Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds
The plant Centaurea cineraria L. subsp. cineraria 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 C. cineraria L. subsp. cineraria 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 Phelipanche ramosa, Orobanche minor, Orobanche crenata, and Orobanche cumana, 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 C. cineraria 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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Format: | artículo biblioteca |
Language: | English |
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Multidisciplinary Digital Publishing Institute
2024-01-02
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Subjects: | Parasitic weeds, Orobanche, Phelipanche, Allelochemicals, Cnicin, Sesquiterpene lactones, Sustainable crop protection, |
Online Access: | http://hdl.handle.net/10261/356399 http://dx.doi.org/10.13039/501100011033 http://dx.doi.org/10.13039/501100003329 |
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dig-ias-es-10261-3563992024-05-09T07:20:41Z Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds Zorrilla, Jesús G. Innangi, Michele Cala, Antonio Soriano, Gabriele Russo, María A. Masi, Marco Fernández-Aparicio, Mónica Cimmino, Alessio Ministerio de Ciencia, Innovación y Universidades (España) Agencia Estatal de Investigación (España) Ministerio de Economía y Competitividad (España) Istituto Nazionale Previdenza Sociale Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection The plant Centaurea cineraria L. subsp. cineraria 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 C. cineraria L. subsp. cineraria 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 Phelipanche ramosa, Orobanche minor, Orobanche crenata, and Orobanche cumana, 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 C. cineraria to produce bioactive compounds for managing parasitic weeds and prompt further studies on its sesquiterpene lactones as tools in developing natural product-based herbicides. This research was funded by the Agencia Estatal de Investigación/Ministerio de Ciencia Innovación (projects PID2020-114668RB-I00 and RYC-2015-18961). This research was carried out within the Agritech National Research Center and received funding from the European Union Next-Generation EU (Piano Nazionale di Ripresa e Resilienza (PNRR)—Missione 4 Componente 2, Investimento 1.4—D.D. 1032 17/06/2022, CN00000022). Authors wish to express gratitude for the Ph.D. grant to Gabriele Soriano funded by INPS (Istituto Nazionale Previdenza Sociale). Peer reviewed 2024-05-09T07:19:00Z 2024-05-09T07:19:00Z 2024-01-02 artículo http://purl.org/coar/resource_type/c_6501 Plants 13(2): 178 (2024) http://hdl.handle.net/10261/356399 10.3390/plants13020178 2223-7747 http://dx.doi.org/10.13039/501100011033 http://dx.doi.org/10.13039/501100003329 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114668RB-I00/ES/MEJORA DE GUISANTES Y ALMORTAS POR RESISTENCIA A ENFERMEDADES Y ADAPTACION A SECANOS MEDITERRANEOS/ info:eu-repo/grantAgreement/MINECO//RYC-2015-18961/ES/RYC-2015-18961/ Publisher's version https://doi.org/10.3390/plants13020178 Sí open application/pdf Multidisciplinary Digital Publishing Institute |
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Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection |
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Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection Zorrilla, Jesús G. Innangi, Michele Cala, Antonio Soriano, Gabriele Russo, María A. Masi, Marco Fernández-Aparicio, Mónica Cimmino, Alessio Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
description |
The plant Centaurea cineraria L. subsp. cineraria 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 C. cineraria L. subsp. cineraria 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 Phelipanche ramosa, Orobanche minor, Orobanche crenata, and Orobanche cumana, 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 C. cineraria to produce bioactive compounds for managing parasitic weeds and prompt further studies on its sesquiterpene lactones as tools in developing natural product-based herbicides. |
author2 |
Ministerio de Ciencia, Innovación y Universidades (España) |
author_facet |
Ministerio de Ciencia, Innovación y Universidades (España) Zorrilla, Jesús G. Innangi, Michele Cala, Antonio Soriano, Gabriele Russo, María A. Masi, Marco Fernández-Aparicio, Mónica Cimmino, Alessio |
format |
artículo |
topic_facet |
Parasitic weeds Orobanche Phelipanche Allelochemicals Cnicin Sesquiterpene lactones Sustainable crop protection |
author |
Zorrilla, Jesús G. Innangi, Michele Cala, Antonio Soriano, Gabriele Russo, María A. Masi, Marco Fernández-Aparicio, Mónica Cimmino, Alessio |
author_sort |
Zorrilla, Jesús G. |
title |
Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
title_short |
Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
title_full |
Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
title_fullStr |
Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
title_full_unstemmed |
Sesquiterpene Lactones Isolated from Centaurea cineraria L. subsp. cineraria Inhibit the Radicle Growth of Broomrape Weeds |
title_sort |
sesquiterpene lactones isolated from centaurea cineraria l. subsp. cineraria inhibit the radicle growth of broomrape weeds |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2024-01-02 |
url |
http://hdl.handle.net/10261/356399 http://dx.doi.org/10.13039/501100011033 http://dx.doi.org/10.13039/501100003329 |
work_keys_str_mv |
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