Bongkrek acid

A toxic compound produced by certain bacteria

Bongkrek acid is a potent respiratory toxin produced by the bacterium Burkholderia gladioli pathovar cocovenenans. It is most commonly associated with foodborne illness resulting from the consumption of contaminated fermented coconut or corn products. The toxin is known for its ability to inhibit adenine nucleotide translocase (ANT) in the mitochondria, leading to cellular respiration failure and potentially fatal outcomes.

Structure and Properties

Bongkrekic acid structure

Bongkrek acid is a polyketide compound with a complex structure that includes multiple hydroxyl groups and a long carbon chain. Its molecular formula is C28H42O7. The compound is characterized by its ability to bind to the adenine nucleotide translocase, a critical component of the mitochondrial inner membrane.

Biosynthesis

Bongkrek acid synthesis mechanism

The biosynthesis of bongkrek acid involves a polyketide synthase (PKS) pathway. The bacterium Burkholderia gladioli utilizes a series of enzymatic reactions to assemble the polyketide chain, which is then modified to produce the active toxin. The synthesis involves the incorporation of acetate and malonate units, followed by cyclization and oxidation steps.

Mechanism of Action

Bongkrek acid exerts its toxic effects by inhibiting the adenine nucleotide translocase (ANT) in the mitochondria. ANT is responsible for the exchange of ADP and ATP across the mitochondrial membrane, a crucial step in cellular energy metabolism. By blocking this exchange, bongkrek acid disrupts ATP synthesis, leading to energy depletion and cell death.

Toxicity and Symptoms

Ingestion of bongkrek acid-contaminated food can lead to severe poisoning. Symptoms typically include abdominal pain, vomiting, diarrhea, and in severe cases, liver failure, kidney failure, and death. The onset of symptoms can occur within hours of consumption, and the severity depends on the dose and individual susceptibility.

Prevention and Control

Preventing bongkrek acid poisoning involves controlling the growth of Burkholderia gladioli in food products. This can be achieved by maintaining proper hygiene during food preparation, avoiding the use of contaminated raw materials, and ensuring adequate fermentation conditions to inhibit bacterial growth.

Related Pages

• Foodborne illness
• Polyketide
• Mitochondrial toxicity
• Burkholderia gladioli