Blighia Hypoglycines

Hypoglycin A from the fruit of Blighia sapida, a tree that grows in Jamaica and Africa, causes hypoglycemia and vomiting in animals and humans. Fatalities, which have occurred, were attributed to a sudden drop in blood sugar. 

Amino acids hypoglycins (Blighia sapida Kwi., Sapindales, Ang., also introduced to the Caribbean BR). 

Hypoglycine A (7), a hypoglycemic compound, was first isolated from the akee plant Blighia sapida Kon. ". This amino acid, together with a-(methylenecyclopropyl)glycine... 

Blighia sapida (akee) contains a large amount of a potent hypoglycemic amino acid, glycylglycylglycine, known as hypoglycin. 

A number of other inhibitors of fatty acid oxidation have been reported in the literature [81,86, 140-142] including 2-bromopalmitoyl-CoA, bromoacetyl-CoA and S-methanesulphonyl-CoA decanoylcamitine, all inhibitors of carnitine palmitoyltransferase, 4-pentenoic acid, an inhibitor of 3-ketoacyl-CoA thiolase and acetoacetyl-CoA thiolase, and hypoglycin, a compound isolated from the Jamaican ackee fruit (Blighia sapida) which potently inhibits several acyl-CoA dehydrogenases. The toxicity associated with these compounds or their expense have precluded further development as hypoglycaemic agents. 

Hypoglycines. H. A [3-((/ )-methylenecyclopropyl)-L-alanine], a non-proteinogenic amino acid with hypoglycemic and teratogenic activity from unripe akee plums (Blighia sapida, Sapindaceae). 

The aril of the unripened fruit is richer in hypoglycin A than the fully matured aril. Both hypoglycin A and B are found in the unripened aril and the seed (Kean, 1976). These two compounds also occur in several species of Blighia and Billia (Hippocastanaceae) and in members of the genus Acer (Aceraceae, the maple family) (Fowden and Pratt, 1973). 

Hypoglycin A is the toxic principle of the unripe ackee fruit (fruits of the tree Blighia sapida E 5.5.3). In animals it undergoes oxidative deamination and decarboxylation to (X-(methylenecyclopropyl)-acetic acid, which strongly inhibits the -oxidation of fatty acids. 

Kean, E. A., Lewis, C. E, Biosynthesis of L-j5-(methylenecyclopropyl)-alanine (hypoglycin) in Blighia sapida. Phytochemistry 20, 2161-2164 (1981)... 

Unsaturated Fatty Acids- Hypoglycin (XVI), a short chain unsaturated amino acid derived from the fruit of Blighia sapida, causes hypoglycemia in... 

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