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...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-10-01
|
| Series: | Toxins |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2072-6651/13/11/759 |
| _version_ | 1797508285660659712 |
|---|---|
| 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 |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T05:00:55Z |
| format | Article |
| id | doaj.art-32029c3f25ac43638975c120067bde88 |
| institution | Directory Open Access Journal |
| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-03-10T05:00:55Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Toxins |
| spelling | doaj.art-32029c3f25ac43638975c120067bde882023-11-23T01:48:37ZengMDPI AGToxins2072-66512021-10-01131175910.3390/toxins13110759Molecular Docking and Comparative Inhibitory Efficacy of Naturally Occurring Compounds on Vegetative Growth and Deoxynivalenol Biosynthesis in <i>Fusarium culmorum</i>Safa Oufensou0Alessandro Dessì1Roberto Dallocchio2Virgilio Balmas3Emanuela Azara4Paola Carta5Quirico Migheli6Giovanna Delogu7Dipartimento di Agraria, Università degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, ItalyIstituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, ItalyIstituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, ItalyDipartimento di Agraria, Università degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, ItalyIstituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, ItalyIstituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, ItalyDipartimento di Agraria, Università degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, ItalyIstituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, ItalyThe 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.https://www.mdpi.com/2072-6651/13/11/759<i>Fusarium culmorum</i>trichothecene Bphenols and hydroxylated biphenylsnatural compoundsplant healthfood safety and security |
| spellingShingle | 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> Toxins <i>Fusarium culmorum</i> trichothecene B phenols and hydroxylated biphenyls natural compounds plant health food safety and security |
| title | 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_short | 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 |
| topic | <i>Fusarium culmorum</i> trichothecene B phenols and hydroxylated biphenyls natural compounds plant health food safety and security |
| url | https://www.mdpi.com/2072-6651/13/11/759 |
| work_keys_str_mv | AT safaoufensou moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT alessandrodessi moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT robertodallocchio moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT virgiliobalmas moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT emanuelaazara moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT paolacarta moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT quiricomigheli moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi AT giovannadelogu moleculardockingandcomparativeinhibitoryefficacyofnaturallyoccurringcompoundsonvegetativegrowthanddeoxynivalenolbiosynthesisinifusariumculmorumi |