Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis
A large number of studies have shown that matrine (<b>MA</b>) possesses various pharmacological activities and is one of the few natural, plant-derived pesticides with the highest prospects for promotion and application. Fifty-eight <b>MA</b> derivatives were prepared, includ...
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MDPI AG
2023-03-01
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| Online Access: | https://www.mdpi.com/1420-3049/28/7/3035 |
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| author | Song Ang Jinfeng Liang Wende Zheng Zhen Zhang Jinxuan Li Zhenping Yan Wing-Leung Wong Kun Zhang Min Chen Panpan Wu |
| author_facet | Song Ang Jinfeng Liang Wende Zheng Zhen Zhang Jinxuan Li Zhenping Yan Wing-Leung Wong Kun Zhang Min Chen Panpan Wu |
| author_sort | Song Ang |
| collection | DOAJ |
| description | A large number of studies have shown that matrine (<b>MA</b>) possesses various pharmacological activities and is one of the few natural, plant-derived pesticides with the highest prospects for promotion and application. Fifty-eight <b>MA</b> derivatives were prepared, including 10 intermediates and 48 target compounds in 3 series, to develop novel mosquitocidal agents. Compounds <b>4b</b>, <b>4e</b>, <b>4f</b>, <b>4m</b>, <b>4n</b>, <b>6e</b>, <b>6k</b>, <b>6m</b>, and <b>6o</b> showed good larvicidal activity against <i>Aedes albopictus</i>, which is both a highly aggressive mosquito and an important viral vector that can transmit a wide range of pathogens. Dipping methods and a bottle bioassay were used for insecticidal activity evaluation. The LC<sub>50</sub> values of <b>4e</b>, <b>4m</b>, and <b>6m</b> reached 147.65, 140.08, and 205.79 μg/mL, respectively, whereas the LC<sub>50</sub> value of <b>MA</b> was 659.34 μg/mL. Structure–activity relationship analysis demonstrated that larvicidal activity could be improved by the unsaturated heterocyclic groups introduced into the carboxyl group after opening the D ring. The <b>MA</b> derivatives with oxidized N-1 lost their mosquitocidal activities, indicating that the bareness of N-1 is crucial to maintain their anti-mosquito activity. However, the activity was not greatly influenced by introducing a cyan group at C-6 or a benzene sulfonyl group at N-16. Additionally, compounds <b>4e</b> and <b>4m</b> exhibited good inhibitory activities against acetylcholinesterase with inhibitory rates of 59.12% and 54.30%, respectively, at a concentration of 250 μg/mL, whereas the inhibitory rate of <b>MA</b> was 9.88%. Therefore, the structural modification and mosquitocidal activity of <b>MA</b> and its derivatives obtained here pave the way for those seeking strong mosquitocidal agents of plant origin. |
| first_indexed | 2024-03-11T05:29:28Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T05:29:28Z |
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| spelling | doaj.art-2bac1a9fac61464eb1de178ba0727d7b2023-11-17T17:12:35ZengMDPI AGMolecules1420-30492023-03-01287303510.3390/molecules28073035Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic AnalysisSong Ang0Jinfeng Liang1Wende Zheng2Zhen Zhang3Jinxuan Li4Zhenping Yan5Wing-Leung Wong6Kun Zhang7Min Chen8Panpan Wu9School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaThe State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, ChinaA large number of studies have shown that matrine (<b>MA</b>) possesses various pharmacological activities and is one of the few natural, plant-derived pesticides with the highest prospects for promotion and application. Fifty-eight <b>MA</b> derivatives were prepared, including 10 intermediates and 48 target compounds in 3 series, to develop novel mosquitocidal agents. Compounds <b>4b</b>, <b>4e</b>, <b>4f</b>, <b>4m</b>, <b>4n</b>, <b>6e</b>, <b>6k</b>, <b>6m</b>, and <b>6o</b> showed good larvicidal activity against <i>Aedes albopictus</i>, which is both a highly aggressive mosquito and an important viral vector that can transmit a wide range of pathogens. Dipping methods and a bottle bioassay were used for insecticidal activity evaluation. The LC<sub>50</sub> values of <b>4e</b>, <b>4m</b>, and <b>6m</b> reached 147.65, 140.08, and 205.79 μg/mL, respectively, whereas the LC<sub>50</sub> value of <b>MA</b> was 659.34 μg/mL. Structure–activity relationship analysis demonstrated that larvicidal activity could be improved by the unsaturated heterocyclic groups introduced into the carboxyl group after opening the D ring. The <b>MA</b> derivatives with oxidized N-1 lost their mosquitocidal activities, indicating that the bareness of N-1 is crucial to maintain their anti-mosquito activity. However, the activity was not greatly influenced by introducing a cyan group at C-6 or a benzene sulfonyl group at N-16. Additionally, compounds <b>4e</b> and <b>4m</b> exhibited good inhibitory activities against acetylcholinesterase with inhibitory rates of 59.12% and 54.30%, respectively, at a concentration of 250 μg/mL, whereas the inhibitory rate of <b>MA</b> was 9.88%. Therefore, the structural modification and mosquitocidal activity of <b>MA</b> and its derivatives obtained here pave the way for those seeking strong mosquitocidal agents of plant origin.https://www.mdpi.com/1420-3049/28/7/3035matrine derivativessynthesisanti-mosquito activitymechanistic analysis |
| spellingShingle | Song Ang Jinfeng Liang Wende Zheng Zhen Zhang Jinxuan Li Zhenping Yan Wing-Leung Wong Kun Zhang Min Chen Panpan Wu Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis Molecules matrine derivatives synthesis anti-mosquito activity mechanistic analysis |
| title | Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis |
| title_full | Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis |
| title_fullStr | Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis |
| title_full_unstemmed | Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis |
| title_short | Novel Matrine Derivatives as Potential Larvicidal Agents against <i>Aedes albopictus</i>: Synthesis, Biological Evaluation, and Mechanistic Analysis |
| title_sort | novel matrine derivatives as potential larvicidal agents against i aedes albopictus i synthesis biological evaluation and mechanistic analysis |
| topic | matrine derivatives synthesis anti-mosquito activity mechanistic analysis |
| url | https://www.mdpi.com/1420-3049/28/7/3035 |
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