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Chemical Composition, Antibacterial Activity and Mechanism of Action of Fermentation Products from Aspergillus Niger xj

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Abstract

Six compounds were isolated and purified from the crude acetone extract of Aspergillus niger xj. Characterization of all compounds was done by NMR and MS. On the basis of chemical and spectral analysis structure, six compounds were elucidated as metazachlor (1), nonacosane (2), palmitic acid (3), 5,5’-oxybis(5-methylene-2-furaldehyde) (4), dimethyl 5-nitroisophthalate (5) and cholesta-3,5-dien-7-one (6), respectively, and compounds 1, 4, 5 and 6 were isolated for the first time from A. niger. To evaluate the antibacterial activity of compounds 1–6 against three plant pathogenic bacteria (Agrobacterium tumefaciens T-37, Erwinia carotovora EC-1 and Ralstonia solanacearum RS-2), and the minimum inhibitory concentrations (MICs) were determined by broth microdilution method in 96-well microtiter plates. Results of the evaluation of the antibacterial activity showed that T-37 strain was more susceptible to metazachlor with the lowest MIC of 31.25 µg/mL. The antibacterial activity of metazachlor has rarely been reported, thus the antibacterial mechanism of metazachlor against T-37 strain were investigated. The permeability of cell membrane demonstrated that cells membranes were broken by metazachlor, which caused leakage of ions in cells. SDS-PAGE of T-37 proteins indicated that metazachlor could damage bacterial cells through the destruction of cellular proteins. Scanning electron microscopy results showed obvious morphological and ultrastructural changes in the T-37 cells, further confirming the cell membrane damages caused by metazachlor. Overall, our findings demonstrated that the ability of metazachlor to suppress the growth of T-37 pathogenic bacteria makes it potential biocontrol agents.

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Data Availability

All data generated or analyzed during this study are included in this published article.

Abbreviations

MIC:

Minimum inhibitory concentration

PDA:

Potato dextrose agar

PDB:

Potato dextrose broth

LB:

Luria-Bertani

CC:

Column chromatography

TLC:

Thin layer chromatography

DMSO:

Dimethyl sulfoxide

CPL:

Chloramphenicol

LC-MS:

Liquid Chromatograph Mass Spectrometer

EI-MS:

Electron ionization mass spectrometry

NMR:

Nuclear magnetic resonance

EC50 :

Half maximal effective concentration

SEM:

Scanning electron microscopy

SDS-PAGE:

Sodium dodecyl sulphate-polyacrylamide gel electrophoresis

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Funding

This work was supported by the Guizhou Province High-level Innovative Talent Project (Qiankehe Platform Talent-GCC[2022]027−1), and the Science and Technology Project of Guizhou Province (grant number [2021]193).

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Author notes

  1. Longfeng Wei, Jiang Ran contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Plant Resource Conservation and Germplasm Innovation in Mountainous Region (Ministry of Education), College of Life Sciences, Institute of Agro-bioengineering, Guizhou University, Guiyang, Guizhou Province, 550025, China

    Longfeng Wei, Jiang Ran, Zhu Li, Qinyu Zhang, Kun Guo, Yudan Xie & Ailin Xie

  2. Guizhou Key Laboratory of Agricultural Biotechnology, Guiyang, 550009, China

    Zhu Li

  3. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, China

    Shuzhen Mu

  4. Institution of Supervision and Inspection Product Quality of Guizhou Province, Guiyang, China

    Yang Xiao

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  1. Longfeng Wei
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  2. Jiang Ran
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  3. Zhu Li
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Contributions

Material preparation, data collection and analysis were performed by Longfeng Wei, Jiang Ran and Zhu Li. The original manuscript was written by Longfeng Wei and Jiang Ran. Qinyu Zhang and Kun Guo analyzed the data. Shuzhen Mu and Yang Xiao contributed to the identification of compounds. Yudan Xie, and Ailin Xie helped to revise the manuscript. All authors read and approved the final manuscript.

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Correspondence to Zhu Li.

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Wei, L., Ran, J., Li, Z. et al. Chemical Composition, Antibacterial Activity and Mechanism of Action of Fermentation Products from Aspergillus Niger xj. Appl Biochem Biotechnol 196, 878–895 (2024). https://doi.org/10.1007/s12010-023-04577-9

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