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Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships
Author(s) -
Cimmino Alessio,
Andolfi Anna,
Avolio Fabiana,
Ali Abbas,
Tabanca Nurhayat,
Khan Ikhlas A.,
Evidente Antonio
Publication year - 2013
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201200358
Subject(s) - aedes aegypti , deet , biting , bioassay , toxicology , chemistry , traditional medicine , dengue fever , biology , larva , botany , virology , medicine , ecology
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 structureactivity 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 LD 50 values, compound 4 ( LD 50 36.8 ppm) was significantly more active than compound 1 ( LD 50 58.2 ppm). However, the activity of these compounds was significantly lower than permethrin.