Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>

The fungal pathogen <i>Fusarium culmorum</i> causes Fusarium head blight in cereals, resulting in yield loss and contamination of the grain by type B trichothecene mycotoxins such as deoxynivalenol (DON), and its acetylated derivatives. Synthesis of trichothecenes is driven by a trichodi...

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Autores principales:	Safa Oufensou, Alessandro Dessì, Roberto Dallocchio, Virgilio Balmas, Emanuela Azara, Paola Carta, Quirico Migheli, Giovanna Delogu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Fusarium culmorum</i> trichothecene B phenols and hydroxylated biphenyls natural compounds plant health food safety and security Medicine R
Acceso en línea:	https://doaj.org/article/32029c3f25ac43638975c120067bde88
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spelling	oai:doaj.org-article:32029c3f25ac43638975c120067bde882021-11-25T19:08:37ZMolecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>10.3390/toxins131107592072-6651https://doaj.org/article/32029c3f25ac43638975c120067bde882021-10-01T00:00:00Zhttps://www.mdpi.com/2072-6651/13/11/759https://doaj.org/toc/2072-6651The fungal pathogen <i>Fusarium culmorum</i> causes Fusarium head blight in cereals, resulting in yield loss and contamination of the grain by type B trichothecene mycotoxins such as deoxynivalenol (DON), and its acetylated derivatives. Synthesis of trichothecenes is driven by a trichodiene synthase (TRI5) that converts farnesyl pyrophosphate (FPP) to trichodiene. In this work, 15 naturally occurring compounds that belong to the structural phenol and hydroxylated biphenyl classes were tested in vitro and in planta (durum wheat) to determine their inhibitory activity towards TRI5. In vitro analysis highlighted the fungicidal effect of these compounds when applied at 0.25 mM. Greenhouse assays showed a strong inhibitory activity of octyl gallate <b>5</b>, honokiol <b>13</b> and the combination propyl gallate <b>4</b> + thymol <b>7</b> on trichothecene biosynthesis. Docking analyses were run on the 3D model of <i>F. culmorum</i> TRI5 containing the inorganic pyrophosphate (PPi) or FPP. Significant ligand affinities with TRI-PPi and TRI-FPP were observed for the same sites for almost all compounds, with 1 and 2 as privileged sites. Octyl gallate <b>5</b> and honokiol <b>13</b> interacted almost exclusively with sites 1 and 2, by concurrently activating strong H-bonds with common sets of amino acids. These results open new perspectives for the targeted search of naturally occurring compounds that may find practical application in the eco-friendly control of FHB in wheat.Safa OufensouAlessandro DessìRoberto DallocchioVirgilio BalmasEmanuela AzaraPaola CartaQuirico MigheliGiovanna DeloguMDPI AGarticle<i>Fusarium culmorum</i>trichothecene Bphenols and hydroxylated biphenylsnatural compoundsplant healthfood safety and securityMedicineRENToxins, Vol 13, Iss 759, p 759 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Fusarium culmorum</i> trichothecene B phenols and hydroxylated biphenyls natural compounds plant health food safety and security Medicine R
spellingShingle	<i>Fusarium culmorum</i> trichothecene B phenols and hydroxylated biphenyls natural compounds plant health food safety and security Medicine R Safa Oufensou Alessandro Dessì Roberto Dallocchio Virgilio Balmas Emanuela Azara Paola Carta Quirico Migheli Giovanna Delogu Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
description	The fungal pathogen <i>Fusarium culmorum</i> causes Fusarium head blight in cereals, resulting in yield loss and contamination of the grain by type B trichothecene mycotoxins such as deoxynivalenol (DON), and its acetylated derivatives. Synthesis of trichothecenes is driven by a trichodiene synthase (TRI5) that converts farnesyl pyrophosphate (FPP) to trichodiene. In this work, 15 naturally occurring compounds that belong to the structural phenol and hydroxylated biphenyl classes were tested in vitro and in planta (durum wheat) to determine their inhibitory activity towards TRI5. In vitro analysis highlighted the fungicidal effect of these compounds when applied at 0.25 mM. Greenhouse assays showed a strong inhibitory activity of octyl gallate <b>5</b>, honokiol <b>13</b> and the combination propyl gallate <b>4</b> + thymol <b>7</b> on trichothecene biosynthesis. Docking analyses were run on the 3D model of <i>F. culmorum</i> TRI5 containing the inorganic pyrophosphate (PPi) or FPP. Significant ligand affinities with TRI-PPi and TRI-FPP were observed for the same sites for almost all compounds, with 1 and 2 as privileged sites. Octyl gallate <b>5</b> and honokiol <b>13</b> interacted almost exclusively with sites 1 and 2, by concurrently activating strong H-bonds with common sets of amino acids. These results open new perspectives for the targeted search of naturally occurring compounds that may find practical application in the eco-friendly control of FHB in wheat.
format	article
author	Safa Oufensou Alessandro Dessì Roberto Dallocchio Virgilio Balmas Emanuela Azara Paola Carta Quirico Migheli Giovanna Delogu
author_facet	Safa Oufensou Alessandro Dessì Roberto Dallocchio Virgilio Balmas Emanuela Azara Paola Carta Quirico Migheli Giovanna Delogu
author_sort	Safa Oufensou
title	Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
title_short	Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
title_full	Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
title_fullStr	Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
title_full_unstemmed	Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>
title_sort	molecular docking and comparative inhibitory efficacy of naturally occurring compounds on vegetative growth and deoxynivalenol biosynthesis in <i>fusarium culmorum</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/32029c3f25ac43638975c120067bde88
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Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>

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