Semisynthesis of Matrinic Acid/Alcohol/Ester Derivatives, Their Pesticidal Activities, and Investigation of Mechanisms of Action against Tetranychus cinnabarinus

Abstract

To discover new natural-product-based potential pesticides, 85 matrinic acid/alcohol/ester derivatives were synthesized by structural modifications of a quinolizidine alkaloid matrine. N-(4-Methyl)benzylmatrinyl n-decylate (76) and N-(2-chloro)benzylmatrinyl n-undecylate (86) exhibited greater than seven-fold more pronounced acaricidal activity than matrine against Tetranychus cinnabarinus; N-(2-chloro)benzylmatrinyl benzoate (80) showed the most promising insecticidal activity against Mythimna separata. The carboxyl group of matrinic acids and introduction of n-decyl/n-undecylcarbonyl into matrinic alcohols were important for the acaricidal activity; introduction of alkyloxy into the carboxyl of matrinic acids and introduction of the electron-withdrawing groups on the N-benzyl of matrinic esters were necessary for the insecticidal activity. Through RT-PCR and qRT-PCR analysis, it was shown that the lactam ring of matrine was vital for action on VGSC; opening the lactam ring of matrine and the alkylcarbonyl of side-chain were two important factors for acting with α1, α2, and α4 nAChR subunits; α1, α2, α4, and β3 subunits may be the target of action of compound 86 against T. cinnabarinus.

High Value-Added Use of Citrus Industrial Wastes in Agriculture: Semisynthesis and Anti-Tobacco Mosaic Virus/Insecticidal Activities of Ester Derivatives of Limonin Modified in the B Ring

“…Antiviral activities of compounds 1–4 , 6 , and 7 against TMV were tested by the half-leaf method. , Insect growth inhibitory (GI) activity of compounds 1–4 , 6 , and 7 against Mythimna separata Walker was evaluated as the previously reported method . The detailed bioassay methods are given in the Supporting Information.…”

“…23,24 Insect growth inhibitory (GI) activity of compounds 1−4, 6, and 7 against Mythimna separata Walker was evaluated as the previously reported method. 38 The detailed bioassay methods are given in the Supporting Information.…”

Semisynthesis and Pesticidal Activities of Derivatives of the Diterpenoid Andrographolide and Investigation on the Stress Response of Aphis citricola Van der Goot (Homoptera: Aphididae)

“…Hsp70 mRNA expressions were evaluated by reverse transcription polymerase chain reaction and quantitative real-time PCR analysis. 16,37,38 ■ RESULTS AND DISCUSSION Preparation of Andrographolide Derivatives. Andrographolide (1) reacting with Al 2 O 3 -pyridine gave 14-deoxy-11,12-didehydroandrographolide (2) (Figure 2), 32 which then reacted with aldehydes R 1 CHO to afford intermediates 3a− Pesticidal Activities.…”

Synthesis and In Vitro Antibacterial Activity of Quaternized 10-Methoxycanthin-6-one Derivatives

“…Although chemical pesticides work quickly, they cause serious environmental pollution, human and animal poisoning, and pesticide residues [8]. Recently, structural modifications of natural products for the discovery of agrochemical candidates have received much attention because of their low toxicity, low residue and environmental friendliness [8,9]. Canthin-6-one 1, mainly from the Rutaceae and Simaroubaceae families, are a subclass of the tryptophan-derived β -carboline alkaloids [10,11].…”