Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Friedrich Schiller University, Lessingstr. 8, D-07743 Jena, Germany.
Org Lett. 2011 Jun 17;13(12):3229-31. doi: 10.1021/ol201114g. Epub 2011 May 23.
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.
我们研究了不寻常的炔酸二坎宁作为藓类植物 Dicranum scoparium 中挥发性氧化脂类前体的作用。二坎宁在苔藓组织受到机械损伤后立即转化为挥发性 C5 和 C6 氧化脂类。使用 LC/MS 分析和多元统计监测合成氘标记二坎宁的转化，以鉴定在挥发性形成过程中产生的极性代谢物。在新形成的氧化脂类中，有一种高度反应性的共轭 C13 丙二烯，其标记程度与 C5 挥发物相似，这表明它是戊烯醛和戊烯酮生物合成的第二个裂解产物。
