Di-D-fructose dianhydride-enriched products by acid ion-exchange resin-promoted caramelization of D-fructose: Chemical analyses

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 3, 2010, Pages 1777-1787

  Suárez Pereira, Elena ^a   Rubio, Enrique M ^b   Pilard, Serge ^c   Ortiz Mellet, Carmen ^a   García Fernández, José M ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^c UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

Caramelization; D fructose; Di D fructose dianhydrides (DFAs); Gas chromatography; Ion exchange resins; Mass spectrometry

Indexed keywords

CARBOHYDRATE; DISACCHARIDE; FRUCTOSE; ION EXCHANGE RESIN; SULFONIC ACID DERIVATIVE;

ARTICLE; CARAMEL; CHEMISTRY;

CARBOHYDRATES; DISACCHARIDES; FRUCTOSE; ION EXCHANGE RESINS; SULFONIC ACIDS;

EID: 76449114017     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf903354y     Document Type: Article

References (50)

1. Gattuso, G.; Nepogodiev, S. A.; Fraser Stoddart, J. F. Synthetic cyclic oligosaccarides. Chem. Rev. 1998, 98, 1919-1958.
2. McDonald, E. J. The polyfructosanes and difructose anhydrides. Adv. Carbohydr. Chem. 1946, 2, 253-277.
3. Manley-Harris, M.; Richards, G. N. Dihexulose dianhydrides. Adv. Carbohydr. Chem. Biochem. 1997, 52, 207-239.
4. García-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M. Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides. Molecules 2008, 13, 1640-1670.
5. Defaye, J.; García Fernández, J. M. Protonic and thermal activation of sucrose and the oligosaccharide composition of caramel. Carbohydr. Res. 1994, 256, C1-C4.
6. Defaye, J.; García Fernández, J. M. The oligosaccharide components of caramel. Zuckerindustrie 1995, 120, 700-704.
7. Defaye, J.; García Fernández, J. M. Les molécules de la caramélization: Structure et méthodologies de détection et d'évaluation. Actual. Chim. 2000, Nov, 24-27.
8. Oosterveld, A.; Voragen, A.G. J.; Schols, H. A. Effect of roasting on the carbohydrate composition of Coffea arabica beans. Carbohydr. Polym. 2003, 54, 183-192.
9. Montilla, A.; Ruíz-Matute, A. I.; Sanz, M. L.; Martínez-Castro, I.; del Castillo, M. D. Difructose anhydrides as quality markers of honey and coffee. Food Res. Int. 2006, 39, 801-806.
10. Waleckx, E.; Gschaedler, A.; Colonna-Ceccaldi, B.; Monsan, P. Hydrolysis of fructans from Agave tequilana Weber var. azul during the cooking step in a traditional tequila elaboration process. Food Chem. 2008, 108, 40-48.
11. Speck, J. C., Jr. The Lobry de Bruyn-Alberda van Ekestein transformation. Adv. Carbohydr. Chem. 1958, 13, 63-103.
12. Kroh, L. W.; Jalyschko, W.; Häseler, J. Non-volatile reaction products by heat-induced degradation of α-glucans. Part I: Analysis of oligomeric maltodextrins and anhydrosugars. Starch/Staerke 1996, 48, 426-433.
13. Jiang, B.; Liu, Y.; Bhandari, B.; Zhou, W. Impact of caramelization in the glass transition temperature of several caramelized sugars. Part I: Chemical analyses. J. Agric. Food Chem. 2008, 56, 5138-5147.
14. Ratsimba, V.; García Fernández, J. M.; Defaye, J.; Nigay, H.; Voilley, A. Qualitative and quantitative evaluation of mono- and disaccharides in D-fructose, D-glucose and sucrose caramels by gas-liquid chromatography-mass spectrometry: Di-D-fructose dianhydrides as tracers of caramel authenticity. J. Chromatogr., A 1999, 884, 283-293.
15. Ruíz-Matute, A. I.; Soria, A. C.; Martínez-Castro, I.; Sanz, M. L. A new methodology based on GC-MS to detect honey adulteration with commercial syrups. J. Agric. Food Chem. 2007, 55, 7264-7269.
16. Tomasik, P.; Palasinski, M.; Wiejak, S. The thermal decomposition of carbohydrates. Part I. The decomposition of mono-, di-, and oligo-saccharides. Adv. Carbohydr. Chem. Biochem. 1989, 47, 203-278.
17. Mineo, H.; Amano, M.; Minaminida, K.; Chiji, H.; Shigematsu, N.; Tomita, F.; Hara, H. Two-week feeding of difructose anhydride III enhances calcium absorptive activity with epithelial cell proliferation in isolated rat cecal mucosa. Nutrition 2006, 22, 312-320. (Pubitemid 43261530)
18. Mitamura, R.; Hara, H. Prolonged feeding of difructose anhydride III increases strength and mineral concentrations of the femur in ovariectomized rats. Br. J. Nutr. 2005, 94, 268-274.
19. Mineo, H.; Amano, M.; Chiji, H.; Shigematsu, N.; Tomita, F.; Hara, H. Indigestible saccharides open tight junctions and enhance net calcium, magnesium and zinc absorption in isolated rat small intestinal epithelium. Dig. Dis. Sci. 2004, 49, 122-132.
20. Matsukawa, N.; Matsumoto, M.; Chiji, H.; Hara, H. Oligosaccharide promotes bioavailability of a water-soluble flavonoid glycoside, αG-rutin, in rats. J. Agric. Food Chem. 2009, 57, 1498-1505.
21. Matsumoto, M.; Matsukawa, N.; Chiji, H.; Hara, H. Difructose anhydride III promotes absorption of the soluble flavonoid αG-rutin in rats. J. Agric. Food Chem. 2007, 55, 4202-4208.
22. Tomita, K.; Shiomi, T.; Okuhara, Y.; Tamura, A.; Shigematsu, N.; Hara, A. Ingestion of difructose anhydride III enhances absorption and retention of calcium in healthy men. Biosci., Biotechnol., Biochem. 2007, 71, 681-687.
23. Kawamura, M.; Uchiyama, T. Chemistry and production of di-Dfructose dianhydrides. In Recent advances in fructooligosaccharides research; Norio, S., Noureddine, B., Shuichi, O., Eds.; Research Signpost: Kerala, India, 2007; pp 273-296.
24. Saito, K.; Tomita, F. Difructose anhydrides: Their mass-production and physiological functions. Biosci., Biotechnol., Biochem. 2000, 64, 1321-1327.
25. Kikuchi, H.; Inoue, M.; Saito, H.; Sakurai, H.; Aritsuka, T.; Tomita, F.; Yokota, A. Industrial production of difructose anhydride III (DFA III) from crude inulin extracted from chicory roots using Arthrobacter sp. H65-7 fructosyltransferase. J. Biosci. Bioeng. 2009, 107, 262-265.
26. Takesue, N.; Sone, T.; Tanaka, M.; Tomita, F.; Asano, K. Effect of an additionally introduced degQ gene on di-D-fructofuranosyl 2,60:20,6 anhydride (DFA IV) production by recombinant Bacillus subtilis in a single culture production system. J. Biosci. Bioeng. 2009, 107, 623-629.
27. Defaye, J.; Gadelle, A.; Pedersen,C. The behaviour of D-fructose and inulin towards anhydrous hydrogen fluoride. Carbohydr. Res. 1985, 136, 53-65.
28. Defaye, J.; García Fernández, J. M. Protonic reactivity of sucrose in anhydrous fluoride. Carbohydr. Res. 1994, 251, 1-15.
29. Defaye, J.; García Fernández, J. M. Synthesis of dispirodioxanyl pseudo-disaccharides by selective protonic activation of isomeric glycosylfructoses in anhydrous hydrogen fluoride. Carbohydr. Res. 1994, 251, 17-31.
30. Defaye, J.; García Fernández, J. M. Selective protonic activation of isomeric glycosylfructoses with pyridinium poly(hydrogen fluoride) and synthesis of spirodioxanyl oligosaccharides. Carbohydr. Res. 1992, 237, 223-247.
31. Simkovis, I.; Surina, I.; Vrican, M. Primary reactions of sucrose thermal degradation. J. Anal. Appl. Pyrolysis 2003, 70, 493-504.
32. Antal, M. J.; Mok, W. S. L.; Richard, G. N. Mechanism of formation of 5-(hydroxymethyl)-2 -furaldehyde from D-fructose and sucrose. Carbohydr. Res. 1990, 199, 91-109.
33. Manley-Harris, M.; Richards, G. N. Di-D-fructose dianhydrides and related oligomers from thermal treatments of inulin and sucrose. Carbohydr. Res. 1996, 287, 183-202.
34. Christian, T. J.; Manley-Harris, M.; Field, R. J.; Parker, B. A. Kinetics of formation of di-D-fructose dianhydrides during thermal treatment of inulin. J. Agric. Food Chem. 2000, 48, 1823-1837.
35. Tanaka, M.; Nakajima, Y.; Nishio, K.; Hashimoto, H. Structure of oligosaccharides prepared by acidic condensation of palatinose. J. Carbohydr. Chem. 1993, 12, 49-61.
36. Orban, J. I.; Patterson, J. A.; Surron, A. L.; Richards, G. N. Effect of sucrose thermal oligosaccharide caramel, dietary vitamin-mineral level, and brooding temperature on growth and intestinal bacterial populations of broiler chickens. Poultry Sci. 1997, 76, 482-490.
37. Böhm, A.; Kaiser, I.; Trebstein, A.; Henle, T. Heat-induced degradation of inulin. Eur. Food Res. Technol. 2005, 220, 466-471.
38. Böhm, A.; Klessen, B.; Henle, T. Effect of dry heated inulin on selected intestinal bactera. Eur. Food Res. Technol. 2006, 222, 737-740.
39. While the term caramelization is well-accepted to refer to the chemical transformations taking place upon thermal treatment of sugars, the name caramel is generally reserved to the home-made or industrial product designed as food additive or ingredient for coloring and/or flavoring food. Although the definition of manufactured caramel changes from a country to another, we are here using the term in a broad sense, conforming to the general text-book description of caramel as the brown product originating from various sugars when they are heated either dry or in concentrated solutions and alone or with certain additives. See: Tomasik, P. Caramel. Properties and analysis. In Encyclopedia of Food Sciences and Nutrition, 2nd ed.; Caballero, B., Trugo, L., Finglas, P., Eds.; Academic Press: New York, 2003; pp 852-858.
40. Okuhara, T. Water-tolerant solid acid catalysts. Chem. Rev. 2002, 102, 3641-3666.
41. Rubio Castillo, E. M.; Gómez-García, M.; Ortiz Mellet, C.; García Fernández, J. M.; A. Zarzuelo Zurita, A.; Gálvez Peralta, J. J.; Duval, R. Novel caramels with a high prebiotic oligosaccharide content. ES Patent WO2008107506 (A1).
42. Looijer-van Langen, M. A. C.; Dieleman, L. A. Prebiotics in chronic intestinal inflammation. Inflamm. Bowel Dis. 2009, 15, 454-462.
43. Tomasik, P. J.; Tomasik, P. Probiotics and prebiotics. Cereal Chem. 2003, 80, 113-117.
44. Benito, J.M.;GómezGarcía, M.; Ortiz Mellet, C.; GarcíaFernández, J. M.; Defaye, J. Carbohydrate-derived spiroketals. Stereoselective synthesis of di-D-fructose dianhydrides by boron trifluoride promoted glycosylation-spiroketalization of acetal precursors. Org. Lett. 2001, 3, 549-552.
45. Benito, J. M.; Rubio, E. M.; Gómez García, M.; Ortiz Mellet, C.; García Fernández, J. M. Carbohydrate-derived spiroketals: stereoselective synthesis of di-D-fructose dianhydrides. Tetrahedron 2004, 60, 5899-5906.
46. 2-symmetric difructose dianhydrides. J. Org. Chem. 2006, 71, 2257-2266.
47. Balbuena, P; Rubio, E. M.; Ortiz Mellet, C.; García Fernández, J. M. The o-xylylene protecting group as an element of conformational control of remote stereochemistry in the synthesis of spiroketals. Chem. Commun. 2006, 2610-2612.
48. Rubio, E. M.; García-Moreno, M. I.; Balbuena, P.; Ortiz Mellet, C.; García Fernández, J. M. Rigid spacer-mediated synthesis of bisspiroketal ring systems: stereoselective synthesis of nonsymmetrical spiro disaccharides. Org. Lett. 2005, 7, 729-731.
49. García Fernández, J. M.; Gadelle, A.; Defaye, J. Difructose dianhydrides from sucrose and fructo-oligosaccharides and their use as building blocks for the preparation of amphiphiles, liquid crystals, and polymers. Carbohydr. Res. 1994, 265, 249-269.
50. Kikuchi, H; Natura, T.; Inoue, M.; Kishida, T.; Sakurai, H.; Yokota, A.; Asano, K.; Tomita, F.; Sayama, K.; Senba, Y. Physical, Chemical and Physiological Properties of difructose anhydride III produced from inulin by enzymatic reaction. J. Appl. Glycosci. 2004, 51, 291-296.