title: Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker.
abstract: To discover the new natural-product-based insecticidal agents, four series of sixty novel 4β-acyloxypodophyllotoxin analogs modified in the C and E rings were prepared, and their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at the concentration of 1 mg/mL. It demonstrated that the position of the dioxo group on the E-ring of 4'-demethylepipodophyllotoxin was regioselectively controlled by the chlorine atom at its C-2' position when 2'-chloro-4'-demethylepipodophyllotoxin was oxidized by sodium periodate. Among all the derivatives, IIIi exhibited the best potent insecticidal activity with the final mortality rate of 63.3%. To alkylacyloxy series, the proper length of the side chain at the C-4 position of Ia-g, IIa-g and IIIa-g was important for their insecticidal activity.
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Zhi
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Xiang
authors.initials: X
authors.lastname: Yu
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Chun
authors.initials: C
authors.lastname: Yang
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Guodong
authors.initials: G
authors.lastname: Ding
authors.affiliation: College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China. Electronic address: orgxuhui@nwsuaf.edu.cn.
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
mesh_terms: D000215:Acylation; D000818:Animals; D002713:Chlorine / Q000737:chemistry; D018360:Crystallography, X-Ray; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry*; D007814:Larva; D015394:Molecular Structure; D009036:Moths; D011034:Podophyllotoxin / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D007306:Insecticides; D002713:Chlorine; D011034:Podophyllotoxin
keywords: 4β-Acyloxypodophyllotoxin; Botanical insecticide; Insecticidal activity; Mythimna separata Walker; Podophyllotoxin; Regioselective; Structural modification