Carboxyatractyloside (CATR) is a highly toxic

diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycoside ...

that inhibits the

ADP/ATP translocase Adenine nucleotide translocator (ANT), also known as the ADP/ATP translocase (ANT), ADP/ATP carrier protein (AAC) or mitochondrial ADP/ATP carrier, exchanges free ATP with free ADP across the inner mitochondrial membrane. ANT is the most abund ...

. It is about 10 times more potent than its analog

atractyloside Atractyloside (ATR) is a natural, toxic glycoside present in numerous plant species worldwide in the daisy family including '' Atractylis gummifera'' and '' Callilepis laureola'', and it's used for a variety of therapeutic, religious, and toxic ...

. While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective. The effects of carboxyatractyloside on the ADP/ATP translocase are not reversed by increasing the concentration of adenine nucleotides, unlike its counterpart atractyloside. Carboxyatractyloside behavior resembles

bongkrekic acid Bongkrek acid (also known as bongkrekic acid) is a respiratory toxin produced in fermented coconut or corn contaminated by the bacterium ''Burkholderia gladioli'' pathovar ''cocovenenans''. It is highly toxic because the compound inhibits the ...

while in the mitochondria. Carboxyatractyloside is poisonous to humans as well as livestock, including cows and horses. Symptoms of carboxyatractyloside poisoning may include abdominal pain, nausea and vomiting, drowsiness, palpitations, sweating and trouble breathing. In severe cases,

convulsions A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ...

, liver failure and loss of consciousness may develop, which can lead to death. Carboxyatractyloside can be found in ''

Xanthium ''Xanthium'' (cocklebur) is a genus of flowering plants in the tribe Heliantheae within the family Asteraceae, native to the Americas and eastern Asia and some parts of south Asia . Description Cockleburs are coarse, herbaceous annual plants ...

'' species plants, including ''

Xanthium strumarium ''Xanthium strumarium'' (rough cocklebur, clotbur, common cocklebur, large cocklebur, woolgarie bur) is a species of annual plants of the family Asteraceae. Some sources claim it originates in southern Europe and Asia, but has been extensively na ...

''. Consumption of ''Xanthium'' containing the toxin led to the deaths of at least 19 people in Sylhet, Bangladesh during a period of food scarcity. Along with

, it is also one of the main poisonous substances in the '' Atractylis gummifera'' thistle.

References

Diterpene glycosides ADP/ATP translocase inhibitors Alkene derivatives Carboxylic acids Plant toxins Sulfate esters {{Biochem-stub