Citrus Limonoids and Their Semisynthetic Derivatives as Antifeedant Agents Against Spodoptera frugiperda Larvae. A Structure−Activity Relationship Study
| Autor: | Corrado Tringali, Giuseppe Ruberto, Monique S J Simmonds, Edoardo Napoli, Agatino Renda |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Limonins
Citrus Insecticides Food Handling Limonin Stereochemistry Industrial Waste Spodoptera Food handling Eating Structure-Activity Relationship chemistry.chemical_compound Furan Animals Benzoxepins Structure–activity relationship Organic chemistry Larva Citrus limon biology Plant Extracts Biological activity General Chemistry biology.organism_classification chemistry General Agricultural and Biological Sciences |
| Zdroj: | Journal of Agricultural and Food Chemistry. 50:6766-6774 |
| ISSN: | 1520-5118 0021-8561 |
| Popis: | The antifeedant activity of Citrus-derived limonoids limonin (1), nomilin (2), and obacunone (3) and their semisynthetic derivatives 4-26 was evaluated against a commercially important pest, Spodoptera frugiperda. Simple chemical conversions were carried out on the natural limonoids obtained from seeds of Citrus limon. These conversions focused on functional groups considered to be important for the biological activity, namely the C-7 carbonyl and the furan ring. In particular, reduction at C-7 afforded the related alcohols, and from these their acetates, oximes, and methoximes were prepared. Hydrogenation of the furan ring was also performed on limonin and obacunone. The known antifeedant properties of the Citrus limonoids are confirmed. Comparison with previously reported data shows that insect species vary in their behavioral responses to these structural modifications. Highly significant antifeedant activity (P < 0.01) for two natural (1 and 3) and three semisynthetic limonoids (4, 8, and 10) was observed against S. frugiperda. |
| Databáze: | OpenAIRE |
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