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Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720

Marine-derived microorganisms possess the unique metabolic pathways to produce structurally novel secondary metabolites with potent biological activities. In this study, bioactivity-guided isolation of the marine deep-sea-derived fungus Aspergillus flavipes DS720 led to the characterization of four...

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Autores principales: Xu, An, Xu, Xiang-Nan, Zhang, Mi, Li, Chun-Lian, Liu, Li, Fu, De-Yuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9355579/
https://www.ncbi.nlm.nih.gov/pubmed/35935239
http://dx.doi.org/10.3389/fmicb.2022.959754
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author Xu, An
Xu, Xiang-Nan
Zhang, Mi
Li, Chun-Lian
Liu, Li
Fu, De-Yuan
author_facet Xu, An
Xu, Xiang-Nan
Zhang, Mi
Li, Chun-Lian
Liu, Li
Fu, De-Yuan
author_sort Xu, An
collection PubMed
description Marine-derived microorganisms possess the unique metabolic pathways to produce structurally novel secondary metabolites with potent biological activities. In this study, bioactivity-guided isolation of the marine deep-sea-derived fungus Aspergillus flavipes DS720 led to the characterization of four indole alkaloids (compounds 1–4) and four polyketides (compounds 5–8), such as two new indoles, flavonoids A (1) and B (2) with a C-6 reversed prenylation, and a new azaphilone, flaviazaphilone A (5). Their chemical structures were unambiguously established by an extensive interpretation of spectroscopic data, such as 1D/2D NMR and HRESIMS data. The absolute configurations of the new compound 5 were solved by comparing the experimental and calculated Electronic Circular Dichroism (ECD) spectra. Since sufficient amount of flavonoids A (1) was obtained, 1 was subjected to a large-scale cytotoxic activity screening against 20 different human tumor cell lines. The results revealed that 1 showed broad-spectrum cytotoxicities against HeLa, 5637, CAL-62, PATU8988T, A-375, and A-673 cell lines, with the inhibition rates of more than 90%. This study indicated that the newly discovered indole alkaloid 1 may possess certain potential for the development of lead compounds in the future.
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spelling pubmed-93555792022-08-06 Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720 Xu, An Xu, Xiang-Nan Zhang, Mi Li, Chun-Lian Liu, Li Fu, De-Yuan Front Microbiol Microbiology Marine-derived microorganisms possess the unique metabolic pathways to produce structurally novel secondary metabolites with potent biological activities. In this study, bioactivity-guided isolation of the marine deep-sea-derived fungus Aspergillus flavipes DS720 led to the characterization of four indole alkaloids (compounds 1–4) and four polyketides (compounds 5–8), such as two new indoles, flavonoids A (1) and B (2) with a C-6 reversed prenylation, and a new azaphilone, flaviazaphilone A (5). Their chemical structures were unambiguously established by an extensive interpretation of spectroscopic data, such as 1D/2D NMR and HRESIMS data. The absolute configurations of the new compound 5 were solved by comparing the experimental and calculated Electronic Circular Dichroism (ECD) spectra. Since sufficient amount of flavonoids A (1) was obtained, 1 was subjected to a large-scale cytotoxic activity screening against 20 different human tumor cell lines. The results revealed that 1 showed broad-spectrum cytotoxicities against HeLa, 5637, CAL-62, PATU8988T, A-375, and A-673 cell lines, with the inhibition rates of more than 90%. This study indicated that the newly discovered indole alkaloid 1 may possess certain potential for the development of lead compounds in the future. Frontiers Media S.A. 2022-07-22 /pmc/articles/PMC9355579/ /pubmed/35935239 http://dx.doi.org/10.3389/fmicb.2022.959754 Text en Copyright © 2022 Xu, Xu, Zhang, Li, Liu and Fu. 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
Xu, An
Xu, Xiang-Nan
Zhang, Mi
Li, Chun-Lian
Liu, Li
Fu, De-Yuan
Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title_full Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title_fullStr Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title_full_unstemmed Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title_short Cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus Aspergillus flavipes DS720
title_sort cytotoxic indole alkaloids and polyketides produced by a marine-derived fungus aspergillus flavipes ds720
topic Microbiology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9355579/
https://www.ncbi.nlm.nih.gov/pubmed/35935239
http://dx.doi.org/10.3389/fmicb.2022.959754
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