A reactive conjugated allene involved in the biosynthesis of volatile oxylipins in the moss Dicranum scoparium.

We addressed the role of the unusual acetylenic fatty acid dicranin as a precursor for volatile oxylipins in the moss Dicranum scoparium. Dicranin is transformed immediately after mechanical wounding of moss tissue to volatile C5- and C6-oxylipins. The transformation of synthetic deuterium labeled dicranin was monitored using LC/MS analysis and multivariate statistics to identify polar metabolites produced during volatile formation. Among the newly formed oxylipins is a highly reactive conjugated C13 allene with similar degrees of labeling compared to the C5 volatiles suggesting that it results as second cleavage product from the biosynthesis of pentenal and pentenone.