Synthesis and antifungal activity of aromatic bis-gamma-lactones analogous to avenaciolide.
Avenaciolide is a bis-gamma-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-gamma-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.
Castelo-Branco
Pedro A
PA
Departamento de Química, CCE, Universidade Federal de Viçosa, 36570-000, Viçosa-MG, Brazil.
Rubinger
Mayura M M
MM
Alves
Leandro de C
Lde C
de Barros
Pauline M
PM
Pereira
Sinval G
SG
de Melo
Vanessa J
VJ
Pilo-Veloso
Dorila
D
Zambolim
Laércio
L
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D020081:Phyllachorales / Q000187:drug effects
D000935:Antifungal Agents; D007783:Lactones; C100081:avenaciolide