- Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity
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Structurally complex natural products have been a fruitful source for the discovery and development of new drugs. In an effort to construct a compound collection populated by architecturally complex members with unique scaffolds, we have used the natural
- Furiassi, Lucia,Hergenrother, Paul J.,Tonogai, Emily J.
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supporting information
p. 16119 - 16128
(2021/06/14)
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- Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study
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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.
- Ruberto, Giuseppe,Renda, Agatino,Tringali, Corrado,Napoli, Edoardo M.,Simmonds, Monique S. J.
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p. 6766 - 6774
(2007/10/03)
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- Studies on the constituents of edible and medicinal plants. III. Effects of seven limonoids on the sleeping time induced in mice by anesthetics
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Effects of seven limonoids, obakunone (1), 7α-obakunol (2), 7β-obakunol (3), limonin (4), 7α-limonol (5), 7β-limonol (6) and nomilin (7), on the sleeping time induced in mice by anesthetics were assayed. All the limonoids, except for 2, shortened the sleeping time induced by α-chloralose and urethane. 7 gave the highest reduction rate of sleeping time, and the order of the reduction rate of sleeping time was as follows; 7 > 1 and 3 > 4, 5 and 6. As the chemical structures of these compounds are similar to each other, the relationship between the structure and the effects of limonoids on sleeping time was discussed.
- Wada,Yagi,Kurihara,Haga
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p. 3079 - 3080
(2007/10/02)
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