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Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue
Author(s) -
CasteloBranco Pedro A,
Rubinger Mayura MM,
Guilardi Silvana,
Leite Vanessa M,
dos Santos Adeliane R,
de C Alves Leandro,
Lariucci Carlito,
Vencato Ivo,
PilóVeloso Dorila,
Zambolim Laércio
Publication year - 2009
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.1640
Subject(s) - chemistry , stereochemistry , orthorhombic crystal system , lactone , absolute configuration , crystal structure , carbon 13 nmr , hydrogen bond , chemical structure , natural product , molecule , organic chemistry
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 P2 1 2 1 2 1 , and the crystal packings are supported by CH···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