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New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

The chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1–8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were e...

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Autores principales: Xiao, Ze’en, Chen, Senhua, Cai, Runlin, Lin, Shao’e, Hong, Kui, She, Zhigang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082600/
https://www.ncbi.nlm.nih.gov/pubmed/27829913
http://dx.doi.org/10.3762/bjoc.12.196
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author Xiao, Ze’en
Chen, Senhua
Cai, Runlin
Lin, Shao’e
Hong, Kui
She, Zhigang
author_facet Xiao, Ze’en
Chen, Senhua
Cai, Runlin
Lin, Shao’e
Hong, Kui
She, Zhigang
author_sort Xiao, Ze’en
collection PubMed
description The chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1–8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were established by analysis of their spectroscopic data and the absolute configuration of compound 2 was unambiguously determined by X-ray structure analysis and ECD calculation. Moreover, the absolute configurations of compounds 3–5 were assigned by comparison of their ECD spectra with isocoumarins described in the literature. Asperisocoumarins C and D (3 and 4) were fully characterized spectroscopically and isolated from a natural source for the first time. Asperisocoumarins A–D (1–4) related to the class of furo[3,2-h]isocoumarins are rarely occurring in natural sources. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC(50) of 87.8, 52.3, and 95.6 μM, respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC(50) values of 125 and 138 μM, respectively.
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spelling pubmed-50826002016-11-09 New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242 Xiao, Ze’en Chen, Senhua Cai, Runlin Lin, Shao’e Hong, Kui She, Zhigang Beilstein J Org Chem Full Research Paper The chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1–8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were established by analysis of their spectroscopic data and the absolute configuration of compound 2 was unambiguously determined by X-ray structure analysis and ECD calculation. Moreover, the absolute configurations of compounds 3–5 were assigned by comparison of their ECD spectra with isocoumarins described in the literature. Asperisocoumarins C and D (3 and 4) were fully characterized spectroscopically and isolated from a natural source for the first time. Asperisocoumarins A–D (1–4) related to the class of furo[3,2-h]isocoumarins are rarely occurring in natural sources. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC(50) of 87.8, 52.3, and 95.6 μM, respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC(50) values of 125 and 138 μM, respectively. Beilstein-Institut 2016-09-23 /pmc/articles/PMC5082600/ /pubmed/27829913 http://dx.doi.org/10.3762/bjoc.12.196 Text en Copyright © 2016, Xiao et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Xiao, Ze’en
Chen, Senhua
Cai, Runlin
Lin, Shao’e
Hong, Kui
She, Zhigang
New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title_full New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title_fullStr New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title_full_unstemmed New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title_short New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242
title_sort new furoisocoumarins and isocoumarins from the mangrove endophytic fungus aspergillus sp. 085242
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082600/
https://www.ncbi.nlm.nih.gov/pubmed/27829913
http://dx.doi.org/10.3762/bjoc.12.196
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