Plant cyanogenic glycosides

Toxicon. 2000 Jan;38(1):11-36. doi: 10.1016/s0041-0101(99)00128-2.


The cyanogenic glycosides belong to the products of secondary metabolism, to the natural products of plants. These compounds are composed of an alpha-hydroxynitrile type aglycone and of a sugar moiety (mostly D-glucose). The distribution of the cyanogenic glycosides (CGs) in the plant kingdom is relatively wide, the number of CG-containing taxa is at least 2500, and a lot of such taxa belong to families Fabaceae, Rosaceae, Linaceae, Compositae and others. Different methods of determination are discussed (including the indirect classical photometrical and the new direct chromatographic ones). The genetic control of cyanogenesis has no unique mechanism, the plants show variation in the amount of the produced HCN. The production of HCN depends on both the biosynthesis of CGs and on the existence (or absence) of its degrading enzymes. The biosynthetic precursors of the CGs are different L-amino acids, these are hydroxylated then the N-hydroxylamino acids are converted to aldoximes, these are turned into nitriles. The last ones are hydroxylated to alpha-hydroxynitriles and then they are glycosilated to CGs. The generation of HCN from CGs is a two step process involving a deglycosilation and a cleavage of the molecule (regulated by beta-glucosidase and alpha-hydroxynitrilase). The tissue level compartmentalisation of CGs and their hydrolysing enzymes prevents large-scale hydrolysis in intact plant tissue. The actual level of CGs is determined by various factors both developmental and ecological ones, which are reviewed too. The last part of the present work demonstrates the biological roles of CGs in plant physiological processes and in plant defence mechanisms as well. The effect of CGs (HCN) on different animals, the symptoms of poisonings are discussed to cows, sheep, donkeys, horses and chicks. Finally, the poisonous effects of cassava (Manihot esculenta) roots are summarised on experimental animals and on the human organism.

Publication types

  • Review

MeSH terms

  • Animals
  • Cyanosis / chemically induced*
  • Glycosides / toxicity*
  • Humans
  • Plants, Toxic / chemistry*


  • Glycosides