Neo-clerodane insect antifeedants from Scutellaria galericulata

Rodríguez, Beatriz; Torre, Marı́a C. de la; Rodrı́guez, Benjamı́n; Bruno, Maurizio; Piozzi, Franco; Savona, Giuseppe; Simmonds, Monique S. J.; Blaney, W. M.; Perales, Aurea

doi:10.1016/0031-9422(93)85509-p

Cited by 53 publications

(41 citation statements)

References 7 publications

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“…173 Two new neo -clerodane diterpenoids with multiple O -containing rings, compounds 439 and 440 , were isolated from an acetone extract of the aerial parts of Scutellaria galericulata . 176,177 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…(Meliaceae), exhibit strong antifeedant activity against the Colorado potato beetle, Leptinotarsa decemlineata (Say) (Coleoptera: Chrysomelidae) and the beet armyworm, Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae). Another abundant source of this kind of compounds are the plants belonging to the genus Scutellaria (family Labiatae), from which several neo-clerodanes with insect antifeedant activity have been isolated (Cole et al, 1990;Rodríguez et al, 1993;Caballero, 2004).…”

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confidence: 99%

Antifeedant activity and effects of terpenoids on detoxication enzymes of the beet armyworm, Spodoptera exigua (Hübner)

Caballero

López-Olguín

Ruíz

et al. 2008

Span. j. agric. res.

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It has been determined the antifeedant activity of a mixture of limonoids 1,7-di-O-acetylhavanensin and 3,7-di-Oacetylhavanensin (F18), isolated from seeds of Trichilia havanensis Jacq. (Meliaceae), and the neo-clerodane diterpene scutecyprol A, isolated from Scutellaria valdiviana (Clos) Epling (Labiatae), on fifth instar larvae of the beet armyworm, Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae). Choice and no-choice feeding assays, nutritional tests, and post-treatment studies indicated that scutecyprol A acts as an insect feeding deterrent against S. exigua, whereas the antifeedant activity of F18 is likely associated with a toxic mode of action. In addition, it was tested the hypothesis that S. exigua larvae will try to metabolize the compounds that are toxic by the induction of their detoxication systems, whereas no such induction happens for those compounds that are deterrents. The mixture of limonoids F18 significantly increased glutathione S-transferases during the treatment and post-treatment periods, whereas esterases were inhibited during the treatment period. On the contrary, scutecyprol A did not have any significant effect on any of the enzymatic processes. Hence, the metabolic response of S. exigua larvae to the ingestion of the secondary metabolites tested depends on their mode of action.Additional key words: esterases, glutathione S-transferases, limonoids, neo-clerodane diterpenes, nutritional indexes, Scutellaria, Trichilia. ResumenActividad antialimentaria de terpenoides y efectos sobre las enzimas de destoxificación de la gardama, Spodoptera exigua (Hübner) Se ha determinado la actividad antialimentaria de una mezcla de limonoides 1,7-di-O-acetilhavanensina y 3,7-di-O-acetilhavanensina (F18), aislados a partir de semillas de Trichilia havanensis Jacq. (Meliaceae), y del diterpeno neo-clerodano scutecyprol A, procedente de Scutellaria valdiviana (Clos) Epling (Labiatae), frente a larvas de 5º estadío de la gardama, Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae). Los resultados de ensayos de preferencia y no preferencia, de ensayos nutricionales y del estudio de los efectos post-ingestivos indican que el scutecyprol A actúa como disuasorio de la alimentación frente a larvas de S. exigua, mientras que la actividad antialimentaria de F18 está asociada a un modo de acción tóxico. Además, se ha comprobado la hipótesis de que las larvas de S. exigua tratan de metabolizar los compuestos que son tóxicos mediante la inducción de enzimas de destoxificación, mientras que esta inducción no es necesaria para aquellos compuestos que son disuasorios de la alimentación. La mezcla de limonoides F18 incrementó de forma significativa la actividad glutatión S-transferasa durante los periodos de tratamiento y post-tratamiento, mientras que la actividad esterasa se redujo durante el periodo de tratamiento. Por el contrario, el scutecyprol A no tuvo ningún efecto significativo sobre estos procesos enzimáticos. Se puede concluir, pues, que la respuesta metabólica en larvas de S. exigua depende del...

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“…6 In fact, a higher field NMR instrument was necessary for a more accurate structural study of the present compounds, since the signal overlap in the 1 H spectra recorded at 300 and 400 MHz compromises the stereochemical analysis. 6,14 The 600 MHz data indicate that the proposed structure of the isolated compound named sacacarin (5) is not correct. The data are in agreement with its 20-oxo-isomer (4) in such a way that it should be called iso-sacacarin.…”

Section: Introductionmentioning

confidence: 90%

NMR and structure review of some natural furoclerodanes

Maciel

Pinto

Kaiser

2003

Magnetic Reson in Chemistry

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The structures of some natural occurring furoclerodanes isolated from Croton cajucara were re-examined using a more powerful NMR instrument (600 MHz for 1 H), 2D NMR experiments, AM1 calculations and 1 H spectrum simulations. This study led to new signal assignments and allowed us to establish the correct structure of the compound named sacacarin, which corresponding to its 20-oxo-isomer, is thus renamed iso-sacacarin.

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Neo-clerodane insect antifeedants from Scutellaria galericulata

Cited by 53 publications

References 7 publications

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

Antifeedant activity and effects of terpenoids on detoxication enzymes of the beet armyworm, Spodoptera exigua (Hübner)

NMR and structure review of some natural furoclerodanes

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