinositolphosphoceramide and compounds VI and VIII are galactosyldimannosylinositolphosphoceramides with isomeric head groups. The chromatographic behavior of compounds II and III indicates that they are similar to the inositolphosphoceramides previously observed in Saccharomyces cerevisiae. Compounds V and VI are virtually absent from the mycelial phase of H. capsulatum. Antibodies that react with compounds V, VI, and VIII have been detected in sera from patients with histoplasmosis.