Methylene cyclopropyl acetic acid

Methylene cyclopropyl acetic acid

Methylene cyclopropyl acetic acid (MCPA) is a chemical compound that is known for its role in the inhibition of fatty acid oxidation. It is a metabolite of hypoglycin, a naturally occurring amino acid found in certain plants, such as the Ackee fruit and Blighia sapida. MCPA is of particular interest in the field of biochemistry and toxicology due to its association with Jamaican vomiting sickness.

Chemical Structure and Properties

Methylene cyclopropyl acetic acid has a unique structure characterized by a cyclopropyl ring attached to an acetic acid moiety. The presence of the methylene group (CH2) linked to the cyclopropyl ring is a distinctive feature of this compound.

Biological Activity

MCPA is known to inhibit the enzyme acyl-CoA dehydrogenase, which is crucial for the beta-oxidation of fatty acids in the mitochondria. This inhibition leads to the accumulation of unmetabolized fatty acids and their derivatives, which can cause severe metabolic disturbances.

Toxicology

Exposure to MCPA, particularly through the ingestion of hypoglycin-containing fruits like the unripe Ackee fruit, can lead to a condition known as Jamaican vomiting sickness. This condition is characterized by severe hypoglycemia, vomiting, and in severe cases, can be fatal. The toxic effects are primarily due to the inhibition of fatty acid oxidation, leading to energy depletion in cells.

Clinical Significance

Understanding the mechanism of action of MCPA is crucial for the diagnosis and treatment of poisoning cases related to hypoglycin ingestion. Treatment typically involves supportive care and the administration of glucose to counteract hypoglycemia.

Related Compounds

MCPA is related to other compounds that inhibit fatty acid oxidation, such as hypoglycin A and hypoglycin B. These compounds share similar toxicological profiles and mechanisms of action.

See Also

• Ackee
• Blighia sapida
• Jamaican vomiting sickness
• Hypoglycin
• Beta-oxidation
• Acyl-CoA dehydrogenase

External Links

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