Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i>
Cardenolide-free extracts from <i>Digitalis obscura</i> showed significant antifeedant effects against the aphid <i>Myzus persicae</i> and this activity correlated with their phenylethanoid content. The content in phenylethanoids of <i>Digitalis obscura</i> has be...
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MDPI AG
2021-05-01
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| Series: | Plants |
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| Online Access: | https://www.mdpi.com/2223-7747/10/5/959 |
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| author | José Francisco Quílez del Moral Álvaro Pérez María José Segura Navarro Alberto Galisteo Azucena Gonzalez-Coloma María Fe Andrés Alejandro F. Barrero |
| author_facet | José Francisco Quílez del Moral Álvaro Pérez María José Segura Navarro Alberto Galisteo Azucena Gonzalez-Coloma María Fe Andrés Alejandro F. Barrero |
| author_sort | José Francisco Quílez del Moral |
| collection | DOAJ |
| description | Cardenolide-free extracts from <i>Digitalis obscura</i> showed significant antifeedant effects against the aphid <i>Myzus persicae</i> and this activity correlated with their phenylethanoid content. The content in phenylethanoids of <i>Digitalis obscura</i> has been studied. Maceration of the aerial parts of <i>D. obscura</i> was used for the selective extraction of the natural compound rengyolone (<b>1</b>) and the aglycone of cornoside (compound <b>3</b>). Pure rengyolone (<b>1</b>) can be obtained from <i>D. obscura</i> in approximately 90% purity from fresh plant from the CHCl<sub>3</sub> soluble fraction of the ethanolic extract (0.8% yield). The ethanol extraction of freshly collected <i>D. obscura</i> showed the presence of compound <b>3</b> as the only phenylethanoid. Compound <b>3</b> was proven to easily evolve to rengyolone. Due to this instability, and although its presence in plants has been previously reported, the spectroscopical data of <b>3</b> are reported herein for the first time. Selective mono-acetylation of compound of <b>3</b> led to the active natural compound hallerone (<b>5</b>). The aphid antifeedant (against <i>Myzus persicae</i>) and nematicidal (against root-knot nematode <i>Meloidogyne javanica</i>) activities of these compounds have been evaluated. Here we report for the first time on the aphid antifeedant effects of <b>1</b>, <b>3</b>, and <b>5</b>. Additionally, the nematicidal activity of hallerone (<b>5</b>) is described here for the first time. |
| first_indexed | 2024-03-10T11:31:02Z |
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| id | doaj.art-c8bd1025446348dbbda10f5a7a8ae21a |
| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-03-10T11:31:02Z |
| publishDate | 2021-05-01 |
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| spelling | doaj.art-c8bd1025446348dbbda10f5a7a8ae21a2023-11-21T19:17:07ZengMDPI AGPlants2223-77472021-05-0110595910.3390/plants10050959Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i>José Francisco Quílez del Moral0Álvaro Pérez1María José Segura Navarro2Alberto Galisteo3Azucena Gonzalez-Coloma4María Fe Andrés5Alejandro F. Barrero6Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainInstitute of Agricultural Sciences, CSIC, 28006 Madrid, SpainInstitute of Agricultural Sciences, CSIC, 28006 Madrid, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainCardenolide-free extracts from <i>Digitalis obscura</i> showed significant antifeedant effects against the aphid <i>Myzus persicae</i> and this activity correlated with their phenylethanoid content. The content in phenylethanoids of <i>Digitalis obscura</i> has been studied. Maceration of the aerial parts of <i>D. obscura</i> was used for the selective extraction of the natural compound rengyolone (<b>1</b>) and the aglycone of cornoside (compound <b>3</b>). Pure rengyolone (<b>1</b>) can be obtained from <i>D. obscura</i> in approximately 90% purity from fresh plant from the CHCl<sub>3</sub> soluble fraction of the ethanolic extract (0.8% yield). The ethanol extraction of freshly collected <i>D. obscura</i> showed the presence of compound <b>3</b> as the only phenylethanoid. Compound <b>3</b> was proven to easily evolve to rengyolone. Due to this instability, and although its presence in plants has been previously reported, the spectroscopical data of <b>3</b> are reported herein for the first time. Selective mono-acetylation of compound of <b>3</b> led to the active natural compound hallerone (<b>5</b>). The aphid antifeedant (against <i>Myzus persicae</i>) and nematicidal (against root-knot nematode <i>Meloidogyne javanica</i>) activities of these compounds have been evaluated. Here we report for the first time on the aphid antifeedant effects of <b>1</b>, <b>3</b>, and <b>5</b>. Additionally, the nematicidal activity of hallerone (<b>5</b>) is described here for the first time.https://www.mdpi.com/2223-7747/10/5/959selective extractionnatural productspesticidesantifeedantnematicidal |
| spellingShingle | José Francisco Quílez del Moral Álvaro Pérez María José Segura Navarro Alberto Galisteo Azucena Gonzalez-Coloma María Fe Andrés Alejandro F. Barrero Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> Plants selective extraction natural products pesticides antifeedant nematicidal |
| title | Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> |
| title_full | Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> |
| title_fullStr | Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> |
| title_full_unstemmed | Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> |
| title_short | Selective Extraction of Bioactive Phenylethanoids from <i>Digitalis obscura</i> |
| title_sort | selective extraction of bioactive phenylethanoids from i digitalis obscura i |
| topic | selective extraction natural products pesticides antifeedant nematicidal |
| url | https://www.mdpi.com/2223-7747/10/5/959 |
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