Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue

BACKGROUND: Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antif...

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Published in:Pest management science 2009-01, Vol.65 (1), p.34-40
Main Authors: Castelo-Branco, Pedro A, Rubinger, Mayura MM, Guilardi, Silvana, Leite, Vanessa M, dos Santos, Adeliane R, de C Alves, Leandro, Lariucci, Carlito, Vencato, Ivo, Piló-Veloso, Dorila, Zambolim, Laércio
Format: Article
Language:English
Subjects:
absolute structural determination
antifungal activity
Aspergillus
avenaciolide analogues
Biological and medical sciences
bis-γ-lactones
Colletotrichum - drug effects
Colletotrichum gloeosporioides
Enzyme kinetics
Fundamental and applied biological sciences. Psychology
Fungi
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Hydrogen bonds
Lactones - chemistry
Lactones - pharmacology
Models, Molecular
Molecular Structure
Pesticides
Spectrum analysis
Studies
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Summary:BACKGROUND: Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antifungal activity, a bis‐γ‐lactone analogous to avenaciolide was prepared and characterized by elemental analysis, mass spectrometry, and infrared and NMR spectroscopy. RESULTS: The absolute structures of this compound and of the synthetic precursor (also a bis‐γ‐lactone) were determined by X‐ray diffraction analysis. The bis‐γ‐lactones synthesized crystallize in the orthorhombic space group P212121, and the crystal packings are supported by CH···O hydrogen bonds. The compound showed antifungal activity against Colletotrichum gloeosporioides (Penz.) Penz. & Sacc., while the synthetic precursor was inactive under the in vitro test conditions employed. CONCLUSION: The results indicate that it is not only the bis‐γ‐lactone skeleton that is important to antifungal activity. The latter also depends on the presence of the exocyclic double bond possibly due to a Michael addition type reaction with the fungal enzymes. Copyright © 2008 Society of Chemical Industry
ISSN:1526-498X
1526-4998
DOI:10.1002/ps.1640