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J Agric Food Chem. 2010 May 12;58(9):5509-14. doi: 10.1021/jf903988f.

New resistance-correlated saponins from the insect-resistant crucifer Barbarea vulgaris.

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  • 1Department of Basic Sciences and Environment, Faculty of Life Sciences, University of Copenhagen, Frederiksberg, Denmark.

Abstract

Isolation and characterization of plant constituents responsible for insect resistance are of the utmost importance for better understanding of insect-host plant interactions, for selection and breeding of resistant plant varieties, and for development of natural insecticides to be used in future sustainable agriculture and food production. In this study, 3-O-cellobiosyl-cochalic acid (1), 3-O-cellobiosyl-gypsogenin (3), and 3-O-cellobiosyl-4-epihederagenin (4) were isolated from the glabrous type of Barbarea vulgaris var. arcuata exhibiting resistance to the flea beetle Phyllotreta nemorum. In addition to the new constituents, 3-O-cellobiosyl-hederagenin (2), a known insect repellant, was identified. The structures were established by one- and/or two-dimensional homo- and heteronuclear NMR experiments acquired at 800 MHz and by fragmentation and high-resolution mass spectrometric analysis. Compounds 1, 3, and 4 are glycosides of cochalic acid, gypsogenin, and 4-epihederagenin, respectively, none of which have previously been identified in Brassicaceae. Compounds 3 and 4 have both recently been targeted as unidentified constituents exhibiting correlation with P. nemorum resistance, but this is the first report of their structures.

PMID:
20387830
DOI:
10.1021/jf903988f
[PubMed - indexed for MEDLINE]
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