Comparative SAR Evaluations of Annonaceous Acetogenins for Pesticidal Activity

Abstract

: The activities of 44 Annonaceous acetogenins, which were originally isolated by monitoring plant fractionations with the brine shrimp lethality test (BST), were evaluated in the yellow fever mosquito larvae microtiter plate (YFM) assay. The results clearly demonstrate that most acetogenins have pesticidal properties. The structureÈactivity relationships indicate that the compounds bearing adjacent bis-THF (tetrahydrofuran) rings with three hydroxyl groups are the most potent. Bullatacin (1) and trilobin (7) (1) and 9É7 ] 10~3 (7) mg litre~1. LC 50 This is the Ðrst report of pesticidal structureÈactivity relationships for a series of Annonaceous acetogenins which are known to act, at least in part, as potent inhibitors of mitochondrial NADH : ubiquinone oxidoreductase.

Toxic effects of annonaceous acetogenins from Annona cherimolia (Magnoliales: Annonaceae) on Spodoptera frugiperda (Lepidoptera: Noctuidae)

“…A previous report (He et al 1997) indicated that acetogenins possessing adjacent bis-THF rings, with three hydroxyl groups, displayed more potent insecticidal eVects against the yellow fever mosquito larvae, in a contact assay. Furthermore, squamocin (5), a bis-THF-trihydroxy acetogenin, has been described as having ovicidal and larvicidal activity on species of Drosophila (Kawasu et al 1989), and insecticidal eVects on Leptinotarsa decemlineata and Myzus persicae adults.…”

Toxic effects of annonaceous acetogenins on Oncopeltus fasciatus

“…Toxic eVects of annonaceous acetogenins have been reported on several insect species (Alali et al 1999;Leatemia and Isman 2004). He et al (1997) indicated that acetogenins possessing adjacent bis-tetra hydrofurane (THF) rings, with three hydroxyl groups, displayed more potent insecticidal eVects against the yellow fever mosquito larvae, in a contact assay. Furthermore, squamocin (1), a bis-THFtrihydroxy acetogenin, has been described as having ovicidal and larvicidal activity on species of Drosophila (Kawasu et al 1989) and insecticidal eVects on Leptinotarsa decemlineata, Myzus persicae adults (Guadaño et al 2000) and Spodoptera frugiperda (Álvarez Colom et al 2007).…”

Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae

“…[30][31][32][33] With squamostatin A and squamostatin B, four OH groups of different positions existed, two OH groups lied in the long alkyl chain of squamostatin A, also conforming that the position of OH groups could significantly affect the inhibition effects. Especially the OH group in long alkyl chain was better than that by the side of c-lactone ring.…”