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J Chem Ecol. 2006 Apr;32(4):755-66. Epub 2006 Apr 27.

Isothiocyanates stimulating oviposition by the diamondback moth, Plutella xylostella.

Author information

1
Boyce Thompson Institute, Ithaca, NY 14853, USA. jar14@cornell.edu

Abstract

Recognition of cabbage as a host plant for the diamondback moth (DBM) has previously been shown to depend on compounds that are extracted by soaking intact foliage in chloroform. Analysis of such chloroform extracts by open column chromatography has now resulted in the isolation of highly active fractions that elicit oviposition on treated filter papers. Further separation of these fractions by high-performance liquid chromatography revealed the presence of two distinct groups of active compounds that may be classified as volatile and non-volatile. The two prominent volatile components were separated and identified by mass spectrometry as the isothiocyanates, iberin (3-methylsulfinylpropyl isothiocyanate) and sulforaphane (4-methylsulfinyl-3-butenyl isothiocyanate). Subsequent bioassays of a range of isothiocyanates showed that iberin and sulforaphane were the most active of those tested. Other isothiocyanates with sulfur in the side chain were also active, whereas alkyl and phenyl isothiocyanates had only limited activity. In electrophysiological experiments, electroantennograms (EAGs) indicated positive responses of moth antennae to the isothiocyanates that were most active in behavioral assays. Since sulforaphane has been identified as a major inducer of anticarcinogenic activity in mouse tissue, a synthetic analog (exo-2-acetyl-5-isothiocyanatonorbornane) that shows similar inducer activity was tested on DBM. This bicyclic analog was highly active in both behavioral and EAG assays, suggesting similarity in receptor sites for the two types of biological activity.

PMID:
16718569
DOI:
10.1007/s10886-006-9036-9
[Indexed for MEDLINE]

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