Nonenzymatic C-glycosylation of flavan-3-ols by oligo- and polysaccharides

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 23, 2007, Pages 9685-9697

  Stark, Timo ^a   Keller, Daniela ^a   Wenker, Kerstin ^a   Hillmann, Hedda ^a   Hofmann, Thomas ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

( ) catechin 8 C D maltopyranoside; C glycosylation; Catechin; Cross links; Epicatechin; Flavan 3 ol; Polysaccharides; Starch

Indexed keywords

AMYLOSE; CATECHIN; CROSS LINKING REAGENT; FLAVAN 3 OL; FLAVAN-3-OL; FLAVONOID; GLUCOSIDE; OLIGOSACCHARIDE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; GLYCOSYLATION; INDICATOR DILUTION CURVE;

AMYLOSE; CATECHIN; CROSS-LINKING REAGENTS; FLAVONOIDS; GLUCOSIDES; GLYCOSYLATION; INDICATOR DILUTION TECHNIQUES; OLIGOSACCHARIDES; POLYSACCHARIDES;

EID: 36749002811     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0719508     Document Type: Article

References (11)

1. Manach, C.; Sealbert, A.; Morand, C.; Rémésy, Ch.; Jiménez, L. Polyphenols: food source and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
2. González-Paramás, A. M.; Lopes da Silva, F.; Martín-López, P.; Macz-Pop, G.; González-Manzano, S.; Alcalde-Eon, Ch.; Joaquin Pérez-Alonso, J.; Escribano-Bailón, M. T.; Rivas-Gonzalo, J. T.; Santos-Buelga, C. Flavanol-anthocyanin condensed pigments in plant extracts. Food Chem. 2006, 94, 428-436.
3. Es-Safi, N. E.; Cheynier, V.; Moutounet, M. Study of the reactions between (+)-catechin and furfural derivatives in the presence or absence of anthocyanins and their implication in food color change. J. Agric. Food Chem. 2000, 48, 5946-5954.
4. Quideau, S.; Jourdes, M.; Saucier, C.; Glories, Y.; Pardon, P.; Baudry, C. DNA topoisomerase inhibitor acutissimin A and other flavano-ellagitannins in red wine. Angew. Chem. Int. Ed. 2003, 42, 6012-6014.
5. Glabasnia, A.; Hofmann, T. Identification and sensory evaluation of dehydro- and deoxy-ellagitannins formed upon toasting of oak wood (Quercus alba L.). J. Agric. Food Chem. 2007, 55, 4109-4118.
6. Stark, T.; Hofmann, T. Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols. J. Agric. Food Chem. 2006, 54, 9510-9521.
7. Wieser, H.; Belitz, H.-D. Studies on the structure/activity relationship of bitter tasting amino acids and peptides (in German). Z. Lebensm.-Unters. Forsch. 1975, 159, 65-72.
8. Scharbert, S.; Holzmann, N.; Hofmann, T. Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse. J. Agric. Food Chem. 2004, 52, 3498-3508.
9. Altona, C.; Haasnoot, C. A. G. Prediction of anti and gauche vicinal proton-proton coupling constants in carbohydrates: a simple additivity rule for pyranose rings. Org. Magn. Reson. 1980, 13, 417-428.
10. 1H nuclear magnetic resonance spectroscopy of flavanoids and their glycosides in hexadeuteriodimethylsulfoxide. In The Flavanoids; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; pp 441-497.
11. Kashiwada, Y.; Nonaka, G.-I.; Nishioka, I. Tannins and related compounds. XLV. Rhubarb. (5). Isolation and characterization of flavan-3-ol and procyanidin glucosides. Chem. Pharm. Bull. 1986, 34, 3208-3222.