Cyanogenic lipids

Due to homologies in structures and biosynthesis, some minor groups of natural products seem to be related to cyanogenic glucosides. These compounds, i.e. cyanogenic lipids, nitrile- and nitro-compounds, are briefly presented in this chapter. 

Selmar, D. (1991) The cleavage of cyanogenic lipids. Physiol. Plantarum, 83, 63-6. 

Selmar, D., Grocholewski, S. and Seigler, D.S. (1990) Cyanogenic lipids utilization during seedling development of Ungnadia speciosa. Plant Physiol., 93,631-6. 

Fig. 1. Naturally occurring cyanogenic glycosides and cyanogenic lipids from various plant sources...

In the family Sapindaceae (and possibly the related family Hippocastanaceae), the a-hydroxynitrile is esterified with a long-chain fatty acid (Cig or C20) to produce cyanogenic lipids (Fig. 16.2) (Mikolajczak, 1977). 

An example of important non-volatile nitriles is 4-hydroxybenzyl cyanide, which is found in mustard pastes made from white mustard seeds Leucosinapis album) containing glucosinolate sinalbin. Nonvolatile nitriles also include cyanogenic glycosides, cyanogenic lipids and amino acids that contain the cyano group. 

Cyanogenic lipids (cyanolipids) occur together with conventional triacylglycerols in the seeds of many plants of the soapberry family (Sapindaceae) in certain cases they represent more than 50% ofthe seed oil. Members of this family have been widely studied for their pharmacological (antioxidant, anti-inflammatory and anti-diabetic properties) and anti-insect activities, and many species have economically valuable tropical fruits and wood. Some cyanogenic lipids also occur in plants of the Hippocastaneaceae and Boraginaceae families, which are not used for human consumption. 

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