Characterization of hemiacetal forms of anthocyanidin 3-O-β- glycopyranosides

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 25, 2006, Pages 9340-9346

  Jordheim, Monica ^a   Fossen, Torgils ^a   Andersen, Øyvind M ^a  

^a UNIVERSITY OF BERGEN   (Norway)

Author keywords

1H and 13C NMR assignments; Anthocyanidin 3 O monoglycopyranosides; Equilibrium proportions; Hemiacetal forms

Indexed keywords

ANTHOCYANIN; DELPHINIDIN; MALVIDIN CHLORIDE; PETUNIDIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; BEAN; CHEMISTRY; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTINIA; PLANT; PLANT SEED;

ANTHOCYANINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT; MAGNETIC RESONANCE SPECTROSCOPY; PHASEOLUS; PHOTINIA; PLANTS; SEEDS;

EID: 33846142865     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0619636     Document Type: Article

References (21)

1. Andersen, Ø. M.; Jordheim, M. The Anthocyanins. In Flavonoids: Chemistry, Biochemistry and Applications; Andersen, Ø. M., Markham, K. R., Eds.; CRC Press: Boca Raton, FL, 2006; pp 471-553.
2. Sondheimer, E. On the relation between spectral changes and pH of the anthocyanin pelargonidin 3-monoglucoside. J. Am. Chem. Soc. 1953, 75, 1507-1508.
3. Jurd, L. Anthocyanins and related compounds. I. Structural transformations of flavylium salts in acidic solutions. J. Org. Chem. 1963, 28, 987-991.
4. Jurd, L.; Geissman, T. A. Anthocyanins and related compounds. II. Structural transformation of some anhydro bases. J. Org. Chem. 1963, 28, 2394-2397.
5. McClelland, R. A.; Gedge, S. Hydration of flavylium ion. J. Am. Chem. Soc. 1980, 102, 5838-5848.
6. Brouillard, R.; Dubois, J. E. Mechanism of the structural transformations of anthocyanins in acidic media. J. Am. Chem. Soc. 1977, 99, 1359-1364.
7. Brouillard, R.; Delaporte, B. Chemistry of anthocyanins pigments. 2. Kinetic and thermodynamic study of proton transfer, hydration, and tautomeric reactions of malvidin 3-glucoside. J. Am. Chem. Soc. 1977, 99, 8461-8468.
8. Pina, F. Thermodynamics and kinetics of flavylium salts. J. Chem. Soc. Faraday Trans. 1998, 94, 2109-2116.
9. Brouillard, R.; Dangles, O. Flavonoids and flower colour. In The Flavonoids: Advances in Research since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; pp 565-588.
10. Cheminat, A.; Brouillard, R. PMR investigation of 3-O-(β- D-glucosyl) malvidin structural transformations in aqueous solutions. Tetrahedron Lett. 1986, 27, 4457-4460.
11. Mistry, T. V.; Cai, Y.; Lilley, T. H.; Haslam, E. Polyphenol interactions. Part 5. Anthocyanin copigmentation. J. Chem. Soc., Perkin Trans. 2. 1991, 8, 1287-1296.
12. Santos, H.; Turner, D. L.; Lima, J. C.; Figueiredo, P.; Pina, F. S.; Macanita, A. L. Elucidation of the multiple equilibria of malvin in aqueous solutions by one- and two-dimensional NMR. Phytochemistry 1993, 33, 1227-1232.
13. Terahara, N.; Suzuki, H.; Toki, K.; Kuwano, H.; Saito, N.; Honda, T. A diacylated anthocyanin from Tibouchina urvilleana flowers. J. Nat. Prod. 1993, 56, 335-340.
14. Bakker, J.; Bridle, P.; Honda, T.; Kuwano, H.; Saito, N.; Terahara, N.; Timberlake, C. F. Identification of an anthocyanin occurring in some red wines. Phytochemistry 1997, 44, 1375-1382.
15. Mazza, G.; Miniati, E. Anthocyanins in Fruits, Vegetables, and Grains; CRC Press: Boca Raton, FL, 1993.
16. Markakis, P. Anthocyanins as Food Colors; Academic Press: New York, 1982.
17. Takeoka, G. R.; Dao, L. T.; Full, G. H.; Wong, R. Y.; Harden, L. A.; Edwards, R. H.; Berrios, J. D. Characterization of black bean (Phaseolus vulgaris L.) anthocyanins. J. Agric. Food Chem. 1997, 45, 3395-3400.
18. Oszmianski, J.; Sapis, J. C. Anthocyanins in fruits of Aronia melanocarpa (chokeberry). J. Food Sci. 1988, 53, 1241-1242.
19. Strigl, A. W.; Leitner, E.; Pfannhauser, W. Qualitative and quantitative analysis of the anthocyanins in black chokeberries (Aronia melanocarpa Michx. Ell.) by TLC, HPLC and UV/vis-spectrometry. Z. Lebensm.-Unters. Forsch. 1995, 91, 177-180.
20. Flavonoids in Health and Disease, 2nd ed.; Rice-Evans, C. A., Packer, L., Eds.; Marcel Dekker: New York, 2003.
21. Cabrita, L.; Fossen, T.; Andersen, Ø. M. Colour and stability of the six common anthocyanidin 3-glucosides in aqueous solutions. Food Chem. 2000, 68, 101-107.