title: The rare cyanogen proteacin, and dhurrin, from foliage of Polyscias australiana, a tropical Araliaceae.
abstract: The tyrosine-derived cyanogenic di-glucoside proteacin and related mono-glucoside dhurrin were identified as the cyanogens in foliage of the tropical tree species Polyscias australiana, present in the approximate ratio 9:1. To date cyanogenic glycosides have not been characterised from the Araliaceae or the Apiales. Concentrations of cyanogenic glycosides varied significantly between plant parts and with leaf age, with the highest concentrations in young emerging leaves (mean 2217.1 μg CN g(-1) dry wt), petioles (rachis; 1487.1 μg CN g(-1) dry wt) and floral buds (265.8 μg CN g(-1) dry wt). Between 2% and 10% of nitrogen in emerging leaves and petioles was present as cyanogenic glycosides. With the exception of floral buds, all tissues apparently lack a specific cyanogenic β-glucosidase to catalyse the first step in the breakdown of these cyanogenic glycosides. Only with the addition of emulsin, an exogenous non-specific β-glucosidase from almonds, were high concentrations of cyanogenic glycosides detected, as much as 20-fold greater than the low to negligible cyanogenic glycoside concentrations determined in the absence of exogenous enzyme. High concentrations of cyanogens in young tissues may confer protection, but may also be a nitrogen source during leaf expansion.
authors.affiliation: School of Biological Sciences, Monash University, Clayton, Victoria 3800, Australia. Rebecca.miller@monash.edu
authors.forename: Rebecca E
authors.initials: RE
authors.lastname: Miller
authors.forename: Kellie L
authors.initials: KL
authors.lastname: Tuck
mesh_terms: D027481:Araliaceae / Q000737:chemistry*; D035264:Flowers / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification*; D018515:Plant Leaves / Q000737:chemistry
chemical_list: D006027:Glycosides; D009570:Nitriles; D010936:Plant Extracts; C007173:cyanogenic glycosides; C011220:dhurrin
keywords: Araliaceae; Chemical defence; Cyanogenesis; Cyanogenic glycoside; Cyanogenic β-glucosidase; Dhurrin; Polyscias australiana; Proteacin