Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran
<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<...
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MDPI AG
2021-11-01
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| 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 |
| collection | DOAJ |
| 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. |
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| publishDate | 2021-11-01 |
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| spelling | doaj.art-2d9573e8f61d4853a5f935444add2c1b2023-11-23T01:49:31ZengMDPI AGToxins2072-66512021-11-01131181210.3390/toxins13110812Phytotoxins Produced by Two <i>Biscogniauxia rosacearum</i> Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in IranMarco Masi0Samaneh Bashiri1Alessio Cimmino2Zeinab Bahmani3Jafar Abdollahzadeh4Antonio Evidente5Departiment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, ItalyDepartment of Plant Protection, Agriculture Faculty, University of Kurdistan, P.O. Box 416, Sanandaj 66177-15175, IranDepartiment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, ItalyDepartment of Plant Protection, Agriculture Faculty, University of Kurdistan, P.O. Box 416, Sanandaj 66177-15175, IranDepartment of Plant Protection, Agriculture Faculty, University of Kurdistan, P.O. Box 416, Sanandaj 66177-15175, IranDepartiment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy<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.https://www.mdpi.com/2072-6651/13/11/812<i>Biscogniauxia rosacearum</i>grapevineoak treesphytotoxinsisocoumarinesSAR studies |
| spellingShingle | 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 Toxins <i>Biscogniauxia rosacearum</i> grapevine oak trees phytotoxins isocoumarines SAR studies |
| 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_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_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_sort | phytotoxins produced by two i biscogniauxia rosacearum i strains causal agents of grapevine trunk diseases and charcoal canker of oak trees in iran |
| topic | <i>Biscogniauxia rosacearum</i> grapevine oak trees phytotoxins isocoumarines SAR studies |
| url | https://www.mdpi.com/2072-6651/13/11/812 |
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