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Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L.
This is the first study to evaluate the phytotoxic activity of three phenolic compounds present in the essential oil of the labdanum of Cistus ladanifer, an allelopathic species of the Mediterranean ecosystem. Propiophenone, 4′-methylacetophenone, and 2′,4′-dimethylacetophenone slightly inhibit tota...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10006901/ https://www.ncbi.nlm.nih.gov/pubmed/36904046 http://dx.doi.org/10.3390/plants12051187 |
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author | Espinosa-Colín, María Hernandez-Caballero, Irene Infante, Celia Gago, Irene García-Muñoz, Javier Sosa, Teresa |
author_facet | Espinosa-Colín, María Hernandez-Caballero, Irene Infante, Celia Gago, Irene García-Muñoz, Javier Sosa, Teresa |
author_sort | Espinosa-Colín, María |
collection | PubMed |
description | This is the first study to evaluate the phytotoxic activity of three phenolic compounds present in the essential oil of the labdanum of Cistus ladanifer, an allelopathic species of the Mediterranean ecosystem. Propiophenone, 4′-methylacetophenone, and 2′,4′-dimethylacetophenone slightly inhibit total germination and radicle growth of Lactuca sativa, and they strongly delay germination and reduce hypocotyl size. On the other hand, the inhibition effect of these compounds on Allium cepa was stronger on total germination than on germination rate, and radicle length compared to hypocotyl size. The position and number of methyl groups will affect the efficacy of the derivative. 2′,4′-dimethylacetophenone was the most phytotoxic compound. The activity of the compounds depended on their concentration and presented hormetic effects. In L. sativa, on paper, propiophenone presented greater inhibition of hypocotyl size at greater concentrations, with IC(50) = 0.1 mM, whereas 4′-methylacetophenone obtained IC(50) = 0.4 mM for germination rate. When the mixture of the three compounds was applied, in L. sativa, on paper, the inhibition effect on total germination and the germination rate was significantly greater compared to the effect of the compounds when they were applied separately; moreover, the mixture inhibited radicle growth, whereas propiophenone and 4′-methylacetophenone did not exert such effect when applied separately. The activity of the pure compounds and that of the mixture also changed based on the substrate used. When the trial was conducted in soil, the separate compounds delayed the germination of the A. cepa to a greater extent compared to the trial on paper, although they stimulated seedling growth. In soil, L. sativa against 4′-methylacetophenone also showed the opposite effect at low concentrations (0.1 mM), with stimulation of germination rate, whereas propiophenone and 4′-methylacetophenone presented a slightly increased effect. |
format | Online Article Text |
id | pubmed-10006901 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100069012023-03-12 Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. Espinosa-Colín, María Hernandez-Caballero, Irene Infante, Celia Gago, Irene García-Muñoz, Javier Sosa, Teresa Plants (Basel) Article This is the first study to evaluate the phytotoxic activity of three phenolic compounds present in the essential oil of the labdanum of Cistus ladanifer, an allelopathic species of the Mediterranean ecosystem. Propiophenone, 4′-methylacetophenone, and 2′,4′-dimethylacetophenone slightly inhibit total germination and radicle growth of Lactuca sativa, and they strongly delay germination and reduce hypocotyl size. On the other hand, the inhibition effect of these compounds on Allium cepa was stronger on total germination than on germination rate, and radicle length compared to hypocotyl size. The position and number of methyl groups will affect the efficacy of the derivative. 2′,4′-dimethylacetophenone was the most phytotoxic compound. The activity of the compounds depended on their concentration and presented hormetic effects. In L. sativa, on paper, propiophenone presented greater inhibition of hypocotyl size at greater concentrations, with IC(50) = 0.1 mM, whereas 4′-methylacetophenone obtained IC(50) = 0.4 mM for germination rate. When the mixture of the three compounds was applied, in L. sativa, on paper, the inhibition effect on total germination and the germination rate was significantly greater compared to the effect of the compounds when they were applied separately; moreover, the mixture inhibited radicle growth, whereas propiophenone and 4′-methylacetophenone did not exert such effect when applied separately. The activity of the pure compounds and that of the mixture also changed based on the substrate used. When the trial was conducted in soil, the separate compounds delayed the germination of the A. cepa to a greater extent compared to the trial on paper, although they stimulated seedling growth. In soil, L. sativa against 4′-methylacetophenone also showed the opposite effect at low concentrations (0.1 mM), with stimulation of germination rate, whereas propiophenone and 4′-methylacetophenone presented a slightly increased effect. MDPI 2023-03-06 /pmc/articles/PMC10006901/ /pubmed/36904046 http://dx.doi.org/10.3390/plants12051187 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Espinosa-Colín, María Hernandez-Caballero, Irene Infante, Celia Gago, Irene García-Muñoz, Javier Sosa, Teresa Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title | Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title_full | Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title_fullStr | Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title_full_unstemmed | Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title_short | Evaluation of Propiophenone, 4-Methylacetophenone and 2′,4′-Dimethylacetophenone as Phytotoxic Compounds of Labdanum Oil from Cistus ladanifer L. |
title_sort | evaluation of propiophenone, 4-methylacetophenone and 2′,4′-dimethylacetophenone as phytotoxic compounds of labdanum oil from cistus ladanifer l. |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10006901/ https://www.ncbi.nlm.nih.gov/pubmed/36904046 http://dx.doi.org/10.3390/plants12051187 |
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