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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
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.
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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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