Phenolic amides (avenanthramides) in oats – a review H. (2015): Phenolic amides (avenanthramides) in oats – a review. Czech J. Food Sci., 33: 399-404.
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Whole grain cereals such as oats are important sources of phenolic compounds. Oats contain phenolic amides, also named avenanthramides (AVAs), which have beneficial health properties because of their antioxidant, anti-inflammatory, and antiproliferative effects. The most common avenanthramides are esters of 5-hydroxyanthranilic acid with p-coumaric (AVA-A), ferulic (AVA-B), or caffeic (AVA-C) acids. The studies related to the stability of AVAs showed that AVA-B is sensitive to alkaline and neutral conditions and this sensitivity increases with higher temperatures. However, has been reported that AVA-A and AVA -C are more stable under the same conditions (alkaline and neutral conditions), and in addition that AVAs content of oats is increasing significantly with the germination process. AVAs help in preventing free radicals from damaging LDL cholesterol while AVAs-enriched extract of oats combined with vitamin C synergistically inhibited LDL oxidation in vitro. Both animal studies and human clinical trials confirmed that oats antioxidants have the potential of reducing cardiovascular risks by lowering serum cholesterol and inhibiting LDL oxidation and peroxidation. Therefore, the consumption of oats and products thereof is extremely important in reducing the risk of cardiovascular diseases.
Bazzano Lydia A., He Jiang, Ogden Lorraine G., Loria Catherine M., Whelton Paul K. (2003): Dietary Fiber Intake and Reduced Risk of Coronary Heart Disease in US Men and Women. Archives of Internal Medicine, 163, 1897-
Biel Wioletta, Bobko Kazimierz, Maciorowski Robert (2009): Chemical composition and nutritive value of husked and naked oats grain. Journal of Cereal Science, 49, 413-418
Bratt Katarina, Sunnerheim Kerstin, Bryngelsson Susanne, Fagerlund Amelie, Engman Lars, Andersson Rolf E., Dimberg Lena H. (2003): Avenanthramides in Oats ( Avena sativa L.) and Structure−Antioxidant Activity Relationships. Journal of Agricultural and Food Chemistry, 51, 594-600
Brown L., Rosner B., Willett W.W., Sacks F.M. (1999): Cholesterol lowering effects of dietary fiber: a meta-analysis. American Journal of Clinical Nutrition, 69: 30–42.
Bryngelsson Susanne, Dimberg Lena H., Kamal-Eldin Afaf (2002): Effects of Commercial Processing on Levels of Antioxidants in Oats ( Avena sativa L.). Journal of Agricultural and Food Chemistry, 50, 1890-1896
Cai Shengbao, Huang Chen, Ji Baoping, Zhou Feng, Wise Mitchell L., Zhang Di, Yang Peiying (2011): In vitro antioxidant activity and inhibitory effect, on oleic acid-induced hepatic steatosis, of fractions and subfractions from oat (Avena sativa L.) ethanol extract. Food Chemistry, 124, 900-905
Chen C.Y.O., Milbury P.E., Collins F.W., Blumberg J.B. (2007): Aventhramides are bioavailable and have antioxidant activity in humans after acute consumption of an enriched mixture from oats. Journal of Nutrition, 137: 1375–1382.
Chen C.Y., Milbury P.E., Kwak H.-K., Collins F.W., Samuel P., Blumberg J.B. (2004): Avenanthramides and phenolic acids from oats are bioavailable and act synergistically with vitamin C to enhance hamster and human LDL resistance to oxidation. Journal of Nutrition, 134: 1459–1466.
Chu Yi-Fang, Wise Mitchell L., Gulvady Apeksha A., Chang Tony, Kendra David F., Jan-Willem van Klinken B., Shi Yuhui, O’Shea Marianne (2013): In vitro antioxidant capacity and anti-inflammatory activity of seven common oats. Food Chemistry, 139, 426-431
Collins F.W., McLachlan D.C., Blackwell B.A. (1991): Oat phenolics: avenalumic acids, a new group of bound phenolic acids from oat groats and hulls. Cereal Chemistry, 68: 184–189.
Collins F. William (1989): Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls. Journal of Agricultural and Food Chemistry, 37, 60-66
Collins F.William, Mullin W.J. (1988): High-performance liquid chromatographic determination of avenanthramides, n-aroylanthranilic acid alkaloids from oats. Journal of Chromatography A, 445, 363-370
Cook N (): Flavonoids--Chemistry, metabolism, cardioprotective effects, and dietary sources. The Journal of Nutritional Biochemistry, 7, 66-76
de Heredia Fátima Pérez, Gómez-Martínez Sonia, Marcos Ascensión (2012): Obesity, inflammation and the immune system. Proceedings of the Nutrition Society, 71, 332-338
Dimberg Lena Häll, Sunnerheim Kerstin, Sundberg Birgitta, Walsh Kevin (2001): Stability of Oat Avenanthramides. Cereal Chemistry, 78, 278-281
Dimberg L.H., Theander O., Lingnert H. (2002): Avenanthramides – a group of phenolic antioxidants in oats. Cereal Chemistry, 70: 637–641.
Dokuyucu Tevrican, Peterson David M., Akkaya Aydin (2003): Contents of Antioxidant Compounds in Turkish Oats: Simple Phenolics and Avenanthramide Concentrations. Cereal Chemistry, 80, 542-543
Dykes (2007): Phenolic Compounds in Cereal Grains and Their Health Benefits. Cereal Foods World, , -
Emmons Cheryld L., Peterson David M. (2001): Antioxidant Activity and Phenolic Content of Oat as Affected by Cultivar and Location. Crop Science, 41, 1676-
Eudes Aymerick, Baidoo Edward E. K., Yang Fan, Burd Helcio, Hadi Masood Z., Collins F. William, Keasling Jay D., Loqué Dominique (2011): Production of tranilast [N-(3′,4′-dimethoxycinnamoyl)-anthranilic acid] and its analogs in yeast Saccharomyces cerevisiae. Applied Microbiology and Biotechnology, 89, 989-1000
Eudes Aymerick, Juminaga Darmawi, Baidoo Edward E K, Collins F, Keasling Jay D, Loqué Dominique (2014): Correction: Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli. Microbial Cell Factories, 13, 8-
Fagerlund Amelie, Sunnerheim Kerstin, Dimberg Lena H. (2009): Radical-scavenging and antioxidant activity of avenanthramides. Food Chemistry, 113, 550-556
Gani A., Wani S.M., Masoodi F.A., Hameed G. (2012): Whole-grain cereal bioactive compounds and their health benefits: a review. Journal of Food Processing & Technology, 3: 146.
Guo Weimin, Nie Lin, Wu Dayong, Wise Mitchell L., Collins F. William, Meydani Simin Nikbin, Meydani Mohsen (2010): Avenanthramides Inhibit Proliferation of Human Colon Cancer Cell Lines In Vitro. Nutrition and Cancer, 62, 1007-1016
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
Inglett George E., Chen Diejun (2012): Antioxidant and Pasting Properties of Oat <i>β</i>-Glucan Hydrocolloids. Food and Nutrition Sciences, 03, 827-835
Ishihara Atsushi, Kojima Kana, Fujita Takeshi, Yamamoto Yuya, Nakajima Hiromitsu (): New series of avenanthramides in oat seed. Bioscience, Biotechnology, and Biochemistry, 78, 1975-1983
Jastrebova J., Skoglund M., Nilsson J., Dimberg L. H. (2006): Selective and Sensitive LC-MS Determination of Avenanthramides in Oats. Chromatographia, 63, 419-423
Li Ji Li, Lay David, Chung Eunhee, Fu Ying, Peterson David M. (2003): Effects of avenanthramides on oxidant generation and antioxidant enzyme activity in exercised rats. Nutrition Research, 23, 1579-1590
Kaukovirta-Norja Anu, Wilhelmson Annika, Poutanen Kaisa (2004): Germination: a means to improve the functionality of oat. Agricultural and Food Science, 13, 100-112
Koenig Ryan, Dickman Jonathan R, Kang Chounghun, Zhang Tianou, Chu Yi-Fang, Ji Li (2014): Avenanthramide supplementation attenuates exercise-induced inflammation in postmenopausal women. Nutrition Journal, 13, 21-
Koenig Ryan T., Dickman Jonathan R., Wise Mitchell L., Ji Li Li (2011): Avenanthramides Are Bioavailable and Accumulate in Hepatic, Cardiac, and Skeletal Muscle Tissue Following Oral Gavage in Rats. Journal of Agricultural and Food Chemistry, 59, 6438-6443
Koenig R.T. (2012): Avenanthramide supplementation in young and older women: Protection against eccentric exercise-induced inflammation and oxidative stress. [Ph.D. Dissertation.] Madison, University of Wisconsin.
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.
Lee-Manion Alison M., Price Ruth K., Strain J. J., Dimberg Lena H., Sunnerheim Kerstin, Welch Robert W. (2009): In Vitro Antioxidant Activity and Antigenotoxic Effects of Avenanthramides and Related Compounds. Journal of Agricultural and Food Chemistry, 57, 10619-10624
Liu Liping, Zubik Ligia, Collins F.William, Marko Melissa, Meydani Mohsen (2004): The antiatherogenic potential of oat phenolic compounds. Atherosclerosis, 175, 39-49
LIU Sen, YANG Nan, HOU Zhao-hua, YAO Yang, LÜ Li, ZHOU Xian-rong, REN Gui-xing (2011): Antioxidant Effects of Oats Avenanthramides on Human Serum. Agricultural Sciences in China, 10, 1301-1305
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
Meydani Mohsen (2009): Potential health benefits of avenanthramides of oats. Nutrition Reviews, 67, 731-735
Andrea Moglia, Cinzia Comino, Sergio Lanteri, Ric de Vos, Pieter de Waard, Teris A. van Beek, Luca Goitre, Saverio Francesco Retta, Jules Beekwilder (2010): Production of novel antioxidative phenolic amides through heterologous expression of the plant’s chlorogenic acid biosynthesis genes in yeast. Metabolic Engineering, 12, 223-232
Molteberg E.L., Solheim R., Dimberg L.H., Frølich W. (1996): Variation in Oat Groats Due to Variety, Storage and Heat Treatment. II: Sensory Quality. Journal of Cereal Science, 24, 273-282
Nayak Balunkeswar, Liu Rui Hai, Tang Juming (): Effect of Processing on Phenolic Antioxidants of Fruits, Vegetables, and Grains—A Review. Critical Reviews in Food Science and Nutrition, 55, 887-918
Nie Lin, Wise Mitchell L., Peterson David M., Meydani Mohsen (2006): Avenanthramide, a polyphenol from oats, inhibits vascular smooth muscle cell proliferation and enhances nitric oxide production. Atherosclerosis, 186, 260-266
Okarter Neal, Liu Rui Hai (2010): Health Benefits of Whole Grain Phytochemicals. Critical Reviews in Food Science and Nutrition, 50, 193-208
Okazaki Yozo, Isobe Taishi, Iwata Yoichi, Matsukawa Tetsuya, Matsuda Fumio, Miyagawa Hisashi, Ishihara Atsushi, Nishioka Takaaki, Iwamura Hajime (2004): Metabolism of avenanthramide phytoalexins in oats. The Plant Journal, 39, 560-572
Orozco-Mena Raul, Salmerón-Ochoa Iván, Ortega-Rivas Enrique, Perez-Vega Samuel (2014): Development of a Sustainable Process for the Solid-Liquid Extraction of Antioxidants from Oat. Sustainability, 6, 1504-1520
Ortiz-Robledo F., Villanueva-Fierro I., Oomah B.D., Lares-Asef I., Proal-Nàjere J.B., Nàvar-Chaidez J.J. (2013): Avenanthramides and nutritional components of four mexican oat (Avena sativa L.) varieties. Agrociencia, 47: 225–232.
Peterson David M. (2001): Oat Antioxidants. Journal of Cereal Science, 33, 115-129
Peterson David M, Hahn Martha J, Emmons Cheryld L (2002): Oat avenanthramides exhibit antioxidant activities in vitro. Food Chemistry, 79, 473-478
Peterson David M., Dimberg Lena H. (2008): Avenanthramide concentrations and hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase activities in developing oats. Journal of Cereal Science, 47, 101-108
Rossi Margherita, Giussani Elena, Morelli Roberto, Lo Scalzo Roberto, Nani Renato C., Torreggiani Danila (2003): Effect of fruit blanching on phenolics and radical scavenging activity of highbush blueberry juice. Food Research International, 36, 999-1005
Sesti F., Tsitsilonis O.E., Kotsinas A., Trougakos I.P. (2012): Oxidative stress mediated biomolecular damage and inflammation in tumorigenesis. In Vivo, 26: 395–402.
Shi Y., Johnson J., O'Shea M., Chu Y.-F. (2014): The Bioavailability and Metabolism of Phenolics, a Class of Antioxidants Found in Grains. Cereal Foods World, 59, 52-58
Singh Rajinder, De Subrata, Belkheir Asma (2013): Avena sativa (Oat), A Potential Neutraceutical and Therapeutic Agent: An Overview. Critical Reviews in Food Science and Nutrition, 53, 126-144
Skoglund Maria, Peterson David M., Andersson Roger, Nilsson Janicka, Dimberg Lena H. (2008): Avenanthramide content and related enzyme activities in oats as affected by steeping and germination. Journal of Cereal Science, 48, 294-303
Stevenson David G., Inglett George E., Chen Diejun, Biswas Atanu, Eller Fred J., Evangelista Roque L. (2008): Phenolic content and antioxidant capacity of supercritical carbon dioxide-treated and air-classified oat bran concentrate microwave-irradiated in water or ethanol at varying temperatures. Food Chemistry, 108, 23-30
Sur Runa, Nigam Anu, Grote Devon, Liebel Frank, Southall Michael D. (2008): Avenanthramides, polyphenols from oats, exhibit anti-inflammatory and anti-itch activity. Archives of Dermatological Research, 300, 569-574
Tian Binqiang, Xie Bijun, Shi John, Wu Jia, Cai Yan, Xu Tuoming, Xue Sophia, Deng Qianchun (2010): Physicochemical changes of oat seeds during germination. Food Chemistry, 119, 1195-1200
Verardo Vito, Serea Cristian, Segal Rodica, Caboni Maria Fiorenza (2011): Free and bound minor polar compounds in oats: Different extraction methods and analytical determinations. Journal of Cereal Science, 54, 211-217
Wise Mitchell L. (2011): Effect of Chemical Systemic Acquired Resistance Elicitors on Avenanthramide Biosynthesis in Oat ( Avena sativa ). Journal of Agricultural and Food Chemistry, 59, 7028-7038
Wu Y.V. (1983): Effect of germination on oats and oat protein. Cereal Chemistry, 60: 418–420.
Yang Jun, Ou Boxin, Wise Mitchell L., Chu YiFang (2014): In vitro total antioxidant capacity and anti-inflammatory activity of three common oat-derived avenanthramides. Food Chemistry, 160, 338-345
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