Journal of Chemical Ecology

, Volume 19, Issue 7, pp 1355–1369 | Cite as

Cardenolides fromErysimum cheiranthoides: Feeding deterrents toPieris rapae larvae

  • K. Sachdev-Gupta
  • Cd. Radke
  • J. A. A. Renwick
  • M. B. Dimock


Larvae of the cabbage butterfly,Pieris rapae, refuse to feed on the wild mustard,Erysimum cheiranthoides, due to the presence of alcoholextractable deterrents. The active components were extracted inton-BuOH, and this extract was separated into four fractions (I–IV) by reverse-phase HPLC. Fractions III and IV retained the feeding deterrent activity. The activity of fraction III was found to be due to the cardenolide diglycosides 1 and 2, which were previously reported as oviposition deterrents for gravidP. rapae butterflies. Three active compounds were isolated from fraction IV by column chromatography on silica gel followed by reverse-phase HPLC. These compounds were identified as a monoglycoside, digitoxigenin 3-O-β-D-glucoside (4), and two diglycosides, glucodigigulomethyloside (5) and glucodigifucoside (6). An additional cardenolide isolated from fraction II was identified as cheirotoxin (7). All compounds were identified by UV, NMR (1H and13C), and mass spectrometry, as well as hydrolysis experiments. The feeding deterrent activity of these compounds was compared with that of related commercially available chemicals and other compounds isolated fromE. cheiranthoides.

Key Words

Pieris rapae Erysimum cheiranthoides feeding deterrents cardenolides digitoxigenin 3-O-β-D-glucoside glucodigigulomethyloside glucodigifucoside erychroside cheirotoxin strophanthidin glycosides digitoxigenin glycosides Lepidoptera Pyridae 


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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • K. Sachdev-Gupta
    • 1
  • Cd. Radke
    • 1
  • J. A. A. Renwick
    • 1
  • M. B. Dimock
    • 1
  1. 1.Boyce Thompson InstituteIthaca

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