Hypoglycin A

Hypoglycin Structural Formula V.1

Hypoglycin A is a naturally occurring amino acid derivative found in the unripe fruit of the Ackee tree (Blighia sapida), which is native to West Africa and widely cultivated in the Caribbean. Hypoglycin A is known for its toxic properties and is the primary cause of Jamaican vomiting sickness.

Chemical Structure and Properties

Hypoglycin A is a non-proteinogenic amino acid with the chemical formula C7H11NO3. It is a derivative of valine and contains a methylenecyclopropyl group. The compound is water-soluble and can be hydrolyzed to produce hypoglycin B, which is also toxic.

Toxicity

The toxicity of Hypoglycin A is due to its ability to inhibit the process of beta-oxidation of fatty acids in the mitochondria. This inhibition leads to the accumulation of toxic intermediates, such as medium-chain acyl-CoA esters, which can cause severe hypoglycemia and metabolic acidosis. Symptoms of poisoning include vomiting, convulsions, and in severe cases, coma and death.

Jamaican Vomiting Sickness

Jamaican vomiting sickness is a potentially fatal condition caused by the ingestion of unripe or improperly prepared ackee fruit containing high levels of Hypoglycin A. The illness is characterized by sudden onset of vomiting, hypoglycemia, and altered mental status. The condition is most commonly reported in Jamaica, where the ackee fruit is a traditional food.

Prevention and Treatment

To prevent Hypoglycin A poisoning, it is essential to consume only fully ripe ackee fruit, as the levels of Hypoglycin A decrease significantly as the fruit matures. Proper preparation methods, such as thorough cooking and discarding the seeds and rind, can also reduce the risk of toxicity.

Treatment for Hypoglycin A poisoning involves supportive care, including the administration of intravenous glucose to manage hypoglycemia and monitoring of metabolic parameters. In severe cases, hospitalization and intensive care may be required.

See Also

• Ackee
• Jamaican vomiting sickness
• Beta-oxidation
• Hypoglycemia
• Metabolic acidosis