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Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities
Six new heptaketides, pleosporalins A–F (1–5, and 7), and a new heptaketide derivative, pleosporalin G (9), together with four biosynthetically related known compounds (6, 8, 10, and 11), were isolated from an endophytic fungus, Pleosporales sp. F46, found in the medicinal plant Mahonia fortunei. Th...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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The Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063763/ https://www.ncbi.nlm.nih.gov/pubmed/35520807 http://dx.doi.org/10.1039/c9ra01956a |
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author | Li, Gang Xu, Ke Chen, Wen-Qi Guo, Zhi-Hao Liu, Yu-Tong Qiao, Ya-Nan Sun, Yong Sun, Gang Peng, Xiao-Ping Lou, Hong-Xiang |
author_facet | Li, Gang Xu, Ke Chen, Wen-Qi Guo, Zhi-Hao Liu, Yu-Tong Qiao, Ya-Nan Sun, Yong Sun, Gang Peng, Xiao-Ping Lou, Hong-Xiang |
author_sort | Li, Gang |
collection | PubMed |
description | Six new heptaketides, pleosporalins A–F (1–5, and 7), and a new heptaketide derivative, pleosporalin G (9), together with four biosynthetically related known compounds (6, 8, 10, and 11), were isolated from an endophytic fungus, Pleosporales sp. F46, found in the medicinal plant Mahonia fortunei. The structures and stereochemistry of these compounds were established by extensive spectroscopic analyses including LC-HRMS, NMR spectroscopy, optical rotations, ECD calculations, and single-crystal X-ray diffraction. The antifungal activities of isolated compounds 1–11 were investigated against Candida albicans, and their cytotoxic activities were evaluated against A549, SMMC-721, and MDA-MB-231 cancer cell lines. Compound 1 was active against C. albicans with an MIC(80) of 128 μg mL(−1), and compound 7 showed moderate cytotoxicity against MDA-MB-231 with an IC(50) of 22.4 ± 1.1 μM. By comparing compounds 1 and 7 with structurally related metabolites, it was revealed that alterations to their C-1 or C-2 substitutions could significantly influence their antifungal or cytotoxic efficacies. |
format | Online Article Text |
id | pubmed-9063763 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90637632022-05-04 Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities Li, Gang Xu, Ke Chen, Wen-Qi Guo, Zhi-Hao Liu, Yu-Tong Qiao, Ya-Nan Sun, Yong Sun, Gang Peng, Xiao-Ping Lou, Hong-Xiang RSC Adv Chemistry Six new heptaketides, pleosporalins A–F (1–5, and 7), and a new heptaketide derivative, pleosporalin G (9), together with four biosynthetically related known compounds (6, 8, 10, and 11), were isolated from an endophytic fungus, Pleosporales sp. F46, found in the medicinal plant Mahonia fortunei. The structures and stereochemistry of these compounds were established by extensive spectroscopic analyses including LC-HRMS, NMR spectroscopy, optical rotations, ECD calculations, and single-crystal X-ray diffraction. The antifungal activities of isolated compounds 1–11 were investigated against Candida albicans, and their cytotoxic activities were evaluated against A549, SMMC-721, and MDA-MB-231 cancer cell lines. Compound 1 was active against C. albicans with an MIC(80) of 128 μg mL(−1), and compound 7 showed moderate cytotoxicity against MDA-MB-231 with an IC(50) of 22.4 ± 1.1 μM. By comparing compounds 1 and 7 with structurally related metabolites, it was revealed that alterations to their C-1 or C-2 substitutions could significantly influence their antifungal or cytotoxic efficacies. The Royal Society of Chemistry 2019-04-26 /pmc/articles/PMC9063763/ /pubmed/35520807 http://dx.doi.org/10.1039/c9ra01956a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Li, Gang Xu, Ke Chen, Wen-Qi Guo, Zhi-Hao Liu, Yu-Tong Qiao, Ya-Nan Sun, Yong Sun, Gang Peng, Xiao-Ping Lou, Hong-Xiang Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title | Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title_full | Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title_fullStr | Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title_full_unstemmed | Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title_short | Heptaketides from the endophytic fungus Pleosporales sp. F46 and their antifungal and cytotoxic activities |
title_sort | heptaketides from the endophytic fungus pleosporales sp. f46 and their antifungal and cytotoxic activities |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063763/ https://www.ncbi.nlm.nih.gov/pubmed/35520807 http://dx.doi.org/10.1039/c9ra01956a |
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