Ferulic acid in cereals – a review

https://doi.org/10.17221/401/2014-CJFSCitation:Boz H. (2015): Ferulic acid in cereals – a review. Czech J. Food Sci., 33: 1-7.
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Phenolic acids represent the most common form of phenolic compounds in the cereal grain and many other plants. The phytochemical ferulic acid is found in the leaves and seeds of many plants, but especially in cereals. It is the most abundant phenolic acid in common cereals, representing up to 90% of total phenolic compounds. Ferulic acid has been reported to have many physiological functions, including antioxidant, antimicrobial, anti-inflammatory, and anti-cancer activities. It is an antioxidant which neutralises free radicals (superoxide, nitric oxide, and hydroxyl radical) which could cause oxidative damage to cell membranes and DNA. Like many other antioxidants, ferulic acid reduces the level of cholesterol and triglyceride, thereby reducing the risk of heart disease.
Abdel-Aal El-Sayed M., Rabalski Iwona (2013): Effect of baking on free and bound phenolic acids in wholegrain bakery products. Journal of Cereal Science, 57, 312-318  https://doi.org/10.1016/j.jcs.2012.12.001
Acosta-Estrada Beatriz A., Lazo-Vélez Marco A., Nava-Valdez Yazel, Gutiérrez-Uribe Janet A., Serna-Saldívar Sergio O. (2014): Improvement of dietary fiber, ferulic acid and calcium contents in pan bread enriched with nejayote food additive from white maize (Zea mays). Journal of Cereal Science, 60, 264-269  https://doi.org/10.1016/j.jcs.2014.04.006
Adom Kafui Kwami, Liu Rui Hai (2002): Antioxidant Activity of Grains. Journal of Agricultural and Food Chemistry, 50, 6182-6187  https://doi.org/10.1021/jf0205099
Andreasan M.F., Kroon P.A., Williamson G., Garcia-Conesa M.T. (2001): Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radical Biology & Medicine, 31: 304–314.
Mateo Anson Nuria, van den Berg Robin, Havenaar Rob, Bast Aalt, Haenen Guido R.M.M. (2009): Bioavailability of ferulic acid is determined by its bioaccessibility. Journal of Cereal Science, 49, 296-300  https://doi.org/10.1016/j.jcs.2008.12.001
Arranz Sara, Silván Jose Manuel, Saura-Calixto Fulgencio (2010): Nonextractable polyphenols, usually ignored, are the major part of dietary polyphenols: A study on the Spanish diet. Molecular Nutrition & Food Research, 54, 1646-1658  https://doi.org/10.1002/mnfr.200900580
Aturki Zeineb, Fanali Salvatore, D'Orazio Giovanni, Rocco Anna, Rosati Chiara (2008): Analysis of phenolic compounds in extra virgin olive oil by using reversed-phase capillary electrochromatography. ELECTROPHORESIS, 29, 1643-1650  https://doi.org/10.1002/elps.200700547
Belobrajdic Damien P, Bird Anthony R (2013): The potential role of phytochemicals in wholegrain cereals for the prevention of type-2 diabetes. Nutrition Journal, 12, 62-  https://doi.org/10.1186/1475-2891-12-62
Bondia-Pons Isabel, Aura Anna-Marja, Vuorela Satu, Kolehmainen Marjukka, Mykkänen Hannu, Poutanen Kaisa (2009): Rye phenolics in nutrition and health. Journal of Cereal Science, 49, 323-336  https://doi.org/10.1016/j.jcs.2009.01.007
Bourne Louise C., Rice-Evans Catherine (1998): Bioavailability of Ferulic Acid. Biochemical and Biophysical Research Communications, 253, 222-227  https://doi.org/10.1006/bbrc.1998.9681
Bunzel Mirko, Ralph John, Marita Jane M, Hatfield Ronald D, Steinhart Hans (2001): Diferulates as structural components in soluble and insoluble cereal dietary fibre. Journal of the Science of Food and Agriculture, 81, 653-660  https://doi.org/10.1002/jsfa.861
Coghe Stefan, Benoot Koen, Delvaux Filip, Vanderhaegen Bart, Delvaux Freddy R. (2004): Ferulic Acid Release and 4-Vinylguaiacol Formation during Brewing and Fermentation:  Indications for Feruloyl Esterase Activity in Saccharomyces cerevisiae. Journal of Agricultural and Food Chemistry, 52, 602-608  https://doi.org/10.1021/jf0346556
Dai Jin, Mumper Russell J. (2010): Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer Properties. Molecules, 15, 7313-7352  https://doi.org/10.3390/molecules15107313
FAZARY Ahmed E, JU Yi-Hsu (2007): Feruloyl Esterases as Biotechnological Tools: Current and Future Perspectives. Acta Biochimica et Biophysica Sinica, 39, 811-828  https://doi.org/10.1111/j.1745-7270.2007.00348.x
Ferguson Lynnette R., Lim Isabel Fong, Pearson Amira E., Ralph John, Harris Philip J. (2003): Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 542, 49-58  https://doi.org/10.1016/j.mrgentox.2003.08.005
Finocchiaro F., Ferrari B., Gianinetti A., Dall’asta C., Galaverna G., Scazzina F., Pellegrini N. (2007): Characterization of antioxidant compounds of red and white rice and changes in total antioxidant capacity during processing. Molecular Nutrition & Food Research, 51: 1006–1019.
Gani A., Wani S.M., Masoodi F.A., Hameed G. (2012): Whole-grain cereal bioactive compounds and their health benefits. Journal of Food Processing & Technology, 3: 146.
Garcia Rebeca, Rakotozafy Lalatiana, Telef Nadège, Potus Jacques, Nicolas Jacques (2002): Oxidation of Ferulic Acid or Arabinose-Esterified Ferulic Acid by Wheat Germ Peroxidase. Journal of Agricultural and Food Chemistry, 50, 3290-3298  https://doi.org/10.1021/jf011355k
Graf E. (1992): Antioxidant potential of ferulic acid. Free Radical Biology & Medicine, 13: 435–448.
Guo Weiwei, Beta Trust (2013): Phenolic acid composition and antioxidant potential of insoluble and soluble dietary fibre extracts derived from select whole-grain cereals. Food Research International, 51, 518-525  https://doi.org/10.1016/j.foodres.2013.01.008
Hahn D.H., Faubion J.M., Rooney L.W. (1983): Sorghum phenolic acids, their high performance liquid chromatography separation and their relation to fungal resistance. Cereal Chemistry, 60: 255–259.
Hingse Swarali S, Digole Shraddha B, Annapure Uday S (2014): Method development for simultaneous detection of ferulic acid and vanillin using high-performance thin layer chromatography. Journal of Analytical Science and Technology, 5, 21-  https://doi.org/10.1186/s40543-014-0021-6
HOLTEKJOLEN A, BAVRE A, RODBOTTEN M, BERG H, KNUTSEN S (2008): Antioxidant properties and sensory profiles of breads containing barley flour. Food Chemistry, 110, 414-421  https://doi.org/10.1016/j.foodchem.2008.02.054
Hübner Florian, Arendt Elke K. (2013): Germination of Cereal Grains as a Way to Improve the Nutritional Value: A Review. Critical Reviews in Food Science and Nutrition, 53, 853-861  https://doi.org/10.1080/10408398.2011.562060
ITAGAKI S, KUROKAWA T, NAKATA C, SAITO Y, OIKAWA S, KOBAYASHI M, HIRANO T, ISEKI K (2009): In vitro and in vivo antioxidant properties of ferulic acid: A comparative study with other natural oxidation inhibitors. Food Chemistry, 114, 466-471  https://doi.org/10.1016/j.foodchem.2008.09.073
Jeong Y.C., Jae H.M., Keun H.P. (2000): Isolation and identification of 3-methoxy-4-hydroxybenzoic acid and 3-methoxy-4- hydroxycinnamic acid from hot water extracts of Hovenia dulcis Thumb and confirmation of their antioxidative and antimicrobial activity. Korean Journal of Food Science and Technology, 32: 1403–1408.
Jilek Margaret L., Bunzel Mirko (2013): Dehydrotriferulic and Dehydrodiferulic Acid Profiles of Cereal and Pseudocereal Flours. Cereal Chemistry, 90, 507-514  https://doi.org/10.1094/CCHEM-11-12-0144-R
Kalt W. (2005): Effects of production and processing factors on major fruit and vegetable antioxidants. Journal of Food Science, 70: R11–R19.
Kandil Amin, Li Jihong, Vasanthan Thava, Bressler David C. (2012): Phenolic Acids in Some Cereal Grains and Their Inhibitory Effect on Starch Liquefaction and Saccharification. Journal of Agricultural and Food Chemistry, 60, 8444-8449  https://doi.org/10.1021/jf3000482
Karamać M., Bucinski A., Pegg R.B., Amarowicz R. (2005): Antioxidant and antiradical activity of ferulates. Czech Journal of Food Sciences, 23: 64–68.
Katina K., Laitila A., Juvonen R., Liukkonen K.-H., Kariluoto S., Piironen V., Landberg R., Åman P., Poutanen K. (2007): Bran fermentation as a means to enhance technological properties and bioactivity of rye. Food Microbiology, 24, 175-186  https://doi.org/10.1016/j.fm.2006.07.012
Kern Sandra M., Bennett Richard N., Mellon Fred A., Kroon Paul Anthony, Garcia-Conesa Maria-Teresa (2003): Absorption of Hydroxycinnamates in Humans after High-Bran Cereal Consumption. Journal of Agricultural and Food Chemistry, 51, 6050-6055  https://doi.org/10.1021/jf0302299
KIM K, TSAO R, YANG R, CUI S (2006): Phenolic acid profiles and antioxidant activities of wheat bran extracts and the effect of hydrolysis conditions. Food Chemistry, 95, 466-473  https://doi.org/10.1016/j.foodchem.2005.01.032
Kim Mi-Jung, Hyun Jong-Nae, Kim Jin-Ae, Park Jong-Chul, Kim Min-Young, Kim Jung-Gon, Lee Sun-Joo, Chun Se-Chul, Chung Ill-Min (2007): Relationship between Phenolic Compounds, Anthocyanins Content and Antioxidant Activity in Colored Barley Germplasm. Journal of Agricultural and Food Chemistry, 55, 4802-4809  https://doi.org/10.1021/jf0701943
Kováčová M., Malinová E. (2007): Ferulic and coumaric acids, total phenolic compounds and their correlation in selected oat genotypes. Czech Journal of Food Sciences, 25: 325–332.
Kroon Paul A., Faulds Craig B., Ryden Peter, Robertson James A., Williamson Gary (1997): Release of Covalently Bound Ferulic Acid from Fiber in the Human Colon. Journal of Agricultural and Food Chemistry, 45, 661-667  https://doi.org/10.1021/jf9604403
Kroon Paul A, Williamson Gary (1999): Hydroxycinnamates in plants and food: current and future perspectives. Journal of the Science of Food and Agriculture, 79, 355-361  https://doi.org/10.1002/(SICI)1097-0010(19990301)79:3<355::AID-JSFA255>3.0.CO;2-G
Ktenioudaki Anastasia, Alvarez-Jubete Laura, Gallagher Eimear (): A Review of the Process-Induced Changes in the Phytochemical Content of Cereal Grains: The Breadmaking Process. Critical Reviews in Food Science and Nutrition, 55, 611-619  https://doi.org/10.1080/10408398.2012.667848
Kuenzig W., Chau J., Norkus E., Holowaschenko H., Newmark H., Mergens W., Conney A.H. (1984): Caffeic and ferulic acid as blockers of nitrosamine formation. Carcinogenesis, 5, 309-313  https://doi.org/10.1093/carcin/5.3.309
Laokuldilok Thunnop, Shoemaker Charles F., Jongkaewwattana Sakda, Tulyathan Vanna (2011): Antioxidants and Antioxidant Activity of Several Pigmented Rice Brans. Journal of Agricultural and Food Chemistry, 59, 193-199  https://doi.org/10.1021/jf103649q
Lin Fu-Hsiung, Lin Jing-Yi, Gupta Ravindra D, Tournas Joshua A, Burch James A, Selim M Angelica, Monteiro-Riviere Nancy A, Grichnik James M, Zielinski Jan, Pinnell Sheldon R (2005): Ferulic Acid Stabilizes a Solution of Vitamins C and E and Doubles its Photoprotection of Skin. Journal of Investigative Dermatology, 125, 826-832  https://doi.org/10.1111/j.0022-202X.2005.23768.x
Liu Rui Hai (2007): Whole grain phytochemicals and health. Journal of Cereal Science, 46, 207-219  https://doi.org/10.1016/j.jcs.2007.06.010
Lo H.H., Chung J.G. (1999): The effects of plant phenolics, caffeic acid, chlorogenic acid and ferulic acid on arylamine N-acetyltransferase activities in human gastrointestinal microflora. Anticancer Research, 19:133–139.
Manach C., Scalbert A., Morand C., Rémésy C., Jiménez L. (2004): Polyphenols: food sources and bioavailability. The American Journal of Clinical Nutrition, 79: 727–747.
Marinova Emma M., Yanishlieva Nedjalka V. (1992): Effect of temperature on the antioxidative action of inhibitors in lipid autoxidation. Journal of the Science of Food and Agriculture, 60, 313-318  https://doi.org/10.1002/jsfa.2740600307
Mathew Sindhu, Abraham T. Emilia (2004): Ferulic Acid: An Antioxidant Found Naturally in Plant Cell Walls and Feruloyl Esterases Involved in its Release and Their Applications. Critical Reviews in Biotechnology, 24, 59-83  https://doi.org/10.1080/07388550490491467
Mattila Pirjo, Pihlava Juha-matti, Hellström Jarkko (2005): Contents of Phenolic Acids, Alkyl- and Alkenylresorcinols, and Avenanthramides in Commercial Grain Products. Journal of Agricultural and Food Chemistry, 53, 8290-8295  https://doi.org/10.1021/jf051437z
Moore Jeffrey, Luther Marla, Cheng Zhihong, Yu Liangli (Lucy) (2009): Effects of Baking Conditions, Dough Fermentation, and Bran Particle Size on Antioxidant Properties of Whole-Wheat Pizza Crusts. Journal of Agricultural and Food Chemistry, 57, 832-839  https://doi.org/10.1021/jf802083x
Mori H., Kawabata K., Yoshimi N., Tanaka T., Murakami T., Okada T., Murai H. (1999): Chemopreventive effects of ferulic acid on oral and rice germ on large bowel carcinogenesis. Anticancer Research, 19: 3775–3778.
Napolitano A., Costabile A., Martin-Pelaez S., Vitaglione P., Klinder A., Gibson G.R., Fogliano V. (2009): Potential prebiotic activity of oligosaccharides obtained by enzymatic conversion of durum wheat in soluble dietary fibre into soluble dietary fibre. Nutrition, Metabolism & Cardiovascular Diseases, 19: 283–290.
Ndolo Victoria U., Beta Trust (2014): Comparative Studies on Composition and Distribution of Phenolic Acids in Cereal Grain Botanical Fractions. Cereal Chemistry Journal, 91, 522-530  https://doi.org/10.1094/CCHEM-10-13-0225-R
Ndolo V.U., Beta T., Fulcher R.G. (2013): Ferulic acid fluorescence intensity profiles and concentration measured by HPLC in pigmented and non-pigmented cereals. Food Research International, 52, 109-118  https://doi.org/10.1016/j.foodres.2013.02.031
Ou Shiyi, Kwok Kin-Chor (2004): Ferulic acid: pharmaceutical functions, preparation and applications in foods. Journal of the Science of Food and Agriculture, 84, 1261-1269  https://doi.org/10.1002/jsfa.1873
Prasad N. Rajendra, Ramachandran Samivel, Pugalendi Kodukkur Viswanathan, Menon Venugopal P. (2007): Ferulic acid inhibits UV-B–induced oxidative stress in human lymphocytes. Nutrition Research, 27, 559-564  https://doi.org/10.1016/j.nutres.2007.06.011
Price Ruth K., Welch Robert W., Lee-Manion Alison M., Bradbury Ian, Strain J. J. (2008): Total Phenolics and Antioxidant Potential in Plasma and Urine of Humans After Consumption of Wheat Bran. Cereal Chemistry, 85, 152-157  https://doi.org/10.1094/CCHEM-85-2-0152
Ralph J., Quideau S., Grabber J.H., Hatfield R.D. (1994): Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. Journal of the Chemical Society, 1: 3485–3498.
Réblová Z. (2012): Effect of temperature on the antioxidant activity of phenolic acids. Czech Journal of Food Sciences, 30: 171–177.
Rice-Evans Catherine A., Miller Nicholas J., Paganga George (1996): Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine, 20, 933-956  https://doi.org/10.1016/0891-5849(95)02227-9
Rocha Luana Dalbem, Monteiro Mariana Costa, Teodoro Anderson Junger (2012): Anticancer Properties of Hydroxycinnamic Acids -A Review. Cancer and Clinical Oncology, 1, -  https://doi.org/10.5539/cco.v1n2p109
Shahidi Fereidoon, Chandrasekara Anoma (2010): Hydroxycinnamates and their in vitro and in vivo antioxidant activities. Phytochemistry Reviews, 9, 147-170  https://doi.org/10.1007/s11101-009-9142-8
Shahidi Fereidoon, Chandrasekara Anoma (2013): Millet grain phenolics and their role in disease risk reduction and health promotion: A review. Journal of Functional Foods, 5, 570-581  https://doi.org/10.1016/j.jff.2013.02.004
Sharma Om Prakash, Bhat Tej Krishan, Singh Bhupinder (1998): Thin-layer chromatography of gallic acid, methyl gallate, pyrogallol, phloroglucinol, catechol, resorcinol, hydroquinone, catechin, epicatechin, cinnamic acid, p-coumaric acid, ferulic acid and tannic acid. Journal of Chromatography A, 822, 167-171  https://doi.org/10.1016/S0021-9673(98)00490-7
Sharma Upendra Kumar, Sharma Nandini, Gupta Ajai Prakash, Kumar Vinod, Kumar Sinha Arun (2007): RP-HPTLC densitometric determination and validation of vanillin and related phenolic compounds in accelerated solvent extract ofVanilla planifolia*. Journal of Separation Science, 30, 3174-3180  https://doi.org/10.1002/jssc.200700229
Singh A K, Rehal Jagbir, Kaur Amarjeet, Jyot Gagan (2013): Enhancement of attributes of Cereals by Germination and Fermentation: A Review. Critical Reviews in Food Science and Nutrition, , 131017103338003-  https://doi.org/10.1080/10408398.2012.706661
Smith M.Meryl, Hartley Roy D. (1983): Occurrence and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants. Carbohydrate Research, 118, 65-80  https://doi.org/10.1016/0008-6215(83)88036-7
Srinivasan Marimuthu, Sudheer Adluri R., Menon Venugopal P. (2007): Recent Advances in Indian Herbal Drug Research Guest Editor: Thomas Paul Asir Devasagayam Ferulic Acid: Therapeutic Potential Through Its Antioxidant Property. Journal of Clinical Biochemistry and Nutrition, 40, 92-100  https://doi.org/10.3164/jcbn.40.92
Tee-ngam Prinjaporn, Nunant Namthip, Rattanarat Poomrat, Siangproh Weena, Chailapakul Orawon (2013): Simple and Rapid Determination of Ferulic Acid Levels in Food and Cosmetic Samples Using Paper-Based Platforms. Sensors, 13, 13039-13053  https://doi.org/10.3390/s131013039
Teixeria J., Gaspar A., Garrido E.M., Garrido J., Borges F. (2013): Hydroxycinnamic acid antioxidants: an electrochemical overview. BioMed Research International, 2013, Article ID 251754, 11 pages. doi: org/10.1155/2013/251754
Tsou M.F., Hung C.F., Lu H.F., Wu L.T., Chang S.H., Chang H.L., Chen G.W., Chung J.G. (2000): Effects of caffeic acid, chlorogenic acid and ferulic acid on growth and arylamine N-acetyltransferase activity in Shigella sonnei (group D): Microbios, 101: 37–46.
Verma B., Hucl P., Chibbar R.N. (2009): Phenolic acid composition and antioxidant capacity of acid and alkali hydrolysed wheat bran fractions. Food Chemistry, 116, 947-954  https://doi.org/10.1016/j.foodchem.2009.03.060
Wang Lan, Yao Yang, He Zhonghu, Wang Desen, Liu Aihua, Zhang Yong (2013): Determination of phenolic acid concentrations in wheat flours produced at different extraction rates. Journal of Cereal Science, 57, 67-72  https://doi.org/10.1016/j.jcs.2012.09.013
Weidner S., Amarowicz R., Karama&#x00107; M., D&#x00105;browski G. (1999): Phenolic acids in caryopses of two cultivars of wheat, rye and triticale that display different resistance to pre-harvest sprouting. European Food Research and Technology, 210, 109-113  https://doi.org/10.1007/s002170050544
Weidner Stanisław, Amarowicz Ryszard, Karamać Magdalena, Frączek Ewa (2000): Changes in endogenous phenolic acids during development of Secale cereale caryopses and after dehydration treatment of unripe rye grains. Plant Physiology and Biochemistry, 38, 595-602  https://doi.org/10.1016/S0981-9428(00)00774-9
Yang, T.K. Basu, B. Ooraikul F. (2001): Studies on germination conditions and antioxidant contents of wheat grain. International Journal of Food Sciences and Nutrition, 52, 319-330  https://doi.org/10.1080/09637480120057567
Young I S (): Antioxidants in health and disease. Journal of Clinical Pathology, 54, 176-186  https://doi.org/10.1136/jcp.54.3.176
Zhouen Zhang, Side Yao, Weizhen Lin, Wenfeng Wang, Yizun Jin, Nianyun Lin (1998): Mechanism of reaction of nitrogen dioxide radical with hydroxycinnamic acid derivatives: A pulse radiolysis study. Free Radical Research, 29, 13-16  https://doi.org/10.1080/10715769800300021
Zhao Zhaohui, Egashira Yukari, Sanada Hiroo (2005): Phenolic Antioxidants Richly Contained in Corn Bran Are Slightly Bioavailable in Rats. Journal of Agricultural and Food Chemistry, 53, 5030-5035  https://doi.org/10.1021/jf050111n
Zhao Zhaohui, Moghadasian Mohammed H. (2008): Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: A review. Food Chemistry, 109, 691-702  https://doi.org/10.1016/j.foodchem.2008.02.039
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