Distribution of cyclolinopeptides in flaxseed fractions and products.

Hydrophobic cyclic peptides, termed cyclolinopeptides, found in flaxseed are known for their immunosuppressive activity. This study is the first report of the occurrence of cyclolinopeptides in flaxseed fractions and products produced by aqueous processing and cold pressing. The distribution of cyclolinopeptides in flaxseed was determined after processing of flaxseed by various industrial and laboratory processes. Extracts of the water-soluble mucilage did not contain cyclolinopeptides. The cotyledon had the highest concentration of cyclolinopeptides, whereas seed coat had lower levels. An oil body fraction separated from seed after homogenization in water, followed by centrifugation, had the highest concentration of cyclolinopeptides of the fractions produced by this method. Further washing of the oil body fraction led to a loss of cyclolinopeptides. When oilseed was extruded using an expeller press, cyclolinopeptides were found in greater concentrations in crude oil and the solid sediment present in the oil fraction than in meal or the unprocessed seed. The concentration of cyclolinopeptides in crude flaxseed oil immediately after pressing was much higher than that observed in flaxseed oils purchased from a retail outlet. The effect of oil refining treatments on the removal of cyclolinopeptides was also tested. Acid degumming using aqueous H(3)PO(4) removed cyclolinopeptides from crude flaxseed oil. Alkali refining was less effective as this treatment failed to remove all peptides equally. This work illustrates ways that cyclolinopeptides may be extracted from flaxseed oil that could be developed for large-scale industrial extraction. The ability to extract cyclolinopeptides on a larger scale would allow faster exploitation of commercial applications of these molecules and provide the flaxseed industry with value-added coproducts.