Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo

• Published in: Bioorganic & medicinal chemistry letters Vol. 21; no. 7; pp. 1974 - 1977
• Main Authors: Xu, Hui, Zhang, Jun-Liang
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.04.2011; Elsevier
• Subjects: 28-Acyloxy derivatives; Animals; Biological and medical sciences; Biological Products - chemical synthesis; Biological Products - chemistry; Biological Products - pharmacology; Chemical control; chemistry; Control; Drugs, Chinese Herbal - chemical synthesis; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - pharmacology; Fundamental and applied biological sciences. Psychology; Insecticidal activity; insecticidal properties; Insecticides; larvae; Melia azedarach; Models, Molecular; Molecular Structure; Moths; Mythimna separata; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Semisynthesis; Toosendanin; Toosendanin; 28-Acyloxy derivatives; Semisynthesis; Insecticidal activity; Insecticide; Insecta; Medicinal plant; Dicotyledones; Angiospermae; Chemical synthesis; Acylate; Hemisynthesis; Terpenoid; Pesticides; Natural compound; Meliaceae; Biological activity; In vivo; Arthropoda; Mythimna separata; Lepidoptera; Triterpene; Spermatophyta; Noctuidae; Invertebrata
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2011.02.031

It indicated that the butanoyloxy or phenylacryloyloxy moiety at the 28-position of toosendanin was important for the insecticidal activity. In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, twelve 28-acyloxy derivatives of toosendanin ( 2a– l) were semisynthesized and preliminarily evaluated their activity against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. Some compounds exhibited the potent insecticidal activity. Especially compounds 2c and 2j displayed the more promising insecticidal activity than their natural precursor, toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. In general, it indicated that the butanoyloxy or phenylacryloyloxy moiety at the 28-position of toosendanin was essential for the insecticidal activity.