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J Agric Food Chem. 2011 Jul 13;59(13):6947-56. doi: 10.1021/jf200412c. Epub 2011 Jun 7.

Polymorphism for novel tetraglycosylated flavonols in an Eco-model crucifer, Barbarea vulgaris.

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University of Copenhagen , Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark.


Nineteen apparent flavonoids were determined by HPLC-DAD in foliage of a chemotype (G-type) of Barbarea vulgaris , and four were isolated. Two were novel tetraglycosylated flavonols with identical glycosylation patterns, kaempferol 3-O-(2,6-di-O-β-d-glucopyranosyl)-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside (1) and quercetin 3-O-(2,6-di-O-β-d-glucopyranosyl)-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside (2). The identification of d/l configuration was tentatively based on susceptibility to α-l-rhamnosidase and β-d-glucosidases. A characteristic feature of 1 and 2 was appreciable water solubility, an expected consequence of the extensive glycosylation. A less complex pair of flavonols comprised 3-O-β-d-glucopyranoside-7-O-α-l-rhamnopyranosides of kaempferol and quercetin. Two natural chemotypes of B. vulgaris differed in levels of 1 and 2, with the P-type deficient in 1 and 2 and the insect-resistant G-type rich in 1 (ca. 3-4 μmol/g dry wt) and with moderate levels of 2 (ca. 0.3-0.8 μmol/g dry wt). However, there was only modest seasonal variation in flavonols 1 and 2, in contrast to a strong seasonal variation in insect resistance.

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