title: Synthesis and insecticidal activity of new deoxypodophyllotoxin derivatives modified in the D-ring.
abstract: In continuation of our program aimed at the discovery of new natural-product-based insecticidal agents, twenty-six deoxypodophyllotoxin derivatives modified in the D-ring were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The configuration of three compounds 3, 4, and IIIi was unambiguously determined by single-crystal X-ray diffraction. It demonstrated that aminolysis of deoxypodophyllotoxin in the presence of pyrrolidine and piperidine could result in complete inversion of the configuration of the carbonyl group at its C-2 position. Five compounds IIa, IIi-k, and IIIh showed the equal or higher insecticidal activity than toosendanin. Especially IIj displayed the most potent insecticidal activity with the final mortality rate of 65.5%.
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Wang
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Xiang
authors.initials: X
authors.lastname: Yu
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, People's Republic of China.
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Zhi
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, People's Republic of China. Electronic address: orgxuhui@nwsuaf.edu.cn.
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004365:Drugs, Chinese Herbal; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D009036:Moths / Q000187:drug effects*; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D004365:Drugs, Chinese Herbal; D007306:Insecticides; C014451:deoxypodophyllotoxin; D011034:Podophyllotoxin
keywords: Deoxypodophyllotoxin; Insecticidal activity; Mythimna separata Walker; Natural-product-based insecticide; Structural modification