Article pubs.acs.org/JAFC
Impact of Wheat Bran Derived Arabinoxylanoligosaccharides and Associated Ferulic Acid on Dough and Bread Properties Jeroen Snelders, Emmie Dornez, Jan A. Delcour, and Christophe M. Courtin* Laboratory of Food Chemistry and Biochemistry & Leuven Food Science and Nutrition Research Centre (LFoRCe), KU Leuven, Kasteelpark Arenberg 20, B-3001 Leuven, Belgium ABSTRACT: The impact of arabinoxylanoligosaccharides (AXOS) with varying bound or free ferulic acid (FA) content on dough and bread properties was studied in view of their prebiotic and antioxidant properties. AXOS with an FA content of 0.1−1.7% caused an increase in dough firmness with increasing AXOS concentration. AXOS with a high FA content (7.2%), on the contrary, resulted in an increase in dough extensibility and a decrease in resistance to extension, similar to that for free FA, when added in levels up to 2%. Higher levels resulted in unmanageable dough. A limited impact on dough gluten network formation was observed. These results suggest that for highly feruloylated AXOS, the FA-mediated dough softening supersedes the firming effect displayed by the carbohydrate moiety of AXOS. The impact of the different AXOS on bread volume, however, was minimal. Furthermore, AXOS in bread were not engaged in covalent cross-linking and significantly increased its antioxidant capacity. KEYWORDS: AXOS, ferulic acid, dough rheology, bread making, antioxidant capacity
■
the FA level during bread making,21,22 suggesting their role in cross-linking with other FA moieties or gluten amino acids. Reaction of FA with gluten might involve reactions associated with the presence of its activated α,β-double bond.23 Only phenolic acids present in the water-soluble fraction, free or present as low molecular weight conjugates, were able to undergo these reactions and form FA-cysteine adducts, while most of the endogenously present FA was present in the insoluble dough fraction.22−24 The presence of a FA-tyrosine cross-linking product in dough was also demonstrated, but its significance toward dough properties is deemed low as it is only present in very low concentrations.25 Other observations, however, suggest that FA moieties do not impact AX functionality significantly. De-esterification of rye WE-AX did not change their impact on gluten−starch separation,17 and the gelling ability of WE-AX was not important for their functionality.18 Furthermore, a decrease in FA content is not always observed as a function of mixing time.19,20 Addition of free FA to the bread making recipe was reported to reduce bread volume. The presence of FA disturbs rearrangements of protein aggregates during dough development, resulting in an increased level of sodium dodecyl sulfate (SDS)extractable proteins.26,27 The mixing tolerance after optimum mixing time decreases as well.22,24,26,27 Beside the effect on gluten agglomeration, the observed reduction in bread volumes upon addition of FA could also be due to inhibition of the yeast, as yeast inhibition has also been observed for other weak acids like benzoic, acetic, and propionic acid.28 In this study, the influence of AXOS with diverse FA content, free or bound, and that of free FA as such on dough and bread
INTRODUCTION Arabinoxylan oligosaccharides (AXOS), hydrolysis product of arabinoxylan (AX), have prebiotic properties.1 They can be produced from AX-rich biomass, such as wheat bran,2 and consist of β-1,4 linked D-xylopyranosyl residues, which can be un-, mono-, or disubstituted with α-L-arabinofuranosyl units on their C-(O)-2 and/or C-(O)-3 position. Ferulic acid (FA) is esterified to some arabinose residues.3,4 FA is a strong natural antioxidant and the most abundant phenolic acid in wheat. The FA content and appearance determine the antioxidant properties of AXOS.5 As bread is a staple food, bread with added AXOS can be an interesting type of functional food. Indeed, functional foods are defined as foods that beneficially affect one or more target functions in the body, beyond adequate nutritional effects, in a way that is relevant to either an improved state of health and well-being and/or reduction of risk of disease.6 The use of AXOS as a bread ingredient and its impact on the bread making procedure and the final product, however, has not been studied. For wheat AX, subdivided into water-extractable (WE-AX) and water-unextractable AX (WU-AX), it is known that they strongly impact the bread making process. WE-AX are beneficial for bread making, whereas WU-AX are not.9 Indeed, WE-AX are believed to increase the stability of the liquid films, surrounding the gas cells, by increasing their viscosity,13,15,16 whereas WU-AX not only compete for water and physically hinder gluten formation but could possibly perforate gas cells as they are present as discrete cell wall fragments without contributing to dough liquor viscosity.9,10,12 Thorough degradation of AX will increase the level of free water and give rise to sticky doughs and inferior breads.7,8,14 The possible role in bread making of FA esterified to AX remains a subject of debate. By cross-linking through, for example, di-FA bridges, WE-AX could form a secondary network, enforcing the gluten network.9,11 Several observations are in line with this hypothesis. Some studies showed a decrease in © 2014 American Chemical Society
Received: Revised: Accepted: Published: 7190
May 15, 2014 July 2, 2014 July 4, 2014 July 4, 2014 dx.doi.org/10.1021/jf502315g | J. Agric. Food Chem. 2014, 62, 7190−7199
Journal of Agricultural and Food Chemistry
Article
Table 1. Overview of the Composition and Structural Characteristics of the AXOS Used in This Articlea AXOS content (% dm) free ara content (% dm) free xyl content (% dm) avDPxylb avDASc oligomeric glucose content (% dm) free FA content (% dm) bound FA content (% dm) total FA content (% dm)
HBFA-AXOS
HFFA-AXOS
MBFA-AXOS
MFFA-AXOS
LFFA-AXOS
73 (±5) 0.05). bLevel of added FA due to addition of AXOS (FA/dm flour expressed in ppm).
0 200 500 1000 1200 1800
FA equiv (ppm FA/dm flour)
Article
a
E DE CD BC B A (±0.1) (±1.7) (±0.5) (±0.8) (±0.8) (±0.3) 11.6 11.9 14.1 16.4 16.7 20.7 Aa Aa Aa Aa Aa Aa (±0.08) (±0.21) (±0.09) (±0.05) (±0.19) (±0.08) 4.01 3.85 4.13 4.11 4.01 4.03 0.00 0.25 0.50 1.00 1.30 2.00 E DE CD BC B A (±0.1) (±1.7) (±0.5) (±0.8) (±0.8) (±0.3) 11.6 11.9 14.1 16.4 16.7 20.7 Aa ABa ABa ABCb BCa BCa (±0.08) (±0.06) (±0.04) (±0.03) (±0.06) (±0.13) 4.01 3.94 3.97 3.83 3.76 3.77
TEAC (μmol Trolox/g dm flour) dose (% dm AXOS/dm flour)
0.00 1.00 2.00 4.00 5.00 8.00
specific volume (cm3/g) specific volume (cm /g)
TEAC (μmol Trolox/g dm flour)
dose (% dm AXOS/dm flour)
HBFA-AXOS MBFA-AXOS
3 b
Table 8. Volume, Specific Volume, and Antioxidant Capacity of Breads with and without the Presence of MBFA-AXOS and HBFA-AXOS As Determined with TEACa
Journal of Agricultural and Food Chemistry
7197
dx.doi.org/10.1021/jf502315g | J. Agric. Food Chem. 2014, 62, 7190−7199
Journal of Agricultural and Food Chemistry
■
Article
(10) Frederix, S. A.; Van hoeymissen, K. E.; Courtin, C. M.; Delcour, J. A. Water-extractable and water-unextractable arabinoxylans affect gluten agglomeration behavior during wheat flour gluten-starch separation. J. Agric. Food Chem. 2004, 52, 7950−7956. (11) Wang, M.; Hamer, R. J.; van Vliet, T.; Gruppen, H.; Marseille, H.; Weegels, P. L. Effect of water unextractable solids on gluten formation and properties: mechanistic considerations. J. Cereal Sci. 2003, 37, 55−64. (12) Wang, M.; Oudgenoeg, G.; van Vliet, T.; Hamer, R. J. Interaction of water unextractable solids with gluten protein: Effect on dough properties and gluten quality. J. Cereal Sci. 2003, 38, 95−104. (13) Gan, Z.; Ellis, P. R.; Schofield, J. D. Gas cell stabilisation and gas retention in wheat bread dough. J. Cereal Sci. 1995, 21, 215−230. (14) Courtin, C. M.; Roelants, A.; Delcour, J. A. Fractionationreconstitution experiments provide insight into the role of endoxylanases in bread-making. J. Agric. Food Chem. 1999, 47, 1870−1877. (15) Courtin, C. M.; Delcour, J. A. Physicochemical and breadmaking properties of low molecular weight wheat-derived arabinoxylans. J. Agric. Food Chem. 1998, 46, 4066−4073. (16) Hoseney, R. C.; Finney, K. F.; Shogren, M. D.; Pomeranz, Y. Functional (breadmaking) and biochemical properties of wheat flour components. 2. Role of water-solubles. Cereal Chem. 1969, 46, 117− 125. (17) Delcour, J. A.; Vanhamel, S.; Hoseney, R. C. Physicochemical and functional-properties of rye nonstarch polysaccharides. 2. Impact of a fraction containing water-soluble pentosans and proteins on gluten-starch loaf volumes. Cereal Chem. 1991, 68, 72−76. (18) Patil, S. K.; Finney, K. F.; Shogren, M. D.; Tsen, C. C. Watersoluble pentosans of wheat-flour 0.3. Effect of water-soluble pentosans on loaf volume of reconstituted gluten and starch doughs. Cereal Chem. 1976, 53, 347−354. (19) Labat, E.; Morel, M. H.; Rouau, X. Effects of laccase and ferulic acid on wheat flour doughs. Cereal Chem. 2000, 77, 823−828. (20) Decamps, K.; Joye, I. J.; Rakotozafy, L.; Nicolas, J.; Courtin, C. M.; Delcour, J. A. The bread dough stability improving effect of pyranose oxidase from Trametes multicolor and Glucose Oxidase from Aspergillus niger: Unraveling the molecular mechanism. J. Agric. Food Chem. 2013, 61, 7848−7854. (21) Yeh, Y. F.; Hoseney, R. C.; Lineback, D. R. Changes in wheatflour pentosans as a result of dough mixing and oxidation. Cereal Chem. 1980, 57, 144−148. (22) Labat, E.; Morel, M.-H.; Rouau, X. Wheat gluten phenolic acids: Occurrence and fate upon mixing. J. Agric. Food Chem. 2000, 48, 6280−6283. (23) Jackson, G. M.; Hoseney, R. C. Fate of ferulic acid in overmixed wheat flour doughs: Partial characterization of a cysteine-ferulic acid adduct. J. Cereal Sci. 1986, 4, 87−95. (24) Jackson, G. M.; Hoseney, R. C. Effect of endogenous phenolic acids on the mixing properties of wheat flour doughs. J. Cereal Sci. 1986, 4, 79−85. (25) Piber, M.; Koehler, P. Identification of dehydro-ferulic acidtyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins. J. Agric. Food Chem. 2005, 53, 5276−5284. (26) Han, H.-M.; Koh, B.-K. Effect of phenolic acids on the rheological properties and proteins of hard wheat flour dough and bread. J. Sci. Food Agric. 2011, 91, 2495−2499. (27) Koh, B.-K.; Ng, P. K. W. Effects of ferulic acid and transglutaminase on hard wheat flour dough and bread. Cereal Chem. 2009, 86, 18−22. (28) Nicks, F.; Richel, A.; Dubrowski, T.; Whatelet, B.; Whatelet, J.P.; Blecker, C.; Paquot, M. Effect of new synthetic PEGylated ferulic acids in comparison to ferulic acid and commercial surfactants on the properties of wheat flour dough and bread. J. Sci. Food Agric. 2013, 93, 2415−2420. (29) Shogren, M. D.; Finney, K. F. Bread-making test for 10 grams of flour. Cereal Chem. 1984, 61, 418−423.
AUTHOR INFORMATION
Corresponding Author
*Tel.: + 32 16 32 19 17. Fax: + 32 16 32 19 97. E-mail:
[email protected]. Funding
Financial support from the “Fonds voor Wetenschappelijk Onderzoek” (FWO, Brussels, Belgium) for the postdoctoral fellowship of E. Dornez and from the European Commission in the Communities seventh Framework Programme (FP7/20072013) for the Biocore Project (grant agreement no. FP7241566) is gratefully appreciated. Notes
The authors declare no competing financial interest.
■
ACKNOWLEDGMENTS This publication reflects only the authors’ views, and the Community is not liable for any use that may be made of the information contained in this publication. Mira Beke, Kristien Thoelen, and Hilde Van den Broeck are gratefully thanked for technical assistance. This research is also part of the Methusalem Programme Food for the Future (2007−2014).
■
ABBREVIATIONS USED 4-VG, 4-vinylguaiacol; AX, arabinoxylan; AXOS, arabinoxylanoligosaccharides; avDAS, average degree of arabinose substitution; avDPxyl, average degree of polymerization of the xylan backbone; FA, ferulic acid; RP-HPLC, reversed-phase high-performance liquid chromatography; SDS, sodium dodecyl sulfate; SE-HPLC, size-exclusion high-performance liquid chromatography; TEAC, Trolox Equivalent Antioxidant Capacity; TFA, trifluoroacetic acid; WE-AX, water-extractable arabinoxylan; WU-AX, water-unextractable arabinoxylan
■
REFERENCES
(1) Broekaert, W. F.; Courtin, C. M.; Verbeke, K.; Van de Wiele, T.; Verstraete, W.; Delcour, J. A. Prebiotic and other health-related effects of cereal-derived arabinoxylans, arabinoxylan-oligosaccharides, and xylooligosaccharides. Crit. Rev. Food Sci. Nutr. 2011, 51, 178−194. (2) Swennen, K.; Courtin, C. M.; Lindemans, G.; Delcour, J. A. Large-scale production and characterisation of wheat bran arabinoxylooligosaccharides. J. Sci. Food Agric. 2006, 86, 1722−1731. (3) Izydorczyk, M. S.; Biliaderis, C. G. Cereal arabinoxylans: Advances in structure and physicochemical properties. Carbohydr. Polym. 1995, 28, 33−48. (4) Zhao, Z.; Moghadasian, M. Bioavailability of hydroxycinnamates: A brief review of in vivo and in vitro studies. Phytochem. Rev. 2010, 9, 133−145. (5) Snelders, J.; Dornez, E.; Delcour, J. A.; Courtin, C. M. Ferulic acid content and appearance determine the antioxidant capacity of arabinoxylanoligosaccharides. J. Agric. Food Chem. 2013, 61, 10173− 10182. (6) Diplock, A. T.; Aggett, P. J.; Ashwell, M.; Bornet, F.; Fern, E. B.; Roberfroid, M. Scientific concepts of functional foods in Europe. Consensus document. Br. J. Nutr. 1999, 81, S1−27. (7) Damen, B.; Pollet, A.; Dornez, E.; Broekaert, W. F.; Van Haesendonck, I.; Trogh, I.; Arnaut, F.; Delcour, J. A.; Courtin, C. M. Xylanase-mediated in situ production of arabinoxylan oligosaccharides with prebiotic potential in whole meal breads and breads enriched with arabinoxylan rich materials. Food Chem. 2012, 131, 111−118. (8) Dornez, E.; Verjans, P.; Broekaert, W. F.; Cappuyns, A. M.; Van Impe, J. F.; Arnaut, F.; Delcour, J. A.; Courtin, C. M. In situ production of prebiotic AXOS by hyperthermophilic Xylanase B from Thermotoga maritima in high-quality bread. Cereal Chem. 2011, 88, 124−129. (9) Courtin, C. M.; Delcour, J. A. Arabinoxylans and endoxylanases in wheat flour bread-making. J. Cereal Sci. 2002, 35, 225−243. 7198
dx.doi.org/10.1021/jf502315g | J. Agric. Food Chem. 2014, 62, 7190−7199
Journal of Agricultural and Food Chemistry
Article
(30) Vanhamel, S.; Vandenende, L.; Darius, P. L.; Delcour, J. A. A volumeter for breads prepared from 10-grams of flour. Cereal Chem. 1991, 68, 170−172. (31) Dunnewind, B.; Sliwinski, E. L.; Grolle, K.; Van Vliet, T. The Kieffer dough and gluten extensibility rig - An experimental evaluation. J. Texture Stud. 2003, 34, 537−560. (32) AOAC. Official Methods of Analysis, Method 990.03, 16th ed.; Association of Official Analytical Chemists: Washington, DC, 1995. (33) Lagrain, B.; Brijs, K.; Veraverbeke, W. S.; Delcour, J. A. The impact of heating and cooling on the physico-chemical properties of wheat gluten-water suspensions. J. Cereal Sci. 2005, 42, 327−333. (34) Loosveld, A. M. A.; Grobet, P. J.; Delcour, J. A. Contents and structural features of water-extractable arabinogalactan in wheat flour fractions. J. Agric. Food Chem. 1997, 45, 1998−2002. (35) Antoine, C.; Peyron, S.; Mabille, F.; Lapierre, C.; Bouchet, B.; Abecassis, J.; Rouau, X. Individual contribution of grain outer layers and their cell wall structure to the mechanical properties of wheat bran. J. Agric. Food Chem. 2003, 51, 2026−2033. (36) Dobberstein, D.; Bunzel, M. Separation and detection of cell wall-bound ferulic acid dehydrodimers and dehydrotrimers in cereals and other plant materials by reversed phase high-performance liquid chromatography with ultraviolet detection. J. Agric. Food Chem. 2010, 58, 8927−8935. (37) Rombouts, I.; Lamberts, L.; Celus, I.; Lagrain, B.; Brijs, K.; Delcour, J. A. Wheat gluten amino acid analysis by high-performance anion-exchange chromatography with integrated pulsed amperometric detection. J. Chromatogr. A 2009, 1216, 5557−5562. (38) Moore, S. On the determination of cystine as cysteic acid. J. Biol. Chem. 1963, 238, 235−237. (39) Serpen, A.; Gökmen, V.; Pellegrini, N.; Fogliano, V. Direct measurement of the total antioxidant capacity of cereal products. J. Cereal Sci. 2008, 48, 816−820. (40) Jekle, M.; Becker, T. Effects of acidification, sodium chloride, and moisture levels on wheat dough: I. Modeling of rheological and microstructural Properties. Food Biophys. 2012, 7, 190−199. (41) Ognean, M.; Ognean, C. F.; Bucur, A. Rheological effects of some xylanase on doughs from high and low extraction flours. Procedia Food Sci. 2011, 1, 308−314. (42) Lagrain, B.; De Vleeschouwer, K.; Rombouts, I.; Brijs, K.; Hendrickx, M. E.; Delcour, J. A. The kinetics of β-elimination of cystine and the formation of lanthionine in gliadin. J. Agric. Food Chem. 2010, 58, 10761−10767. (43) MacRitchie, F. Mechanical degradation of gluten proteins during high-speed mixing of doughs. J. Polym. Sci. Polym. Symp. 1975, 49, 85− 90. (44) Okada, K.; Negishi, Y.; Nagao, S. Factors affecting dough breakdown during overmixing. Cereal Chem. 1987, 64, 428−434. (45) Shahidi, F.; Naczk, M. Nutritional and pharmacological effects of food phenolics. In Food Phenolics: Sources, Chemistry, Effects and Applications; Shahidi, F., Naczk, M., Eds.; Technomic Publishing Co., Inc.: Lancaster, PA, 1995; pp 171−191. (46) Siebert, K. J.; Troukhanova, N. V.; Lynn, P. Y. Nature of polyphenol-protein interactions. J. Agric. Food Chem. 1996, 44, 80−85. (47) Coghe, S.; Benoot, K.; Delvaux, F.; Vanderhaegen, B.; Delvaux, F. R. Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: indications for feruloyl esterase activity in Saccharomyces cerevisiae. J. Agric. Food Chem. 2004, 52, 602−608. (48) Lagrain, B.; Thewissen, B. G.; Brijs, K.; Delcour, J. A. Impact of redox agents on the extractability of gluten proteins during bread making. J. Agric. Food Chem. 2007, 55, 5320−5325. (49) Cloetens, L.; De Preter, V.; Swennen, K.; Brockaert, W. F.; Courtin, C. M.; Delcour, J. A.; Rutgeerts, P.; Verbeke, K. Doseresponse effect of arabinoxylooligosaccharides on gastrointestinal motility and on colonic bacterial metabolism in healthy volunteers. J. Am. Coll. Nutr. 2008, 27, 512−518. (50) Euromonitor International. Who Eats What: Identifying International Food Consumption Trends, 1st ed.; Euromonitor International: London, UK, 2009.
7199
dx.doi.org/10.1021/jf502315g | J. Agric. Food Chem. 2014, 62, 7190−7199
