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Phenolic Compounds in Cereal Grains and Their Health Benefits

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Phenolic Compounds in Cereal Grains and Their Health Benefits and antioxidant activity are reported in the Phenolic Compounds in Cereal literature. Unfortunately, it is difficult to make comparisons of phenol and anti- Grains and Their Health Benefits oxidant activity levels in cereals since different methods have been used. The ➤ Whole grain cereals are a good source of phenolics. purpose of this article is to give an overview ➤ Black sorghums contain high levels of the unique 3-deoxyanthocyanidins. of phenolic compounds reported in whole ➤ Oats are the only source of avenanthramides. grain cereals and to compare their phenol and antioxidant activity levels. ➤ Among cereal grains, tannin sorghum and black rice contain the highest antioxidant activity in vitro. Phenolic Acids Phenolic acids are derivatives of benzoic and cinnamic acids (Fig. 1) and are present in all cereals (Table I). There are two Most of the literature on plant phenolics classes of phenolic acids: hydroxybenzoic L. DYKES AND L. W. ROONEY focuses mainly on those in fruits, acids and hydroxycinnamic acids. Hy- TEXAS A&M UNIVERSITY vegetables, wines, and teas (33,50,53,58, droxybenzoic acids include gallic, p- College Station, TX 74). However, many phenolic compounds hydroxybenzoic, vanillic, syringic, and in fruits and vegetables (i.e., phenolic acids protocatechuic acids. The hydroxycinna- esearch has shown that whole grain and flavonoids) are also reported in cereals. mic acids have a C6-C3 structure and Rconsumption helps lower the risk of The different species of grains have a great include coumaric, caffeic, ferulic, and cardiovascular disease, ischemic stroke, deal of diversity in their germplasm sinapic acids. The phenolic acids reported type II diabetes, metabolic syndrome, and resources, which can be exploited. Some in cereals occur in both free and bound gastrointestinal cancers (36,37). In addi- phenols are unique to one plant species, forms. Sorghum and millet have the widest tion to dietary fiber, whole grains contain such as the oat avenanthramides (12). variety of phenolic acids. Free phenolic many health-promoting components such Different methods of analysis for phenols acids are located in the outer layer of the as vitamins, minerals, and phytochemicals, which include phenolic compounds. Phenolic compounds have antioxidant Table I. Phenolic acids reported in cereal grains properties and can protect against degen- Phenolic Acid Grain References erative diseases (i.e., heart disease and Hydroxybenzoic acids: cancer) in which reactive oxygen species Gallic Milleta, rice, sorghum 29, 67, 75 (i.e., superoxide anion, hydroxyl radicals, Protocatechuic Barley, maize, milletb, oat, rice, rye, and peroxy radicals) are involved (32,57). sorghum, wheat 29, 41, 43, 44, 66, 67, 69 The general definition of a phenolic p-Hydroxybenzoic Barley, maize, milletc, oat, rice, rye, compound is any compound containing a sorghum, wheat 29, 39, 41, 43, 44, 66, 69 Gentisic Milletd, sorghum 44, 70 benzene ring with one or more hydroxyl Salicylic Barley, sorghum, wheat 39, 43, 70 groups. Phenolic acids, flavonoids, con- Vanillic Barley, maize, milletd, oat, rice, rye, densed tannins, coumarins, and alkyl- sorghum, wheat 29, 39, 41, 43, 44, 66, 67, 69, 75 resorcinols are examples. All plant-based Syringic Barley, maize, milletd, oat, rice, rye, foods have phenols, which affect their sorghum, wheat 39, 41, 43, 44, 66, 69, 70, 75 appearance, taste, odor, and oxidative Hydroxycinnamic acids: stability (45). In cereal grains, these Ferulic Barley, maize, milletd, oat, rice, rye, compounds are located mainly in the sorghum, wheat 3, 29, 39, 41, 43, 44, 66, 67, 69, 75 Caffeic Maize, milletd, oat, rice, rye, pericarp, and they can be concentrated by sorghum, wheat 29, 39, 41, 44, 66, 67, 75 decorticating the grain to produce bran, o-Coumaric Barley 43 which can be incorporated into a food m-Coumaric Barley 43 product (i.e., breads, cookies, and tortillas) p-Coumaric Barley, maize, milletd, oat, rice, rye, with increased dietary fiber levels and sorghum 3, 29, 39, 41, 43, 44, 66, 67, 69, 75 nutraceutical properties. Cinnamic Milletd, sorghum, wheat 29, 44 Sinapic Barley, millete, oat, rice, rye, sorghum 3, 41, 43, 44, 66, 69, 70 a Detected in finger millet. b Detected in finger, pearl, and teff millets. c Detected in finger, pearl, and foxtail millets. doi:10.1094 / CFW-52-3-0105 d Detected in finger, pearl, teff, and foxtail millets. © 2007 AACC International, Inc. e Detected in finger and pearl millets. CEREAL FOODS WORLD / 105 pericarp and are extracted using organic aromatic rings joined by a three-carbon deoxyanthocyanidins are the yellow solvents (29,30,41,66,67). Bound phenolic link; they include anthocyanins, flavanols, apigeninidin and the orange luteolinidin acids are esterified to cell walls; acid or flavones, flavanones, and flavonols (Fig. (18). Sorghums with a black pericarp have base hydrolysis is required to release these 1). More than 5,000 flavonoids have been higher levels of 3-deoxyanthocyanins than bound compounds from the cell matrix identified in nature (74). Flavonoids are red sorghums (19). Decortication of black (29,30,39,41,59,66,67). The major phenolic located in the pericarp of all cereals. Thus sorghum grain to produce bran concen- acids in cereals are ferulic and p-coumaric far, sorghum has the widest variety of trates anthocyanin levels almost seven- acids (29,34,41,44,66,75). Phenolic acid flavonoids reported (Table III). fold. For example, in our laboratory, the levels vary among cereals; their brans Anthocyanins are water-soluble pig- grain and bran of Tx430 black have concentrate these compounds threefold ments that contribute the blues, purples, anthocyanin levels of 944 (Table IV) and (Table II). and reds in plant foods (i.e., blueberries, 6,695 µg/g, respectively (unpublished blackberries, and strawberries) and are data). Flavonoids the major flavonoids studied in cereals. Other flavonoids found in fruits and Flavonoids are compounds with a C6- The six common anthocyanidins in na- vegetables are also reported in cereals. For C3-C6 skeleton that consists of two ture are cyanidin, delphinidin, malvinidin, example, the flavone apigenin, a compound pelargonidin, petunidin, and peonidin. found in parsley and celery (58,74), is also Table II. Phenolic acid content in cereal grains These compounds have been reported in reported in millet, oat, and sorghum (Table Amount the pericarp of pigmented varieties of III). Flavanones, which are compounds Sample (µg/g) References barley, maize, rice, rye, and wheat (Table mainly reported in citrus (58,74), are also Whole grains: III); the amounts are reported in Table IV. reported in cereals such as sorghum and Barley 450–1346 34, 41 Milling these cereals into bran con- oat (Table III). Flavonoids are reported to Finger millet 612 44 centrates the anthocyanins. For example, have antioxidant, anticancer, anti-allergic, Foxtail millet 3907 44 blue and purple whole wheat and bran anti-inflammatory, anticarcinogenic, and Maize 601 41 have anthocyanin levels of 93–152 and gastroprotective properties (13,32,58,74). Oat 472 41 236–453 µg/g, respectively (1). Pearl millet 1478 44 Rice 197–376 41 Sorghums contain unique anthocyanins Condensed Tannins Rye 1362–1366 41 called 3-deoxyanthocyanins, which lack Condensed tannins, which are also call- Sorghum 385–746 29 the hydroxyl group in the 3 position of the ed proanthocyanidins or procyanidins, Wheat 1342 41 C-ring (Fig. 2). This feature is believed to consist of polymerized flavanol units (Fig. Brans: increase their stability at high pH com- 1), and they contribute to astringency in Oat 651 41 pared to common anthocyanins (6,22), foods. These compounds are found in Rye 4190 41 which could make them good natural food sorghum with a pigmented testa layer, red Wheat 4527 41 colorants. The two main sorghum 3- finger millets, and barley (18,21). Fig. 1. Chemical structure of classes of phenolic compounds in cereal grains. 106 / MAY-JUNE 2007, VOL. 52, NO. 3 Over the years, it has been difficult to have been used to measure condensed Normal-phase HPLC with fluorescence determine tannins in foods due to the lack tannins (18). However, these methods can detection separates and quantifies condens- of appropriate standards. For many years, over-estimate or yield false-positive results ed tannin according to the degree of colorimetric methods (i.e., the vanillin/ since monomeric phenols react with the polymerization (23,31). For instance, HCl, butanol/HCl, or the 4-dimethylami- reagents (18). tannin levels in barley and in tannin no–cinnamaldehyde [DMACA] assays) sorghum are 0.74 mg/g and 7.88–21.97 mg/g, respectively (4,24). The tannins in barley are monomers, dimers, and trimers, Table III. Flavonoids reported in cereal grains whereas those found in tannin sorghums Compound Grains References are polymers (4,23,24,34). Anthocyanins: Tannins bind to proteins, carbohydrates, Apigeninidin Sorghum 6, 47 and minerals, which decrease digestibility Apigeninidin 5-glucoside Sorghum 46, 47, 73 of these nutrients and reduce feed efficiency Cyanidin Barley 43 of ruminants and monogastrics during Cyanidin 3-galactoside Maize, wheat 1, 43 feeding (18). Plants containing high tannin Cyanidin 3-glucoside Barley, maize, rice, rye, wheat 1, 2, 43 Cyanidin 3-rutinoside Maize, rice, wheat 2 levels are not preferred by birds and Delphinidin Barley 43 insects. However, humans have acquired a Delphinidin 3-glucoside Wheat 2 taste for moderately astringent foodstuff Delphinidin 3-rutinoside Rye, wheat 2 (i.e., dark chocolate and cranberries) or Luteolinidin
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