Reports on the distribution of aromatic cyanogenic glycosides in Australian tropical rainforest tree species of the Lauraceae and Sapindaceae.

The aromatic cyanogenic glycosides taxiphyllin [(R)-4-hydroxymandelonitrile β-D-glucoside] and prunasin [(R)-mandelonitrile β-D-glucoside] were identified as the main cyanogenic compounds in tissues of Australian endemic tropical rainforest tree taxa in the Lauraceae and Sapindaceae families, respectively. The tyrosine-derived taxiphyllin was the main cyanogenic glycoside in foliage of Beilschmiedia collina. This is the first reported cyanogenic compound from the Lauraceae. In addition, substantial quantitative variation in the capacity for cyanogenesis was detected in leaves from 40 individuals, with taxiphyllin concentrations ranging from 23 to 1263 μg CN g(-1) dry wt. No acyanogenic individuals were detected. Concentrations of taxiphyllin were, on average, 2.2-fold greater in young leaves than in old leaves. Prunasin was the dominant cyanogenic compound in tissues of Mischocarpus grandissimus (leaves) and Mischocarpus exangulatus (leaves and seed capsule). Better known for cyanolipids in seed oils, this is the first time a phenylalanine-derived cyanogenic glycoside has been reported in the Sapindaceae. The concentrations of prunasin varied widely, over an order of magnitude, among individuals and different tissue types in these species, with the higher concentrations found in seed capsules and young leaves.