Identification of bitter off-taste compounds in the stored cold pressed linseed oil

Brühl L, Matthäus B, Fehling E, Wiege B, Lehmann B, Luftmann H, Bergander K, Quiroga K, Scheipers A, Frank O, Hofmann T

Abstract

Whereas freshly pressed linseed oil provides a delicate nutty flavor, a lingering bitter off-taste is developing upon storage at room temperature. Using a sensory guided fractionation approach, the key bitter compound was identified in stored linseed oil, and its structure was determined as the methionine sulfoxide-containing, cyclic octapeptide cyclo(PLFIM OLVF) by means of FTIR, LC-MS, NMR spectroscopy, and amino acid analysis. Although this peptide is known in the literature as cyclolinopeptide E, the bitter taste activity of this compound has not previously been described. Sensory evaluation revealed a recognition threshold concentration of 12.3 μmol/L water.