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

Pest Manag Sci. 2004 Nov;60(11):1131-6. doi: 10.1002/ps.922.

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 48h 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Assay
  • Dose-Response Relationship, Drug
  • Drugs, Chinese Herbal
  • Insecticides / chemistry*
  • Insecticides / isolation & purification
  • Insecticides / pharmacology
  • Juniperus / chemistry*
  • Larva
  • Lepidoptera / drug effects*
  • Lethal Dose 50
  • Podophyllotoxin* / analogs & derivatives*
  • Podophyllotoxin* / chemistry
  • Podophyllotoxin* / isolation & purification
  • Podophyllotoxin* / pharmacology
  • Spectrum Analysis / methods

Substances

  • Drugs, Chinese Herbal
  • Insecticides
  • deoxypodophyllotoxin
  • Podophyllotoxin