Ceramide aminoethylphosphonate in the fungus Pythium prolatum.

Ceramide aminoethylphosphonate was characterized from the lower fungus Pythium prolatum. The compound was purified by silicic acid column chromatography, DEAE-cellulose column chromatography, the action of phospholipase D, and two-dimensional thin-layer chromatography. Infrared spectra lacked ester bands and suggested the presence of a bonded NH group. The compound was hydrolyzed by strong acid. Sphingosine comprised 98% of the long chain bases. The predominant fatty acids were palmitate, oleate, linoleate, and an unidentified long chain acid. The aqueous portion of the hydrolysis products gave an elemental analysis consistent with 2-aminoethylphosphonate. On paper and thin layer chromatograms, the ammonium salt of the aqueous hydrolysis product chromatographed with 2-aminoethylphosphoate but not 1-aminoethylphosphonate, 2-aminoethanol, serine or alanine. This appears to be the first report of a phosphonolipid from fungi.