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Critical Reviews in Food Science and Nutrition


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Ferulic Acid and its Position Among the Phenolic Compounds of Wheat
Joanna Klepacka & ucja Fornal
a a b

Institute of Commodities Science and Food Quality Evaluation, University of Warmia and Mazury in Olsztyn, Poland
b

Chair of Food Plants Chemistry and Processing, University of Warmia and Mazury in Olsztyn, Poland Available online: 18 Jan 2007

To cite this article: Joanna Klepacka & ucja Fornal (2006): Ferulic Acid and its Position Among the Phenolic Compounds of Wheat, Critical Reviews in Food Science and Nutrition, 46:8, 639-647 To link to this article: http://dx.doi.org/10.1080/10408390500511821

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Critical Reviews in Food Science and Nutrition, 46:639647 (2006) Copyright C Taylor and Francis Group, LLC ISSN: 1040-8398 DOI: 10.1080/10408390500511821

Ferulic Acid and its Position Among the Phenolic Compounds of Wheat
JOANNA KLEPACKA
Institute of Commodities Science and Food Quality Evaluation, University of Warmia and Mazury in Olsztyn, Poland

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LUCJA FORNAL
Chair of Food Plants Chemistry and Processing, University of Warmia and Mazury in Olsztyn, Poland

Ferulic acid (3-methoxy-4-hydroxycinnamic acid) is the main phenolic acid occurring in cell walls of monocotyledones. Due to its blue-and-white uorescence it is easily identied and is located in the cereal grain morphological parts. Its 40-fold greater concentration was found in the cells walls of the seed coat and aleuronic layer than in the cells walls of endosperm. Most often, it is linked by ester bonds with hemicellulose chains, mainly with arabinose residues and it also polymerizes with lignin through ether bonds. However, ferulic acid in the pentosane molecules forms specic complexes with proteins through chemical bonds with amino acids. It is interesting to mention the theory of the pentosane gel formation in which a great role is assigned to ferulic acid. An oxidized form of ferulic aciddiferulic acidproduces gel formation by linking two pentosane or protein molecules. The blue-and-white uorescence of ferulic acid can be applied to determine our contamination with grain coat particles and its ability to form complexes with pentosanes and proteins is important in the formation of dough texture with its semi-elastic properties. Keywords ferulic acid, phenolic compounds, wheat, cereal grains

INTRODUCTION Interest in phenolic compounds originates mainly from their well-known antioxidant features(Onyeneho and Hettiarachchy, 1992; Sikorski, 1994; Buchwald and Czapska, 1995; Amiot et al., 1996; Maillard et al., 1996; Bourne and Rice-Evans, 1998; Deighton et al., 2000; Zieli ski and Koz lowska, 2000). n Particular attention has been paid to their role as free radical scavengers and has provoked numerous studies into phenolic compounds in many plants, including cereals. The antioxidant activity of extracts from cereal products has been found to correlate with the content of plant phenols occurring in these cereals (Zieli ski and Koz lowska, 2000; Burda n et al., 2001). Cereals contain a wide range of phenolic compounds, of different chemical structures, of which phenolic acids are of great signicance (K hk nen et al., 1999). In wheat grains, a o ferulic acid occurs in the highest amounts (McKeehen, 1999). Due to the valuable functions and content of phenolic compounds, including ferulic acid, cereal products may constitute a valuable source of phenolic compounds in the human diet (Parr
Address correspondence to Joanna Klepacka, Institute of Commodities Science and Food Quality Evaluation, University of Warmia and Mazury, PLAC CIES2YWSKI 1, Olsztyn, 10-718. Poland. E-mail: klepak@uwm.edu.pl

and Bolwell, 2000). The phenolic compounds, especially ferulic acid, occurring in cereals also exhibit technological functions. What, therefore, is current the stage of knowledge of the chemical structure and properties of phenolic compounds, particularly the role of the ferulic acid in wheat grain? CLASSIFICATION AND PROPERTIES OF POLYPHENOLS Phenolic compounds appear only in plants and are their major secondary metabolites. Phenylalanine and tyrosine are their precursors. Phenolic compounds are characterized by a high diversity of chemical structure. They occur in a free as well as a bound form with such compounds as saccharides and organic acids. Over 800 aglycones have been identied and ca. 4000 of these compounds occur in the form of glycosides, esters as well as in other combinations (Oszmia ski, 1988; Lachman et al., n 1991; Ashraf et al., 1994; Rozes and Peres, 1998; Scalbert and Williamson, 2000). Due to the structure of the basic carbon skeleton, polyphenolic compounds can be divided into three subgroups: C6 C1 phenyl-carboxyl acidsderivatives of benzoic acid, e.g. protocatechuic acid and gallic acid;

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Figure 1

Benzoic acid and its derivatives (Borkowski, 1993).

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C6 C3 phenyl-propene acidsderivatives of cinnamic acid, e.g. ferulic acid or caffeic acid; C6 C3 C6 avonoids which include: avones and avonols, e.g. quercetin and rutin; avanones, e.g. hesperidin and naringin; avanols: catechins, leuco- and proanthocyanins; anthocyanins, e.g. cyanin and malvidin; chalcones, e.g. phlorizidin; isoavones and auronesrarely occurring in food. The most important groups of polyphenols which affect the sensory properties of food include: anthocyaninsresponsible for the red color of many fruit and ower species; and phenolic acids, catechins, and proanthocyanidins which as the precursors of tannins and substrates of enzymatic browning are responsible for the color, avor and odor of many food products (Sikorski, 1994). To date, no toxic effect of plant- originated polyphenols has been found in human diet, although their role and metabolism in the human organism has not yet been fully studied. Flavonoids are the most known and described for their protective role against cardiovascular diseases resulting mainly from their stabilizing activity on the walls of capillary vessels (Feng and McDonald, 1989; Chu et al., 2000; Parr and Bolwell, 2000; Kris-Etherton et al., 2002). CLASSIFICATION, PROPERTIES AND OCCURRENCE OF PHENOLIC ACIDS IN CEREAL GRAINS Two sequences of phenolic acids are of signicant importancederivatives of benzoic and cinnamic acids which

have been the subject of research since at least the 1970s (Koz lowska et al., 1977; Salomonsson et al., 1978; S lomi ski, n 1980; Krygier et al., 1982; Dabrowski and Sosulski, 1984; Nordkvist et al., 1984; Rotkiewicz et al., 1984; Collins et al., 1991; Szajdak and Zyczy ska-Ba loniak, 1994; Bocchi et al., 1996; n Dimberg et al., 1996; Stefanowska et al., 1996; Opoku et al., 1997; Phelps and Young, 1997; Sharma et al., 1998; Watanabe et al., 1998; Andreasen et al., 1999; Kennedy et al., 1999; McKeehen et al., 1999; Amakura et al., 2000; Parr and Bolwell, 2000; Silva et al., 2000). The chemical structures of benzoic and cinnamic acids as well as their derivatives are presented in Figures 1 and 2. The results of studies on the quality and content of phenolic acids in wheat grains are not equivocal. They are different in terms of the range of the acid contents as well as the form in which they occur in. Sosulski et al. (1982) analyzed the phenolic acids occurring in rice, oat, maize, and wheat. They found cisferulic and vanillic acids among the acids released from ester bonds while in insoluble fraction trans-ferulic acid which occurs in the highest amounts in maize (Table 1). Among the free phenolic acids in triticale, Maga and Lorenz (1974) also found vanillic, ferulic, and p-coumaric acids. Hatcher and Kruger (1997) also characterized three fractions of phenolic acids in wheat grain: free acids, acids in soluble ester bonds and acids occurring in insoluble complexes. In the latter, only ferulic acid was found. Depending on the wheat variety, its content ranged from 274.8 to 337.6 ppm. Free phenolic acids constituted 23.5% of the total phenolic acids. Of all free phenolic acids, ferulic acid was found to dominate. Its content ranged from 0.2 to 6.3 ppm, depending on the wheat variety. In ester bonds, sinapic, ferulic, vanillic and syringic acids were found in the highest amounts reaching: 16.9 30.5 ppm, 8.6 17.6 ppm,

Figure 2

Cinnamic acid and its derivatives (Borkowski, 1993).

FERULIC ACID
Table 1 Content of phenolic acids released from ester bonds and from insoluble fraction (Sosulski et al., 1982) Grain [ppm] Phenolic acids cis-ferulic trans-ferulic Vanillic cis-ferulic trans-ferulic Rice Oat Maize Wheat trace 3,8 3,0 trace 58,6

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Phenolic acids released from ester bonds 1,6 1,9 5,1 9,6 6,7 44,9 0,8 3,5 2,7 Phenolic acids released from insoluble fraction trace 0,7 0,8 63,1 54,6 208,6

4 7.2 ppm, and 1.76.5 ppm, respectively. Therefore, the results of the studies by Hatcher and Kruger (1997), support the thesis that the content of ferulic acid is a variety-dependent trait. Weidner et al. (1999) analyzed the content of phenolic acids in kernels of Polish varieties of wheat, rye, and triticale. The characteristics covered three fractions: free phenolic acids, acids released from soluble ester bonds, and acids released from soluble glycosides. The results of these studies clearly indicate a higher content of ferulic acid in grain depending on the variety (Elena, Alba variety), especially when determined in ester or glycoside bonds. Besides ferulic acid, sinapic, p-coumaric, and caffeic acids were present in all the analyzed phenolic fractions in wheat, rye, and triticale. Papers by Boskov-Hansen et al. (2002) also support the thesis that the following acids occur in the highest amounts in rye: ferulic (1079 g/g d.m.), sinapic (76 g/g d.m.) and p-coumaric (35 g/g d.m.). Ciska et al. (2003) analyzed the content of phenolic acids in ve cereal varieties: wheat, barley, rye, oat and buckwheat. The following acids occurring in a free or ester-bonded form were identied in the analyzed grains: vanillic, syringic, ferulic, and coumaric. Rye, oat, and buckwheat grain also contained sinapic and caffeic acids. Ferulic acid predominated among the phenolic acids found in the analyzed varieties of wheat and barley while syringic acid predominated in the grain of oat, rye, and buckwheat. The total amount of phenolic acids occurring in both forms was the highest in rye and oat.

FERULIC ACID IN WHEAT GRAINITS PROPERTIES AND OCCURRENCE Studies into the occurrence of phenolic acids in cereal grains support the thesis of the distinguished content of ferulic acid among the phenolic compounds of wheat grain. This results from, among others, the fact that ferulic acid (3-methoxy-4hydroxycinnamic acid) is the major phenolic acid occurring in the cell walls of monocotyledones (Smith and Hartley, 1983; Micard et al., 1994; Cabrera et al., 1995; Bartolom et al., 1997; e Kroon et al., 1997; Lempereur et al., 1997; Madhavi et al., 1997; Wakabayashi et al., 1997; Rousseau and Rosazza, 1998; Zupfer et al., 1998; Muheim and Lerch, 1999). The following acids

are its precursors: p-coumaric (p-hydroxycinnamic) and caffeic (3,4-dihydroxycinnamic). They are synthesized in plants from phenylalanine and L-tyrosine on the shikimic pathway (Bourne and Rice-Evans, 1998). Ferulic acid appears in the form of cis- and trans-isomers (Sosulski et al., 1982). Molecules of ferulic acid may bind oxygen atoms forming dimers (Ishii, 1997; Oosterveld et al., 1997; Saulnier and Thibault, 1999). Numerous dehydrodimers of ferulic acid, including 5-5 -diferulic acid [(E,E)-4,4 -dihydroxy-5,5 -dimethoxy-3,3 -bicinnamic] occurring in the largest amounts in cereal grain were found in the pentosane fraction of wheat (Ng et al., 1997; Andreasen et al., 2000a,b; Bunzel et al., 2000; Renger and Steinhart, 2000). The blue autouorescence of ferulic acid conrms its presence in the cell walls of the wheat kernel aleurone layer (Smart and OBrien, 1979; Seitz, 1989; Morales et al., 1996; Regnier and Macheix, 1996). Ferulic acid esters reveal blue uorescence at pH 5.8 and change their color into green at pH 10 (Ishii, 1997 after Harris and Hartley, 1976). Fulcher et al. (1972) noted that the blue-white autouorescence of wheat kernel cell walls is exactly the same as that revealed by pure crystals of ferulic acid. It indicates that ferulic acid, whose concentration in the aleurone layer is very high, may be responsible for the uorescence of cell walls. It was supported by the studies of Smart and OBrien (1979). Rotkiewicz et al. (1984) found that the ferulic acid content in wheat kernels in all its forms amounts to 31.0 g/g. On the other hand, Pussnawin and Wetzel (1987) determined the total ferulic acid content at the level of 500 g/g. Rybka et al. (1993) conrmed the predominating character of this acid among free phenolic acids and those in ester bonds. Lempereur et al. (1997) showed a high genetic (variety-dependent) diversity of the ferulic acid content in durum wheat grains (from 0.693 to 2.443 mg/g d.m.). The mean content of that acid was higher compared to that reported for Triticum aestivum. Hatcher and Kruger (1997) analyzed the content of phenolic acids, including ferulic acid, in grains and our of different purity obtained from ve quality classes of Canadian wheat: CWSWS (Canadian Western Soft White Spring), CPSR (Canadian Prairie Spring Red), CWRW (Canadian Western Red Winter), CWRS (Canadian Western Red Spring), and CWES (Canadian Western Extra Strong). They isolated three fractions of phenolic acids: free phenolic acids, acids bound into insoluble complexes, and acids occurring in soluble ester linkages. The highest share (80%) in the total sum of phenolic acids was reported for acids occurring in insoluble complexes. Of all the acids in this fraction, only ferulic acid could be determined quantitatively; its content in the whole kernels ranged from 274.8 to 337.6 g/g, depending on the quality class of wheat. The lowest content was found in CWRW and CWES class grain. These classes represent the highest quality. This suggests a relation between high technological quality of wheat kernels and low content of ferulic acid in insoluble linkages. The content of ferulic acid determined in the soluble ester linkages of wheat grains reached 8.617.6 g/g, while in the fraction of free phenolic acidsfrom 0.2 to 6.3 g/g, depending on the wheat variety.

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The results obtained by other authors also conrm the thesis of the predominating character of ferulic acid, however, its content found in wheat kernels indicates great discrepancies which result from the varied properties of the analyzed varieties (Hatcher and Kruger, 1997; Weidner et al., 1999).

CONTENT OF FERULIC ACID IN BRAN Quoting the studies of Munck et al. (1979), Symons and Dexter (1993) claimed that determination of components revealing uorescence, e.g. ferulic acid, and occurring in high concentrations in selected layers of the kernel may indicate the purity of our. Jensen et al. (1982) used uorescence to determine the contamination of our with particles of aleurone layer and seed coat. Pussayanawin and Wetzel (1987) showed that ferulic acid may indicate the degree of our purity, which may then be helpful in determining its milling quality. Kelfkens (1995) veried whether the determination of the ferulic acid content in our is more efcient for estimating the presence of seed coat particles in the our, compared to determination of the ash content. The thesis of his studies was based on the assumption that the content of ferulic acid in the seed coat is about 40-fold higher than that determined in the endosperm. However, further studies indicated that the above correlations are characterized by an unexpectedly large variability. In the bran of durum and soft wheat, ferulic acid can occur in bonds with polisaccharides and proteins (Regnier and Macheix, 1996; Saulnier et al., 1999; Bartolome et al., 2000). It can be linked by ester bonds with hemicellulose chains, mainly with arabinose residues (Jung and Shalita-Jones, 1990; Hosny and Rosazza 1997; Andreasen et al. 2000a,b). Moreover, it may polymerize with lignin forming bonds resistant to the activity

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of alkaline compounds (Rybka et al., 1993; Lozovaya et al., 1999). Ester linkages of ferulic acid with arabinoxylans and their role in the formation of arabinoxylanic structures have been widely described (Ciacco and DAppolonia, 1982; Michniewicz et al., 1990; Izydorczyk et al., 1991; Izydorczyk and Biliaderis, 1993; Rybka et al., 1993; Raczy ska- Bojanowska and Rybka, 1994; n Ralet et al., 1994; Rattan et al., 1994; Ishii, 1997; FigueroaEspinoza and Rouau, 1998; Figueroa- Espinoza et al., 1999; Andreasen et al., 2000a,b; Lu et al., 2000). Ferulic acid and its dimers play an important role in the formation and functional properties of dietary ber (Ishii, 1997; Ng et al., 1997; Bunzel et al., 2000; Renger and Steihart, 2000). This acid binds with polysaccharides by ester linkages, while its binding with lignin also proceeds with ether linkages (Andreasen et al., 2000a,b; Lozovaya et al., 1999 and 2000; Renger and Steinhart, 2000; Weidner et al., 2000). Renger and Steinhart (2000) reported that over 60% of ferulic acid contained in dietary ber occurred in ether bonds. It is possible that ether linkages of ferulic acid bind together molecules of arabinoxylans and lignin. Klepacka et al. (2000) found that the total content of phenolic compounds in bran is greater than in our and their relationship is variety dependent (Figure 3). On the other hand, ferulic acid in the analyzed bran varieties occurs mainly in ester linkages (Figure 4). These results also indicate a varied content of ferulic acid in bran of low and high technological quality varieties (Elena, Begra). Similar correlations were observed by Hatcher and Kruger (1997) who indicated the highest content of ferulic acid occurring in insoluble linkages in Canadian wheat kernels of high technological quality. Few studies indicate a correlation between the content of ferulic acid and kernel size. Lempereur et al. (1997) reported that in small kernels of Primadur Durum wheat the

Figure 3

Content of total phenolic compounds in our and brans of wheat varieties (Klepacka et al., 2000).

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Figure 4

Content of ferulic acid in brans of wheat varieties (Klepacka et al., 2000).

content of arabinoxylans and ferulic acid is higher than in varieties characterized by larger kernels. Based on the studies by Klepacka et al. (2002), the content of ferulic acid in wheat bran varies between the studied varieties and is kernel-size dependent (Table 2). The differences were found to be statistically signicant within certain sized kernels.

CONTENT OF FERULIC ACID IN FLOUR The results of studies on the ferulic acid content in particular layers of wheat kernel as well as in milling fractions are not clear. Sosulski et al. (1982) found that in our directly after milling, the trans-ferulic acid content reaches 63.6 g/g, while in our stored for 6 months it drops to 23.3 g/g. These results refer to the content of total ferulic acid, i.e. the total sum of its contents in the fraction of free phenolic acids, soluble esters and insoluble fraction. Hatcher and Kruger (1997) reported that a high correlation (r>0.93, <0.05) was found between the ferulic acid content in insoluble fraction and the ash content in the our of all analyzed wheat varieties, which may be explained by the presence of this fraction of phenolic acids in the bran.

Lempereur et al. (1997) reported that ferulic acid determined in the fraction of medium our makes up 55.6 % of the ferulic acid content in the whole kernel (ca. 429 g/g). Symons and Dexter (1993) determined the ferulic acid content in particular milling fractions of wheat. In the medium our, its content ranged from 25 to 177.5 g/g, depending on the break-sieving stage. Lempereur et al. (1997) characterized the content of ferulic acid in particular milling fractions of the French wheat variety Ardente. The content of ferulic acid determined by these authors in the whole kernels of wheat durum ranged from 780 to 1980 g/g, depending on the variety, while that determined in semolina was substantially lower. The lower the our yield, the lower was the content of ferulic acid occurring in that our. Nishizawa et al. (1998) obtained similar results in the ferulic acid content in milling fractions of wheat. The differences in the ferulic acid contents reported by different authors may have causes, the most signicant of which include genetic and environmental conditions as well as different analytical techniques applied (Hatcher ad Kruger, 1997). Preparation of grain for analyses involves its disintegration, which may proceed under different conditions, thus resulting in different sizes of the particles obtained, which in turn affects the results of the determinations. The application of different mills for the preparation of selected milling fractions, as well as different

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Table 2

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Statistical analysis of ferulic acid content in the bran depending on variety and grain size of wheat (Klepacka et al., 2002) Quality grade( ) winter spring winter spring A C A B A C A B A C A C A A A(E) A(E) Fraction F>1,7 25mm Content of ferulic acid[mg/100g dry matter] 36,41b 29,62a 42,81d 40,46c 32,66a 32,06a 42,44c 34,78b 49,80b,e 52,29a 65,25c 50,59b 47,94d 49,02e 43,44f 39,99g

Wheat variety Zyta Elena Torka Henika Zyta Elena Torka Henika Zyta Elena Begra Almari Torka Jasna Ismena Nawra

2,5<F3 <2,8 25mm

winter

2,8<F2 <3,2 25mm

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spring

There are no statistically signicant differences between the values marked with same letters in the column. ( )grade of technological value in accordance with multiple evaluation method applied in the evaluation of varieties in Poland: Eelite wheat, Aquality wheat, Bbread wheat, Cother wheat (feed). The brackets indicate proximity of other group (Kaczy ski, 1999). n

milling conditions, may contribute to obtaining not homogenous experimental material. Various methods applied in the determination of the ferulic acid content and different interpretation of the results obtained may have caused the discrepancies in its content quoted in different papers.

FERULIC ACID AND DOUGH RHEOLOGICAL PROPERTIES Ferulic acid is a component of glycoproteins of wheat our (Smart and OBrien, 1979). Arabinoxylans belong to pentosanes, substances of a non-starch fraction of polysaccharides, and their presence in the our of bread cereal affects, among others, rheological properties of dough and bread quality (Ciacco and DAppolonia, 1982; Michniewicz et al., 1990; Izydorczyk et al., 1991; Graybosch et al., 1993; Andreasen et al., 2000b). Chemical bonds have been found in pentosane molecules between groups of ferulic acid and amino acids, e.g. tyrosine or cysteine. Such linkages create the formation of very strong bonds between peptide substances and pentosane molecules or cellulose. Many authors claim that pentosane gel is formed by phenolic acids, especially ferulic acid which occurs in the highest quantities. In the presence of oxygen, it oxidizes into diferulic acid by binding two or more neighboring pentosane molecules or peptide subunits (Smart and OBrien, 1979; Michniewicz, 1995 after Geissman and Neukom, 1973; Hoseney, 1984; Jacksonem and Hoseney, 1986; Markwalder and Neukom, 1976). In their studies, scientists have tended to ignore waterinsoluble pentosanes as they are thought to have too high of an esterication degree of ferulic acid groups to actively participate in the formation of pentosane gel (Michniewicz, 1995). Ferulic acid makes up from 0.09 to 0.30% of water-soluble pentosane

substances (Ciacco and DAppolonia, 1982), and ca. 0.11% of water-insoluble pentosanes (Michniewicz et al., 1990). Huang and Hoseney (1999) carried out studies on the wheat our components responsible for the formation of dough viscosity. They stated that compounds which produced such defect of dough are water-soluble, have a carbohydrate-like structure, and absorb UV light. They suggested that the most crucial component creating a dough viscosity is the molecule of trans-ferulic acid bound to - glucan chain at 71 anhydrous glucose. The production of food from whole grain ours, due to increased content of ferulic acid, might face such problems as the occurrence of undesirable properties of dough and changes in its color, most probably caused by the reactions of enzymatic browning. When considered in terms of wheat grain milling, the quality of our depends to a high extent on the content of polyphenol oxidase. The milling fraction characterized by a our yield higher than 70% makes its content substantially higher. Phenolic acids, especially ferulic acid, occurring in high quantities may be potential substrates of this enzyme. Oxidative processes, involving the participation of polyphenol oxidase, lead to the formation of labile chinones, which in turn cause chromatosis of products through polymerization with other components, e.g. amines or thiols (Hatcher and Kruger, 1997; Koh and Hoseney, 1994).

CONCLUSION Present knowledge of phenolic compounds in cereal grain, particularly wheat grain, indicates a series of correlations. The most important is the variety-dependence of phenolic compound content, however, the variability of this trait for different varieties affected by biotic and abiotic factors has not yet been explained.

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On the other hand, it was found that the content of ferulic acid is many times greater in the seed coat of wheat and its content in ester linkages is many times greater than in insoluble complexes. These ndings may be a starting point for further studies into the application of ferulic acid content as a discriminate of ash content in our. Moreover, provided quick methods based on uorescence measurement can be developed, they can serve as another milling quality technique to be applied in mills. REFERENCES
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