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Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus sabina L, and related lignans against larvae of Pieris rapae L

Authors

  • Rong Gao,

    1. Department of Neurotoxicology, Applied Institute of Toxicology, Nanjing Medical University, Nanjing 210029, China
    2. Research and Development Center of Biorational Pesticide, Northwest Science and Technology University of Agriculture and Forestry, Yangling, Shaanxi 712100, China
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  • Congfen Gao,

    1. Key Laboratory of Monitoring and Management of Plant Diseases and Insects, Ministry of Agriculture, Nanjing Agriculture University, Nanjing 210095, China
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  • Xuan Tian,

    1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu Lanzhou 730000, China
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  • Xiangyang Yu,

    1. Research and Development Center of Biorational Pesticide, Northwest Science and Technology University of Agriculture and Forestry, Yangling, Shaanxi 712100, China
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  • Xudong Di,

    1. Department of Neurotoxicology, Applied Institute of Toxicology, Nanjing Medical University, Nanjing 210029, China
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  • Hang Xiao,

    1. Department of Neurotoxicology, Applied Institute of Toxicology, Nanjing Medical University, Nanjing 210029, China
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  • Xing Zhang

    Corresponding author
    1. Research and Development Center of Biorational Pesticide, Northwest Science and Technology University of Agriculture and Forestry, Yangling, Shaanxi 712100, China
    • Department of Neurotoxicology, Applied Institute of Toxicology, Nanjing Medical University, Nanjing 210029, China
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Abstract

In the course of screening for naturally occurring insecticides from plants from the northwestern part of China, a petroleum ether extract of Juniperus sabina L was found to show insecticidal activity against fifth-instar larvae of Pieris rapae L. From the extract, an insecticidal compound was isolated by bioassay-guided fractionation. The compound was identified as deoxypodophyllotoxin (1) by comparison of its spectroscopic characteristics with literature data. In bioassays, 1 showed antifeedant activity against fifth-instar larvae of P rapae at 0.05–1.00 g litre−1 and its AFC50 (concentration for 50% antifeedant activity) values at 12 and 48 h were 0.170 and 0.060 g litre−1, respectively. In that concentration range, all treated insects died within 48 h after treatment and compound 1 showed delayed insecticidal activity. At 0.015–0.100 g litre−1, 1 showed insecticidal activity, with an LC50 of 0.020 g litre−1. The related compound deoxypicropodophyllotoxin (2), however, showed lower antifeedant and insecticidal activities than 1 in bioassay. This indicated that the trans-lactone ring is an important moiety for enhancing activity in these compounds. Comparison of the insecticidal activities of 1 and another related compound, podophyllotoxin (3), suggested that varying the substituent at C-4 is an exciting possibility for synthesizing more potent analogues. Copyright © 2004 Society of Chemical Industry

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