Validamycin A

Validamycin A

Validamycin A (CAS No. 37248-47-8) is a naturally occurring antifungal agent produced by the fermentation of Streptomyces hygroscopicus. It is primarily used in agriculture to protect crops, particularly rice, from fungal diseases such as sheath blight caused by Rhizoctonia solani.

Chemical and Physical Properties

• CAS Number: 37248-47-8
• MDL Number: MFCD09028089
• EINECS: 609-372-4
• Molecular Formula: C₂₀H₃₅NO₁₃
• Molecular Weight: 497.49 g/mol
• Boiling Point: 813.7°C at 760 mmHg
• Melting Point: 130–135°C
• Density: 1.69 g/cm³
• Appearance: White powder
• Storage: Store at 2–8°C for long-term stability (months).

Structure and Composition

Validamycin A is a complex molecule with multiple hydroxyl groups and a cyclic structure that contribute to its biological activity. The compound features a unique arrangement of functional groups that enhance its antifungal properties, particularly through the inhibition of trehalase, an enzyme critical for fungal carbohydrate metabolism.

Mechanism of Action

This antifungal agent acts as a competitive inhibitor of trehalase, an enzyme essential for the digestion of trehalose, a storage carbohydrate in fungi. By blocking this enzyme, it disrupts fungal growth and reproduction, making it effective against a wide range of crop-related fungal pathogens.

Applications

1. Agricultural Use: Validamycin A is widely used as a biopesticide to control sheath blight in rice and other crops like potatoes, strawberries, and tobacco.
2. Research Applications: It is also utilized in scientific studies to understand fungal metabolism and the mechanisms of antifungal resistance.

Safety and Toxicity

Validamycin A exhibits low toxicity to mammals and fish, with an oral LD50 greater than 20 g/kg in rats. It is generally considered safe for use in agricultural applications when applied according to recommended guidelines. However, it should be handled with care due to its biological activity.

Storage Recommendations

For optimal stability, Validamycin A should be stored at temperatures between 2–8°C and protected from light. When prepared in solution, it should be kept under nitrogen to prevent degradation.

In summary, Validamycin A is an important antifungal agent with significant applications in agriculture for crop protection. Its unique mechanism of action and low toxicity profile make it a valuable tool for managing fungal diseases in various crops.

Citations:

1. https://www.glpbio.com/validamycin-a.html
2. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7236710.htm
3. https://pubchem.ncbi.nlm.nih.gov/compound/Validamycins
4. https://file.medchemexpress.com/batch_PDF/HY-B0856/Validamycin-A-COA-68017-MedChemExpress.pdf
5. https://en.wikipedia.org/wiki/Validamycin
6. http://sitem.herts.ac.uk/aeru/bpdb/Reports/677.htm
7. https://www.drugfuture.com/chemdata/validamycins.html
8. https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sa=X&ved=2ahUKEwj70sSTtaeMAxWVsVYBHVjHEP8Q_B16BAgDEAI