Identification of Antibacterial Metabolites from Endophytic Fungus Isolated from Leaves (Fabaceae), Utilizing Metabolomic and Molecular Docking Techniques

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2022 Feb 15

PMID 35164382

Authors

Mai E Hussein

Osama G Mohamed

Ahlam M El-Fishawy

Hesham I El-Askary

Amira S El-Senousy

Ahmed A El-Beih

Eman S Nossier

Ahmed M Naglah

Abdulrahman A Almehizia

Ashootosh Tripathi

Ahmed A Hamed

Affiliations

Soon will be listed here.

Abstract

The rapid spread of bacterial infection caused by has become a problem to public health despite the presence of past trials devoted to controlling the infection. Thus, the current study aimed to explore the chemical composition of the extract of endophytic fungus , isolated from leaves, and investigate the antimicrobial activity of isolated metabolites and their probable mode of actions. The chemical investigation of the fungal extract via UPLC/MS/MS led to the identification of at least forty-two metabolites, as well as the isolation and complete characterization of eight reported metabolites. The antibacterial activities of isolated metabolites were assessed against using agar disc diffusion and microplate dilution methods. Compounds ergosterol, helvolic acid and monomethyl sulochrin-4-sulphate showed minimal inhibitory concentration (MIC) values of 15.63, 1.95 and 3.90 µg/mL, respectively, compared to ciprofloxacin. We also report the inhibitory activity of the fungal extract on DNA gyrase and topoisomerase IV, which led us to perform molecular docking using the three most active compounds isolated from the extract against both enzymes. These active compounds had the required structural features for DNA gyrase and topoisomerase IV inhibition, evidenced via molecular docking.

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References

Kojima Y, Honda C, Kobayashi I, Katsuta R, Matsumura S, Wagatsuma I . Transglycosylation Forms Novel Glycoside Ethyl α-Maltoside and Ethyl α-Isomaltoside in Sake during the Brewing Process by α-Glucosidase A of . J Agric Food Chem. 2020; 68(5):1419-1426. DOI: 10.1021/acs.jafc.9b06936. View

Hamed A, Soldatou S, Qader M, Arjunan S, Miranda K, Casolari F . Screening Fungal Endophytes Derived from Under-Explored Egyptian Marine Habitats for Antimicrobial and Antioxidant Properties in Factionalised Textiles. Microorganisms. 2020; 8(10). PMC: 7594075. DOI: 10.3390/microorganisms8101617. View

Mohamed O, Khalil Z, Salim A, Cui H, Blumenthal A, Capon R . Lincolnenins A-D: Isomeric Bactericidal Bianthracenes from . J Org Chem. 2020; 86(16):11011-11018. DOI: 10.1021/acs.joc.0c02492. View

Correia-da-Silva M, Sousa E, Pinto M . Emerging sulfated flavonoids and other polyphenols as drugs: nature as an inspiration. Med Res Rev. 2013; 34(2):223-79. DOI: 10.1002/med.21282. View

Chen Y, Dong J, Liu J, Xu W, Wei Z, Li Y . Network Pharmacology-Based Investigation of Protective Mechanism of on Lipopolysaccharide-Induced Acute Lung Injury. Int J Mol Sci. 2019; 20(3). PMC: 6387216. DOI: 10.3390/ijms20030543. View

El-Hawary S, Sayed A, Rateb M, Bakeer W, AbouZid S, Mohammed R . Secondary metabolites from fungal endophytes of Solanum nigrum. Nat Prod Res. 2017; 31(21):2568-2571. DOI: 10.1080/14786419.2017.1327859. View

Nagia M, El-Metwally M, Shaaban M, El-Zalabani S, Hanna A . Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Org Med Chem Lett. 2012; 2(1):9. PMC: 3349564. DOI: 10.1186/2191-2858-2-9. View

Cano P, Jamin E, Tadrist S, Bourdaudhui P, Pean M, Debrauwer L . New untargeted metabolic profiling combining mass spectrometry and isotopic labeling: application on Aspergillus fumigatus grown on wheat. Anal Chem. 2013; 85(17):8412-20. DOI: 10.1021/ac401872f. View

Ferreira E, Torres M, da Silva A, Colares L, Pires K, Lotufo T . Prospecting Anticancer Compounds in Actinomycetes Recovered from the Sediments of Saint Peter and Saint Paul's Archipelago, Brazil. Chem Biodivers. 2016; 13(9):1149-1157. DOI: 10.1002/cbdv.201500514. View

10.

Li H, Xiao J, Gao Y, Tang J, Zhang A, Gao J . Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. J Agric Food Chem. 2014; 62(17):3734-41. DOI: 10.1021/jf500390h. View

11.

Nielsen K, Mansson M, Rank C, Frisvad J, Larsen T . Dereplication of microbial natural products by LC-DAD-TOFMS. J Nat Prod. 2011; 74(11):2338-48. DOI: 10.1021/np200254t. View

12.

Liang Z, Zhang T, Zhang X, Zhang J, Zhao C . An alkaloid and a steroid from the endophytic fungus Aspergillus fumigatus. Molecules. 2015; 20(1):1424-33. PMC: 6272270. DOI: 10.3390/molecules20011424. View

13.

Tamiya H, Ochiai E, Kikuchi K, Yahiro M, Toyotome T, Watanabe A . Secondary metabolite profiles and antifungal drug susceptibility of Aspergillus fumigatus and closely related species, Aspergillus lentulus, Aspergillus udagawae, and Aspergillus viridinutans. J Infect Chemother. 2015; 21(5):385-91. DOI: 10.1016/j.jiac.2015.01.005. View

14.

Frisvad J, Rank C, Nielsen K, Larsen T . Metabolomics of Aspergillus fumigatus. Med Mycol. 2008; 47 Suppl 1:S53-71. DOI: 10.1080/13693780802307720. View

15.

Ge H, Yu Z, Zhang J, Wu J, Tan R . Bioactive alkaloids from endophytic Aspergillus fumigatus. J Nat Prod. 2009; 72(4):753-5. DOI: 10.1021/np800700e. View

16.

Jiao R, Xu S, Liu J, Ge H, Ding H, Xu C . Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Org Lett. 2006; 8(25):5709-12. DOI: 10.1021/ol062257t. View

17.

Han J, Liu M, Jenkins I, Liu X, Zhang L, Quinn R . Genome-Inspired Chemical Exploration of Marine Fungus MF071. Mar Drugs. 2020; 18(7). PMC: 7401266. DOI: 10.3390/md18070352. View

18.

Tomasic T, Katsamakas S, Hodnik Z, Ilas J, Brvar M, Solmajer T . Discovery of 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site. J Med Chem. 2015; 58(14):5501-21. DOI: 10.1021/acs.jmedchem.5b00489. View

19.

Sajjad-Ur-Rahman , Rasool M, Rafi M . Penicillin production by wild isolates of Penicillium chrysogenum in Pakistan. Braz J Microbiol. 2013; 43(2):476-81. PMC: 3768827. DOI: 10.1590/S1517-83822012000200007. View

20.

El-Elimat T, Figueroa M, Ehrmann B, Cech N, Pearce C, Oberlies N . High-resolution MS, MS/MS, and UV database of fungal secondary metabolites as a dereplication protocol for bioactive natural products. J Nat Prod. 2013; 76(9):1709-16. PMC: 3856222. DOI: 10.1021/np4004307. View