New Resistance-Correlated Saponins from the Insect-Resistant Crucifer Barbarea vulgaris

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 su...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2010-05, Vol.58 (9), p.5509-5514
Main Authors: Nielsen, Nikoline J, Nielsen, John, Staerk, Dan
Format: Article
Language:English
Subjects:
3-O-cellobiosyl-4-epihederagenin
3-O-cellobiosyl-cochalic acid
3-O-cellobiosyl-gypsogenin
Animals
Barbarea - chemistry
Barbarea vulgaris
Biological and medical sciences
chemical analysis
chemical compounds
Chromatography, High Pressure Liquid
Coleoptera - chemistry
correlation
Crop and Animal Protection Chemistry
Food industries
Fundamental and applied biological sciences. Psychology
isolation
Magnetic Resonance Spectroscopy
pest management
pest resistance
phytochemicals
plant extracts
saponins
Saponins - analysis
selection criteria
Spectrometry, Mass, Electrospray Ionization
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Summary: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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf903988f