Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
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 antim...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Shaaban, Mohamed [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2022 |
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| Anmerkung: |
© 2022 Walter de Gruyter GmbH, Berlin/Boston |
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| Übergeordnetes Werk: |
Enthalten in: Zeitschrift für Naturforschung. C, Biosciences - De Gruyter, 1973, 78(2022), 3-4 vom: 18. März, Seite 149-156 |
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| Übergeordnetes Werk: |
volume:78 ; year:2022 ; number:3-4 ; day:18 ; month:03 ; pages:149-156 |
| Links: |
|---|
| DOI / URN: |
10.1515/znc-2021-0284 |
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OLC2143421575 |
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| 520 | |a 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. | ||
| 700 | 1 | |a Nasr, Hamdi |4 aut | |
| 700 | 1 | |a Mohamed, Tahia K. |4 aut | |
| 700 | 1 | |a Mahmoud, Samy F. |4 aut | |
| 700 | 1 | |a El-Metwally, Mohammad M. |4 aut | |
| 700 | 1 | |a Abdelwahab, Ahmed B. |4 aut | |
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10.1515/znc-2021-0284 doi (DE-627)OLC2143421575 (DE-B1597)znc-2021-0284-p DE-627 ger DE-627 rakwb eng 500 VZ 570 VZ 12 ssgn BIODIV DE-30 fid Shaaban, Mohamed verfasserin (orcid)0000-0001-9281-2505 aut Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity 2022 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © 2022 Walter de Gruyter GmbH, Berlin/Boston 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. Nasr, Hamdi aut Mohamed, Tahia K. aut Mahmoud, Samy F. aut El-Metwally, Mohammad M. aut Abdelwahab, Ahmed B. aut Enthalten in Zeitschrift für Naturforschung. C, Biosciences De Gruyter, 1973 78(2022), 3-4 vom: 18. März, Seite 149-156 (DE-627)129307394 (DE-600)124636-7 (DE-576)014504936 0939-5075 nnns volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 https://doi.org/10.1515/znc-2021-0284 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-FOR GBV_ILN_70 GBV_ILN_121 GBV_ILN_252 GBV_ILN_2237 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4277 GBV_ILN_4302 GBV_ILN_4320 AR 78 2022 3-4 18 03 149-156 |
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10.1515/znc-2021-0284 doi (DE-627)OLC2143421575 (DE-B1597)znc-2021-0284-p DE-627 ger DE-627 rakwb eng 500 VZ 570 VZ 12 ssgn BIODIV DE-30 fid Shaaban, Mohamed verfasserin (orcid)0000-0001-9281-2505 aut Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity 2022 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © 2022 Walter de Gruyter GmbH, Berlin/Boston 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. Nasr, Hamdi aut Mohamed, Tahia K. aut Mahmoud, Samy F. aut El-Metwally, Mohammad M. aut Abdelwahab, Ahmed B. aut Enthalten in Zeitschrift für Naturforschung. C, Biosciences De Gruyter, 1973 78(2022), 3-4 vom: 18. März, Seite 149-156 (DE-627)129307394 (DE-600)124636-7 (DE-576)014504936 0939-5075 nnns volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 https://doi.org/10.1515/znc-2021-0284 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-FOR GBV_ILN_70 GBV_ILN_121 GBV_ILN_252 GBV_ILN_2237 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4277 GBV_ILN_4302 GBV_ILN_4320 AR 78 2022 3-4 18 03 149-156 |
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10.1515/znc-2021-0284 doi (DE-627)OLC2143421575 (DE-B1597)znc-2021-0284-p DE-627 ger DE-627 rakwb eng 500 VZ 570 VZ 12 ssgn BIODIV DE-30 fid Shaaban, Mohamed verfasserin (orcid)0000-0001-9281-2505 aut Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity 2022 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © 2022 Walter de Gruyter GmbH, Berlin/Boston 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. Nasr, Hamdi aut Mohamed, Tahia K. aut Mahmoud, Samy F. aut El-Metwally, Mohammad M. aut Abdelwahab, Ahmed B. aut Enthalten in Zeitschrift für Naturforschung. C, Biosciences De Gruyter, 1973 78(2022), 3-4 vom: 18. März, Seite 149-156 (DE-627)129307394 (DE-600)124636-7 (DE-576)014504936 0939-5075 nnns volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 https://doi.org/10.1515/znc-2021-0284 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-FOR GBV_ILN_70 GBV_ILN_121 GBV_ILN_252 GBV_ILN_2237 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4277 GBV_ILN_4302 GBV_ILN_4320 AR 78 2022 3-4 18 03 149-156 |
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10.1515/znc-2021-0284 doi (DE-627)OLC2143421575 (DE-B1597)znc-2021-0284-p DE-627 ger DE-627 rakwb eng 500 VZ 570 VZ 12 ssgn BIODIV DE-30 fid Shaaban, Mohamed verfasserin (orcid)0000-0001-9281-2505 aut Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity 2022 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © 2022 Walter de Gruyter GmbH, Berlin/Boston 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. Nasr, Hamdi aut Mohamed, Tahia K. aut Mahmoud, Samy F. aut El-Metwally, Mohammad M. aut Abdelwahab, Ahmed B. aut Enthalten in Zeitschrift für Naturforschung. C, Biosciences De Gruyter, 1973 78(2022), 3-4 vom: 18. März, Seite 149-156 (DE-627)129307394 (DE-600)124636-7 (DE-576)014504936 0939-5075 nnns volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 https://doi.org/10.1515/znc-2021-0284 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-FOR GBV_ILN_70 GBV_ILN_121 GBV_ILN_252 GBV_ILN_2237 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4277 GBV_ILN_4302 GBV_ILN_4320 AR 78 2022 3-4 18 03 149-156 |
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10.1515/znc-2021-0284 doi (DE-627)OLC2143421575 (DE-B1597)znc-2021-0284-p DE-627 ger DE-627 rakwb eng 500 VZ 570 VZ 12 ssgn BIODIV DE-30 fid Shaaban, Mohamed verfasserin (orcid)0000-0001-9281-2505 aut Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity 2022 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © 2022 Walter de Gruyter GmbH, Berlin/Boston 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. Nasr, Hamdi aut Mohamed, Tahia K. aut Mahmoud, Samy F. aut El-Metwally, Mohammad M. aut Abdelwahab, Ahmed B. aut Enthalten in Zeitschrift für Naturforschung. C, Biosciences De Gruyter, 1973 78(2022), 3-4 vom: 18. März, Seite 149-156 (DE-627)129307394 (DE-600)124636-7 (DE-576)014504936 0939-5075 nnns volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 https://doi.org/10.1515/znc-2021-0284 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-FOR GBV_ILN_70 GBV_ILN_121 GBV_ILN_252 GBV_ILN_2237 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4277 GBV_ILN_4302 GBV_ILN_4320 AR 78 2022 3-4 18 03 149-156 |
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Enthalten in Zeitschrift für Naturforschung. C, Biosciences 78(2022), 3-4 vom: 18. März, Seite 149-156 volume:78 year:2022 number:3-4 day:18 month:03 pages:149-156 |
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bioactive secondary metabolites from trichoderma viride mm21: structure elucidation, molecular docking and biological activity |
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Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity |
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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. © 2022 Walter de Gruyter GmbH, Berlin/Boston |
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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. © 2022 Walter de Gruyter GmbH, Berlin/Boston |
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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. © 2022 Walter de Gruyter GmbH, Berlin/Boston |
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