Insect Antifeedant Ryanodane Diterpenes from <i>Persea indica</i>

González-Coloma⊥, Azucena; Terrero, David; Perales, Aurea; Escoubas, Pierre; Fraga, Braulio M.

doi:10.1021/jf9500593

Cited by 57 publications

(48 citation statements)

References 12 publications

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“…For E. paenulata , adults, which are faster feeders than larvae (unpublished results), were tested individually (10-15 replicates per extract). In the case of S. littoralis (5 replicates per extract), two larvae were placed in each plate (González-Coloma et al, 1996). …”

Section: Methodsmentioning

confidence: 99%

“…To measure deterrent activity, a visual score of area consumed (0, 25, 50, 75 or 100%) was assigned for all discs within the plate, and a percent feeding reduction index (% FR) was determined for each replicate using the formula % FR = [1 - (treatment consumption/ control consumption)] × 100 (González-Coloma et al, 1995; González-Coloma et al, 1996). Since no previous reports of bioassays with E. paenulata were available, nicotine and rotenone (100 μg each) were tested under the same conditions for comparison purposes.…”

Section: Methodsmentioning

confidence: 99%

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Screening of Uruguayan plants for deterrent activity against insects

Castillo

González-Coloma⊥

González

et al. 2009

Industrial Crops and Products

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We evaluated the anti-insectan activity of extracts from different vegetative parts of ten plant species native to Uruguay. The selected plants belong to five families: Bignoniaceae: Clytostoma callistegioides, Dolichandra cynanchoides, Macfadyena unguis-cati; Sapindaceae: Dodonaea viscosa, Allophylus edulis, Serjania meridionalis; Lamiaceae: Salvia procurrens, Salvia guaranitica; Solanaceae: Lycium cestroides; and Phytolaccaceae: Phytolacca dioica. The extracts were evaluated in independent bioassays against four insect pests and one beneficial insect. Aphid settling inhibition was evaluated with a grass specialist, Rhopalosiphum padi, and a feeding generalist, Myzus persicae (both Hemiptera: Aphididae). Antifeedant activity was tested with adults of the specialist Epilachna paenulata (Coleoptera: Coccinellidae) and larvae of the generalist Spodoptera littoralis (Lepidoptera: Noctuidae). Finally, contact toxicity was assessed with honey bees, Apis mellifera (Hymenoptera: Apidae). Strong settling inhibition (SI) activity (expressed as % SI, where 100% means complete inhibition by the extract) was found only for the twig extracts of A. edulis (Sapindaceae) against M. persicae (% SI = 77 ± 4). Antifeedant activity (expressed as % of feeding reduction (FR), where 100% means no consumption on extract-treated diet) against E. paenulata was significant for the leaf extracts of L. cestroides (Solanaceae) (% FR = 100 ± 0) as well as of all Bignoniaceae and Sapindaceae species. No extracts were active against S. littoralis larvae, and most of them were innocuous to honey bees, with the exception of L. cestroides and S. meridionalis leaf extracts.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Screening of Uruguayan plants for deterrent activity against insects

Castillo

González-Coloma⊥

González

et al. 2009

Industrial Crops and Products

Self Cite

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“…Very recently, compounds of this family were also isolated from Persea indica by Fraga and co-workers (26). These natural diterpenes are closely related to ryanodol (8), being its 3-deoxy analogs.…”

Section: Synthetic Achievementsmentioning

confidence: 95%

Ryanoids and related compounds. Identification of five new ryanoids from the plantRyaniaspeciosaVahl. Formal total syntheses of 3-deoxyryanodol (cinnzeylanol), 10-O-acetyl-3-deoxyryanodol (cinnzeylanine), 2-deoxyryanodol, 2-deoxy-2-epiryanodol, 2,3-dideoxy-2,3-dihydroryanodol, 2-deoxy-3-epiryanodol, and 2-deoxy-3-epiryanodine

Ruest¹,

Dodier²

1996

Can. J. Chem.

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In the course of a preliminary investigation on the relationships between the chemical structure of ryanoids and their affinity to the ryanodine binding site, we have isolated, from the plant Ryarzia speciosn Vahl, four new members of this family of natural insecticidal compounds (ryanoids 3,4,5, and 6) and corrected the reported structure of a fifth one (ryanoid 7). In addition, we have synthesized, from anhydroryanodol (lo), new members of this family having fewer hydroxyl groups in ring A: cinnzeylanol (14) and cinnzeylanine (15). 2,3-dideoxy-2,3-dihydroryanodol (16), 2-deoxy-3-epiryanodol (IS), and 2-deoxy-3-epiryanodine (19), 2-deoxyryanodol (20), and 2-deoxy-2-epiryanodol(21).Key words: ryanoids synthesis, cinnzeylanine, 2-deoxyryanodols, 2-deoxy-3-epiryanodine.Resume : Dans le cadre d'une ttude prCliminaire des relations structures chimiques -activitC biologique des ryanoi'des et de leur affinitC au site rCcepteur de la ryanodine, nous avons isole de la plante Ryania speciosa Vahl, quatre nouveaux membres de cette famille d'insecticides naturels (les ryanoi'des 3 , 4 , 5 et 6) et conigC la structure dCjB rapportCe d'un cinquikme (le ryanoi'de 7). Par ailleurs, B partir de l'anhydroryanodol (lo), nous avons synthCtisC quelques membres de cette famille, moins oxygtnCs au cycle A : le cinnzeylanol(14) et la cinnzeylanine (IS), le 2,3-didCoxy-2,3-dihydroryanodol(16), le 2-dCoxy-3-Cpiryanodol(1S) et la 2-dCoxy-3-Cpiryanodine (19), le 2-dCoxyryanodol(20) et le 2-dCoxy-2-Cpiryanodol (21).

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“…Observa-se que todas estas amidas apresentam ligações duplas conjugadas, a maioria com configuração E, e apenas dois compostos (8 e 9) 51 84 com esqueleto ent-labdano acetilado em C-3, obtido de Copaifera reticulata (Leguminosae), espécie pertencente ao gênero das copaíbas, mostrou-se cerca de cem vezes mais ativo que seu precursor hidroxilado (58). 84 Os diterpenos com esqueleto do tipo ryanodano ocorrem, principalmente, em espécies de Lauraceae, particularmente nos gêneros Cinnamomum e Persea, havendo relatos de seu efeito antifeedant frente a insetos, 85 porém, apenas para um membro deste grupo (56) foi relatada atividade larvicida.…”

Section: Produtos Naturais De Origem Vegetal Com Atividade Larvicidaunclassified

“…Diterpenos com atividade larvicida isolados de plantas [82][83][84][85][86] Os triterpenos são compostos muito frequentes em plantas e com inúmeras atividades biológicas a eles atribuídas. Porém, apenas dois compostos desta classe apresentaram atividade contra larvas de Aedes aegypti (Figura 15), sendo o primeiro destes (62) um triterpeno com esqueleto tetracíclico.…”

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Naturally Occurring Plant Compounds with Larvicidal Activity AgainstAedes aegypti

Garcez¹,

Garcez²,

Silva³

et al. 2013

Revista Virtual De Química

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Abstract:The mosquito Aedes aegypti is a vector that carries the arboviroses responsible for dengue and dengue hemorrhagic fevers, diseases which are considered as major worldwide public health problems. The most widely adopted strategy for decreasing the incidence of these diseases resides in controlling the mosquito larvae population. The increasingly incidence of resistant mosquito populations due to the continuous use of synthetic insecticides, in addition to the public concern over environmental pollution and toxicity of the current commercial pesticides to nontarget organisms, have stimulated the search for alternative methods for mosquito control. In this regard, plant-derived compounds have emerged as a promising efficient and environmentally safe tool for reducing the larval population of Aedes aegypti mosquitoes. This review provides a survey on naturally occurring plant compounds belonging to different classes of secondary metabolites which have been shown to be active against Aedes aegypti.Keywords: Dengue; larvicidal compounds; bioactive natural products; Aedes aegypti. ResumoO mosquito Aedes aegypti é o vetor que transmite as arboviroses responsáveis pela dengue e a dengue hemorrágica, doenças consideradas um importante problema de saúde pública mundial. A estratégia mais amplamente adotada para diminuir a incidência dessas doenças consiste em controlar a população de larvas do mosquito. A ocorrência cada vez maior de populações resistentes de mosquitos, devido ao uso contínuo de inseticidas sintéticos, além da poluição ambiental e toxicidade dos pesticidas comerciais atualmente em uso a organismos não-alvo, tem estimulado a procura por métodos alternativos para o controle do mosquito. Neste sentido, compostos de origem vegetal surgem como uma estratégia promissora, eficiente e ambientalmente segura para reduzir a população de larvas de mosquitos Aedes aegypti. Esta revisão trata de pesquisas sobre compostos naturais originados de plantas pertencentes a diferentes classes de metabólitos secundários, que mostraram atividade contra larvas de Aedes aegypti.Palavras-chave: Dengue; substâncias larvicidas; produtos naturais bioativos; Aedes aegypti.

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Insect Antifeedant Ryanodane Diterpenes from Persea indica

Cited by 57 publications

References 12 publications

Screening of Uruguayan plants for deterrent activity against insects

Screening of Uruguayan plants for deterrent activity against insects

Naturally Occurring Plant Compounds with Larvicidal Activity AgainstAedes aegypti

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