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  • 1
    Electronic Resource
    Electronic Resource
    A chemical basis for differential acceptance ofErysimum cheiranthoides by twoPieris species (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 195-210 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Pieris napi oleracea ; Lepidoptera ; Pieridae ; Erysimum cheiranthoides ; oviposition ; stimulants ; deterrents ; glucosinolates ; glucoiberin ; glucocheirolin ; cardenolides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Wormseed mustard,Erysimum cheiranthoides, is unacceptable as a host for the cabbage butterfly,Pieris rapae. However, it is preferred for oviposition byPieris napi oleracea in the greenhouse. Isolation and identification of the oviposition stimulants toP. napi oleracea were accomplished by C18 open-column chromatography, TLC, ion-exchange chromatography, HPLC, UV, and NMR spectroscopy. Glucoiberin and glucocheirolin were identified as the most active stimulants. The extracted glucoiberin was as stimulatory as glucocheirolin, although its concentration in theErysimum plants was about 10 times lower than that of glucocheirolin. These glucosinolates were only weak stimulants toP. rapae. Furthermore,P. rapae was strongly deterred by the cardenolides, erysimoside and erychroside, fromE. cheiranthoides, andP. napi oleracea was less sensitive to these compounds. No other deterrent toP. napi oleracea was detected in this plant species. The results explain the differential acceptance ofE. cheiranthoides by these twoPieris species.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00993689
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  • 2
    Electronic Resource
    Electronic Resource
    Chemical constituents of an unacceptable crucifer,Erysimum cheiranthoides, deter feeding byPieris rapae (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 525-533 
    Details
    ISSN: 1573-1561
    Keywords: Feeding deterrents ; Cruciferae ; Erysimum cheiranthoides ; cardenolides ; Pieris rapae ; cabbage butterfly ; Lepidoptera ; Pieridae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The wild cruciferErysimum cheiranthoides was found to contain extractable constituents that deterred feeding by larvae of the crucifer specialistPieris rapae when applied to cabbage leaf disks in both choice and nochoice bioassays. High-performance liquid chromatography was used to separate the extract into several fractions, two of which retained the feeding deterrent activity of the extract. UV-absorption spectra of the fractions suggested that one contained cardenolides similar or identical to those reported to deter oviposition byP. rapae onE. cheiranthoides. The other active fraction evidently contains a compound that deters larval feeding but not adult oviposition. The results suggest that the chemical defense ofE. cheiranthoides depends on two types of compounds acting on separate developmental stages of the insect.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982123
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  • 3
    Electronic Resource
    Electronic Resource
    Isolation and identification of oviposition deterrents to cabbage butterfly,Pieris rapae, fromErysimum cheiranthoides (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 1059-1067 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pieridae ; Pieris rapae ; cabbage butterfly ; Erysimum cheiranthoides ; Cruciferae ; oviposition deterrents ; cardenolides ; erysimoside ; erychroside ; erycordin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Avoidance of some crucifer species by the crucifer specialist,Pieris rapae, has been attributed to the presence of oviposition deterrents in these plants. Studies on one such unacceptable plant,Erysimum cheiranthoides, have resulted in the isolation ofn-butanol-soluble deterrents from the alcoholic extract of foliage. The active fraction contained three cardiac glycosides, which were isolated by reversed-phase HPLC and by open column chromatography on silica gel. Chemical and spectral evidence (UV, [1H]NMR, and FAB-MS) led to the characterization of these compounds as erysimoside (1), erychroside (2), and erycordin (3). Erysimoside and erychroside were strongly deterrent toPieris rapae, but erycordin was inactive. Both active compounds have the same aglycone, strophanthidin (5) and the inner sugar in both cases is a 2,6-dideoxy hexose to which the outer sugar is attached at position C-4. These structural features, which are absent in the inactive compound (3), may represent specific requirements for oviposition deterrent activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021010
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  • 4
    Electronic Resource
    Electronic Resource
    Cardenolides fromErysimum cheiranthoides: Feeding deterrents toPieris rapae larvae (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1355-1369 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Erysimum cheiranthoides ; feeding deterrents ; cardenolides ; digitoxigenin 3-O-β-D-glucoside ; glucodigigulomethyloside ; glucodigifucoside ; erychroside ; cheirotoxin ; strophanthidin glycosides ; digitoxigenin glycosides ; Lepidoptera ; Pyridae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984881
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