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Tytuł:
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Discovery of evodiamine derivatives as potent insecticide candidates.
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Autorzy:
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Liu J; College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, PR China. Electronic address: .
Shi Y; College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, PR China.
Chen S; College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, PR China.
Li F; College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, PR China. Electronic address: .
Wen W; College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, PR China.
Wang Y; College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, PR China.
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Źródło:
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Bioorganic & medicinal chemistry [Bioorg Med Chem] 2022 May 15; Vol. 62, pp. 116727. Date of Electronic Publication: 2022 Mar 28.
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Typ publikacji:
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Journal Article; Research Support, Non-U.S. Gov't
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Język:
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English
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Imprint Name(s):
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Publication: Oxford : Elsevier Science
Original Publication: Oxford : New York : Pergamon Press, c1993-
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MeSH Terms:
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Insecticides*/chemistry
Insecticides*/pharmacology
Moths*/metabolism
Animals ; Calcium ; Larva ; Molecular Structure ; Quinazolines ; Rotenone ; Ryanodine Receptor Calcium Release Channel/metabolism
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Contributed Indexing:
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Keywords: Evodiamine; Insecticidal activity; Mode of action; Structure activity relationships
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Substance Nomenclature:
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0 (Insecticides)
0 (Quinazolines)
0 (Ryanodine Receptor Calcium Release Channel)
03L9OT429T (Rotenone)
C01825BVNL (evodiamine)
SY7Q814VUP (Calcium)
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Entry Date(s):
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Date Created: 20220402 Date Completed: 20220419 Latest Revision: 20220508
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Update Code:
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20240104
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DOI:
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10.1016/j.bmc.2022.116727
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PMID:
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35366437
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In the search for novel more effective insecticides, natural products could be used as ideal template compounds due to their good environmental compatibility, various bioactivities, unique scaffolds and mode of action. We have found that natural product evodiamine, the main active component from the fruits of Evodia rutaecarpa (Juss.) Benth, displayed obvious insecticidal activities against lepidoptera pests. To continue our research, a series of evodiamine derivatives 3a-3aa were rationally designed and synthesized. The larvicidal activities results indicated that most of target compounds displayed better efficacy than evodiamine, matrine, and rotenone against Mythimna separata, Plutella xylostella and Helicoverpa armigera, among which 3z exhibited excellent larvicidal activities (65% at 2.5 mg/L against M. separata, 75% at 1.0 mg/L against P. xylostella, and 85% 10 mg/L against H. armigera, respectively), much better than evodiamine (0%), matrine (0%), and rotenone (0%). The preliminary structure activity relationships demonstrated that the fluorine atom at the E ring of evodiamine had a positive influence on the larvicidal activity. The calcium imaging experiment studies indicated that 3z could act on the ryanodine receptor (RyR) of M. separata and was an effective calcium activator for RyR.
(Copyright © 2022 Elsevier Ltd. All rights reserved.)
