Czech J. Food Sci., 2015, 33(5):399-404 | DOI: 10.17221/696/2014-CJFS

Phenolic amides (avenanthramides) in oats - a reviewReview

Hüseyin BOZ
Gastronomy and Culinary Arts Department, Tourism Faculty, Atatürk University, Erzurum, Turkey

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.

Keywords: bioactive compounds; antioxidant; antiproliferative

Published: October 31, 2015  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
BOZ H. Phenolic amides (avenanthramides) in oats - a review. Czech J. Food Sci. 2015;33(5):399-404. doi: 10.17221/696/2014-CJFS.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Azuma H., Banno K., Yoshimura T. (1976): Pharmacological properties of N-(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5), a new anti-atopic agent. British Journal of Pharmacology, 58: 483-488. Go to original source... Go to PubMed...
    2. Bazzano L.A., He J., Ogden L.G., Loria C.M., Whelton P.K. (2003): Dietary fiber intake and reduced risk of coronary heart disease in US men and women: the National Health and Nutrition Examination Survey I Epidemiologic Followup Study. Archives of Internal Medicine, 163: 1897-1904. Go to original source... Go to PubMed...
    3. Biel W., Bobko K., Maciorowski R. (2009): Chemical composition and nutritive value of husked and naked oat grains. Journal of Cereal Science, 49: 413-418. Go to original source...
    4. Bratt K., Sunnerheim K., Bryngelsson S., Fagerlund A., Engman L., Andersson R.E., Dimberg L.H. (2003): Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. Journal of Agricultural and Food Chemistry, 51: 594-600. Go to original source... Go to PubMed...
    5. 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. Go to original source... Go to PubMed...
    6. Bryngelsson S., Dimberg L.H., Kamal-Eldin A. (2002): Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.). Journal of Agricultural and Food Chemistry, 50: 1890-1896. Go to original source... Go to PubMed...
    7. Cai S., Huang C., Ji B., Zhou F., Wise M.L., Zhang D., Yang P. (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. Go to original source...
    8. 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. Go to original source... Go to PubMed...
    9. 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. Go to original source... Go to PubMed...
    10. Chu Y.-F, Wise M.L., Gulvady A.A., Chang T., Kendra D.F., van Klinken B.J.-W., Shi Y., O'Shea M. (2013): In vitro antioxidant capacity and anti-inflammatory activity of seven common oats. Food Chemistry, 139: 426-431. Go to original source... Go to PubMed...
    11. 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.
    12. Collins F.W. (1989): Oat phenolics: Avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls. Journal of Agricultural and Food Chemistry, 37: 60-66. Go to original source...
    13. Collins F.W., Mullin W.J. (1988): High-performance liquid chromatographic determination of avenanthramides, N-aroylanthranilic acid alkaloids from oats. Journal of Chromatography A, 45: 363-370. Go to original source...
    14. Cook N.C., Samman S. (1996): Flavonoids - chemistry, metabolism, cardioprotective effects, and dietary sources. The Journal of Nutritional Biochemistry, 7: 66-76. Go to original source...
    15. de Heredia F.P., Gómez-Martinez S., Marcos A. (2012): Obesity, inflammation and the immune system. Proceedings of the Nutrition Society, 71: 332-338. Go to original source... Go to PubMed...
    16. Dimberg L.H., Sunnerheim K., Sundberg B., Walsh K. (2001): Stability of oat avenanthramides. Cereal Chemistry, 78: 278-281. Go to original source...
    17. Dimberg L.H., Theander O., Lingnert H. (2002): Avenanthramides - a group of phenolic antioxidants in oats. Cereal Chemistry, 70: 637-641.
    18. Dokuyucu T., Peterson D.M., Akkaya A. (2003): Contents of antioxidant compounds in turkish oats: simple phenolics and avenanthramide concentrations. Cereal Chemistry, 80: 542-543. Go to original source...
    19. Dykes L., Roney L.W. (2007): Phenolic compounds in cereal grains and their health benefits. Cereal Food World, 52: 105-111. Go to original source...
    20. Emmons C.L., Peterson D.M. (2001): Antioxidant activity and phenolic content of oat as affected by cultivar and location. Crop Science, 41: 1678-1681. Go to original source...
    21. Eudes A., Baidoo E.E.K., Tang F., Burd H., Hadi M.Z., Collins F.W., Keasling J.D., Loqué D. (2011): Production of tranilast [N-(3',4'-dimethoxycinnamoyl)-anthranilic acid] and its analogs in yeast Saccharomyces cerevisiae. Applied Microbiology and Biotechnology, 89: 989-1000. Go to original source... Go to PubMed...
    22. Eudes A., Juminaga D., Baidoo E.E.K., Collins F.W., Keasling J.D., Loqué D. (2014): Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli. Microbial Cell Factories, 13: 8. Go to original source...
    23. Fagerlund A., Sunnerheim K., Dimberg L.H. (2009): Radicalscavenging and antioxidant activity of avenanthramides. Food Chemistry, 113: 550-556. Go to original source...
    24. Gani A., Wani S.M., Masoodi F.A., Hameed G. (2012): Wholegrain cereal bioactive compounds and their health benefits: a review. Journal of Food Processing & Technology, 3: 146. Go to original source...
    25. Guo W., Nie L., Wu D., Wise M.L., Collins F.W., Meydani S.N., Meydani M. (2010): Avenanthramides inhibit proliferation of human colon cancer cell lines in vitro. Nutrition and Cancer, 62: 1007-1016. Go to original source... Go to PubMed...
    26. Hübner F., Arendt E.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. Go to original source... Go to PubMed...
    27. Inglett G.E., Chen D. (2012): Antioxidant and pasting properties of oat β-glucan hydrocolloids. Food and Nutrition Sciences, 3: 827-835. Go to original source...
    28. Ishihara A., Kojima K., Fujita T., Yamamato Y., Nakajima H. (2014): New series of avenanthramides in oat seed. Bioscience, Biotechnology, and Biochemistry, 78: 1975-1983. Go to original source... Go to PubMed...
    29. Jastrebova J., Skoglund M., Nilson J., Dimberg L.H. (2006): Selective and sensitive LC-MS determination of avenanthramides in oats. Chromatographia, 63: 419-423. Go to original source...
    30. Ji L.L., Lay D., Chung E., Fu Y. Peterson D.M. (2003): Effect of avenathramides on oxidant generation and antioxidant enzyme activity in exercised rats. Nutrition Research, 23: 1579-1590. Go to original source...
    31. Kaukovirta-Norja A., Wilhelmson A., Poutanen K. (2004): Germination: a means to improve, the functionality of oat. Agricultural and Food Science, 13: 100-112. Go to original source...
    32. Koenig R., Dickman J.R., Kang C., Zhang T., Chu Y-F., Ji L.L. (2014): Avenanthramide supplementation attenuates exercise-induced inflammation in postmenopausal women. Nutrition Journal, 13: 21. Go to original source... Go to PubMed...
    33. Koenig R., Dickman J.R., Wise M.L., Ji L.L. (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. Go to original source... Go to PubMed...
    34. 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. Go to original source...
    35. Kováèová 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. Go to original source...
    36. Lee-Manion A.M., Price R.K., Strain J.J., Dimberg L.H., Sunnerheim K., Welch R.W. (2009): In vitro antioxidant activity and antigenotoxic effects of avenanthramides and related compounds. Journal of Agricultural and Food Chemistry, 57: 10619-10624. Go to original source... Go to PubMed...
    37. Liu L., Zubik L., Collins F.W., Marko M., Meydani M. (2004): The antiatherogenic potential of oat phenolic compounds. Atherosclerosis, 175: 39-49. Go to original source... Go to PubMed...
    38. Liu S., Yand N., Hou Z.-H., Yao Y., Lü L., Zhou X.-R. (2011): Antioxidant effects of oats avenanthramides on human serum. Agricultural Sciences in China, 10: 1301-1305. Go to original source...
    39. Mattila P., Pihlava J.M., Hellström J. (2005): Contents of phenolic acids, alkyl- and alkenylresorcinols, and avenanthramides in commercial grain products. Journal of Agricultural and Food Chemistry, 53: 8290-8295. Go to original source... Go to PubMed...
    40. Meydani M. (2009): Potential health benefits of avenanthramides of oats. Nutrition Reviews, 67: 731-735. Go to original source... Go to PubMed...
    41. Moglia A., Comino C., Lanteri S., de Vos R., de Waard P., van Beek T.A., Luca G., Retta S.F., Beekwilder J. (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. Go to original source... Go to PubMed...
    42. 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. Go to original source...
    43. Nayak B., Liur H., Tang J. (2014): Effect of processing on phenolic antioxidants of fruits, vegetables and grains - a review. Critical Reviews in Food Science and Nutrition, 55: 887-918. Go to original source... Go to PubMed...
    44. Nie L., Wise M.L., Peterson D.M., Meydani M. (2006): Avenanthramide, a polyphenol from oats, inhibits vascular smooth muscle cell proliferation and enhances nitric oxide production. Atherosclerosis, 186: 260-266. Go to original source... Go to PubMed...
    45. Okarter N., Liu R.H. (2010): Health benefits of whole grain phytochemicals. Critical Reviews in Food Science and Nutrition, 50: 193-208. Go to original source... Go to PubMed...
    46. Okazaki Y., Iwata Y., Matsukawa T., Matsuda F., Miyagawa H., Ishihara A., Nishioka T., Iwamura H. (2004): Metabolism of avenanthramide phytoalexins in oats. The Plant Journal, 39: 560-572. Go to original source... Go to PubMed...
    47. Orozco-Mena R., Salmerón-Ochoa I., Ortega-Rivas E., Perez-Vega S. (2014): Development of a sustainable process for the solid-liquid extraction of antioxidants from oat. Sustainability, 6: 1504-1520. Go to original source...
    48. Ortiz-Robledo F., Villanueva-Fierro I., Oomah B.D., LaresAsef 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.
    49. Peterson D.M. (2001): Oat antioxidants. Journal of Cereal Science, 33: 115-129. Go to original source...
    50. Peterson D.M., Hahn M.J., Emmons C.L. (2002): Oat avenanthramides exhibit antioxidant activities in vitro. Food Chemistry, 79: 473-478. Go to original source...
    51. Peterson D.M., Dimberg L.H. (2008): Avenanthramide concentrations and hydroxycinnamoyl-CoA: hydroxyanthranilate N-hydroxycinnamoyltransferase activities in developing oats. Journal of Cereal Science, 47: 101-108. Go to original source...
    52. Rossi M., Giussani E., Morelli R., Lo Scalzo R., Nani R.C., Torreggiani D. (2003): Effect of fruit blanching on phenolics and radical scavenging activity of highbush blueberry juice. Food Research International, 36: 999-1005. Go to original source...
    53. 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.
    54. Shi Y., Johnson Y.S., 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. Go to original source...
    55. Singh R., De S., Belkheir A. (2013): Avena sativa (oat), a potential neutraceutical and therapeutic agent: an overview. Critical Reviews in Food Science and Nutrition, 53: 26-144. Go to original source... Go to PubMed...
    56. Skoglund M., Peterson D.M., Andersson R., Nilsson J., Dimberg L.H. (2008): Avenanthramide content and related enzyme activities in oats as affected by steeping and germination. Journal of Cereal Science, 48: 294-303. Go to original source...
    57. Stevenson D.G., Inglett G.E., Chen D., Biswas A., Eller F.J., Evangelista R.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. Go to original source...
    58. Sur R., Nigam A., Grote D., Liebel F., Southall M.D. (2008): Avenanthramides, polyphenols from oats, exhibit antiinflammatory and anti-itch activity. Archives of Dermatological Research, 300: 569-574. Go to original source... Go to PubMed...
    59. Tian B., Xie B., Shi J., Wu J., Cai Y., Xu T., Xue S., Deng Q. (2010): Physicochemical changes in oat seeds during germination. Food Chemistry, 119: 1195-1200. Go to original source...
    60. Verardo V., Serea C., Segal R., Caboni M.F. (2011): Free and bound minor polar compounds in oats: Different extraction methods and analytical determinations. Journal of Cereal Science, 54: 211-217. Go to original source...
    61. Wise M.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. Go to original source... Go to PubMed...
    62. Wu Y.V. (1983): Effect of germination on oats and oat protein. Cereal Chemistry, 60: 418-420.
    63. Yang J., Ou B., Wise M.L., Chu Y.F. (2014): In vitro total antioxidant capacity and anti-inflammatory activity of three common oat-derived avenanthramides. Food Chemistry, 160: 338-345. Go to original source... Go to PubMed...

    This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.


    Return to the content