Flavonol glycosides from Montcalm dark red kidney bean: implications for the genetics of seed coat color in Phaseolus vulgaris L.
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).
Beninger
C W
CW
USDA, Agricultural Research Service, Sugarbeet and Bean Research, Department of Crop and Soil Sciences, Michigan State University, East Lansing, Michigan 48824, USA.
Hosfield
G L
GL
D002851:Chromatography, High Pressure Liquid; D007887:Fabaceae / Q000737:chemistry* / Q000235:genetics*; D005419:Flavonoids / Q000032:analysis* / Q000302:isolation & purification; D006027:Glycosides / Q000032:analysis; D044949:Kaempferols; D009682:Magnetic Resonance Spectroscopy; D010858:Pigmentation / Q000235:genetics*; D010946:Plants, Medicinal; D011794:Quercetin / Q000031:analogs & derivatives / Q000032:analysis; D012639:Seeds
D005419:Flavonoids; D006027:Glycosides; D044949:Kaempferols; C006552:kaempferol; D011794:Quercetin