Volume 49 Number 3

Antibacterial and antioxidant aromatic butenolide derivatives from the endophytic fungus Aspergillus flavipes XC5-7

Lulu Liu^a, Pan Wu^b, Rongya Zhang^a, Yaping Ma^a, Zhishun Chai^a, Yongwei Liang^b, Honghui Dong^b, Guofeng Yu^c,*, Ting Zhou^a, Lei Xing^a,*, Tianxiao Li^b,*

 
ABSTRACT:     Five bioactive aromatic butenolide derivatives were isolated from ethyl acetate (EtOAc) extracts of the endophytic fungus Aspergillus flavipes XC5-7, which was isolated from tobacco in China. Their structures were identified by 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectrometry (MS) spectroscopic analyses as aspernolide C (1), aspernolide H (2), butyrolactone II (3), aspulvinone P (4), and aspulvinone Q (5). Compound 1 exhibited significant antimicrobial activity against ten strains of bacteria with minimal inhibitory concentrations (MICs) in the range of 6.6 to 27.9 ?g/ml, especially against Enterococcus faecalis (MIC = 7.7 ?g/ml) and Escherichia coli (MIC = 6.6 ?g/ml). Aspulvinone P (4) and aspulvinone Q (5) were found to exhibit prominent antioxidant effects for the first time, with potencies [EC50 (half effective) = 13.3 and 16.0 ?M] that were two-fold greater than those of the positive control Trolox (EC50 = 32.7 ?M) in 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl free radical (DPPH) assays. In addition, the antibacterial and antioxidant structure-function relationships of these compounds were also studied and discussed.

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* Corresponding author, E-mail: jingyu825158@163.com, 304083106@qq.com, litianxiao1012@163.com

Received 30 Jul 2023, Accepted 21 Apr 2024