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Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships

Identifieur interne : 001B13 ( Main/Exploration ); précédent : 001B12; suivant : 001B14

Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships

Auteurs : Alessio Cimmino ; Anna Andolfi ; Fabiana Avolio ; Abbas Ali [États-Unis] ; Nurhayat Tabanca [États-Unis] ; Ikhlas A. Khan [États-Unis] ; Antonio Evidente [Italie]

Source :

Chemistry & Biodiversity [ 1612-1872 ] ; 2013-07.

RBID : ISTEX:0590B512DBBBF65C99D164B923024E24D639AB21

English descriptors

Teeft :
- Aedes aegypti, Aegypti, Bioassay, Biodiversity, Butenolide ring, Cdcl3, Chemistry biodiversity, Corresponding base, Cupressi, Cyclopaldic, Cyclopaldic acid, Deet, Derivative, Etoh, Evidente, Fungal, Fungal phytotoxins, Larva, Larval, Larval diet, Larvicidal, Larvicidal activities, Lethal metabolism, Methyl ester, Mosquito, Papyracillic acid, Positive control, Pyridine, Resp, Reversible esterification, Seiridin, Semisynthetic derivatives, Soln, Solvent control, Sparapano, Sphaeropsidin, Test compounds, Toxin, White crystals.

Abstract

Aedes aegypti L. is the major vector of the arboviruses responsible for dengue fever, one of the most devastating human diseases. From a preliminary screening of fungal phytotoxins, cyclopaldic acid (1), seiridin (2), sphaeropsidin A (4), and papyracillic acid (5) were evaluated for their biting deterrent and larvicidal activities against Ae. aegypti L. Because compounds 1, 2, 4, and 5 exhibited mosquito biting deterrent activities and 1 and 4 demonstrated larvicidal activities, further structureactivity relationship studies were initiated on these toxins. In biting‐deterrence bioassays, 1, 2, 4, and 5, 3,8‐didansylhydrazone of cyclopaldic acid, 1F, 5‐azidopentanoate of cyclopaldic acid A, 1G, the reduced derivative of cyclopaldic acid, 1 H, isoseiridin (3), 2′‐O‐acetylseiridin (2A), 2′‐oxoseiridin (2C), 6‐O‐acetylsphaeropsidin A (4A), 8,14‐methylensphaeropsidin A methyl ester (4B), and sphaeropsidin B (4C) showed activities higher than the solvent control. Sphaeropsidin B (4C) was the most active compound followed by 2A, while the other compounds were less active. Biting‐deterrence activity of compound 4C was statistically similar to DEET. In the larvicidal screening bioassays, only compounds 1 and 4 demonstrated larvicidal activities. Based on LD50 values, compound 4 (LD50 36.8 ppm) was significantly more active than compound 1 (LD50 58.2 ppm). However, the activity of these compounds was significantly lower than permethrin.

Url:

https://api.istex.fr/ark:/67375/WNG-0G969K2X-N/fulltext.pdf

DOI: 10.1002/cbdv.201200358

Affiliations:

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Le document en format XML

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<term>Biodiversity</term>
<term>Butenolide ring</term>
<term>Cdcl3</term>
<term>Chemistry biodiversity</term>
<term>Corresponding base</term>
<term>Cupressi</term>
<term>Cyclopaldic</term>
<term>Cyclopaldic acid</term>
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<term>Methyl ester</term>
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<term>Positive control</term>
<term>Pyridine</term>
<term>Resp</term>
<term>Reversible esterification</term>
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<term>Solvent control</term>
<term>Sparapano</term>
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<front><div type="abstract" xml:lang="en">Aedes aegypti L. is the major vector of the arboviruses responsible for dengue fever, one of the most devastating human diseases. From a preliminary screening of fungal phytotoxins, cyclopaldic acid (1), seiridin (2), sphaeropsidin A (4), and papyracillic acid (5) were evaluated for their biting deterrent and larvicidal activities against Ae. aegypti L. Because compounds 1, 2, 4, and 5 exhibited mosquito biting deterrent activities and 1 and 4 demonstrated larvicidal activities, further structureactivity relationship studies were initiated on these toxins. In biting‐deterrence bioassays, 1, 2, 4, and 5, 3,8‐didansylhydrazone of cyclopaldic acid, 1F, 5‐azidopentanoate of cyclopaldic acid A, 1G, the reduced derivative of cyclopaldic acid, 1 H, isoseiridin (3), 2′‐O‐acetylseiridin (2A), 2′‐oxoseiridin (2C), 6‐O‐acetylsphaeropsidin A (4A), 8,14‐methylensphaeropsidin A methyl ester (4B), and sphaeropsidin B (4C) showed activities higher than the solvent control. Sphaeropsidin B (4C) was the most active compound followed by 2A, while the other compounds were less active. Biting‐deterrence activity of compound 4C was statistically similar to DEET. In the larvicidal screening bioassays, only compounds 1 and 4 demonstrated larvicidal activities. Based on LD50 values, compound 4 (LD50 36.8 ppm) was significantly more active than compound 1 (LD50 58.2 ppm). However, the activity of these compounds was significantly lower than permethrin.</div>
</front>
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Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships

Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships

Source :

English descriptors

Abstract

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Le document en format XML

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