New Highly Stable Dimeric 3-Deoxyanthocyanidin Pigments from Sorghum bicolor Leaf Sheath

The growing interest in natural alternatives to synthetic petroleum-based dyes for food applications necessitates looking at nontraditional sources of natural colors. Certain sorghum varieties accumulate large amounts of poorly characterized pigments in their nongrain tissue. We used High Performance Liquid Chromatography-Tandem Mass Spectroscopy to characterize sorghum leaf sheath pigments and measured the stability of isolated pigments in the presence of bisulfite at pH 1.0 to 7.0 over a 4-wk period. Two new 3-deoxyanthocyanidin compounds were identified: apigeninidin-flavene dimer and apigenin-7-O-methylflavene dimer. The dimeric molecules had near identical UV-Vis absorbance profiles at pH 1.0 to 7.0, with no obvious sign of chalcone or quinoidal base formation even at the neutral pH, indicating unusually strong resistance to hydrophilic attack. The dimeric 3-deoxyanthocyanidins were also highly resistant to nucleophilic attack by SO2; for example, apigeninidin-flavene dimer lost less than 20% of absorbance, compared to apigeninidin monomer, which lost more than 80% of absorbance at lambda(max) within 1 h in the presence of SO2. The increased molecular complexity of the dimeric 3-deoxyanthocyanidins compared to their monomers may be responsible for their unusual stability in the presence of bisulfite; these compounds present new interesting opportunities for food applications.