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New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003

Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumari...

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Autores principales: Xu, Xiuli, Li, Jiangpeng, Zhang, Kai, Wei, Shangzhu, Lin, Rui, Polyak, Steven W., Yang, Na, Song, Fuhang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227774/
https://www.ncbi.nlm.nih.gov/pubmed/34071288
http://dx.doi.org/10.3390/md19060313
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author Xu, Xiuli
Li, Jiangpeng
Zhang, Kai
Wei, Shangzhu
Lin, Rui
Polyak, Steven W.
Yang, Na
Song, Fuhang
author_facet Xu, Xiuli
Li, Jiangpeng
Zhang, Kai
Wei, Shangzhu
Lin, Rui
Polyak, Steven W.
Yang, Na
Song, Fuhang
author_sort Xu, Xiuli
collection PubMed
description Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A (12), paraphamide B (13), and paraphamide C (14), together with five known compounds, oospolactone (7), 8-O-methyloospolactone (8), 10-hydroxyoospolactone (9), 9,10-dihydroxyoospolactone (10), and oospoglycol (11), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12–14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL.
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spelling pubmed-82277742021-06-26 New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003 Xu, Xiuli Li, Jiangpeng Zhang, Kai Wei, Shangzhu Lin, Rui Polyak, Steven W. Yang, Na Song, Fuhang Mar Drugs Article Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A (12), paraphamide B (13), and paraphamide C (14), together with five known compounds, oospolactone (7), 8-O-methyloospolactone (8), 10-hydroxyoospolactone (9), 9,10-dihydroxyoospolactone (10), and oospoglycol (11), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12–14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL. MDPI 2021-05-28 /pmc/articles/PMC8227774/ /pubmed/34071288 http://dx.doi.org/10.3390/md19060313 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Xu, Xiuli
Li, Jiangpeng
Zhang, Kai
Wei, Shangzhu
Lin, Rui
Polyak, Steven W.
Yang, Na
Song, Fuhang
New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title_full New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title_fullStr New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title_full_unstemmed New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title_short New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
title_sort new isocoumarin analogues from the marine-derived fungus paraphoma sp. cugbmf180003
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227774/
https://www.ncbi.nlm.nih.gov/pubmed/34071288
http://dx.doi.org/10.3390/md19060313
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