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Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity

  • Mohamed Shaaban ORCID logo EMAIL logo , Hamdi Nasr , Tahia K. Mohamed , Samy F. Mahmoud , Mohammad M. El-Metwally and Ahmed B. Abdelwahab
Published/Copyright: March 18, 2022
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Zeitschrift für Naturforschung C
From the journal Zeitschrift für Naturforschung C Volume 78 Issue 3-4

Abstract

Four bioactive metabolites; ergosterol (1), peroxy ergosterol (2), α-cyclopiazonic acid (3) and kojic acid (4), were isolated from the fungal sp. Trichoderma viride MM21. Their structures were assigned by cumulative analysis of NMR and mass spectra, and comparison with literature. The antimicrobial activity of the fungus supernatant, mycelial cake, cumulative crude extract and compounds 1–4 was broadly studied against 11 diverse pathogens, revealing auspicious activity results. Based on the molecular docking, ergosterol (1) and peroxy ergosterol (2) were picked up to be computationally tested against topoisomerase IV of Staphylococcus aureus. The nominated enzyme is a possible target for the antibacterial activity of triterpenoidal/steroidal compounds. Compounds 1, 2 showed a deep inserting inside the enzyme groove recording a good binding affinity of −8.1 and −8.4 kcal/mol, respectively. Noteworthy that the antibacterial activity of ergosterol was higher (14–17 mm) than peroxy ergosterol (11–14 mm), although ergosterol formed only one hydrogen bond with the target, while peroxy ergosterol formed three hydrogen bonds. Such higher antibacterial activity of ergosterol may be attributed to its interference with other proteins included in this inhibition. The cytotoxic activity was tested against brine shrimp, revealing 100% mortality for the supernatant, crude extract and whole isolated compounds. Such strong cytotoxicity is attributed most likely to the abundant productivity/concentration of α-cyclopiazonic acid and kojic acid.

Keywords: antimicrobial activity; bioactive compounds; cytotoxicity; molecular docking; Trichoderma viride MM21
Corresponding author: Mohamed Shaaban, Chemistry of Natural Compounds Department, Pharmaceutical Industries Research Institute, National Research Centre, El-Behoos St. 33, Dokki, Cairo 12622, Egypt; and Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany, E-mail:

Acknowledgment

The authors also are grateful to Prof. Laatsch for lab facilities in institute of organic and biomolecular chemistry, Göttingen, providing spectral and analytical data for the research work done. We are indebted to Mrs. F. Lissy for antimicrobial and cytotoxicity testing and Mr. A. Kohl for technical assistance.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: We appreciate and thank Taif University for the financial support for Taif University Researchers Supporting Project (TURSP-2020/138), Taif University, Taif, Saudi Arabia.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-09-01
Accepted: 2022-02-19
Published Online: 2022-03-18
Published in Print: 2023-03-28

© 2022 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Organic chemistry and medicinal applications
  4. Research Articles
  5. Nitroimidazoles Part 10. Synthesis, crystal structure, molecular docking, and anticancer evaluation of 4-nitroimidazole derivatives combined with piperazine moiety
  6. Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents
  7. Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
  8. Design, synthesis, and molecular docking study of novel cinnoline derivatives as potential inhibitors of tubulin polymerization
  9. Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon
  10. Thermodynamic control synthesis of spiro[oxindole-3,3′-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline
  11. Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
  12. 8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
https://doi.org/10.1515/znc-2021-0284
Keywords for this article
antimicrobial activity; bioactive compounds; cytotoxicity; molecular docking; Trichoderma viride MM21

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Organic chemistry and medicinal applications
  4. Research Articles
  5. Nitroimidazoles Part 10. Synthesis, crystal structure, molecular docking, and anticancer evaluation of 4-nitroimidazole derivatives combined with piperazine moiety
  6. Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents
  7. Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
  8. Design, synthesis, and molecular docking study of novel cinnoline derivatives as potential inhibitors of tubulin polymerization
  9. Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon
  10. Thermodynamic control synthesis of spiro[oxindole-3,3′-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline
  11. Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
  12. 8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
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