A MANNOSE- AND ERYTHRITOL-CONTAINING GLYCOLIPID FROM USTILAGO MAYDIS

Erythritol- and mannose-containing glycolipids have been found in the intracellular lipids of a strain of the com smut fungus, Ustilago maydis. The lipids have been fractionated by Florisil column chromatography and the major component has been obtained in relatively pure form. This compound contains equimolar amounts of mannose and erythritol. The chromatographic behavior and infrared spectrum indicated that the material contained unsubstituted hydroxyl groups. Fatty acid analysis showed only four acyl residues per molecule of erythritol mannoside. The glycolipid was oxidizable with lead tetraacetate which resulted in the destruction of the erythritol subunit, but not the mannose. The nature of the lead tetraacetate oxidation products indicates that all of the mannose hydroxyl groups are substituted and that the three free hydroxyl groups are on erythritol. The fatty acid constituents were found to range from C12 to C18 with the C16 acids predominating. It is proposed that the major glycolipid component has the structure 4-O-(2,3,4,6-tetra-O-acyl-β-D-mannopyranosyl)-D-erythritol. © 1969, American Chemical Society. All rights reserved.