Abstract
Annonaceous acetogenins (ACG), belonging to the family Annonaceae, represent a class of bioactive compounds whose toxic effects have been reported for several spe-cies of insects. Given their insecticidal properties, we first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods. ACG analogues were semi-synthesized and characterized by spec-troscopic techniques (1H and 13C-NMR). We isolated ten natural acetogenins: squamo-cin, molvizarin, motrilin, rolliniastatin-2, almunequin, cherimolin-1, cherimolin-2, an-nonacin, squamocin D and asiminecin. The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lep-idoptera: Noctuidae). The natural ACGs squamocin and molvizarin killed 100% of S. frugiperda larvae, followed by motrilin (80%). Acetylated derivatives had less toxic and nutritional effects that led to pupal mortality and adult fatal malformations. The addition of MOM derivatives to the larval diet has not toxic effects on larvae, but significantly reduces growth rate and efficiency in conversion of ingested food into biomass, affecting adult survival.
Highlights
We first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods
The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
We first carried out the isolation of adjacent and no-adjacent, bis-THF ACGs with OH groups flanking the THF: squamocin (1), molvizarin (2), motrilin (3), rolliniastatin-2 (4), almuñequin (5), cherimolin-1 (6), cherimolin-2 (7), annonacin (8), squamocin D (9), asiminecin (10) (Figure 1) from Annona squamosa
Summary
(Annonaceae), is a 6 - 8 m tall tree distributed in tropical and subtropical regions of America, and the Caribbean (Puerto Rico, Cuba, etc.), and is common in El Salvador, Colombia, Peru, Venezuela, Brazil and eastern Bolivia, whose edible fruit is currently incorporated to commercial fruit juices Characteristic constituents of these plants are the annonaceous acetogenins that possess unique structures [1] and anticancer [2] [3], cytotoxic [4], insecticidal [5] [6], antiparasitic activities and as a highly interesting new generation of antitumor drugs [7] [8] [9] [10] [11]. The aim of this work is the search of the most active structure of ACG with insecticide action on the polyphagous lepidopteran S. frugiperda For this purpose, we first carried out the isolation of adjacent and no-adjacent, bis-THF ACGs with OH groups flanking the THF: squamocin (1), molvizarin (2), motrilin (3), rolliniastatin-2 (4), almuñequin (5), cherimolin-1 (6), cherimolin-2 (7), annonacin (8), squamocin D (9), asiminecin (10) (Figure 1) from Annona squamosa. Their acetylated (OAc) derivatives: squamocin (3 OAc) (11), molvizarin (3 OAc) (12), motrilin (3 OAc) (13) and methoxy methylated (MOM): squamocin (MOM) (14) and motrilin (MOM) (15), were prepared (Figure 2)
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
