Abstract
This review provides an overview of the current status of the chemistry and biology of di-d-fructose dianhydrides (DFAs) with a focus on their potential as functional foods. The history of this family of cyclic ketodisaccharides has expanded for almost 100 years and offers a paradigmatic example of artificial synthetic molecules that were identified as natural products later on and finally encountered in our own table. Issued from fundamental investigations on the reactivity of carbohydrates in strongly acidic media, DFAs remained laboratory curiosities for decades. Early reports on their isolation from plants raised doubts, until the formation of some DFA representatives by the action of microorganisms on fructans was reported in the middle 1980s. Since then, research on DFAs has run in parallel in the areas of microbiology and carbohydrate chemistry. Evidence of the potential of these compounds as functional food was accumulated from both sides, with the development of biotechnological processes for mass production of selected candidates and of chemical methodologies to prepare DFA-enriched products from sucrose or inulin. In 1994 a decisive discovery in the field took place in the laboratory of Jacques Defaye in Grenoble, France: the presence of DFAs in a commercial sucrose caramel was evidenced in a quite significant 18% mass proportion! The development of an efficient analytical protocol for DFAs and the stereoselective synthesis of individual standards allowed one to demonstrate that DFAs and their glycosylated derivatives (glycosyl-DFAs) are universally formed during caramelization reactions. They are not potential food products; they have actually always been in our daily food. Most important, they seem to exert beneficial effects: they are acariogenic, low-caloric, and promote the growth of beneficial microflora in the gut.
Most recent evidence indicates that DFAs can even protect the intestinal tract against agressive agents favor the assimilation of antioxidants, and act as a drug-like food for the treatment of colon ailments such as inflammatory bowel disease (Crohn disease). The development of efficient methodologies for the preparation of DFA-enriched caramels, compatible with the food and agricultural industry regulations, may lead to new natural functional foods and nutraceuticals based on DFAs in the near future.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Diplock AT, Aggett PJ, Ashwell M, Bornet F, Fern EB, Robertfroid MB (1999) Br J Nutr 81 (4 Suppl 1):S1
Gibson GR, Roberfroid MB (1995) Br J Nutr 125:1401–1412
Gibson GR, Probert HM, van Loo J, Rastall RA, Roberfroid M (2004) Nutr Res Rev 17:259–275
Pszczola DE (1992) Food Technol 46:77–79
Lomax AR, Calder PC (2009) Br J Nutr 101:633–658
Hugenholtz J, Smid EJ (2002) Curr Opin Biotechnol 13:497–507
Fooks LJ, Fuller R, Gibson GR (1999) Int Dairy J9:53–61
Delzene NM (2003) Proc Nutr Soc 62:177–182
Bounik Y, Raskine L, Simoneau G, Vicaut E, Neut C, Flourie B, Brouns F, Bornet F (2004) J Nutr 80:1658–1664
Zentec J, Marquart B, Pietrzak T (2002) J Nutr 132:S1682–S1684
Olano-Martín E, Williams MR, Gibson GR, Rastall RA (2003) FEMS Microbiol Lett 218:101–105
Morgan AJ, Mul AJ, Beldman G, Voragen AGJ (1992) AGRO Food Industry High Technol Nov/Dec 3:35–38
Campbell JM, Fahy GC, Wolf BW (1997) J Nutr 127:130–136
Macfarlane GT, Steed H, Macfarlane S (2008) J Appl Microbiol 104:305–344
Gattuso G, Nepogodiev SA, Stoddart JF (1998) Chem Rev 98:1919–1958
McDonald EJ (1946) Adv Carbohydr Chem 2:53–277
Manley-Harris M, Richards GN (1997) Adv Carbohydr Chem Biochem 52:207–239
García-Moreno MI, Benito JM, Ortiz Mellet C, García Fernández JM (2008) Molecules 13:1640–1670
Defaye J, García Fernández JM (1994) Carbohydr Res 256:C1–C4
This H, Rutledge D (2009) Anal Bional Chem 394:659–661
This H (2009) Acc Chem Res 42:575–583
McNaught AD (1996) Pure Appl Chem 68:1919
Shlubach HH, Knoop H (1993) Justus Liebigs Ann Chem 504:19–30
Strepkov SM (1958) Zh Obshch Khim 28:3143–3147
Uchiyama T (1983) Agric Biol Chem 47(2):437–439
Li H-Y, Hagiwara H, Zhu W, Yokoyama C, Harada N (1997) Carbohydr Res 299:301–305
Uchiyama T, Niwa S, Tanaka K (1973) Biochim Biophys 315:412–420
Tanaka K, Uchiyama T, Ito A (1972) Biochim Biophys 284:248–256
Kawamura M, Uchiyama T (2007) Chemistry and production of di-d-fructose dianhydrides. In: Norio S, Noureddine B, Shuichi O (eds) Recent advances in fructooligosaccharides research. Research Signpost, Kerala, India, pp 273–296
Uchiyama T (1975) Biochim Biophys Acta 397:153–163
Tanaka K, Kawaguchi H, Ohno K, Shohji K (1981) J Biochem 90:1545–1548
Tanaka K, Uchiyama T, Yamamuchi K, Suzuki Y, Hashiguchi S (1982) Carbohydr Res 99:197–204
Tanaka K, Karigane T, Yamaguchi F, Nishikawa S, Yoshida N (1983) J Biochem 94:1569–1578
Defaye J, Gadelle A, Pedersen C (1985) Carbohydr Res 136:53–65
Chu YD, Shiau LD, Berglund KA (1989) J Crystal Growth 97:689–696
Wolfrom ML, Blair MG (1948) J Am Chem Soc 70:2406–2409
Nguyen SK, Sophonputtanaphoca S, Kim E, Penner MH (2009) Appl Biochem Biotechnol 158:352–361
Benito JM, Ortiz Mellet C, García Fernández JM (2005) Identificación y cuantificacción de azúcares resultantes de la dimerización de la sacarosa y de la d-fructosa (dianhídridos de fructosa) formados en la raíz de la remolacha o durante su procesado industrial. In: Echevarría C, Morillo-Valverde R (eds) Aspectos fisiológicos de la remolacha azucarera de siembra otoñal, 1st edn. Junta de Andalucía, Seville, Spain
García Fernández JM, Gadelle A, Defaye J (1994) Carbohydr Res 265:249–269
Defaye J, García Fernández JM (1994) Carbohydr Res 251:17–31
García Fernández JM, Defaye J (1992) Carbohydr Res 237:223–247
Defaye J, García Fernández JM (1994) Carbohydr Res 251:1–15
García Fernández JM, Defaye J (1992) Tetrahedron Lett 33(51):7861–7864
García Fernández JM, Ortiz Mellet C, Defaye J (1998) J Org Chem 63:3572–3580
Defaye J, Gadelle A, Pedersen C (1988) Carbohydr Res 174:323–329
García Fernández JM, Schnelle R-R, Defaye J (1995) Tetrahedron Asymmetry 6:307–312
Gerber-Lemaire S, Vogel P (2009) Carbohydr Chem 35:13–32
Takaoka LR, Buckmelter AJ, LaCruz TE, Rychnovsky SD (2005) J Am Chem Soc 127:528
Benito JM, Gómez-García M, Ortiz Mellet C, García Fernández JM, Defaye J (2001) Org Lett 3:549–552
Benito JM, Rubio EM, Gómez-García M, Ortiz Mellet C, García Fernández JM (2004) Tetrahedron 60:5899–5906
Balbuena P, Rubio EM, Ortiz Mellet C, García Fernández JM (2006) Chem Commun 2610–2612
Rubio EM, Ortiz Mellet C, García Fernández JM (2003) Org Lett 5(6):873–876
Rubio EM, García Moreno MI, Balbuena P, Lahoz FJ, Alvarez E, Ortiz Mellet C, García Fernández JM (2006) J Org Chem 71:2257–2266
Rubio EM, García Moreno MI, Balbuena P, Ortiz Mellet C, García Fernández JM (2005) Org Lett 7(4):729–731
Louis F, García Moreno MI, Balbuena P, Ortiz Mellet C, García Fernández JM (2008) Tetrahedron 64:2792–2800
Saito K, Tomita F (2000) Biosci Biotechnol Biochem 64:1321–1327
Seki K, Haraguchi K, Kishimoto S, Kobayashi S, Kainuma K (1988) Starch-Stärke 40:440–442
Seki K, Haraguchi K, Kishimoto S, Kobayashi S, Kainuma K (1989) Agric Biol Chem 53:2089–2090
Kushibe S, Sashida R, Morimoto Y, Ohkishi H (1993) Biosci Biotechnol Biochem 57:2054–2058
Haraguchi K, Yoshida M, Ohtsubo K (2003) Biotechnol Lett 25:1049–1053
Haraguchi K, Yoshida M, Yamanaka T, Ohtsubo K (2003) Carbohydr Polym 53:501–505
Yokota A, Hirayama S, Enemoto K, Miura Y, Takao S, Tomita F (1991) J Ferment Bioeng 72:258–261
Yokota A, Enemoto K, Tomita F (1991) J Ferment Bioeng 72:262–265
Kikuchi H, Inoue M, Saito H, Sakurai H, Aritsuka T, Tomita F, Yokota A (2009) J Biosci Bioeng 107(3):262–265
Haraguchi K, Yoshida M, Ohtsubo K (2005) Carbohydr Polym 59:411–416
Haraguchi K, Yoshida M, Ohtsubo K (2006) Carbohydr Polym 66:75–80
Cha J, Park NH, Yang SJ, Lee TH (2001) J Biotechnol 91:49–61
Jang K-H, Ryu E-J, Park B-S, Song K-B, Kang SA, Kim CH, Uhm T-B, Park Y-I, Rhee S-K (2003) J Agric Food Chem 51:2635–2636
Jang K-H, Jang E-K, Kim SH, Kim I-H, Kang SA, Koh I, Park Y-I, Kim Y-J, Ha -D, Kim CH (2006) J Microbiol Biotechnol 16:102–108
Jang E-K, Jang K-H, Koh I, Kim I-H, Kim SH, Kang SA, Kim CH, Ha S-D, Rhee S-K (2002) J Microbiol Biotechnol 12:603–609
Takesue N, Sone T, Tanaka M, Tomita F, Asano K (2007) Enzyme Microb Technol 41:673–676
Takesue N, Sone T, Tanak M, Tomita F, Asano K (2009) J Biosci Bioeng 107(6):623–629
Tomasik P, Palasinski M, Wiejak S (1989) Adv Carbohydr Chem Biochem 47:203–278
Queneau Y, Jarosz S, Lewandowski B, Fitremann J (2007) Adv Carbohydr Chem Biochem 61:217–292
Defaye J, García Fernández JM (1995) Zuckerindustrie 120:700–704
Defaye J, García Fernández JM (2000) Actual Chim Novembre:24–27
Oosterveld A, Voragen AGJ, Schols HA (2003) Carbohydr Polym 54:183–192
Montilla A, Ruíz-Matute AI, Sanz ML, Martínez-Castro I, del Castillo MD (2006) Food Res Int 39:801–806
Waleckx E, Gschaedler A, Colonna-Ceccaldi B, Monsan P (2008) Food Chem 108:40–48
Speck JC Jr (1958) Adv Carbohydr Chem 13:63–103
Kroh LW, Jalyschko W, Häseler J (1996) Starch/Stärke 48:426–433
Jiang B, Liu Y, Bhandari B, Zhou W (2008) J Agric Food Chem 56:5138–5147
Simkovis I, Surina I, Vrican M (2003) J Anal Appl Pyrolysis 70:493–504
Antal MJ, Mok WSL, Richard GN (1990) Carbohydr Res 199:91–109
Ratsimba V, García Fernández JM, Defaye J, Nigay H, Voilley A (1999) J Chromatogr A 884:283–293
Ruíz-Matute AI, Soria AC, Martínez-Castro I, Sanz ML (2007) J Agric Food Chem 55:7264–7269
Manley-Harris M, Richards GN (1994) Zuckerindustrie 114:924–928
Manley-Harris M, Richards GN (1994) Carbohydr Res 254:195–202
Manley-Harris M, Richards GN (1996) Carbohydr Res 287:183–202
Christian TJ, Manley-Harris M, Field RJ, Parker BA (2000) J Agric Food Chem 48:1823–1837
Tanaka M, Nakajima Y, Nishio K, Hashimoto H (1993) J Carbohydr Chem 12:49–61
Suárez-Pereira E, Rubio EM, Pilard S, Ortiz Mellet C, García Fernández JM (2010) J Agric Food Chem 58:1777–1787
Rechner AR, Wagner E, Van Buren L, Van De Put F, Wiseman S, Rice-Evans CA (2002) Free Radical Res 36:1127–1135
Saito K, Hira T, Suzuki T, Hara H, Yokota A, Tomita F (1999) Biosci Biotechnol Biochem 63:655–661
Minamida K, Sujaya IN, Tamura A, Shigematsu N, Sone T, Yokota A, Asano K, Benno Y, Tomita F (2004) J Biosci Bioeng 98:244–250
Minamida K, Shiga K, Sujaya IN, Sone T, Yokota A, Hara H, Asano K, Tomita F (2005) J Biosci Bioeng 99:230–236
Minamida K, Asakawa C, Sujaya IN, Kaneko M, Abe A, Sone T, Hara H, Asano K, Tomita F (2006) J Biosci Bioeng 101:149–156
Minamida K, Kaneko M, Ohashi M, Sujaya IN, Sone T, Wada M, Yokota A, Hara H, Asano K, Tomita F (2005) J Biosci Bioeng 99:548–554
Hara H, Kondo K (2005) Biosci Biotechnol Biochem 69:839–841
Mineo H, Amano M, Chiji H, Shigematsu N, Tomita F, Hara H (2004) Dig Dis Sci 49:122–132
Afsana K, Shiga K, Ishizuka S, Hara H (2003) J Nutr 133:553–3560
Shiga K, Hara H, Okano G, Ito M, Minami A, Tomita F (2003) J Nutr 133:4207–4211
Mineo H, Hara H, Shigematsu N, Okuhara Y, Tomita F (2002) J Nutr 132:3394–3399
Suzuki T, Hara H (2006) Life Sci 79:401–410
Matsumoto M, Matsukawa N, Chiji H, Hara H (2007) J Agric Food Chem 55:4202–4208
Matsuwaka N, Matsumoto M, Chiji H, Hara H (2009) J Agric Food Chem 57:1498–1505
Kashimura J, Nakajima Y, Benno Y, Endo K, Mitsuoka T (1989) Bifidobacteria Microflora 8:45–50
Orban JI, Patterson JA, Surron AL, Richards GN (1997) Poultry Sci 76:482–490
Rubio Castillo EM, Gómez García M, Ortiz Mellet C, García Fernández JM, Zarzuelo Zurita A, Gálvez Peralta JJ, Duval R (2007) Novel caramels with a high prebiotic oligosaccharide content, ES Patent WO2008107506
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer
About this chapter
Cite this chapter
Mellet, C.O., Fernández, J.M.G. (2010). Difructose Dianhydrides (DFAs) and DFA-Enriched Products as Functional Foods. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development I. Topics in Current Chemistry, vol 294. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_50
Download citation
DOI: https://doi.org/10.1007/128_2010_50
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-14836-1
Online ISBN: 978-3-642-14837-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)