Flavonol Glycosides from Montcalm Dark Red Kidney Bean:  Implications for the Genetics of Seed Coat Color in Phaseolus vulgaris L.

Abstract

Three flavonol glycosides were isolated and identified from the commercial dark red kidney bean (Phaseolus vulgaris L.) cultivar Montcalm. In order of highest to lowest concentration these compounds were 3',4',5,7-tetrahydroxyflavonol 3-O-beta-D-glucopyranosyl (2-->1) O-beta-D-xylopyranoside (compound 1), quercetin 3-O-beta-D-glucopyranoside (compound 2), and kaempferol 3-O-beta-D-glucopyranoside (compound 3). Compound 1 is a flavonol glycoside that has not been reported before in P. vulgaris L. These three flavonol glycosides were yellow compounds that do not contribute to the garnet red color of Montcalm seed coats. Red-colored compounds which tested positive for proanthocyanidins are most likely responsible for the red seed coat color of Montcalm. Previous work on the chemistry of the compounds produced from the multi-allelic seed coat gene series C-C(r)()-c(u) indicated that neither anthocyanins nor flavonol glycosides were detected from seed coat extracts in the presence of the c(u)() locus. However, the seed coat color genotype of Montcalm is c(u) J g B v rk(d) and three flavonol glycosides were found. Technological advances such as modern HPLC analysis of seed coat extracts may allow for detection of small amounts of compounds which previously could not be seen using paper chromatography. Alternatively, the change of the Rk allele to rk(d) may allow for the synthesis of flavonol glycosides in the presence of c(u).

Composition and content of seed flavonoids in forage and grain legume crops

“…The identification of compound 2 was confirmed by the injection of authentic standard and by comparison of their retention times and spectral data. These findings were in agreement with several literature data reporting the presence of kaempferol 3-O-glucoside [22,23,36,37] and kaempferol 3-acetylglucoside [22] in various Phaseolus genotypes.…”

Effect of processing on antioxidant contents in selected dry beans (Phaseolus spp. L.)

“…It has been reported that higher condensed tannins or proanthocyanidin content are seen in colored beans than in pale (in yellow and white) colored beans (Beninger & Hosfield, 1999). However, Cardador-Martinez, Loarca-Pina, and Oomah, 2002 suggested that the highest antioxidant activity in white seeds might be due to their condensed tannin content.…”

Measurement of the geometrical features and surface color of rapeseeds using digital image analysis

“…Seed coat pigment in the brown-seeded line of Brassica consisting of proanthocyanidins (condensed tannins). The normally colorless proanthocyanidins undergo secondary changes during seed maturation to form oxidized complexes with the cell wall, polysaccharides and other phenolics in the seed coat, causing it to darken (Beninger & Hosfield, 1999;Marles, Gruber, Scoles, & Muir, 2003). The mean value of a* attribute was negative in all cases, indicating the presence of green color.…”