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Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton

A novel polyphenolic natural product, galewone, with undescribed carbon skeleton, was isolated as a racemate from the culture of Daldinia eschscholzii IFB-TL01, a fungus obtained from the mantis (Tenodera aridifolia) gut. The galewone structure was elucidated by a combination of MS and NMR spectra,...

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Autores principales: Zhang, Ai Hua, Jiang, Nan, Wang, Xing Qi, Tan, Ren Xiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6778108/
https://www.ncbi.nlm.nih.gov/pubmed/31586120
http://dx.doi.org/10.1038/s41598-019-50868-9
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author Zhang, Ai Hua
Jiang, Nan
Wang, Xing Qi
Tan, Ren Xiang
author_facet Zhang, Ai Hua
Jiang, Nan
Wang, Xing Qi
Tan, Ren Xiang
author_sort Zhang, Ai Hua
collection PubMed
description A novel polyphenolic natural product, galewone, with undescribed carbon skeleton, was isolated as a racemate from the culture of Daldinia eschscholzii IFB-TL01, a fungus obtained from the mantis (Tenodera aridifolia) gut. The galewone structure was elucidated by a combination of MS and NMR spectra, and substantiated by X-ray crystallographic diffraction. The absolute stereochemistry of each galewone enantiomers was determined by the CD spectrum. In compliance of the structural similarities, galewone might be the shunt products of the dalesconol biosynthetic pathway. Both (−)- and ( + )-galewones were evaluated to be anti-fibrotic against activated hepatic stellate cell line, CFSC-8B, with the IC(50) values being 3.73 ± 0.21 and 10.10 ± 0.41 μM, respectively. Thus, galewone may serve as a starting molecule for the discovery of new anti-fibrotic drug.
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spelling pubmed-67781082019-10-09 Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton Zhang, Ai Hua Jiang, Nan Wang, Xing Qi Tan, Ren Xiang Sci Rep Article A novel polyphenolic natural product, galewone, with undescribed carbon skeleton, was isolated as a racemate from the culture of Daldinia eschscholzii IFB-TL01, a fungus obtained from the mantis (Tenodera aridifolia) gut. The galewone structure was elucidated by a combination of MS and NMR spectra, and substantiated by X-ray crystallographic diffraction. The absolute stereochemistry of each galewone enantiomers was determined by the CD spectrum. In compliance of the structural similarities, galewone might be the shunt products of the dalesconol biosynthetic pathway. Both (−)- and ( + )-galewones were evaluated to be anti-fibrotic against activated hepatic stellate cell line, CFSC-8B, with the IC(50) values being 3.73 ± 0.21 and 10.10 ± 0.41 μM, respectively. Thus, galewone may serve as a starting molecule for the discovery of new anti-fibrotic drug. Nature Publishing Group UK 2019-10-04 /pmc/articles/PMC6778108/ /pubmed/31586120 http://dx.doi.org/10.1038/s41598-019-50868-9 Text en © The Author(s) 2019 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
Zhang, Ai Hua
Jiang, Nan
Wang, Xing Qi
Tan, Ren Xiang
Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title_full Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title_fullStr Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title_full_unstemmed Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title_short Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton
title_sort galewone, an anti-fibrotic polyketide from daldinia eschscholzii with an undescribed carbon skeleton
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6778108/
https://www.ncbi.nlm.nih.gov/pubmed/31586120
http://dx.doi.org/10.1038/s41598-019-50868-9
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