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Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods
Determination of the absolute configrations for natural products is one of the most important and challenging tasks, especially when the molecules display high conformational flexibility. In this paper, eight new prenylxanthones, aspergixanthones A-H (1–8), and one known analogue (9), were isolated...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6045578/ https://www.ncbi.nlm.nih.gov/pubmed/30006520 http://dx.doi.org/10.1038/s41598-018-28996-5 |
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author | Zhu, Ao Yang, Meng-Yue Zhang, Ya-Hui Shao, Chang-Lun Wang, Chang-Yun Hu, Lian-Dong Cao, Fei Zhu, Hua-Jie |
author_facet | Zhu, Ao Yang, Meng-Yue Zhang, Ya-Hui Shao, Chang-Lun Wang, Chang-Yun Hu, Lian-Dong Cao, Fei Zhu, Hua-Jie |
author_sort | Zhu, Ao |
collection | PubMed |
description | Determination of the absolute configrations for natural products is one of the most important and challenging tasks, especially when the molecules display high conformational flexibility. In this paper, eight new prenylxanthones, aspergixanthones A-H (1–8), and one known analogue (9), were isolated from the marine-derived fungus Aspergillus sp. ZA-01. The absolute configurations of C-14 and C-15 in 1–8 were difficult to be assigned due to the high conformational flexibility of the chains. To solve this problem, the experimental ECD, ORD, and VCD spectra of 1 were combined for analysis with the corresponding theoretical predictions for its different diastereomers. This study suggested that a concerted application of more than one chiroptical methods could be used as a preferable approach for the stereochemical characterizations of flexible molecules. Compounds 1–9 were evaluated for their cytotoxic and antibacterial activities. Among them, 6 showed cytotoxicity against the A-549 cell line with the IC(50) value of 1.1 μM, and 7 exhibited antibacterial activity against Micrococcus lysodeikticus with the MIC value of 0.78 μg/mL. |
format | Online Article Text |
id | pubmed-6045578 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-60455782018-07-16 Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods Zhu, Ao Yang, Meng-Yue Zhang, Ya-Hui Shao, Chang-Lun Wang, Chang-Yun Hu, Lian-Dong Cao, Fei Zhu, Hua-Jie Sci Rep Article Determination of the absolute configrations for natural products is one of the most important and challenging tasks, especially when the molecules display high conformational flexibility. In this paper, eight new prenylxanthones, aspergixanthones A-H (1–8), and one known analogue (9), were isolated from the marine-derived fungus Aspergillus sp. ZA-01. The absolute configurations of C-14 and C-15 in 1–8 were difficult to be assigned due to the high conformational flexibility of the chains. To solve this problem, the experimental ECD, ORD, and VCD spectra of 1 were combined for analysis with the corresponding theoretical predictions for its different diastereomers. This study suggested that a concerted application of more than one chiroptical methods could be used as a preferable approach for the stereochemical characterizations of flexible molecules. Compounds 1–9 were evaluated for their cytotoxic and antibacterial activities. Among them, 6 showed cytotoxicity against the A-549 cell line with the IC(50) value of 1.1 μM, and 7 exhibited antibacterial activity against Micrococcus lysodeikticus with the MIC value of 0.78 μg/mL. Nature Publishing Group UK 2018-07-13 /pmc/articles/PMC6045578/ /pubmed/30006520 http://dx.doi.org/10.1038/s41598-018-28996-5 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Zhu, Ao Yang, Meng-Yue Zhang, Ya-Hui Shao, Chang-Lun Wang, Chang-Yun Hu, Lian-Dong Cao, Fei Zhu, Hua-Jie Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title | Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title_full | Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title_fullStr | Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title_full_unstemmed | Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title_short | Absolute Configurations of 14,15-Hydroxylated Prenylxanthones from a Marine-Derived Aspergillus sp. Fungus by Chiroptical Methods |
title_sort | absolute configurations of 14,15-hydroxylated prenylxanthones from a marine-derived aspergillus sp. fungus by chiroptical methods |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6045578/ https://www.ncbi.nlm.nih.gov/pubmed/30006520 http://dx.doi.org/10.1038/s41598-018-28996-5 |
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