Cyanogenesis in Aralia spinosa (Araliaceae).

A systematic survey of Aralia spinosa (Araliaceae), covering an entire growing season and including aboveground organs at various developmental stages, revealed that only about half of all samples collected showed cyanogenesis. Cyanogenesis was detected in inflorescences and leaves but is apparently restricted to certain harvest times or developmental stages. The structurally unusual triglochinin, characterized by a hex-2-enedioic acid partial structure, was the only cyanogenic glycoside detected. This is the first description of triglochinin in this species and in the family of Araliaceae. Triglochinin is biogenetically derived from tyrosine, which is in good agreement with the few cyanogenic glycosides previously detected in members of the Araliaceae family. Triglochinin was identified, characterized, and quantified by modern chromatographic methods, and the amount of enzymatically releasable hydrocyanic acid was determined qualitatively and quantitatively. Two isomers of triglochinin were detected chromatographically at minor levels. The isomeric pattern agreed well with literature data from other triglochinin-containing plants. This was confirmed in the two species, Triglochin maritima and Thalictrum aquilegiifolium, which were comparatively studied. In the case of A. spinosa, inflorescence buds harvested in July showed the highest content of triglochinin, just under 0.2% on a dry weight basis. The detection of triglochinin adds to the knowledge of toxicological properties and the dereplication of U(H)PLC/MS² data provides a comprehensive phytochemical profile of A. spinosa.