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Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai

Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensiv...

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Autores principales: Li, Hong-Lei, Li, Xiao-Ming, Yang, Sui-Qun, Meng, Ling-Hong, Li, Xin, Wang, Bin-Gui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891482/
https://www.ncbi.nlm.nih.gov/pubmed/31653083
http://dx.doi.org/10.3390/md17110605
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author Li, Hong-Lei
Li, Xiao-Ming
Yang, Sui-Qun
Meng, Ling-Hong
Li, Xin
Wang, Bin-Gui
author_facet Li, Hong-Lei
Li, Xiao-Ming
Yang, Sui-Qun
Meng, Ling-Hong
Li, Xin
Wang, Bin-Gui
author_sort Li, Hong-Lei
collection PubMed
description Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL.
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spelling pubmed-68914822019-12-18 Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai Li, Hong-Lei Li, Xiao-Ming Yang, Sui-Qun Meng, Ling-Hong Li, Xin Wang, Bin-Gui Mar Drugs Article Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL. MDPI 2019-10-24 /pmc/articles/PMC6891482/ /pubmed/31653083 http://dx.doi.org/10.3390/md17110605 Text en © 2019 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Li, Hong-Lei
Li, Xiao-Ming
Yang, Sui-Qun
Meng, Ling-Hong
Li, Xin
Wang, Bin-Gui
Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title_full Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title_fullStr Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title_full_unstemmed Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title_short Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
title_sort prenylated phenol and benzofuran derivatives from aspergillus terreus en-539, an endophytic fungus derived from marine red alga laurencia okamurai
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891482/
https://www.ncbi.nlm.nih.gov/pubmed/31653083
http://dx.doi.org/10.3390/md17110605
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