Chaconine

Chaconine1

Chaconine is a glycoalkaloid poison found in plants of the Solanaceae family, which includes potatoes, tomatoes, and eggplants. It is a natural defense mechanism of these plants against pests and pathogens. Chaconine, along with solanine, is one of the primary glycoalkaloids found in potatoes.

Chemical Structure and Properties

Chaconine is a steroidal glycoalkaloid, which means it consists of a steroidal aglycone (solanidine) attached to a sugar moiety. The chemical formula of chaconine is C45H73NO14. It is structurally similar to solanine, differing only in the sugar residues attached to the solanidine backbone.

Biosynthesis

Chaconine is synthesized in the Solanaceae plants through the mevalonate pathway, which is a crucial metabolic pathway for the production of isoprenoids. The biosynthesis involves several enzymatic steps, starting from acetyl-CoA and leading to the formation of solanidine, which is then glycosylated to form chaconine.

Toxicity

Chaconine is toxic to humans and animals when ingested in large quantities. It can cause gastrointestinal and neurological symptoms such as nausea, vomiting, diarrhea, and headaches. In severe cases, it can lead to more serious conditions like respiratory distress and even death. The toxicity of chaconine is due to its ability to disrupt cell membranes and inhibit the enzyme acetylcholinesterase, which is essential for nerve function.

Occurrence in Potatoes

The concentration of chaconine in potatoes varies depending on the variety, growing conditions, and storage. Higher levels are typically found in the skin and sprouts of potatoes. Green potatoes, which have been exposed to light, tend to have higher concentrations of chaconine and solanine. Proper storage and handling of potatoes can help minimize the risk of glycoalkaloid poisoning.

Health Implications

While the levels of chaconine in commercially available potatoes are generally safe for consumption, it is important to avoid eating green or sprouted potatoes. Cooking can reduce the glycoalkaloid content to some extent, but it does not eliminate it completely. Individuals with sensitivity to glycoalkaloids should be particularly cautious.

Related Compounds

• Solanine
• Solanidine
• Tomatine

See Also

• Glycoalkaloid
• Solanaceae
• Potato
• Tomato
• Eggplant