Phytotoxins Produced by Two Biscogniauxia rosacearum Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran

Biscogniauxia rosacearum, recognized for the first time as a pathogen involved in grapevine trunk diseases in Paveh (west of Iran) vineyards, produced meso-2,3-butanediol (1) as the only phytotoxin. Nectriapyrone (2), (3<...

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Autores principales:	Marco Masi, Samaneh Bashiri, Alessio Cimmino, Zeinab Bahmani, Jafar Abdollahzadeh, Antonio Evidente
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Biscogniauxia rosacearum</i> grapevine oak trees phytotoxins isocoumarines SAR studies Medicine R
Acceso en línea:	https://doaj.org/article/2d9573e8f61d4853a5f935444add2c1b
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spelling	oai:doaj.org-article:2d9573e8f61d4853a5f935444add2c1b2021-11-25T19:09:01ZPhytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran10.3390/toxins131108122072-6651https://doaj.org/article/2d9573e8f61d4853a5f935444add2c1b2021-11-01T00:00:00Zhttps://www.mdpi.com/2072-6651/13/11/812https://doaj.org/toc/2072-6651<i>Biscogniauxia rosacearum,</i> recognized for the first time as a pathogen involved in grapevine trunk diseases in Paveh (west of Iran) vineyards, produced <i>meso</i>-2,3-butanediol (<b>1</b>) as the only phytotoxin. Nectriapyrone (<b>2</b>), (3<i>R</i>)-5-methylmellein (<b>3</b>), (3<i>R</i>)-5-methyl-6-methoxymellein (<b>4</b>), and tyrosol (<b>5</b>) were instead produced as phytotoxins from a strain of the same fungus isolated from oak trees in Zagros forests of Gilan-e Gharb, Kermanshah Province. They were identified comparing their <sup>1</sup>H and <sup>13</sup>C NMR, ESIMS, and specific optical rotation data with those already reported in the literature. The phytotoxicity of metabolites (<b>1–5</b>) was estimated by leaf puncture assay on <i>Quercus ilex</i> L. and <i>Hedera helix</i> L., and by leaf absorption assay on grapevine (<i>Vitis vinifera</i> L.) at a concentration of 5 × 10<sup>−3</sup> and 10<sup>−3</sup> M. Tested on grapevine, <i>meso</i>-2,3-butanediol (<b>1</b>) and (3<i>R</i>)-5-methyl-6-methoxymellein (<b>4</b>) resulted to be the most phytotoxic compounds. On <i>Q. ilex</i>, nectriapyrone (<b>2</b>) and tyrosol (<b>5</b>) showed severe necrosis at the highest concentration while none of the compounds (<b>1</b>–<b>5</b>) was active on <i>H. helix</i>. Furthermore, the phytotoxicity of compounds <b>3</b> and <b>4</b> was also compared with that of some related natural melleins to perform a structure-activity relationship (SAR) study. The results of this study were also discussed.Marco MasiSamaneh BashiriAlessio CimminoZeinab BahmaniJafar AbdollahzadehAntonio EvidenteMDPI AGarticle<i>Biscogniauxia rosacearum</i>grapevineoak treesphytotoxinsisocoumarinesSAR studiesMedicineRENToxins, Vol 13, Iss 812, p 812 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Biscogniauxia rosacearum</i> grapevine oak trees phytotoxins isocoumarines SAR studies Medicine R
spellingShingle	<i>Biscogniauxia rosacearum</i> grapevine oak trees phytotoxins isocoumarines SAR studies Medicine R Marco Masi Samaneh Bashiri Alessio Cimmino Zeinab Bahmani Jafar Abdollahzadeh Antonio Evidente Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
description	<i>Biscogniauxia rosacearum,</i> recognized for the first time as a pathogen involved in grapevine trunk diseases in Paveh (west of Iran) vineyards, produced <i>meso</i>-2,3-butanediol (<b>1</b>) as the only phytotoxin. Nectriapyrone (<b>2</b>), (3<i>R</i>)-5-methylmellein (<b>3</b>), (3<i>R</i>)-5-methyl-6-methoxymellein (<b>4</b>), and tyrosol (<b>5</b>) were instead produced as phytotoxins from a strain of the same fungus isolated from oak trees in Zagros forests of Gilan-e Gharb, Kermanshah Province. They were identified comparing their <sup>1</sup>H and <sup>13</sup>C NMR, ESIMS, and specific optical rotation data with those already reported in the literature. The phytotoxicity of metabolites (<b>1–5</b>) was estimated by leaf puncture assay on <i>Quercus ilex</i> L. and <i>Hedera helix</i> L., and by leaf absorption assay on grapevine (<i>Vitis vinifera</i> L.) at a concentration of 5 × 10<sup>−3</sup> and 10<sup>−3</sup> M. Tested on grapevine, <i>meso</i>-2,3-butanediol (<b>1</b>) and (3<i>R</i>)-5-methyl-6-methoxymellein (<b>4</b>) resulted to be the most phytotoxic compounds. On <i>Q. ilex</i>, nectriapyrone (<b>2</b>) and tyrosol (<b>5</b>) showed severe necrosis at the highest concentration while none of the compounds (<b>1</b>–<b>5</b>) was active on <i>H. helix</i>. Furthermore, the phytotoxicity of compounds <b>3</b> and <b>4</b> was also compared with that of some related natural melleins to perform a structure-activity relationship (SAR) study. The results of this study were also discussed.
format	article
author	Marco Masi Samaneh Bashiri Alessio Cimmino Zeinab Bahmani Jafar Abdollahzadeh Antonio Evidente
author_facet	Marco Masi Samaneh Bashiri Alessio Cimmino Zeinab Bahmani Jafar Abdollahzadeh Antonio Evidente
author_sort	Marco Masi
title	Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
title_short	Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
title_full	Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
title_fullStr	Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
title_full_unstemmed	Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
title_sort	phytotoxins produced by two <i>biscogniauxia rosacearum</i> strains, causal agents of grapevine trunk diseases, and charcoal canker of oak trees in iran
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/2d9573e8f61d4853a5f935444add2c1b
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Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran

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