Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds
The plant <i>Centaurea cineraria</i> L. subsp<i>. cineraria</i> has been investigated as a potential source of inhibitors of broomrape radicle growth. The latter are weeds that pose a threat to agriculture and for which there are few methods available for the control of infes...
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MDPI AG
2024-01-01
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| author | Jesús G. Zorrilla Michele Innangi Antonio Cala Peralta Gabriele Soriano Maria Teresa Russo Marco Masi Mónica Fernández-Aparicio Alessio Cimmino |
| author_facet | Jesús G. Zorrilla Michele Innangi Antonio Cala Peralta Gabriele Soriano Maria Teresa Russo Marco Masi Mónica Fernández-Aparicio Alessio Cimmino |
| author_sort | Jesús G. Zorrilla |
| collection | DOAJ |
| description | The plant <i>Centaurea cineraria</i> L. subsp<i>. cineraria</i> has been investigated as a potential source of inhibitors of broomrape radicle growth. The latter are weeds that pose a threat to agriculture and for which there are few methods available for the control of infestations. Four sesquiterpene lactones have been isolated from <i>C. cineraria</i> L. subsp<i>. cineraria</i> aerial parts and identified as isocnicin, cnicin, salonitenolide, and 11β,13-dihydrosalonitenolide using spectroscopic, spectrometric, and optical methods. Salonitenolide and 11β,13-dihydrosalonitenolide have been isolated for the first time from this plant. Tested at 1.0–0.1 mM against the broomrape species <i>Phelipanche ramosa</i>, <i>Orobanche minor</i>, <i>Orobanche crenata</i>, and <i>Orobanche cumana</i>, isocnicin, cnicin, and salonitenolide demonstrated remarkable inhibitory activity (over 80% in most of the cases) at the highest concentrations. Structure-activity relationship conclusions indicated the significance of the α,β-unsaturated lactone ring. In addition, the synthetic acetylated derivative of salonitenolide showed the strongest activity among all compounds tested, with inhibitions close to 100% at different concentrations, which has been related to a different lipophilicity and the absence of H-bond donor atoms in its structure. Neither the extracts nor the compounds exhibited the stimulating activity of broomrape germination (induction of suicidal germination). These findings highlight the potential of <i>C. cineraria</i> to produce bioactive compounds for managing parasitic weeds and prompt further studies on its sesquiterpene lactones as tools in developing natural product-based herbicides. |
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| institution | Directory Open Access Journal |
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| last_indexed | 2024-03-08T09:48:55Z |
| publishDate | 2024-01-01 |
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| spelling | doaj.art-96ae9306c9204aa1b86e7eb7db313d5d2024-01-29T14:10:44ZengMDPI AGPlants2223-77472024-01-0113217810.3390/plants13020178Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape WeedsJesús G. Zorrilla0Michele Innangi1Antonio Cala Peralta2Gabriele Soriano3Maria Teresa Russo4Marco Masi5Mónica Fernández-Aparicio6Alessio Cimmino7Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 80126 Naples, ItalyEnvixLab, Department of Biosciences and Territory, University of Molise, Contrada Fonte Lappone, 86090 Pesche, ItalyAllelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, s/n, 11510 Puerto Real, SpainDepartment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 80126 Naples, ItalyDepartment of Plant Breeding, Institute for Sustainable Agriculture (IAS), CSIC, Avenida Menéndez Pidal s/n, 14004 Córdoba, SpainDepartment of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, 80126 Naples, ItalyThe plant <i>Centaurea cineraria</i> L. subsp<i>. cineraria</i> has been investigated as a potential source of inhibitors of broomrape radicle growth. The latter are weeds that pose a threat to agriculture and for which there are few methods available for the control of infestations. Four sesquiterpene lactones have been isolated from <i>C. cineraria</i> L. subsp<i>. cineraria</i> aerial parts and identified as isocnicin, cnicin, salonitenolide, and 11β,13-dihydrosalonitenolide using spectroscopic, spectrometric, and optical methods. Salonitenolide and 11β,13-dihydrosalonitenolide have been isolated for the first time from this plant. Tested at 1.0–0.1 mM against the broomrape species <i>Phelipanche ramosa</i>, <i>Orobanche minor</i>, <i>Orobanche crenata</i>, and <i>Orobanche cumana</i>, isocnicin, cnicin, and salonitenolide demonstrated remarkable inhibitory activity (over 80% in most of the cases) at the highest concentrations. Structure-activity relationship conclusions indicated the significance of the α,β-unsaturated lactone ring. In addition, the synthetic acetylated derivative of salonitenolide showed the strongest activity among all compounds tested, with inhibitions close to 100% at different concentrations, which has been related to a different lipophilicity and the absence of H-bond donor atoms in its structure. Neither the extracts nor the compounds exhibited the stimulating activity of broomrape germination (induction of suicidal germination). These findings highlight the potential of <i>C. cineraria</i> to produce bioactive compounds for managing parasitic weeds and prompt further studies on its sesquiterpene lactones as tools in developing natural product-based herbicides.https://www.mdpi.com/2223-7747/13/2/178parasitic weeds<i>Orobanche</i><i>Phelipanche</i>allelochemicalscnicinsesquiterpene lactones |
| spellingShingle | Jesús G. Zorrilla Michele Innangi Antonio Cala Peralta Gabriele Soriano Maria Teresa Russo Marco Masi Mónica Fernández-Aparicio Alessio Cimmino Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds Plants parasitic weeds <i>Orobanche</i> <i>Phelipanche</i> allelochemicals cnicin sesquiterpene lactones |
| title | Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds |
| title_full | Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds |
| title_fullStr | Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds |
| title_full_unstemmed | Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds |
| title_short | Sesquiterpene Lactones Isolated from <i>Centaurea cineraria</i> L. subsp. <i>cineraria</i> Inhibit the Radicle Growth of Broomrape Weeds |
| title_sort | sesquiterpene lactones isolated from i centaurea cineraria i l subsp i cineraria i inhibit the radicle growth of broomrape weeds |
| topic | parasitic weeds <i>Orobanche</i> <i>Phelipanche</i> allelochemicals cnicin sesquiterpene lactones |
| url | https://www.mdpi.com/2223-7747/13/2/178 |
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