Research Progress on Distribution, Forms and Preparation Methods of Ferulic Acid in Wheat

SONG Wei; XIN Jiaying; LU Xuechun; XIAO Jinghong; LI Yue

doi:10.13386/j.issn1002-0306.2021070224

Volume 43 Issue 14

Jul. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(14): 445-452. > DOI: 10.13386/j.issn1002-0306.2021070224

SONG Wei, XIN Jiaying, LU Xuechun, et al. Research Progress on Distribution, Forms and Preparation Methods of Ferulic Acid in Wheat[J]. Science and Technology of Food Industry, 2022, 43(14): 445−452. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021070224.

Citation:

PDF (2445 KB)

Research Progress on Distribution, Forms and Preparation Methods of Ferulic Acid in Wheat

1.
Key Laboratory of Food Science and Engineering, Harbin University of Commerce, Harbin 150028, China
2.
State Key Laboratory of Carbonyl Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

More Information

Received Date: July 19, 2021
Available Online: May 07, 2022

Graphical Abstract

Abstract

Abstract

Ferulic acid is a beneficial human health phenolic acid that reduces the risk of serious diseases such as diabetes, cholesterol, heart disease and cancer. Ferulic acid is the highest content phenolic acid in wheat, mainly concentrated in wheat bran. With the improvement of people’s awareness of health care, the preparation and function of ferulic acid in wheat bran have been paid more and more attention. The methods of preparing ferulic acid from wheat bran generally include alkaline hydrolysis, biological enzyme and biological fermentation, and many studies have assisted the above preparation methods by physical means, such as ultrasonic and high temperature steam, etc. In this paper, the distribution and form of ferulic acid in wheat and the method of preparing ferulic acid from wheat bran are summarized, and the advantages and disadvantages of the method of preparing ferulic acid from wheat bran are analyzed, so as to provide some references and ideas for the development, research and industrial production of ferulic acid in wheat bran.
- wheat,
- ferulic acid,
- distribution,
- form of existence,
- wheat bran,
- preparation

FullText(HTML)

References (65)

References

[1]	孙晓明, 辛嘉英, 林雪, 等. 阿魏酸及其衍生物在食品添加剂领域研究进展[J]. 中国食品添加剂,2019,30(1):170−176. [SUN X M, XIN J Y, LIN X, et al. Research progress of ferulic acid and its derivatives in food additives[J]. China Food Additives,2019,30(1):170−176. SUN X M, XIN J Y, LIN X, et al. Research progress of ferulic acid and its derivatives in food additives[J]. China Food Additives, 2019, 030(001): 170-176.
[2]	LIU K W, MAO-RUN F U. Research progress of ferulic acid[J]. Jiangsu Condiment and Subsidiary Food, 2016.
[3]	LI D, RUI Y X, GUO S D, et al. Ferulic acid: A review of its pharmacology, pharmacokinetics and derivatives[J]. Life Sciences,2021,284:119921. doi: 10.1016/j.lfs.2021.119921
[4]	BARBARA L, SOFIA C, GIOVANNI M. Wheat bran phenolic acids: Bioavailability and stability in whole wheat-based foods[J]. Molecules,2015,20(9):15666−15685. doi: 10.3390/molecules200915666
[5]	YU L, WANG Y, WEN H, et al. Synthesis and evaluation of acetylferulic paeonol ester and ferulic paeonol ester as potential antioxidants to inhibit fish oil oxidation[J]. Food Chemistry,2021(8):130384.
[6]	TANSKA M, MIKOLAJCZAK N, KONOPKA I. Comparison of the effect of sinapic and ferulic acids derivatives (4-vinylsyringol vs. 4-vinylguaiacol) as antioxidants of rapeseed, flaxseed, and extra virgin olive oils[J]. Food Chemistry,2017,240:679−685.
[7]	PRITAM C, GOUTAM B, SUKANTA K, et al. Cleaner production of vanillin through biotransformation of ferulic acid esters from agroresidue by Streptomyces sannanensis[J]. Biosystems Engineering, 2018.
[8]	刘延照, 李想, 刘功继, 等. 辣根过氧化物酶催化阿魏酸交联果胶物化特性[J]. 食品科学,2020,41(14):9−14. [LIU Y Z, LI X, LIU G J, et al. Physicochemical properties of pectin modified by cross-linking with ferulic acid under the catalysis of horseradish peroxidase[J]. Food Science,2020,41(14):9−14. doi: 10.7506/spkx1002-6630-20190729-399 LIU Y Z, LI X, LIU G J, et al. Physicochemical properties of pectin modified by cross-linking with ferulic acid under the catalysis of horseradish peroxidase[J]. Food Science, 2020, 41(14): 9-14. doi: 10.7506/spkx1002-6630-20190729-399
[9]	贾超, 王利强, 卢立新, 等. 阿魏酸对马铃薯淀粉基复合膜性能的影响[J]. 食品工业科技,2013,34(7):82−85. [JIA C, WANG L Q, LU L X, et al. Effect of ferulic acid on properties of potato starch-based composite films[J]. Science and Technology of Food Industry,2013,34(7):82−85. JIA C, WANG L Q, LU L X, et al. Effect of ferulic acid on properties of potato starch-based composite films[J]. Science and Technology of Food Industry, 2013, 34(7): 82-85.
[10]	SHI Y G, BIAN L Q, ZHU Y J, et al. Multifunctional alkyl ferulate esters as potential food additives: Antibacterial activity and mode of action against Listeria monocytogenes and its application on American sturgeon caviar preservation[J]. Food Control,2019,96:390−402. doi: 10.1016/j.foodcont.2018.09.030
[11]	TAKAHASHI H, KASHIMURA M, KOISO H, et al. Use of ferulic acid as a novel candidate of growth inhibiting agent against Listeria monocytogenes in ready-to-eat food[J]. Food Control,2013,33(1):244−248. doi: 10.1016/j.foodcont.2013.03.013
[12]	国家卫生和计划生育委员会. GB 2760-2014文后附录B [S]. 北京: 中国标准出版社, 2014. People's Republic of China National Health and Family Planning Commission. GB 2760-2014 Appendix B [S]. Beijing: Standards Press of China, 2014.
[13]	吴凡, 蔡红燕, 沈汪洋, 等. 小麦麸皮的营养特性与应用进展[J]. 食品工业,2020,41(5):284−287. [WU F, CAI H Y, SHEN W Y, et al. Nutritional characteristics and application progress of wheat bran[J]. Food Industry,2020,41(5):284−287. WU F, CAI H Y, SHEN W Y, et al. Nutritional characteristics and application progress of wheat bran[J]. Food Industry, 2020, 41(5): 284-287.
[14]	M PRÜCKLER, SIEBENHANDL-EHN S, APPRICH S, et al. Wheat bran-based biorefinery 1: Composition of wheat bran and strategies of functionalization[J]. LWT-Food Science and Technology,2014,56(2):211−221. doi: 10.1016/j.lwt.2013.12.004
[15]	BING Z, YZ A, HL A, et al. A review on insoluble-bound phenolics in plant-based food matrix and their contribution to human health with future perspectives[J]. Trends in Food Science & Technology,2020,105:347−362.
[16]	KUMAR N, GOEL N. Phenolic acids: Natural versatile molecules with promising therapeutic applications[J]. Biotechnology Reports,2019,24:e00370. doi: 10.1016/j.btre.2019.e00370
[17]	WEIDNER S, AMAROWICZ R, KARAMA M, et al. Changes in endogenous phenolic acids during development of Secalecereale caryopses and after dehydration treatment of unripe rye grains[J]. Plant Physiology & Biochemistry,2000,38(7−8):595−602.
[18]	PATRICIA R R, ALFONSO V L, TY FORBES-HERNÁNDEZ, et al. Phenolic compounds isolated from olive oil as nutraceutical tools for the prevention and management of cancer and cardiovascular diseases[J]. International Journal of Molecular Sciences,2018,19(8):2305−2325. doi: 10.3390/ijms19082305
[19]	BARRON C, SURGET A, ROUAU X. Relative amounts of tissues in mature wheat (Triticumaestivum L.) grain and their carbohydrate and phenolic acid composition[J]. Journal of Cereal Science,2007,45(1):88−96. doi: 10.1016/j.jcs.2006.07.004
[20]	ANTOINE C. Wheat bran tissue fractionation using biochemical markers[J]. Journal of Cereal Science,2004,39(3):387−393. doi: 10.1016/j.jcs.2004.02.001
[21]	王薇薇, 潘奕鸥, 王丽, 等. 谷物中阿魏酸的分布及其生理活性的研究进展[J]. 粮油食品科技, 2019, 27(5): 43-48. WANG W W, PAN Y O, WANG L, et al. Research advances on the distribution and physiological activity of ferulic acid in grain[J]. Science and Technology of Cereals, Oils and Foods, 2019, 27(5): 43-48.
[22]	ZHAO Z, MOGHADASIAN M H. Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: A review[J]. Food Chemistry,2008,109(4):691−702. doi: 10.1016/j.foodchem.2008.02.039
[23]	A K SINGH, JAGBIR, REHAL, et al. Enhancement of attributes of cereals by germination and fermentation: A review[J]. Critical Reviews in Food Science and Nutrition,2015,55(11):1575−1589. doi: 10.1080/10408398.2012.706661
[24]	ADOM K K, LIU R H. Antioxidant activity of grains[J]. Journal of Agricultural & Food Chemistry,2002,50(21):6182−7.
[25]	KAUR A, SINGH B, YADAV M P, et al. Isolation of arabinoxylan and cellulose-rich arabinoxylan from wheat bran of different varieties and their functionalities[J]. Food Hydrocolloids,2021,112:106287. doi: 10.1016/j.foodhyd.2020.106287
[26]	张璟. 黑曲霉液体发酵法产酶制备阿魏酸和低聚糖的研究[D]. 广州: 暨南大学, 2004. ZHANG J. Production of enzymes from Aspergillus niger by liquid culture and their application in preparation of trans-ferulic acid and oligosaccharide[D]. Guangzhou: Jinan University, 2004.
[27]	MARQUEZ-ESCALANTE J A, CARVJAL-MILLAN E, YADAV M P, et al. Rheology and microstructure of gels based on wheat arabinoxylans enzymatically modified in arabinose to xylose ratio.[J]. Journal of the Science of Food and Agriculture,2018,98(3):914−922. doi: 10.1002/jsfa.8537
[28]	C EL MODAFAR, E EL BOUSTANI. Cell wall-bound phenolic acid and lignin contents in date palm as related to its resistance to Fusarium oxysporum[J]. Biologia Plantarum,2001,44(1):125−130. doi: 10.1023/A:1017942927058
[29]	YOSHIDA-SHIMOKAWA T, YOSHIDA S, KAKEGAWA K, et al. Enzymicferuloylation of arabinoxylan-trisaccharide by feruloyl-CoA: Arabinoxylan-trisaccharide O-hydroxycinnamoyltransferase from Oryza sativa[J]. Planta,2001,212(3):470−474. doi: 10.1007/s004250000490
[30]	MCCALLUM J A, TAYLOR I, TOWERS G. Spectrophotometric assay and electrophoretic detection of trans-feruloyl esterase activity[J]. Analytical Biochemistry,1991,196(2):360−366. doi: 10.1016/0003-2697(91)90479-D
[31]	RALET M C, FAULDS C B, WILLIAMSON G, et al. Degradation of feruloylated oligosaccharides from sugar-beet pulp and wheat bran by ferulic acid esterases from Aspergillus niger[J]. Carbohydrate Research,1994,263(2):257−269. doi: 10.1016/0008-6215(94)00177-4
[32]	RHODES D I, SADEK M, B A STONE. Hydroxycinnamic acids in walls of wheat aleurone cells[J]. Journal of Cereal Science,2002,36(1):67−81. doi: 10.1006/jcrs.2001.0449
[33]	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. doi: 10.1016/S0008-6215(99)00110-X
[34]	TANG Y, HAO J, FAN C, et al. Preparative separation of high-purity trans- and cis-ferulic acid from wheat bran by pH-zone-refining counter-current chromatography[J]. Journal of Chromatography A,2020,1636:461772.
[35]	WANG P, HOU C, ZHAO X, et al. Molecular characterization of water-extractable arabinoxylan from wheat bran and its effect on the heat-induced polymerization of gluten and steamed bread quality[J]. Food Hydrocolloids,2018,87:570−581.
[36]	ROBBINS R J. Phenolic acids in foods: An overview of analytical methodology[J]. Journal of Agricultural & Food Chemistry,2003,51(10):2866−2887.
[37]	IDEIA P, SOUSAFERREIRA I , CASTILHO P C. A novel and simpler alkaline hydrolysis methodology for extraction of ferulic acid from brewer’s spent grain and its (partial) purification through adsorption in a synthetic resin[J]. Foods, 2020, 9(5).
[38]	AI M, SAKKA M, KOSUGI A, et al. Significance of a family-6 carbohydrate-binding module in a modular feruloyl esterase for removing ferulic acid from insoluble wheat arabinoxylan.[J]. Enzyme and Microbial Technology,2020,138:109546. doi: 10.1016/j.enzmictec.2020.109546
[39]	NISHANT G, MADHAVAN N K. Biorefining of wheat bran for the purification of ferulicacid[J]. Biocatalysis & Agricultural Biotechnology,2018,15:304−310.
[40]	WANG X, XIN G, EGASHIRA Y, et al. Release of ferulic acid from wheat bran by an inducible feruloyl esterase from an intestinal bacterium Lactobacillus acidophilus[J]. Food Science and Technology Research,2005,11(3):241−247. doi: 10.3136/fstr.11.241
[41]	龚燕燕, 殷欣, 唐存多, 等. 宇佐美曲霉阿魏酸酯酶与木聚糖酶协同作用降解小麦麸皮制备阿魏酸[J]. 中国生物制品学杂志,2014,27(2):262−266. [GONG Y Y, YIN X, TANG C D, et al. Synergistic effect of feruloyl esterase and xylanase from Aspergillus usamii in preparation of ferulic acid by degradation of wheat bran[J]. Chinese Journal of Biologicals,2014,27(2):262−266. GONG Y Y, YIN X, TANG C D, et al. Synergistic effect of feruloyl esterase and xylanase from Aspergillus usamii in preparation of ferulic acid by degradation of wheat bran[J]. Chinese Journal of Biologicals, 2014, 27(2) : 262-266.
[42]	YIN Z N, YAO K, MIN T, et al. Antioxidant and anti-inflammatory capacity of ferulic acid released from wheat bran by solid-state fermentation of Aspergillus niger[J]. Biomedical and Environmental Sciences,2019,32(1):11−21.
[43]	WONG D W. Feruloyl esterase: A key enzyme in biomass degradation[J]. Applied Biochemistry & Biotechnology Part A Enzyme Engineering & Biotechnology,2006,133(2):87−112.
[44]	FAULDS C B, WILLIAMSON G. Release of ferulic acid from wheat bran by a ferulic acid esterase (FAE-III) from Aspergillusniger[J]. Applied Microbiology & Biotechnology,1995,43(6):1082−1087.
[45]	LI H, GAN L, JIAN L, et al. High efficiency co-production of ferulic acid and xylooligosaccharides from wheat bran by recombinant xylanase and feruloylesterase[J]. Biochemical Engineering Journal,2017,120:41−48. doi: 10.1016/j.bej.2017.01.001
[46]	DUPOIRON S, LAMELOISE M L, POMMET M, et al. A novel and integrative process: From enzymatic fractionation of wheat bran with a hemicellulasic cocktail to the recovery of ferulic acid by weak anion exchange resin[J]. Industrial Crops & Products,2017,105:148−155.
[47]	WANG R, YANG J, JIN M J, et al. Efficient ferulic acid and xylo-oligosaccharides production by a novel multi-modular bifunctional xylanase/feruloyl esterase using agricultural residues as substrates[J]. Bioresource Technology,2019,297:122487.
[48]	MFA B, AH C, GZ A, et al. Advances in combined enzymatic extraction of ferulic acid from wheat bran[J]. New Biotechnology,2020,56:38−45. doi: 10.1016/j.nbt.2019.10.010
[49]	尹志娜. 小麦麸皮固态发酵过程中活性成分释放的机理研究[D]. 广州: 华南理工大学, 2018. YIN Z N. Study on mechanism of active component released by solid-state fermentation of wheat bran[D]. Guangzhou: South China University of Technology, 2018.
[50]	TOPAKAS E, VAFIADI C, CHRISTAKOPOULOS P. Microbial production, characterization and applications of feruloyl esterases[J]. Process Biochemistry,2007,42(4):497−509. doi: 10.1016/j.procbio.2007.01.007
[51]	MAO M, WANG P, SHI K, et al. Effect of solid state fermentation by Enterococcus faecalis M2 on antioxidant and nutritional properties of wheat bran[J]. Journal of Cereal Science,2020,94:102997. doi: 10.1016/j.jcs.2020.102997
[52]	孙晓明. 好食脉孢菌发酵小麦麸皮释放阿魏酸及其衍生物研究[D]. 哈尔滨: 哈尔滨商业大学, 2019. SUN X M. Ferulic acid and its derivatives release from wheat bran by Neurospora sitophila fermentation[D]. Harbin: Harbin University of Commerce, 2019.
[53]	高鹏. 好食脉孢菌发酵麸皮制备游离阿魏酸及其改性研究[D]. 哈尔滨: 哈尔滨商业大学, 2020. GAO P. Study on the preparation and modification of free Ferulic acid from fermentation bran of Neurospora fastidious[D]. Harbin: Harbin University of Commerce, 2020.
[54]	胡博涵. 利用发酵法释放麦麸中束缚型酚酸及其抗氧化活性的研究[D]. 广州: 华南理工大学, 2015. HU B H. Using fermentation release type bound phenolic acids in the wheat bran and its antioxidant activity[D]. Guangzhou: South China University of Technology, 2015.
[55]	尹志娜, 吴晖, 赖富饶, 等. 两种丝状真菌发酵小麦麸皮中酚酸的释放及与阿魏酸酯酶和木聚糖酶的关系[J]. 现代食品科技,2017(3):81−87. [YIN Z N, WU H, LAI F R, et al. Release of phenolic acid by two filamentous fungi during the fermentation of wheat bran with ferulic acid esterase and xylanase[J]. Modern Food Science and Technology,2017(3):81−87. YIN Z N, WU H, LAI F R, et al. Release of phenolic acid by two filamentous fungi during the fermentation of wheat bran with ferulic acid esterase and xylanase[J]. Modern Food Science And Technology, 2017(3): 81-87.
[56]	YIN Z, WU W, SUN C, et al. Comparison of releasing bound phenolic acids from wheat bran by fermentation of three Aspergillus species[J]. International Journal of Food Science & Technology,2017,53(5):1120−1130.
[57]	吴非, 李钊, 周琪, 等. 超声波辅助水酶法提取米胚油及其成分分析[J]. 食品科学,2020,41(24):233−241. [WU F, LI Z, ZHOU Q, et al. Ultrasonic-assisted aqueous enzymatic extraction and chemical composition of rice germ oil[J]. Food Science,2020,41(24):233−241. doi: 10.7506/spkx1002-6630-20200426-343 WU F, L Z, ZHOU Q, et al. Ultrasonic-assisted aqueous enzymatic extraction and chemical composition of rice germ oil[J]. Food Science, 2020, 41(24): 233-241. doi: 10.7506/spkx1002-6630-20200426-343
[58]	ALEXANDRE E, CA STRO L, MOREIRA S A, et al. Comparison of emerging technologies to extract high-added value compounds from fruit residues: Pressure- and electro-based technologies[J]. Food Engineering Reviews,2017,9(3):190−212. doi: 10.1007/s12393-016-9154-2
[59]	L F CĂLINOIU, C V DAN. Thermal processing for the release of phenolic compounds from wheat and oat bran[J]. Biomolecules,2019,10(1):21. doi: 10.3390/biom10010021
[60]	QIAO L, YE X, SUN Y, et al. Sonochemical effects on free phenolic acids under ultrasound treatment in a model system[J]. Ultrasonics-Sonochemistry,2013,20(4):1017−1025. doi: 10.1016/j.ultsonch.2012.12.007
[61]	CHERIF M M, GRIGORAKIS S, HALAHLAH A, et al. High-efficiency extraction of phenolics from wheat waste biomass (bran) by combining deep eutectic solvent, ultrasound-assisted pretreatment and thermal treatment[J]. Environmental Processes:An International Journal,2020,7(3):845−859. doi: 10.1007/s40710-020-00449-0
[62]	ITAGAKI S, KUROKAWA T, NAKATA C, et al. In vitro and in vivo antioxidant properties of ferulic acid: A comparative study with other natural oxidation inhibitors[J]. Food Chemistry,2009,114(2):466−471. doi: 10.1016/j.foodchem.2008.09.073
[63]	LIU L, ZHAO M, LIU X, et al. Effect of steam explosion‐assisted extraction on phenolic acid profiles and antioxidant properties of wheat bran[J]. Journal of the Science of Food & Agriculture,2016,96(10):3484−3491.
[64]	CHEN Y, ZHANG R, LIU C, et al. Enhancing antioxidant activity and antiproliferation of wheat bran through steam flash explosion[J]. Journal of Food Science & Technology,2016,53(7):3028−3034.
[65]	SLA C, XJA C, JING G, et al. Impact of wheat bran micronization on dough properties and bread quality: Part I-bran functionality and dough properties[J]. Food Chemistry,2021,353(6):129407.

Supplements (0)

Cited By

Cited by

Periodical cited type(7)

1.	张柱，黄钧，周荣清，张宿义，秦辉，董异，王超，王小军，雷梓伦，唐秋香，万营东，张毅. 红曲霉对高温大曲的扰动及制曲工艺探究. 食品与发酵工业. 2025(02): 275-284 .
2.	刘晓柱，黄名正，唐维媛，于志海，许存宾. 酱香型白酒酿造微生物多样性研究进展. 食品工业. 2024(01): 145-150 .
3.	罗小叶，刘婉琳，郎莹，李豆南，潘凤爽，吴伯天，龙尧，邱树毅. 王茅大曲微生物菌群多样性分析. 食品科技. 2024(01): 9-18 .
4.	楚京嬴，吕嘉枥，曹丹，许双双，金成勇，张永利，张宇航. 三种凤香型大曲中心区域细菌群落、理化特性及非靶向代谢物的差异性和相关性分析. 陕西科技大学学报. 2024(06): 40-51 .
5.	唐绍培，朱国军，李银强，吴长贵，罗方雯，周燊，张良，赵金松. 酱香型白酒下造沙不同阶段细菌群落结构多样性特征分析. 酿酒科技. 2024(12): 52-60 .
6.	邓皖玉，许永明，陈波，王西，邓俊，聂正东，聂宏芳，张春香，李素. 制曲工艺关键控制点对冬季高温大曲质量的影响. 中国酿造. 2023(08): 153-157 .
7.	贾一清，孙昭，廖博曦，陈建新. 不同堆积醅对芝麻香型白酒发酵过程中主要微生物演替及代谢的影响. 中国酿造. 2023(11): 34-39 .