Cyanogenesis in Plants

Cyanogenesis is the process by which plants produce hydrogen cyanide gas

(HCN) to defend themselves against herbivores. HCN is poisonous not only to animals
that eat plants, but to the plants themselves. To prevent poisoning themselves, the plants
store cyanogenic glycosides1 in a vacuole of the cell and an enzyme that acts to produce
HCN in a separate compartment. When the cell is damaged, the compartment walls are
breached, allowing the reaction to take place. In this way, HCN is produced only when
needed.

Equation of Cyanogenesis:
N N

glucose C HC N O
C

O HO HO
B glucosidase hydroxynitrile lyase
glucose
OH OH OH

We can visualize the production of HCN using Feigl-Anger strips. These strips
change color in the presence of cyanide gas, from nearly white to blue or purple. This
method is a qualitative rather than quantitative one; in other words, we will be noting
whether or not HCN is produced, but not how much. Although cyanide is toxic to
people, the amounts we will be producing are small enough not to bother us.

Procedure:
Obtain about 2-3 apple seeds, or a portion of another fruit seed. In order to
release HCN, we will have to damage the cells. Using mortar and pestle, carefully grind
your sample. Don’t spend too much time grinding. If the sample is too dry, add one or
two drops of water. Too much water will mess up the experiment, so only add water is it
is absolutely necessary. Also, be careful not to get the Feigl-Anger strips wet. Transfer
the sample to a tube. Place one Feigl-Anger strip over the top of the tube and cork in
place. Look for color change.
A color change signals that cyanide is being released. The strips will turn from
pale blue-green to bright blue or purple in the presence of cyanide gas. The color change
may take a few minutes, so be patient. While waiting, prepare another sample in a
separate beaker.

Equation for Fiegl-Anger strip:

2 CuAc2 + C17H22N2 + 2 HCN  2 CuCN + [C17H22N2]Ac + 3 HAc
(Note: For simplicity the original article abbreviated copper II ethylacetoacetate as
CuAc2; CuAc2 in full would be C12H18CuO6)

Can you come up with a hypotheses for why some samples released cyanide gas
and others didn’t? Think about what parts of a plant are more important evolutionarily.
 According to Extoxnet, an internet source for toxicity of various compounds,
almonds, cassava root, sorghum and lima beans all produce hydrogen cyanide. Cassava
is an important food in many parts of the world. Based on our experiment, how do you
think people can safely eat cassava?
1
cyanogenic means producing cyanide; glycosides are sugar containing compounds

Sources:
Brinker, A.M. and Seigler, D.S. 1989. Methods for the detection and quantitative
determination of cyanide in plant materials. Phytochemical Bulletin 21(2): 24-31.
Feigl, F. and Anger, V. 1966. Replacement of benzidine by copper ethylacetoacetate
and tetra base as spot-test reagent for hydrogen cyanide and cyanogen. Analyst, 91: 282-
284.