α-Chaconine

 α-Chaconine

α-Chaconine, with the CAS number 20562-03-2, is a glycoalkaloid primarily found in potatoes (Solanum tuberosum). It is known for its toxic properties and is one of the major components responsible for the bitter taste in green potatoes. This compound has garnered attention due to its biological activities and potential applications in both agriculture and medicine.

Chemical Identity

• CAS Number: 20562-03-2
• MDL Number: MFCD09039102
• Molecular Formula: C45H73NO14
• Molecular Weight: 852.06 g/mol
• EINECS Number: Not specified

Physical and Chemical Properties

1. Appearance: Typically appears as a white to off-white solid or powder.
2. Melting Point: Ranges from 228 to 236 °C, indicating a stable structure that withstands heat.
3. Boiling Point: Not specified, but expected to be high due to the complexity of the molecule.
4. Solubility: Soluble in pyridine at a concentration of 10 mg/mL, appearing clear and very faintly yellow.

Biological Activities

α-Chaconine exhibits several important biological functions:

1. Toxicity: It acts as a natural pesticide, providing protection to the potato plant against herbivores and pathogens. However, it can be toxic to humans and animals when consumed in large amounts, particularly in green or sprouted potatoes.
2. Cellular Effects: Research indicates that α-chaconine can induce apoptosis (programmed cell death) in various cell types by disrupting cellular membranes and affecting mitochondrial function. This property has implications for its use in cancer research.
3. Anti-inflammatory Effects: Studies suggest that α-chaconine may possess anti-inflammatory properties, potentially making it useful in treating conditions associated with inflammation.
4. Impact on Gut Health: It has been shown to affect intestinal permeability, which could have implications for gut health and conditions like leaky gut syndrome.

Applications

α-Chaconine has several applications across different fields:

1. Agriculture: As a natural pesticide, it helps protect crops from pests, contributing to sustainable farming practices.
2. Pharmaceutical Research: Its effects on cell proliferation and apoptosis make it a candidate for further investigation in cancer therapies and treatments for inflammatory diseases.
3. Food Safety: Understanding its toxicity is crucial for food safety regulations regarding potato consumption, especially concerning green or sprouted potatoes.
4. Nutraceuticals: Due to its biological activities, there is potential for α-chaconine to be explored as an ingredient in dietary supplements aimed at enhancing health.

Safety Information

While α-chaconine is naturally occurring in potatoes, it can be toxic at higher concentrations:

• Avoid consumption of green or sprouted potatoes to minimize exposure.
• Standard laboratory safety practices should be followed when handling the compound, including the use of personal protective equipment (PPE).

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5773055.htm
2. https://pubchem.ncbi.nlm.nih.gov/compound/Alpha-Chaconine
3. https://en.wikipedia.org/wiki/Chaconine
4. https://pubchem.ncbi.nlm.nih.gov/compound/Alpha-solanine
5. https://www.frontiersin.org/journals/plant-science/articles/10.3389/fpls.2021.673774/full
6. https://www.sciencedirect.com/topics/chemistry/alpha-chaconine
7. https://www.sciencedirect.com/topics/neuroscience/alpha-chaconine
8. https://www.chemfaces.com/natural/alpha-Chaconine-CFN00450.html