Research Progress on Preparation, Characterization and Structure-Activity Relationship of Feruloylated Arabinoxylan Oligosaccharides

Abstract

Abstract: In our country, a large amount of cereal bran is produced by cereal processing each year, which is rich in phenolic acids and non-digestible polysaccharides. However, the low utilization of cereal bran results in its low added value. In recent years, feruloyl arabinoxylan-oligosaccharides (F-AXOs) have been prepared from cereal bran. F-AXOs are functional oligosaccharides, which have been identified as having the dual physiological activities of ferulic acid and oligosaccharide, such as antioxidant and biogenic properties, and have broad application prospects. This review summarizes the preparation, characterization and known structure of F-AXOs from cereal bran. Finally, this review focuses on the relationship between the structure of F-AXOs and their biological activities and the application of F-AXOs in food industry. It is expected to provide valuable information for future preparation and application of F-AXOs.

Key words: feruloyl arabinoxylan-oligosaccharides, preparation, characterization, structure-activity correlations

CLC Number:

TS209

Feng-Hong DENG. Research Progress on Preparation, Characterization and Structure-Activity Relationship of Feruloylated Arabinoxylan Oligosaccharides[J]. FOOD SCIENCE, 0, (): 0-0.

References

[1] Ou J, Sun Z. Feruloylated oligosaccharides: Structure, metabolism and function[J]. Journal of Functional Foods, 2014, 7: 90-100. DOI: 10.1016/j.jff.2013.09.028.
[2] Antoine C, Peyron S, Mabille F, et al. Individual contribution of grain outer layers and their cell wall structure to the mechanical properties of wheat bran[J]. Journal of Agricultural and Food Chemistry, 2003, 51(7): 2026-2033. DOI: 10.1021/jf0261598.
[3] Hashimoto S, Shogren M D, Bolte L C, et al. Cereal pentosans: Their estimation and significance. 3. Pentosans in abraded grains and milling by-products[J]. Cereal Chemistry, 1987, 64(1): 39-41.
[4] Marcotuli I, Hsieh Y S Y, Lahnstein J, et al. Structural variation and content of arabinoxylans in endosperm and bran of durum wheat (triticum turgidum l.)[J]. Journal of Agricultural and Food Chemistry, 2016, 64(14): 2883-2892. DOI: 10.1021/acs.jafc.6b00103.
[5] Zhang Z X, Smith C, Li W L, et al. Characterization of nitric oxide modulatory activities of alkaline-extracted and enzymatic-modified arabinoxylans from corn bran in cultured human monocytes[J]. Journal of Agricultural and Food Chemistry, 2016, 64(43): 8128-8137. DOI: 10.1021/acs.jafc.6b02896.
[6] Zheng X L, Li L M, Wang X X. Molecular characterization of arabinoxylans from hull-less barley milling fractions[J]. Molecules, 2011, 16(4): 2743-2753. DOI: 10.3390/molecules16042743.
[7] Saeed F, Pasha I, Anjum F M, et al. Arabinoxylans and arabinogalactans: A comprehensive treatise[J]. Critical Reviews in Food Science and Nutrition, 2011, 51(5): 467-476. DOI: 10.1080/10408391003681418.
[8] Mathew S, Abraham T E. Ferulic acid: An antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications[J]. Critical Reviews in Biotechnology, 2004, 24(2-3): 59-83. DOI: 10.1080/07388550490491467.
[9] Schendel R R, Becker A, Tyl C E, et al. Isolation and characterization of feruloylated arabinoxylan oligosaccharides from the perennial cereal grain intermediate wheat grass (thinopyrum intermedium)[J]. Carbohydrate Research, 2015, 407: 16-25. DOI: 10.1016/j.carres.2015.01.006.
[10] Bhatia R, Winters A, Bryant D N, et al. Pilot-scale production of xylo-oligosaccharides and fermentable sugars from miscanthus using steam explosion pretreatment[J]. Bioresource Technology, 2020, 296: 122285. DOI: 10.1016/j.biortech.2019.122285.
[11] Rose D J, Inglett G E. Production of feruloylated arabinoxylo-oligosaccharides from maize (zea mays) bran by microwave-assisted autohydrolysis[J]. Food Chemistry, 2010, 119(4): 1613-1618. DOI: 10.1016/j.foodchem.2009.09.053.
[12] Pazo-Cepeda M V, Aspromonte S G, Alonso E. Extraction of ferulic acid and feruloylated arabinoxylo-oligosaccharides from wheat bran using pressurized hot water[J]. Food Bioscience, 2021, 44: 101374. DOI: 10.1016/j.fbio.2021.101374.
[13] Li K Y, Lai P, Lu S, et al. Optimization of acid hydrolysis conditions for feruloylated oligosaccharides from rice bran through response surface methodolgy[J]. Journal of Agricultural and Food Chemistry, 2008, 56(19): 8975-8978. DOI: 10.1021/jf801736z.
[14] 葛丽花. 阿魏酸低聚糖的制备及其抗氧化性质的研究[D]; 东北林业大学, 2007.
[15] 解春艳. 茶薪菇发酵制备麦麸膳食纤维与阿魏酰低聚糖及其生物活性研究[D]; 南京农业大学, 2010.
[16] Coda R, Katina K, Rizzello C G. Bran bioprocessing for enhanced functional properties[J]. Current Opinion in Food Science, 2015, 1: 50-55. DOI: 10.1016/j.cofs.2014.11.007.
[17] Schendel R R, Puchbauer A-K, Britscho N, et al. Feruloylated wheat bran arabinoxylans: Isolation and characterization of acetylated ando–2-monosubstituted structures[J]. Cereal Chemistry Journal, 2016, 93(5): 493-501. DOI: 10.1094/cchem-12-15-0250-r.
[18] Lequart C, Nuzillard J M, Kurek B, et al. Hydrolysis of wheat bran and straw by an endoxylanase: Production and structural characterization of cinnamoyl-oligosaccharides[J]. Carbohydrate Research, 1999, 319(1-4): 102-111. DOI: 10.1016/s0008-6215(99)00110-x.
[19] Vardakou M, Katapodis P, Samiotaki M, et al. Mode of action of family 10 and 11 endoxylanases on water-unextractable arabinoxylan[J]. International Journal of Biological Macromolecules, 2003, 33(1-3): 129-134. DOI: 10.1016/s0141-8130(03)00077-1.
[20] Katapodis P, Vardakou M, Kalogeris E, et al. Enzymic production of a feruloylated oligosaccharide with antioxidant activity from wheat flour arabinoxylan[J]. European Journal of Nutrition, 2003, 42(1): 55-60. DOI: 10.1007/s00394-003-0400-z.
[21] 姚惠源, 胡敏, 袁小平, 等. 酶法制备阿魏酰低聚糖的研究[J].食品与机械, 2008, (04): 3-7. DOI: 10.13652/j.issn.1003-5788.2008.04.007.
[22] 仪鑫, 孙元琳, 陈树俊, 等. 酶法制备黑小麦麸皮阿魏酰低聚木糖的工艺优化[J].食品工业科技, 2016, 37(06): 191-195. DOI: 10.13386/j.issn1002-0306.2016.06.031.
[23] Gottschalk L M F, Oliveira R A, Bon E P D. Cellulases, xylanases, beta-glucosidase and ferulic acid esterase produced by trichoderma and aspergillus act synergistically in the hydrolysis of sugarcane bagasse[J]. Biochemical Engineering Journal, 2010, 51(1-2): 72-78. DOI: 10.1016/j.bej.2010.05.003.
[24] Pedersen M, Hollensted M, Lange L, et al. Screening for cellulose and hemicellulose degrading enzymes from the fungal genus ulocladium[J]. International Biodeterioration & Biodegradation, 2009, 63(4): 484-489. DOI: 10.1016/j.ibiod.2009.01.006.
[25] 潘海晓, 刘海顺, 王静, 等. 玉米麸皮中阿魏酰低聚糖的制备[J].北京工商大学学报(自然科学版), 2011, 29(03): 33-37.
[26] 张晓娜, 周素梅, 王世平. 二次回归正交旋转组合设计对麦麸中阿拉伯木聚糖酶解工艺的优化[J]. 食品科学, 2008, (01): 141-145.
[27] Hromadkova Z, Kost'alova Z, Ebringerova A. Comparison of conventional and ultrasound-assisted extraction of phenolics-rich heteroxylans from wheat bran[J]. Ultrason Sonochemistry, 2008, 15(6): 1062-1068. DOI: 10.1016/j.ultsonch.2008.04.008.
[28] 解春艳, 游雪娇, 侯晓强, 等. 物理处理玉米皮渣对酶法提取阿魏酰低聚糖的影响[J].食品工业科技, 2016, 37(08): 272-275. DOI: 10.13386/j.issn1002-0306.2016.08.048.
[29] Ruthes A C, Martínez-Abad A, Tan H-T, et al. Sequential fractionation of feruloylated hemicelluloses and oligosaccharides from wheat bran using subcritical water and xylanolytic enzymes[J]. Green Chemistry, 2017, 19(8): 1919-1931. DOI: 10.1039/c6gc03473j.
[30] Yuan X P, Wang J, Yao H Y. Production of feruloyl oligosaccharides from wheat bran insoluble dietary fibre by xylanases from bacillus subtilis[J]. Food Chemistry, 2006, 95(3): 484-492. DOI: 10.1016/j.foodchem.2005.01.043.
[31] Singh A, Eligar S M. Bioactive feruloylated xylooligosaccharides derived from pearl millet (pennisetum glaucum) bran with antiglycation and antioxidant properties[J]. Journal of Food Measurement and Characterization, 2021, 15: 5695-5706. DOI: 10.1007/s11694-021-01139-7.
[32] 袁小平. 酶解麦麸制备阿魏酰低聚糖及其生物活性的研究[D]; 江南大学, 2006.
[33] Saulnier L, Vigouroux J, Thibault J-F. Isolation and partial characterization of feruloylated oligosaccharides from maize bran[J]. Carbohydrate Research, 1995, 272(2): 241-253. DOI: 10.1016/0008-6215(95)00053-V.
[34] Lequart C, Nuzillard J-M, Kurek B, et al. Hydrolysis of wheat bran and straw by an endoxylanase: Production and structural characterization of cinnamoyl-oligosaccharides[J]. Carbohydrate Research, 1999, 319(1): 102-111. DOI: 10.1016/S0008-6215(99)00110-X.
[35] Ishii T, Hiroi T. Isolation and characterization of feruloylated arabinoxylan oligosaccharides from bamboo shoot cell-walls[J]. Carbohydrate Research, 1990, 196: 175-183. DOI: 10.1016/0008-6215(90)84117-d.
[36] Schendel R R, Meyer M R, Bunzel M. Quantitative profiling of feruloylated arabinoxylan side-chains from graminaceous cell walls[J]. Frontiers in Plant Science, 2015, 6: 1249. DOI: 10.3389/fpls.2015.01249.
[37] Bunzel M, Allerdings E, Ralph J, et al. Cross-linking of arabinoxylans via 8-8-coupled diferulates as demonstrated by isolation and identification of diarabinosyl 8-8 (cyclic)-dehydrodiferulate from maize bran[J]. Journal of Cereal Science, 2008, 47(1): 29-40. DOI: 10.1016/j.jcs.2006.12.005.
[38] Allerdings E, Ralph J, Schatz P F, et al. Isolation and structural identification of diarabinosyl 8-o-4-dehydrodiferulate from maize bran insoluble fibre[J]. Phytochemistry, 2005, 66(1): 113-124. DOI: 10.1016/j.phytochem.2004.10.026.
[39] Kylli P, Nousiainen P, Biely P, et al. Antioxidant potential of hydroxycinnamic acid glycoside esters[J]. Journal of Agricultural and Food Chemistry, 2008, 56(12): 4797-4805. DOI: 10.1021/jf800317v.
[40] 冯丽然. 阿魏酰低聚糖酯结构单元间相互作用及抗氧化机制研究[D]; 河南工业大学, 2021. DOI: 10.27791/d.cnki.ghegy.2021.000270.
[41] Lin Q L, Ou S Y, Wen Q B. In vitro antioxidant activity of feruloyl arabinose isolated from maize bran by acid hydrolysis[J]. Journal of Food Science and Technology-Mysore, 2014, 51(7): 1356-1362. DOI: 10.1007/s13197-012-0643-x.
[42] Ruthes A C, Martinez-Abad A, Tan H T, et al. Sequential fractionation of feruloylated hemicelluloses and oligosaccharides from wheat bran using subcritical water and xylanolytic enzymes[J]. Green Chemistry, 2017, 19(8): 1919-1931. DOI: 10.1039/c6gc03473j.
[43] Malunga L N, Beta T. Antioxidant capacity of arabinoxylan oligosaccharide fractions prepared from wheat aleurone using trichoderma viride or neocallimastix patriciarum xylanase[J]. Food Chemistry, 2015, 167: 311-319. DOI: 10.1016/j.foodchem.2014.07.001.
[44] Zhao W, Chen H, Wu L, et al. Antioxidant properties of feruloylated oligosaccharides of different degrees of polymerization from wheat bran[J]. Glycoconjugate Journal, 2018, 35(6): 547-559. DOI: 10.1007/s10719-018-9847-2.
[45] Snelders J, Dornez E, Delcour J A, et al. Ferulic acid content and appearance determine the antioxidant capacity of arabinoxylanoligosaccharides[J]. Journal of Agricultrual and Food Chemistry, 2013, 61(42): 10173-10182. DOI: 10.1021/jf403160x.
[46] Jia Y, He Y, Lu F C. The structure-antioxidant activity relationship of dehydrodiferulates[J]. Food Chemistry, 2018, 269: 480-485. DOI: 10.1016/j.foodchem.2018.07.038.
[47] Veenashri B R, Muralikrishna G. In vitro anti-oxidant activity of xylo-oligosaccharides derived from cereal and millet brans – a comparative study[J]. Food Chemistry, 2011, 126(3): 1475-1481. DOI: 10.1016/j.foodchem.2010.11.163.
[48] Yang J Y, Bindels L B, Munoz R R S, et al. Disparate metabolic responses in mice fed a high-fat diet supplemented with maize-derived non-digestible feruloylated oligoand polysaccharides are linked to changes in the gut microbiota[J]. Plos One, 2016, 11(1): 17. DOI: 10.1371/journal.pone.0146144.
[49] Wende G, Buchanan C J, Fry S C. Hydrolysis and fermentation by rat gut microorganisms of 2-o-β-d-xylopyranosyl (5-o-feruloyl)-l-arabinose derived from grass cell wall arabinoxylan[J]. Journal of the Science of Food and Agriculture, 1997, 73(3): 296-300. DOI: 10.1002/(SICI)1097-0010(199703)73:3<296::AID-JSFA737>3.0.CO;2-0.
[50] Gong L, Wang H, Wang T, et al. Feruloylated oligosaccharides modulate the gut microbiota in vitro via the combined actions of oligosaccharides and ferulic acid[J]. Journal of Functional Foods, 2019, 60: 103453. DOI: 10.1016/j.jff.2019.103453.
[51] Snelders J, Olaerts H, Dornez E, et al. Structural features and feruloylation modulate the fermentability and evolution of antioxidant properties of arabinoxylanoligosaccharides during in vitro fermentation by human gut derived microbiota[J]. Journal of Functional Foods, 2014, 10: 1-12. DOI: 10.1016/j.jff.2014.05.011.
[52] Zhang X W, Chen T T, Lim O B, et al. Fabrication of a soluble crosslinked corn bran arabinoxylan matrix supports a shift to butyrogenic gut bacteria[J]. Food & Function, 2019, 10(8): 4497-4504. DOI: 10.1039/c8fo02575d.
[53] Van Craeyveld V, Swennen K, Dornez E, et al. Structurally different wheat-derived arabinoxylooligosaccharides have different prebiotic and fermentation properties in rats[J]. Journal of Nutrition, 2008, 138(12): 2348-2355. DOI: 10.3945/jn.108.094367.
[54] Damen B, Verspreet J, Pollet A, et al. Prebiotic effects and intestinal fermentation of cereal arabinoxylans and arabinoxylan oligosaccharides in rats depend strongly on their structural properties and joint presence[J]. Molecular Nutrition & Food Research, 2011, 55(12): 1862-1874. DOI: 10.1002/mnfr.201100377.
[55] Pollet A, Van Craeyveld V, Van de Wiele T, et al. In vitro fermentation of arabinoxylan oligosaccharides and low molecular mass arabinoxylans with different structural properties from wheat (triticum aestivum l.) bran and psyllium (plantago ovata forsk) seed husk[J]. Journal of Agricultural and Food Chemistry, 2012, 60(4): 946-954. DOI: 10.1021/jf203820j.
[56] Pastell H, Westermann P, Meyer A S, et al. In vitro fermentation of arabinoxylan-derived carbohydrates by bifidobacteria and mixed fecal microbiota[J]. Journal of Agricultural and Food Chemistry, 2009, 57(18): 8598-8606. DOI: 10.1021/jf901397b.
[57] Macfarlane G T, Macfarlane S. Bacteria, colonic fermentation, and gastrointestinal health[J]. Journal of AOAC INTERNATIONAL, 2019, 95(1): 50-60. DOI: 10.5740/jaoacint.SGE_Macfarlane.