Synthesis and antifungal activity of aromatic bis-γ-lactones analogous to avenaciolide

被引:14
作者
Castelo-Branco, Pedro A. [1 ,2 ]
Rubinger, Mayura M. M. [1 ]
Alves, Leandro de C. [1 ]
de Barros, Pauline M. [1 ]
Pereira, Sinval G. [1 ]
de Melo, Vanessa J. [1 ]
Pilo-Veloso, Dorila [2 ]
Zambolim, Laercio [3 ]
机构
[1] Univ Fed Vicosa, Dept Quim, CCE, BR-36570000 Vicosa, MG, Brazil
[2] Univ Fed Minas Gerais, Dept Quim, ICEx, BR-31270901 Belo Horizonte, MG, Brazil
[3] Univ Fed Vicosa, Dept Fitopatol, CCA, BR-36570000 Vicosa, MG, Brazil
关键词
D O I
10.1002/cbdv.200790223
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
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收藏
页码:2745 / 2754
页数:10
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