Structural investigations and biological activity of inositol sphingophospholipids from Phytophthora capsici

Inositol sphingophospholipids that protect pepper (Capsicum annuum c.v. Yolo Wonder) against pathogen have been isolated by chromatographic methods from the mycelium of Phytophthora capsici. The structure of the major compound was determined by chemical methods and mass spectrometry. Phosphodiester bond cleavage of the phospholipid by mild alkaline hydrolysis liberated a ceramide which contained a C16-sphingosine. This long-chain base was identified by gas chromatography and mass spectrometry of its trimethylsilyl derivative. One of the amide-linked fatty acids was found to be 4-hydroxy-2 docosenoic acid. Fast-atom-bombardment mass spectrometry and fast-atom-bombardment collison-induced tandem mass spectrometry were used to characterize the ceramide as N(4-hydroxy-2-docosenoyl)C16-sphingosine. These sphingolipids have a protective effect on cotyledons of young peppers against necrotic lesions induced by the pathogen P. capsici.