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Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi
Three new antibacterial spirooxindole alkaloids, spirobrefeldins A–C (1–3), together with four known analogs, spirotryprostatin M (4), spirotryprostatin G (5), 12β-hydroxyverruculogen TR-2 (6), and 12α-hydroxyverruculogen TR-2 (7), were isolated from terrestrial fungus Penicillium brefeldianum. All...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9702524/ https://www.ncbi.nlm.nih.gov/pubmed/36452922 http://dx.doi.org/10.3389/fmicb.2022.1046099 |
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author | Shi, Huajun Jiang, Jinyan Zhang, Hang Jiang, Haimei Su, Zijie Liu, Dandan Jie, Ligang He, Fei |
author_facet | Shi, Huajun Jiang, Jinyan Zhang, Hang Jiang, Haimei Su, Zijie Liu, Dandan Jie, Ligang He, Fei |
author_sort | Shi, Huajun |
collection | PubMed |
description | Three new antibacterial spirooxindole alkaloids, spirobrefeldins A–C (1–3), together with four known analogs, spirotryprostatin M (4), spirotryprostatin G (5), 12β-hydroxyverruculogen TR-2 (6), and 12α-hydroxyverruculogen TR-2 (7), were isolated from terrestrial fungus Penicillium brefeldianum. All the new compounds were elucidated extensively by the interpretation of their NMR (1D and 2D) spectra and high-resolution mass data, and their absolute configurations were determined by computational chemistry and CD spectra. The absolute configurations of spiro carbon C-2 in spirotryprostatin G (5) and spirotryprostatin C in literature were reported as S, which were revised to R based on experimental and calculated CD spectra. All the compounds were evaluated for their antimicrobial activities toward Pseudomonas aeruginosa PAO1, Dickeya zeae EC1, Staphylococcus epidermidis, Escherichia coli, and Sporisorium scitamineum. Compound 7 displayed moderate inhibitory activity toward dimorphic switch of pathogenic smut fungi Sporisorium scitamineum at 25 μM. Compounds 3 and 6 showed weak antibacterial activities against phytopathogenic bacterial Dickeya zeae EC1 at 100 μM. |
format | Online Article Text |
id | pubmed-9702524 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-97025242022-11-29 Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi Shi, Huajun Jiang, Jinyan Zhang, Hang Jiang, Haimei Su, Zijie Liu, Dandan Jie, Ligang He, Fei Front Microbiol Microbiology Three new antibacterial spirooxindole alkaloids, spirobrefeldins A–C (1–3), together with four known analogs, spirotryprostatin M (4), spirotryprostatin G (5), 12β-hydroxyverruculogen TR-2 (6), and 12α-hydroxyverruculogen TR-2 (7), were isolated from terrestrial fungus Penicillium brefeldianum. All the new compounds were elucidated extensively by the interpretation of their NMR (1D and 2D) spectra and high-resolution mass data, and their absolute configurations were determined by computational chemistry and CD spectra. The absolute configurations of spiro carbon C-2 in spirotryprostatin G (5) and spirotryprostatin C in literature were reported as S, which were revised to R based on experimental and calculated CD spectra. All the compounds were evaluated for their antimicrobial activities toward Pseudomonas aeruginosa PAO1, Dickeya zeae EC1, Staphylococcus epidermidis, Escherichia coli, and Sporisorium scitamineum. Compound 7 displayed moderate inhibitory activity toward dimorphic switch of pathogenic smut fungi Sporisorium scitamineum at 25 μM. Compounds 3 and 6 showed weak antibacterial activities against phytopathogenic bacterial Dickeya zeae EC1 at 100 μM. Frontiers Media S.A. 2022-11-14 /pmc/articles/PMC9702524/ /pubmed/36452922 http://dx.doi.org/10.3389/fmicb.2022.1046099 Text en Copyright © 2022 Shi, Jiang, Zhang, Jiang, Su, Liu, Jie and He. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Microbiology Shi, Huajun Jiang, Jinyan Zhang, Hang Jiang, Haimei Su, Zijie Liu, Dandan Jie, Ligang He, Fei Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title | Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title_full | Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title_fullStr | Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title_full_unstemmed | Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title_short | Antibacterial spirooxindole alkaloids from Penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
title_sort | antibacterial spirooxindole alkaloids from penicillium brefeldianum inhibit dimorphism of pathogenic smut fungi |
topic | Microbiology |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9702524/ https://www.ncbi.nlm.nih.gov/pubmed/36452922 http://dx.doi.org/10.3389/fmicb.2022.1046099 |
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