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Natural phenolic inhibitors of trichothecene biosynthesis by the wheat fungal pathogen Fusarium culmorum: a computational insight into the structure-activity relationship

Pani, Giovanna and Dessì, Alessandro and Dallocchio, Roberto and Scherm, Barbara and Azara, Emanuela and Delogu, Giovanna and Migheli, Quirico (2016) Natural phenolic inhibitors of trichothecene biosynthesis by the wheat fungal pathogen Fusarium culmorum: a computational insight into the structure-activity relationship. PLoS One, Vol. 11 (6), e0157316. ISSN 1932-6203. Article.

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DOI: 10.1371/journal.pone.0157316

Abstract

A model of the trichodiene synthase (TRI5) of the wheat fungal pathogen and type-B trichothecene producer Fusarium culmorum was developed based on homology modelling with the crystallized protein of F. sporotrichioides. Eight phenolic molecules, namely ferulic acid 1, apocynin 2, propyl gallate 3, eugenol 4, Me-dehydrozingerone 5, eugenol dimer 6, magnolol 7, and ellagic acid 8, were selected for their ability to inhibit trichothecene production and/or fungal vegetative growth in F. culmorum. The chemical structures of phenols were constructed and partially optimised based on Molecular Mechanics (MM) studies and energy minimisation by Density Functional Theory (DFT). Docking analysis of the phenolic molecules was run on the 3D model of F. culmorum TRI5. Experimental biological activity, molecular descriptors and interacting-structures obtained from computational analysis were compared. Besides the catalytic domain, three privileged sites in the interaction with the inhibitory molecules were identified on the protein surface. The TRI5-ligand interactions highlighted in this study represent a powerful tool to the identification of new Fusarium-targeted molecules with potential as trichothecene inhibitors.

Item Type:Article
ID Code:11712
Status:Published
Refereed:Yes
Uncontrolled Keywords:Phenols, crystal structure, protein interactions, biosynthesis, Fusarium, dimers (chemical physics), fungicides, free energy
Subjects:Area 07 - Scienze agrarie e veterinarie > AGR/12 Patologia vegetale
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Agraria
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Public Library of Science
ISSN:1932-6203
Copyright Holders:© 2016 Pani et al.
Deposited On:17 May 2017 16:42

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