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Synthesis and Antifungal Activity of Aromatic Bis‐ γ ‐lactones Analogous to Avenaciolide
Author(s) -
CasteloBranco Pedro A.,
Rubinger Mayura M. M.,
Alves Leandro de C.,
de Barros Pauline M.,
Pereira Sinval G.,
de Melo Vanessa J.,
PiloVeloso Dorila,
Zambolim Laércio
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790223
Subject(s) - chemistry , antifungal , organic chemistry , stereochemistry , microbiology and biotechnology , biology
Avenaciolide is a bis‐ γ ‐lactone isolated from Aspergillus avenaceus and possesses antifungal activity. Here, we describe the total syntheses and characterization by elemental analyses, and IR and NMR spectroscopy of three new bis‐ γ ‐lactones analogous to avenaciolide, where the octyl group of the natural product was replaced by aromatic groups. The effects of the avenaciolide, the novel compounds, and their synthetic precursors on the mycelia development and conidia germination of Colletotrichum gloeosporioides were evaluated in vitro. The new compounds were as active as avenaciolide in the tested conditions, while the synthetic precursors were inactive. The preparation and characterization of 15 new synthetic intermediates are also described.