Abstract
Three hydroxybenzoic acids: p-hydroxybenzoic acid, vanillic acid and syringic acid; six hydroxycinnamic acids: p-coumaric acid, ferulic acid and four ferulic acid derivatives and a flavonoid (apigenin) were identified and quantified in 34 accessions corresponding to 19 cultivars of wheat applying HPLC coupled to diode array detector. Considerable differences between the wheat cultivars were observed in the phenolic contents. Some cultivars (Colorado, Del País, Barbilla, Jallado, Raspinegro Canario and Plaganudo) could be selected according to the high levels of phenolic compounds. Ferulic acid was the major phenolic acid compound followed by syringic and p-hydroxybenzoic acids. The proportion of ferulic acid present as dimeric forms ranged from 4.2 to 8.6% across all of the wheat cultivars analyzed. Apigenin, p-hydroxybenzoic and syringic acids did not show significant correlations. Many correlations between the determined hydroxycinnamic acids were observed. The ferulic acid and all the ferulic acid derivatives showed highly significant correlations, suggesting that the concentrations of diferulic acids depend on the concentration of ferulic acid.
Similar content being viewed by others
Abbreviations
- RT:
-
Retention time
- 8-O-4´-diFA:
-
(Z)-β-{4-[(E)-2-carboxyvinyl]-2-methoxy-phenoxy}-4-hydroxy-3-methoxycinnamic acid
- 8-5´-diFA benzofuran form:
-
trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid
- 5-5´-diFA:
-
(E,E)-4,4´-dihydroxy-5,5´-dimethoxy-3,3´-bicinnamic acid
- 8-5´-diFA:
-
(E,E)-4,4´-dihydroxy-3,5´-dimethoxy-β,3´-bicinnamic acid
References
Slavin J, Jacobs D, Marquart L (1997) Whole-grain consumption and chronic disease: Protective mechanisms. Nutr Cancer 27:14–21
Mateo Anson N, Van den Berg R, Havenaar R, Bast A, Haenen G (2008) Ferulic acid from aleurone determines the antioxidant potency of wheat grain (Triticum aestivum L.). J Agric Food Chem 56:5589–5594
Zhou K, Laux JJ, Yu L (2004) Antioxidant properties of bran extracts from “Trego” wheat grown at different locations. J Agric Food Chem 52:1112–1117
Zhou K, Laux JJ, Yu L (2004) Comparison of swiss red wheat grain and fractions for their antioxidant properties. J Agric Food Chem 52:1118–1123
Hung P, Maeda T, Miyatake K, Morita N (2009) Total phenolic compounds and antioxidant capacity of wheat graded flours by polishing method. Food Res Int 42:185–190
Li L, Shewry P, Ward J (2008) Phenolic acids in wheat varieties in the health grain diversity screen. J Agric Food Chem 56:9732–9739
Kern SM, Bennett RN, Mellon FA, Kroon PA, García-Conesa MT (2003) Absorption of hydroxycinnamates in humans after high-bran cereal consumption. J Agric Food Chem 51:6050–6055
Karakaya S (2004) Bioavailability of phenolic compounds. Crit Rev Food Sci 44:453–464
Andreasen M, Kroon P, Williamson G, García-Conesa MT (2001) Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radical Biol Med 31:304–314
Price RK, Welch RW, Lee-Manion AM, Bradbury L, Strain JJ (2008) Total phenolics and antioxidant potential in plasma and urine of humas after consumption of wheat bran. Cereal Chem 85:152–157
Klepacka J, Fornal L (2008) Research into correlations between the content of some selected phenolic compounds and the milling quality of wheat grain. Zywnosc-Nauka Technologia Jakosc 15:55–64
Hemery Y, Rouau X, Lullien-Pellerin V, Barron C, Abecassis J (2007) Dry processes to develop wheat fractions and products with enhanced nutritional quality. J Cereal Sci 46:327–347
Hemery Y, Lullien-Pellerin V, Rouau X, Abecassis J, Samson M, Åman P, Von Reding W, Spoerndli C, Barron C (2009) Biochemical markers: Efficient tools for the assessment of wheat grain tissue proportions in milling fractions. J Cereal Sci 49:55–64
Zuchowski J, Kapusta I, Szajwaj B, Jonczyk K, Oleszek W (2009) Phenolic acid content of organic and conventionally grown winter wheat. Cereal Res Commun 37:189–197
Andreasen M, Christensen L, Meyer A, Hansen Å (2000) Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties. J Agric Food Chem 48:2837–2842
Olenichenko NA, Ossipov VI, Zagoskina NV (2006) Effect of cold hardening on the phenolic complex of winter wheat leaves. Russ J Plant Physiol 53:495–500
Beato VM, Orgaz F, Mansilla F, Montaño (2011) Changes in phenolic compounds in garlic (Allium sativum L.) owing to the cultivar and location growth. Plant Foods Hum Nutr 66:218–223
Klepacka J, Gujska E, Michalak J (2011) Phenolic compounds as cultivar- and variety-distinguishing factors in some plant products. Plant Foods Hum Nutr 66:64–69
Gallardo C, Jiménez L, García-Conesa MT (2006) Hydroxycinnamic acid composition and in vitro antioxidant activity of selected grain fractions. Food Chem 99:455–463
Andreasen M, Kroon P, Williamson G, García-Conesa MT (2001) Esterase activity able to hydrolyze dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals. J Agric Food Chem 49:5679–5684
Andreasen M, Christensen L, Meyer A, Hansen Å (1999) Release of hydroxycinnamic and hydroxybenzoic acids in rye by commercial plant cell wall degrading enzyme preparations. J Sci Food Agric 79:411–413
Andreasen M, Christensen L, Meyer A, Hansen Å (2000) Ferulic acid dehydrodimers in rye (Secale cereale L.). J Cereal Sci 31:303–307
Andreasen M, Landbo AK, Christensen L, Hansen Å, Meyer A (2001) Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins. J Agric Food Chem 49:4090–4096
García-Conesa MT, Plumb GW, Waldron KW, Ralph J, Williamson G (1997) Ferulic acid dehydrodimers from wheat bran: Isolation, purification and antioxidant properties of 8-O-4-diferulic acid. Redox Rep 3:319–323
Waldron K, Parr AJ, Ng A, Ralph J (1996) Cell wall esterified phenolic dimers: Identification and quantification by reverse phase high performance liquid chromatography and diode array detection. Phytochem Anal 7:305–312
García-Conesa MT, Wilson PD, Plumb GW, Ralph J, Williamson G (1999) Antioxidant properties of 4,4´-dihydroxy-3-3´-dimethoxy-β, β´-bicinnamic acid (8-8´-diferulic acid, non-cyclic form). J Sci Food Agric 79:379–384
Adom KK, Sorrells ME, Liu RH (2005) Phytochemicals and antioxidant activity of milled fractions of different wheat varieties. J Agric Food Chem 53:2297–2306
Barron C, Surget A, Rouau X (2007) Relative amounts of tissues in mature wheat (Triticum aestivum L.) grain and their carbohydrate and phenolic acid composition. J Cereal Sci 45:88–96
Sun RC, Sun XF, Zhang SH (2001) Quantitative determination of hydroxycinnamic acids in wheat, rice, rye and barley straws, maize stems, oil palm frond fiber, and fast-growing poplar wood. J Agric Food Chem 49:5122–5129
Lempereur L, Rouau X, Abecassis J (1997) Genetic and agronomic variation in arabinoxylan and ferulic acid contents of durum wheat (Triticum durum L.) grain and its milling fractions. J Cereal Sci 25:103–110
Adom KK, Sorrells ME, Liu RH (2003) Phytochemical profiles and antioxidant activity of wheat varieties. J Agric Food Chem 51:7825–7834
Pussayanawin V, Wetzel D (1987) High-performance liquid chromatographic determination of ferulic acid in wheat milling fractions as a measure of bran contamination. J Chromatogr 391:243–255
Krygier K, Sosulski F, Hogge L (1982) Free, esterified and insoluble-bound phenolic acids. 1. Extraction and purification procedure. J Agric Food Chem 30:330–334
Asenstorfer RE, Wang Y, Mares DJ (2006) Chemical structure of flavonoid compounds in wheat (Triticum aestivum L.) flour that contribute to the yellow colour of Asian alkaline noodles. J Cereal Sci 43:106–119
Acknowledgements
We acknowledge to European Project Interreg III B “Germobanco Agrícola de la Macaronesia” and Structuring Project, Ref. ULL APD-08/01, Canary Government, Spain. We also gratefully acknowledge the help of Patrick Dennis for revising and checking the English in this paper.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hernández, L., Afonso, D., Rodríguez, E.M. et al. Phenolic Compounds in Wheat Grain Cultivars. Plant Foods Hum Nutr 66, 408–415 (2011). https://doi.org/10.1007/s11130-011-0261-1
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11130-011-0261-1