“…Plumbagin, 5-hydroxy-2-methyl-1,4-naphthoquinone (C 11 H 8 O 3 ), is an important secondary metabolite and bioactive compound in plants originally isolated from the medicinal plant Plumbago zeylanica and has been reported to exhibit potent larvicidal activity against several insect pests, including S. litura (Tokunaga et al, 2004;Rajendra Prasad et al, 2012), Achaea Janata (Rajendra Prasad et al, 2012), Trichoplusia ni (Akhtar et al, 2012a), Musca domestica (Pavela, 2013), Helicoverpa armigera , Pieris rapae , Mythimna separate (Shang et al, 2019), Nilaparvata lugens (Shang et al, 2019), S. littoralis (Davila-Lara et al, 2021;Rahman-Soad et al, 2021), Aedes aegypti (de Oliveira et al, 2022), and three aphid species (Akhtar et al, 2012b), as well as acaricidal activity against the herbivorous mite Tetranychus urticae (Akhtar et al, 2012b). The results of these studies have indicated that plumbagin has great potential to be developed as a potent botanical insecticide and an alternative to synthetic insecticides.…”
IntroductionPlumbagin is an important phytochemical and has been reported to exhibit potent larvicidal activity against several insect pests, However, the insecticidal mechanism of plumbagin against pests is still poorly understood. This study aimed to investigate the insecticidal activities of plumbagin and the underlying molecular mechanisms against a devastating agricultural pest, the fall armyworm Spodoptera frugiperda.MethodsThe effects of plumbagin on S. frugiperda larval development and the activities of two detoxification enzymes were initially examined. Next, transcriptomic changes in S. frugiperda after plumbagin treatment were investigated. Furthermore, RNA-seq results were validated by qPCR.ResultsPlumbagin exhibited a high larvicidal activity against the second and third instar larvae of S. frugiperda with 72 h LC50 of 0.573 and 2.676 mg/g, respectively. The activities of the two detoxification enzymes carboxylesterase and P450 were significantly increased after 1.5 mg/g plumbagin treatment. Furthermore, RNA-seq analysis provided a comprehensive overview of complex transcriptomic changes in S. frugiperda larvae in response to 1.5 mg/g plumbagin exposure, and revealed that plumbagin treatment led to aberrant expression of a large number of genes related to nutrient and energy metabolism, humoral immune response, insect cuticle protein, chitin-binding proteins, chitin synthesis and degradation, insect hormone, and xenobiotic detoxification. The qPCR results further validated the reproducibility and reliability of the transcriptomic data.DiscussionOur findings provide a valuable insight into understanding the insecticidal mechanism of the phytochemical plumbagin.
“…Plumbagin, 5-hydroxy-2-methyl-1,4-naphthoquinone (C 11 H 8 O 3 ), is an important secondary metabolite and bioactive compound in plants originally isolated from the medicinal plant Plumbago zeylanica and has been reported to exhibit potent larvicidal activity against several insect pests, including S. litura (Tokunaga et al, 2004;Rajendra Prasad et al, 2012), Achaea Janata (Rajendra Prasad et al, 2012), Trichoplusia ni (Akhtar et al, 2012a), Musca domestica (Pavela, 2013), Helicoverpa armigera , Pieris rapae , Mythimna separate (Shang et al, 2019), Nilaparvata lugens (Shang et al, 2019), S. littoralis (Davila-Lara et al, 2021;Rahman-Soad et al, 2021), Aedes aegypti (de Oliveira et al, 2022), and three aphid species (Akhtar et al, 2012b), as well as acaricidal activity against the herbivorous mite Tetranychus urticae (Akhtar et al, 2012b). The results of these studies have indicated that plumbagin has great potential to be developed as a potent botanical insecticide and an alternative to synthetic insecticides.…”
IntroductionPlumbagin is an important phytochemical and has been reported to exhibit potent larvicidal activity against several insect pests, However, the insecticidal mechanism of plumbagin against pests is still poorly understood. This study aimed to investigate the insecticidal activities of plumbagin and the underlying molecular mechanisms against a devastating agricultural pest, the fall armyworm Spodoptera frugiperda.MethodsThe effects of plumbagin on S. frugiperda larval development and the activities of two detoxification enzymes were initially examined. Next, transcriptomic changes in S. frugiperda after plumbagin treatment were investigated. Furthermore, RNA-seq results were validated by qPCR.ResultsPlumbagin exhibited a high larvicidal activity against the second and third instar larvae of S. frugiperda with 72 h LC50 of 0.573 and 2.676 mg/g, respectively. The activities of the two detoxification enzymes carboxylesterase and P450 were significantly increased after 1.5 mg/g plumbagin treatment. Furthermore, RNA-seq analysis provided a comprehensive overview of complex transcriptomic changes in S. frugiperda larvae in response to 1.5 mg/g plumbagin exposure, and revealed that plumbagin treatment led to aberrant expression of a large number of genes related to nutrient and energy metabolism, humoral immune response, insect cuticle protein, chitin-binding proteins, chitin synthesis and degradation, insect hormone, and xenobiotic detoxification. The qPCR results further validated the reproducibility and reliability of the transcriptomic data.DiscussionOur findings provide a valuable insight into understanding the insecticidal mechanism of the phytochemical plumbagin.
There are many indole alkaloids that contain diverse functional groups attached to the benzene ring on the indole core. Promising biological activities of these alkaloids have been reported. Herein, we report the indole C5‐selective bromination of indolo[2,3‐a]quinolizidine alkaloids by adding nearly equimolar amounts of Br3·PyH and HCl in MeOH. The resulting reaction plausibly proceeds through an indoline intermediate by the nucleophilic addition of MeOH to the C3‐brominated indolenine intermediate. Data support the intermediacy of a C3‐, C5‐dibrominated indolenine intermediate as a brominating agent. These conditions demonstrate excellent selectivity for indole C5 bromination of natural products and their derivatives. Thus, these simple, mild, and metal‐free conditions allow for selective, late‐stage bromination followed by further chemical modifications. The utility of the brominated product prepared from naturally occurring yohimbine was demonstrated through various derivatizations, including a bioinspired heterodimerization reaction.
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