Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against Aedes aegypti (Diptera: Culicidae): StructureActivity Relationships. Issue 7 (12th July 2013)

• Record Type: Journal Article
• Authors: Cimmino, Alessio; Andolfi, Anna; Avolio, Fabiana; Ali, Abbas; Tabanca, Nurhayat; Khan, Ikhlas A.; Evidente, Antonio
• Is Part Of: Chemistry & biodiversity. Volume 10:Issue 7(2013:Jul.)
• Page Start: 1239
• Page End: 1251
• Publication Date: 2013-07-12
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201200358
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p> <italic>Aedes aegypti</italic> 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 (<bold>1</bold>), seiridin (<bold>2</bold>), sphaeropsidin A (<bold>4</bold>), and papyracillic acid (<bold>5</bold>) were evaluated for their biting deterrent and larvicidal activities against <italic>Ae. aegypti</italic> L. Because compounds <bold>1, 2, 4</bold>, and <bold>5</bold> exhibited mosquito biting deterrent activities and <bold>1</bold> and <bold>4</bold> demonstrated larvicidal activities, further structureactivity relationship studies were initiated on these toxins. In biting‐deterrence bioassays, <bold>1, 2, 4</bold>, and <bold>5</bold>, 3, 8‐didansylhydrazone of cyclopaldic acid, <bold>1F</bold>, 5‐azidopentanoate of cyclopaldic acid A, <bold>1G</bold>, the reduced derivative of cyclopaldic acid, <bold>1 H</bold>, isoseiridin (<bold>3</bold>), 2′‐<italic>O</italic>‐acetylseiridin (<bold>2A</bold>), 2′‐oxoseiridin (<bold>2C</bold>), 6‐<italic>O</italic>‐acetylsphaeropsidin A (<bold>4A</bold>), 8, 14‐methylensphaeropsidin A methyl ester (<bold>4B</bold>), and sphaeropsidin B (<bold>4C</bold>) showed activities higher than the solvent control. Sphaeropsidin B (<bold>4C</bold>) was the most active compound followed by <bold>2A</bold>, while the other compounds were less active. Biting‐deterrence activity of compound <bold>4C</bold> was statistically similar to DEET. In the larvicidal screening bioassays, only compounds <bold>1</bold> and <bold>4</bold> demonstrated larvicidal activities. Based on <italic>LD</italic><sub>50</sub> values, compound <bold>4</bold> (<italic>LD</italic><sub>50</sub> 36.8 ppm) was significantly more active than compound <bold>1</bold> (<italic>LD</italic><sub>50</sub> 58.2 ppm). However, the activity of these compounds was significantly lower than permethrin.</p> </abstract>