Date published: 2025-10-16

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Avenaciolide (CAS 16993-42-3)

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Application:
Avenaciolide is a bicyclic bis-butyrolactone antifungal agent
CAS Number:
16993-42-3
Purity:
>95%
Molecular Weight:
266.33
Molecular Formula:
C15H22O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Avenaciolide is a naturally occurring heterocyclic compound, specifically a 12-membered lactone, known for its unique structure and biological activity. It is primarily derived from various species of fungi, including those belonging to the Aspergillus and Fusarium genera. Avenaciolide′s biochemical significance lies in its capability to act as a bioactive molecule influencing plant-fungal interactions. The compound′s mechanism of action involves disrupting cellular processes in fungi, contributing to its role as a natural antifungal agent. In agricultural research, avenaciolide has been studied for its potential to protect crops by naturally controlling pathogenic fungi, thereby reducing reliance on synthetic fungicides. Its mode of action is thought to involve the disruption of the fungal cell membrane integrity or interference with key enzymatic pathways critical for fungal survival and proliferation. Additionally, avenaciolide′s chemical structure has attracted interest from organic chemists looking to synthesize analogs and derivatives with improved or diversified biological activities. The study of avenaciolide not only enhances understanding of natural fungal defense mechanisms but also aids in the development of new strategies for managing crop diseases and understanding ecological balances within soil microbiomes.


Avenaciolide (CAS 16993-42-3) References

  1. Possible mechanisms of the efflux of glutamate from kidney mitochondria generated by the activity of mitochondrial glutaminase.  |  Kovacević, Z. 1975. Biochim Biophys Acta. 396: 325-34. PMID: 1174515
  2. Synthesis and antifungal activity of aromatic bis-gamma-lactones analogous to avenaciolide.  |  Castelo-Branco, PA., et al. 2007. Chem Biodivers. 4: 2745-54. PMID: 18081084
  3. Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue.  |  Castelo-Branco, PA., et al. 2009. Pest Manag Sci. 65: 34-40. PMID: 18785221
  4. Avenaciolide Induces Apoptosis in Human Malignant Meningioma Cells through the Production of Reactive Oxygen Species.  |  Katsuzawa, T., et al. 2022. Biol Pharm Bull. 45: 517-521. PMID: 35370277
  5. Avenaciolide inhibition of anion transport in mitochondria.  |  Godinot, C. 1974. FEBS Lett. 46: 138-40. PMID: 4370621
  6. Is avenaciolide another ionophore?  |  Harris, EJ. and Wimhurst, JM. 1973. Nat New Biol. 245: 271-3. PMID: 4518992
  7. Effects of Bacillus subtilis protease, type 8 (subtilopeptidase A) on isolated adipose cells. Fructose utilization and its inhibition by avenaciolide, piericidin A and puromycin.  |  Kuo, JF. 1968. Biochim Biophys Acta. 165: 208-17. PMID: 4971641
  8. Two new mould metabolites related to avenaciolide.  |  Aldridge, DC. and Turner, WB. 1971. J Chem Soc Perkin 1. 13: 2431-2. PMID: 5166602
  9. Avenaciolide: a specific inhibitor of glutamate transport in rat liver mitochondria.  |  McGivan, JD. and Chappell, JB. 1970. Biochem J. 116: 37P-38P. PMID: 5435480
  10. The actions of avenaciolide and ethanol on glucose metabolism and on related enzyme activities in the isolated perfused rat liver.  |  Wimhurst, JM. and Harris, EJ. 1976. Biochim Biophys Acta. 437: 51-61. PMID: 949510

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Avenaciolide, 0.5 mg

sc-391742
0.5 mg
$250.00