Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), an...

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Main Authors:	Zhe Guo, Zhong-Mei Zou
Format:	Article
Language:	English
Published:	MDPI AG 2020-09-01
Series:	Molecules
Subjects:	epigenetic regulation NMR comparison Monosporascus eutypoides cyclopropane derivatives cytotoxic activities
Online Access:	https://www.mdpi.com/1420-3049/25/18/4192

id	doaj-f137404172034f099695e7e771515cf4
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spelling	doaj-f137404172034f099695e7e771515cf42020-11-25T02:31:44ZengMDPI AGMolecules1420-30492020-09-01254192419210.3390/molecules25184192Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>Zhe Guo0Zhong-Mei Zou1Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, ChinaInstitute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, ChinaOverexpression of the histone acetyltransferase and the <sup>1</sup>H NMR spectroscopic experiments of the endophytic fungus <i>Monosporascus eutypoides</i> resulted in the isolation of two new compounds, monosporasols A (<b>1</b>) and B (<b>2</b>), and two known compounds, pestaloficin C (3) and arthrinone (<b>4</b>). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds <b>1–2</b> were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.https://www.mdpi.com/1420-3049/25/18/4192epigenetic regulationNMR comparisonMonosporascus eutypoidescyclopropane derivativescytotoxic activities
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Zhe Guo Zhong-Mei Zou
spellingShingle	Zhe Guo Zhong-Mei Zou Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i> Molecules epigenetic regulation NMR comparison Monosporascus eutypoides cyclopropane derivatives cytotoxic activities
author_facet	Zhe Guo Zhong-Mei Zou
author_sort	Zhe Guo
title	Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>
title_short	Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>
title_full	Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>
title_fullStr	Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>
title_full_unstemmed	Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>
title_sort	discovery of new secondary metabolites by epigenetic regulation and nmr comparison from the plant endophytic fungus <i>monosporascus eutypoides</i>
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-09-01
description	Overexpression of the histone acetyltransferase and the <sup>1</sup>H NMR spectroscopic experiments of the endophytic fungus <i>Monosporascus eutypoides</i> resulted in the isolation of two new compounds, monosporasols A (<b>1</b>) and B (<b>2</b>), and two known compounds, pestaloficin C (3) and arthrinone (<b>4</b>). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds <b>1–2</b> were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.
topic	epigenetic regulation NMR comparison Monosporascus eutypoides cyclopropane derivatives cytotoxic activities
url	https://www.mdpi.com/1420-3049/25/18/4192
work_keys_str_mv	AT zheguo discoveryofnewsecondarymetabolitesbyepigeneticregulationandnmrcomparisonfromtheplantendophyticfungusimonosporascuseutypoidesi AT zhongmeizou discoveryofnewsecondarymetabolitesbyepigeneticregulationandnmrcomparisonfromtheplantendophyticfungusimonosporascuseutypoidesi
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Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus <i>Monosporascus eutypoides</i>

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