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In Oats – a Review Czech J. Food Sci., 33, 2015 (5): 399–404 Review doi: 10.17221/696/2014-CJFS Phenolic Amides (Avenanthramides) in Oats – A review Hüseyin BOZ Gastronomy and Culinary Arts Department, Tourism Faculty, Atatürk University, Erzurum, Turkey Abstract Boz H. (2015): Phenolic amides (avenanthramides) in oats – a review. Czech J. Food Sci., 33: 399–404. 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-inflamma- tory, 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 Oats (Avena sativa L.) is a cereal consumed at 1989; Bratt et al. 2003; Dokuyucu et al. 2003; lower rates than wheat and rice all over the World. Peterson & Dımberg 2008; Wıse 2011). However the dietary fiber content and nutritional AVAs are low molecular weight soluble phenolic value of oats are high. Oats contain many essen- compounds. Among cereals, only oats contain AVAs tial amino acids (methionine, cysteine, threonine, (Kováčová & Malinová 2007; Moglia et al. 2010; isoleucine, tryptophan, valine, leucine, histidine, Shi et al. 2014). These compounds are antipathogens methionine, phenylalanine, and tyrosine) necessary (phytoalexins), which are produced by the plant in for human body (Biel 2009), and high antioxidant response to the exposure to pathogens such as fungus activity components such as tocopherols, tocotrien- (Collins & Mullin 1988; Collins 1989; Oka- ols, and flavanoids (Peterson 2001; Liu et al. 2011; zaki et al. 2004). The three most abundant AVAs in Koenig et al. 2014). oats are AVA-A, AVA-B, and AVA-C, which contain In recent years, there has been considerable interest hydroxyanthranilic acid and a kind of hydroxycin- in the influence of phenolic amides from plant-based namic acids like p-coumaric, caffeic, or ferulic acids, foods on human health. These phenolic amides have respectively (Peterson et al. 2002; Okazaki et al. antioxidant properties and potential therapeutic ben- 2004; Gani et al. 2012). efits including antiinflammatory, antiproliferative, and antigenotoxic effects (Eudes et al. 2011). AVAs (anthranilic acid amides) are a group of naturally Antioxidant properties occurring phenolic amides in oats. Oats contain a unique group of approximately 40 different types of Oxidative stress and inflammation play a critical AVAs that consist of an anthranilic acid derivatives roles in the development of many health problems and hydroxycinnamic acid derivatives (Collins such as cancer, obesity, and cardiovascular diseases 399 Review Czech J. Food Sci., 33, 2015 (5): 399–404 doi: 10.17221/696/2014-CJFS (de Heredia et al. 2012; Sesti et al. 2012; Chu et ing oats AVAs on human body and found that oats al. 2013). Beneficial effects on human health of the extract containing AVAs possessed a high antioxidant phenolic compounds obtained from herbal products activity on humans (Liu et al. 2011). have been reported in many studies. Epidemiological studies suggest that a relationship exists between whole grain consumption and chronic diseases. Phytochemi- Effects of avenanthramides on health cals with antioxidant properties found in cereals have been show to protect cells against oxidative damage Whole grain cereals such as oats are important (Okarter & Liu 2010; Chu et al. 2013). sources of phenolic compounds. Phenolic compounds Oat (Avena sativa L.) has been recognised as healthy, are of interest because of their high antioxidant due to its containing antioxidants, such as vitamin E capacity and potential health benefits. Especially in and many kinds of phenolic compounds, which have recent years, there has been interest in oats and oat been proved to have strong antioxidant activities in vitro products as bioactive high-value sources for human and in vivo (Cai et al. 2011). Oat phenolics may serve health in industries such as food, pharmaceutical, as potent antioxidants by scavenging reactive oxygen and cosmetic (Chu et al. 2013; Orozco-Mena et and nitrogen species and/or by chelating transition al. 2014). minerals (Chen et al. 2004). AVAs are important phe- Oats and oats products are generally considered nolic compounds found in oats. They are constitutively healthy and the consumption of oat bran is believed expressed in the kernels, appearing in almost all mill- to lower LDL cholesterol (Brown et al. 1999; Liu et ing fractions, but occur in the highest concentration al. 2004; Singh et al. 2013). AVAs helps in prevent- in the bran and outer layers of the kernel (Peterson ing free radicals from damaging LDL cholesterol et al. 2002; Jastrebova et al. 2006; Meydani 2009). (Singh et al. 2013) and AVAs-enriched extract of Their concentrations are affected by the genotype and oats combined with vitamin C synergistically inhib- growing environment, in one location the combined its LDL oxidation in vitro (Meydani 2009). Both concentration of A, B and C having exceeded 300 mg/kg animal studies and human clinical trials confirmed (Emmons & Peterson 2001; Peterson et al. 2002). that oats antioxidants have the potential of reducing They have been reported to contribute to the fresh cardiovascular risks by lowering serum cholesterol, taste of products made from oats (Molteberg et al. inhibiting LDL cholesterol oxidation and peroxida- 1996). Oat flakes (whole grain) contain more AVAs tion (Cook & Samman 1996; Ji et al. 2003; Inglett (26–27 µg/g) than oat bran (13 µg/g) (Mattila et al. & Chen 2012). Therefore, it is emphasised that the 2005; Dykes & Roney 2007). consumption of oats and oats products is extremely The antioxidant activity of AVAs has been found important to reduce the risk of cardiovascular disease to be 10–30 times higher than those of the typical (Bazzano et al. 2003; Chen et al. 2004, 2007; Singh cereal components ferulic acid, gentisic acid, phy- et al. 2013). Another study has indicated that the droxybenzoic acid, protocatechuic acid, syringic consumption of oats and oats bran may reduce the acid, vanillic acid, and vanillin (Dimberg et al. 2002; risk of colon cancer not only because of their high Meydani 2009; Verardo et al. 2011; Orozco-Mena fiber contents but also due to AVAs (Guo et al. 2010). et al. 2014; Yang et al. 2014). The AVAs differ in In a study on laboratory animals, the supplementa- the antioxidant activity, AVA-C having the highest tion of the diet of rats with AVAs-enriched extract of activity, followed by AVA-B and AVA-A (Peterson oats at 100 mg/kg diet has been reported to increase et al. 2002; Ji et al. 2003). They are reported to be superoxide dismutase activity in skeletal muscle, stopping the oxidation of lipid and linoleic acid in liver, and kidneys, and to enhance glutathione per- foods (Fagerlund et al. 2009; Singh et al. 2013). oxidase activity in heart and skeletal muscles (Ji et Fagerlund et al. (2009) found that, compared with al. 2003; Meydani 2009). Liu et al. (2004) indicated α-tocopherol, AVAs protected linoleic acid from that oats AVAs provide another potential protective oxidation initially to a smaller extent initially. Also, mechanism by which the consumption of oats may to prevent the oxidative reaction of unsaturated fatty contribute to the reduction of the risk of atheroscle- acids, AVAs can easily be used in the food industry rosis through inhibiting vascular smooth muscle cells (Ishihara et al. 2014) due to the radical scavenging proliferation. AVAs enriched oat extracts and syn- effect (Singh et al. 2013). Similarly, Liu et al. (2011) thetic dihydroavenanthramide-D and AVA-C methyl studied the antioxidant ability of capsules contain- ester (CH3-AVA-C) have been shown to inhibit the 400 Czech J. Food Sci., 33, 2015 (5): 399–404 Review doi: 10.17221/696/2014-CJFS activation of the NF-κB transcription factor, which 5-hydroxyanthranilic acid with p-coumaric, caffeic, is the master regulator of infection and inflamma- or ferulic acids (Collins & Mullin 1988; Collins tion (Eudes et al. 2014). NFκ-B inhibitory and other et al. 1991; Singh et al. 2014). functional properties of AVAs make it a candidate The most commonly used solvents for the extraction for supplementation in the cause of decreasing in- of AVAs are methanol, ethanol, acetonitrile, formic flammation and muscle damage in post-menopausal acid, and their combinations. AVAs are generally women (Koening et al. 2014). determined by various chromatographic methods. It is interesting that AVAs are very similar in their For the determination of the AVAs amounts, high- chemical structure to tranilast (N-3,4-dimethoxy- performance liquid chromatography (HPLC) (Bryn- cinnamoylanthranilic acid), which is an antiallergic gelsson et al. 2002; Peterson et al. 2002; Chen drug used to treat asthma and autoimmune diseases et al. 2004; Mattila et al. 2005; Jastrebova et al. (Azuma et al. 1976; Ishihara et al. 2014). AVAs, 2006; Peterson & Dimberg 2008; Skoglund et having a similar structure to that of tranilast, can al. 2008; Wise et al. 2011; Ortiz-Robledo et al.
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