Synthesis, characterization of two matrine derivatives and their cytotoxic effect on Sf9 cell of Spodoptera frugiperda

Abstract

The invasion of Spodoptera frugiperda has imposed a serious impact on global food security. Matrine is a botanical pesticide with a broad spectrum of insecticidal activity which was recommended for controlling Spodoptera frugiperda. In order to discover effective insecticide for Spodoptera frugiperda, two matrine derivatives modified with carbon disulfide and nitrogen-containing groups were systhesized. And their inhibition activities on Sf9 cell were evaluated. The structural configuration of compounds were characterized by IR, HPLC, MS, NMR and XRD, with yields of 52% and 65%, respectively. The IC50 of the two newly synthesized compounds on Sf9 cell reduced to 0.648 mmol/L and 1.13 mmol/L, respectively, compared with that of matrine (5.330 mmol/L). In addition, microscopic observation of Sf9 cell treated with the compounds showed that the number of adherent cells decreased, the cells shrunk, vacuolated and apoptotic bodies appeared. The two newly synthesized compounds exhibited better inhibitory effect on Sf9 cell than that of the parent matrine, suggesting that the positive effect of the introduction of 1-pyrrolidinecarbodithioate and diethylcarbamodithioate groups to matrine. The morphological observation of Sf9 cell induced by derivatives indicated that apoptosis induction may be a mechanism that inhibits insect cell proliferation and exerts insecticidal effect.

Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions

“…A content increase for 9 was observed from PE3-7, but no longer detected from PE9. This compound is vital due to its antimicrobial [ 55 , 58 ], antiparasitic [ 59 ], cytotoxic [ 60 ], anticarcinogenic [ 61 ], antiviral, [ 62 ] and antimalarial properties [ 63 , 64 ].…”

Advances in Control Strategies against Spodoptera frugiperda. A Review

“…In this same sense, new compounds have been synthesized from active molecules of natural origin with insecticidal activity, such as matrine, a heterocyclic compound derived from quinolizidine isolated from the roots of Sophora flavescens (Aiton) and Sophora alopecuroides L. These molecules were introduced to groups of 1-pyrrolidinecarbodithioate and diethylcarbamodithioate to improve their activity through chemical synthesis, enhancing this activity at low concentrations; the structures of these new matrine derivatives are shown in Figure 4 [ 1 ].…”

“…Mortality and time of death were evaluated, and the authors concluded that halogenated flavones had insecticide activity. In this same sense, new compounds have been synthesized from active molecules of natural origin with insecticidal activity, such as matrine, a heterocyclic compound derived from quinolizidine isolated from the roots of Sophora flavescens (Aiton) and Sophora alopecuroides L. These molecules were introduced to groups of 1-pyrrolidinecarbodithioate In this same sense, new compounds have been synthesized from active molecules of natural origin with insecticidal activity, such as matrine, a heterocyclic compound derived from quinolizidine isolated from the roots of Sophora flavescens (Aiton) and Sophora alopecuroides L. These molecules were introduced to groups of 1-pyrrolidinecarbodithioate and diethylcarbamodithioate to improve their activity through chemical synthesis, enhancing this activity at low concentrations; the structures of these new matrine derivatives are shown in Figure 4 [1]. Other compounds tested are gamma-aminobutyric acid (GABA) antagonists, which resulted in an exciting drug target in lepidopteran and other plagues.…”

“…Smith, 1797), is a lepidopteran insect of the family Noctuidae. The larval stage of this pest has a food preference for leaves and tender shoots, especially buds, becoming a chewer of plant tissue [ 1 ]. Its feeding habits make it a polyphagous, migrating, destructive pest of crops in the Western Hemisphere.…”

Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities

“…Using Lawson reagent to replace the oxygen atom on the carbonyl group of matrine with a sulfur atom and undergo a nucleophilic addition reaction with the active group at position C13, a series of thiomatrine derivatives were synthesized, which have antiliver fibrosis and antihepatitis activities [ 16 , 17 ]. Additionally, the introduction of nitrogen-containing and sulfur-containing derivatives synthesized at the C13 position of matrine has good insecticidal activity against Lipaphis erysimi , root knot nematode and Spodoptera frugiperda [ 18 , 19 , 20 ]. The derivative that was obtained by introducing dimethyl carbonate group condensed ester at the C14 position of matrine, and then reduced to alcohols and decarbonylated by lithium aluminum hydride has a significantly higher antitobacco mosaic virus and plant fungicidal activities than matrine [ 21 ].…”