Structural Factors of Annonaceous Acetogenins and Their Semisynthetic Analogues Related with the Toxicity on Spodoptera frugiperda

Abstract

Toxic and nutritional effects of annonaceous acetogenins and their semisynthetic analogues on Spodoptera frugiperda were evaluated. Structural modification of the natural ACG, blocking the OH flanking THF with MOM, allowed us to suggest the mode of action of ACG in the membrane. Our study emphasizes the role of the flanking OH and acetyl groups of THF with the membrane hydrophilic polar head groups. They are essential structural factors in the ACG that facilitate the intermolecular interaction that dehydrates the membrane and makes it potentially toxic against Spodoptera frugiperda.

Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith

“…These results are in agreement with a previous report from our team for other ACGs isolated from different species of Annonaceae [14]. Since hydroxyls groups flanking the THF have been blocked in MOM and acetylated derivatives a decrease in insecticidal activity is observed.…”

“…ACG acetylated (OAc) derivatives: squamocin (3 OAc) (11), molvizarin (3 OAc) (12) and motrilin (3 OAc) (13), and their methoxy methylated (MOM) derivatives: squamocin (MOM) (14) and motrilin (MOM) (15) (Figure 2) were synthesized and purified, and then characterized by spectroscopic techniques (Table 1 and Table 2). …”

“…Methoxy methylated derivatives, squamocin (MOM) (14) and motrilin (MOM) (15) were obtained by adding N,N-diisopropylethylamine and methoxymethyl chloride to a dichloromethanic solution of natural ACG under a nitrogen atmosphere. (3 g), boiled and milled bean (250 g), wheat germ (12.5 g), ascorbic acid (1.5 g), agar agar (12.5 g), methyl p-hydroxybenzoate (1.5 g), formaldehyde (4 mL of a 38 % water solution), and water (500 mL).…”

“…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. Then, 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). …”

“…Furthermore, acetogenin cytotoxicity would be strongly related to the conformation adopted in the membrane [12] [13] [14].…”