Torachrysone-8-O-β-D-glucoside

Torachrysone-8-O-β-D-glucoside

Torachrysone-8-O-β-D-glucoside is a natural compound derived from the plant Polygonum multiflorum Thunb., known for its various biological activities, particularly its anti-inflammatory and antioxidant properties. Below is a comprehensive overview of its properties, applications, and safety information.

Chemical Properties

• CAS Number: 64032-49-1
• MDL Number: MFCD20274770
• Molecular Formula: C20H24O9
• Molecular Weight: 408.40 g/mol
• Boiling Point: 626.9 °C at 760 mmHg
• Melting Point: 171-173 °C
• Density: Approximately 1.5 g/cm³ (predicted)
• Solubility: Soluble in DMSO and other organic solvents; requires ultrasonic treatment for optimal solubility.

Structural Information

Torachrysone-8-O-β-D-glucoside features a naphthalene ring structure with a glucosyl group attached at the 8-position. This structure enhances its solubility and bioactivity. The compound can be represented by the following SMILES notation:

COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(O)c(C(C)=O)c(C)cc2c1\text{COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(O)c(C(C)=O)c(C)cc2c1}COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(O)c(C(C)=O)c(C)cc2c1

Biological Activities

Torachrysone-8-O-β-D-glucoside exhibits several important biological properties:

1. Anti-inflammatory Activity: It has been shown to inhibit inflammatory pathways, making it beneficial in conditions characterized by excessive inflammation.
2. Antioxidant Effects: The compound acts as an antioxidant, helping to reduce oxidative stress in cells and tissues.
3. Aldose Reductase Inhibition: It effectively inhibits aldose reductase (AR), an enzyme involved in the metabolism of carbohydrates, which may have implications for managing diabetic complications.
4. Alpha-glucosidase Inhibition: Torachrysone-8-O-β-D-glucoside has demonstrated alpha-glucosidase inhibitory activities, suggesting potential use in managing type 2 diabetes.

Applications

Torachrysone-8-O-β-D-glucoside is utilized in various fields:

• Pharmaceutical Research: Investigated for its therapeutic potential in treating inflammatory diseases and metabolic disorders such as diabetes.
• Natural Product Development: Explored for incorporation into nutraceuticals aimed at promoting health and preventing disease.
• Biochemical Studies: Used to study the mechanisms of glycosylation reactions and their effects on cellular processes.

Safety Information

While specific hazard classifications may not be detailed, general safety precautions should be observed:

1. Storage Conditions: Store at -20 °C in a sealed container to maintain stability; protect from moisture and light.
2. Handling Precautions: Use appropriate personal protective equipment (PPE), such as gloves and goggles, to prevent exposure.
3. First Aid Measures:
   • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
   • Skin Contact: Wash thoroughly with soap and water; consult a physician if irritation persists.
   • Eye Contact: Rinse eyes with water for at least 15 minutes; seek medical help if irritation develops.
   • Ingestion: Do not induce vomiting; rinse mouth and seek immediate medical assistance.

Synonyms

The compound is known by several alternative names, including:

• Torachrysone 8-O-beta-D-glucoside
• Torachrysone 8-O-b-D-glucopyranoside
• Torachrysone glucoside

This detailed description highlights the significance of Torachrysone-8-O-β-D-glucoside in scientific research and potential therapeutic applications, emphasizing its chemical properties, biological activities, applications, and safety considerations.

Citations:

1. https://www.benchchem.com/product/b155671
2. https://pubchem.ncbi.nlm.nih.gov/compound/Torachrysone-8-glucoside
3. https://www.biorbyt.com/torachrysone-8-o-b-d-glucoside-orb1297186.html
4. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB72562460.htm
5. https://pubchem.ncbi.nlm.nih.gov/compound/11972479
6. https://www.targetmol.com/compound/Torachrysone-8-O-b-D-glucoside
7. https://www.glpbio.com/torachrysone-8-o-b-d-glucoside.html
8. https://file.medchemexpress.com/batch_PDF/HY-N1141/Torachrysone-8-O-b-D-glucoside-COA-145593-MedChemExpress.pdf