Chemical modification produces species-specific changes in cucurbitacin antifeedant effect
Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant cap...
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2013
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218561_v61_n23_p5534_Lang http://hdl.handle.net/20.500.12110/paper_00218561_v61_n23_p5534_Lang |
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paper:paper_00218561_v61_n23_p5534_Lang2023-06-08T14:42:17Z Chemical modification produces species-specific changes in cucurbitacin antifeedant effect anti-insect antiherbivory cucurbitacins deterrent semisynthesis triterpenoid anti-insect antiherbivory Cucurbitacins deterrent Semisynthesis Triterpenoids Musculoskeletal system Chemical modification cucurbitacin plant extract animal article beetle chemical structure chemistry Cucurbitaceae drug effect feeding behavior Lepidoptera physiology species difference Animals Beetles Cucurbitaceae Cucurbitacins Feeding Behavior Lepidoptera Molecular Structure Plant Extracts Species Specificity Coccinellidae Coleoptera Cucurbitaceae Epilachna paenulata Hexapoda Lepidoptera Mythimna Noctuidae Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only 15 of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton. © 2013 American Chemical Society. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218561_v61_n23_p5534_Lang http://hdl.handle.net/20.500.12110/paper_00218561_v61_n23_p5534_Lang |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
anti-insect antiherbivory cucurbitacins deterrent semisynthesis triterpenoid anti-insect antiherbivory Cucurbitacins deterrent Semisynthesis Triterpenoids Musculoskeletal system Chemical modification cucurbitacin plant extract animal article beetle chemical structure chemistry Cucurbitaceae drug effect feeding behavior Lepidoptera physiology species difference Animals Beetles Cucurbitaceae Cucurbitacins Feeding Behavior Lepidoptera Molecular Structure Plant Extracts Species Specificity Coccinellidae Coleoptera Cucurbitaceae Epilachna paenulata Hexapoda Lepidoptera Mythimna Noctuidae |
| spellingShingle |
anti-insect antiherbivory cucurbitacins deterrent semisynthesis triterpenoid anti-insect antiherbivory Cucurbitacins deterrent Semisynthesis Triterpenoids Musculoskeletal system Chemical modification cucurbitacin plant extract animal article beetle chemical structure chemistry Cucurbitaceae drug effect feeding behavior Lepidoptera physiology species difference Animals Beetles Cucurbitaceae Cucurbitacins Feeding Behavior Lepidoptera Molecular Structure Plant Extracts Species Specificity Coccinellidae Coleoptera Cucurbitaceae Epilachna paenulata Hexapoda Lepidoptera Mythimna Noctuidae Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| topic_facet |
anti-insect antiherbivory cucurbitacins deterrent semisynthesis triterpenoid anti-insect antiherbivory Cucurbitacins deterrent Semisynthesis Triterpenoids Musculoskeletal system Chemical modification cucurbitacin plant extract animal article beetle chemical structure chemistry Cucurbitaceae drug effect feeding behavior Lepidoptera physiology species difference Animals Beetles Cucurbitaceae Cucurbitacins Feeding Behavior Lepidoptera Molecular Structure Plant Extracts Species Specificity Coccinellidae Coleoptera Cucurbitaceae Epilachna paenulata Hexapoda Lepidoptera Mythimna Noctuidae |
| description |
Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only 15 of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton. © 2013 American Chemical Society. |
| title |
Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| title_short |
Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| title_full |
Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| title_fullStr |
Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| title_full_unstemmed |
Chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| title_sort |
chemical modification produces species-specific changes in cucurbitacin antifeedant effect |
| publishDate |
2013 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218561_v61_n23_p5534_Lang http://hdl.handle.net/20.500.12110/paper_00218561_v61_n23_p5534_Lang |
| _version_ |
1768545450037608448 |