Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities

Cheng, Xiangdong; He, Hongchao; Dong, Fangyun; Xu, Chunbao; Zhang, Hanhui; Liu, Zhanmei; Lv, Xiaojing; Wu, Yan‐Chao; Jiang, Xuhong; Qin, Xiangjing

doi:10.3390/molecules27154974

Cited by 10 publications

(4 citation statements)

References 36 publications

(33 reference statements)

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“…Various botanical derivatives, such as limonoids and osthol, inhibited different severe diseases caused by fungi [47,48]. In this study, compound FPL001 inhibited the mycelial growth of C. gloeosporioides more effectively than plant-derivative fungicides, such as halopyrazole matrine derivatives [49]. Conidial germination, appressorium formation, and invasive hyphae development are critical phases in the early stages of infection of host plants by C. gloeosporioides to suppress fungal infection.…”

Section: Discussionmentioning

confidence: 72%

Evaluation of the Antifungal Activity of Polysubstituted Cyclic 1,2-Diketones against Colletotrichum gloeosporioides

Wang

Meng

Sun

et al. 2023

Forests

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(1) Anthracnose caused by Colletotrichum damages crops, ornamentals, and forest trees severely, resulting in enormous economic losses to agricultural and forestry systems. Overusing traditional chemical fungicides leads to fungicide resistance, environmental pollution, and potential risks to public health. Therefore, priorities should be given to developing efficient and environmentally friendly approaches to pest management, including anthracnose. (2) In this study, the antifungal activity of botanical derivative polysubstituted cyclic 1,2-diketones (FPL001) against C. gloeosporioides was examined. (3) FPL001 significantly inhibited the vegetative growth of C. gloeosporioides with an EC50 of 160.23 µg/mL. When the concentration of FPL001 reached 30 µg/mL, the conidial germination and appressorium formation of C. gloeosporioides were completely inhibited. FPL001 also significantly suppressed the invasive hyphae development and plant infection of C. gloeosporioides. FPL001 did not exhibit toxicity to model organisms such as alfalfa and silkworm larvae. (4) These results indicate that compound FPL001 is a potential and efficient agent for green control of C. gloeosporioides.

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Section: Discussionmentioning

confidence: 72%

Evaluation of the Antifungal Activity of Polysubstituted Cyclic 1,2-Diketones against Colletotrichum gloeosporioides

Wang

Meng

Sun

et al. 2023

Forests

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“…The matrine derivative ZS17, which was designed and synthesized under the condition of retaining the amide ring, had a more effective anti-tumor effect than matrine itself by activating the ROS-JNK-P53 signaling pathway [20]. The derivatives showed stronger insecticidal and fungicidal activities than matrine when the halogenated pyrazole groups were introduced on matrine C13 [21]. Finding the active part of the compounds is conducive to the study of its mechanism and the development and utilization of new veterinary drugs.…”

Section: Discussionmentioning

confidence: 99%

Target Discovery of Matrine against PRRSV in Marc-145 Cells via Activity-Based Protein Profiling

Ling

Cao

Sun

et al. 2023

IJMS

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Porcine reproductive and respiratory syndrome (PRRS) seriously endangers the sustainable development of the pig industry. Our previous studies have shown that matrine can resist porcine reproductive and respiratory syndrome virus (PRRSV) infection. This study aimed to explore the anti-PRRSV targets of matrine in Marc-145 cells. Biotin-labeled matrine 1 and 2 were used as probes. MTT assay was used to determine the maximum non-cytotoxic concentration (MNTC) of each probe in Marc-145 cells. The anti-PRRSV activity of each probe was evaluated via MTT, qPCR and Western blot, and its anti-inflammatory activity was evaluated via qPCR and Western blot. The targets of matrine in Marc-145 cells were searched using activity-based protein profiling (ABPP), and compared with the targets predicted via network pharmacology for screening the potential targets of matrine against PRRSV. The protein–protein interaction networks (PPI) of potential targets were constructed using a network database and GO/KEGG enrichment analysis was performed. ACAT1, ALB, HMOX1, HSPA8, HSP90AB1, PARP1 and STAT1 were identified as potential targets of matrine, and their functions were related to antiviral capacity and immunity. Matrine may play an anti-PRRSV role by directly acting on ACAT1, ALB, HMOX1, HSPA8, HSP90AB1, PARP1 and STAT1.

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“…One benign alternative to synthetic insecticides is plant extracts and their derived compounds. Crude plant extracts could control P. xylostella in various ways, including via insecticidal [6] and repellent effects, growth and oviposition inhibition [7], and reducing their feeding [8]. Beyond their insecticidal properties, plant extracts have several advantages over traditional insecticides.…”

Section: Introductionmentioning

confidence: 99%

Behavioral, Electrophysiological, and Toxicological Responses of Plutella xylostella to Extracts from Angelica pubescens

Zheng

Zhao

et al. 2023

Insects

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Plutella xylostella L. is a destructive pest affecting cruciferous vegetables, causing massive economic losses worldwide. Plant−based insecticides are considered promising insect control agents. The Angelica pubescens extract inhibited female oviposition, with an oviposition deterrence index (ODI) of 61.65% at 12.5 mg/mL. We aimed to identify the bioactive compounds in A. pubescens extract. The compounds from A. pubescens extract were analyzed using LC−MS techniques. The toxicity and behavioral responses of larvae and adults of P. xylostella to ten compounds were investigated. We found that the caryophyllene oxide and 3,4-dimethoxycinnamic acid inhibited female oviposition; the ODIs were 98.31% and 97.59% at 1.25 mg/mL, respectively. The A. pubescens extract, caryophyllene oxide, and 3,4-dimethoxycinnamic acid caused larval mortality, with LC50 values of 21.31, 4.56, and 5.52 mg/mL, respectively. The EAG response of females was higher than that of males under A. pubescens extract conditions, while the EAG response of males was higher than that of females in caryophyllene oxide and 3,4-dimethoxycinnamic acid conditions. The A. pubescens extract and caryophyllene oxide showed repellent activity against both female and male adults, while the 3,4-dimethoxycinnamic acid did not elicit any notable behavioral responses from P. xylostella adults. A. pubescens extract and caryophyllene oxide are potential insecticides, oviposition deterrents, and behavioral regulators against P. xylostella, and they could be potential candidates for the development of biological insecticides to control P. xylostella.

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Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities

Cited by 10 publications

References 36 publications

Evaluation of the Antifungal Activity of Polysubstituted Cyclic 1,2-Diketones against Colletotrichum gloeosporioides

Evaluation of the Antifungal Activity of Polysubstituted Cyclic 1,2-Diketones against Colletotrichum gloeosporioides

Target Discovery of Matrine against PRRSV in Marc-145 Cells via Activity-Based Protein Profiling

Behavioral, Electrophysiological, and Toxicological Responses of Plutella xylostella to Extracts from Angelica pubescens

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