Abstract

Whole-wheat flour of purple wheat varieties contains anthocyanins and other phenolic compounds with high antioxidant activity, which makes it a potential raw material for functional foods. The content and composition of phenolic compounds in whole-wheat flour depends on the genotype and weather conditions; in the bread, however, they also depend on the bread-making technology. This article offers a comparative analysis of phenolic compounds in purple whole-wheat flour and bread baked from this flour.
The study featured purple soft spring wheat (Triticum aestivum L.) of two varieties, Nadira and Line 193, which were harvested in 2016 and 2017, and corresponding bread samples. The antioxidant activity and phenolic content were measured spectrophotometrically while the qualitative analysis relied on the method of high-performance liquid chromatography (HPLC).
In the hot and dry year of 2016, the content of bound phenolic acids reached 2.0–2.4 mg/g dry weight in the flour of both genotypes. In the cool and humid year of 2017, the content of anthocyanins in the Nadira flour increased by 2.7 times and amounted to 0.65 mg/g dry weight. However, the corresponding bread sample had a much lower phenolic content: soluble phenolics were halved, anthocyanins dropped by 3–4 times, and bound phenolic acids went down by 7–17 times. The content of bound phenolic acids in the flour correlated positively with the content of free phenolic acids in the bread. The HPLC analysis revealed an increase in the content of free hydroxycinnamic acids in the bread: p-coumaric acid was the most abundant and amounted to 0.14–0.22 mg/g dry weight.
Conventional State Standard 27669-88 for bread making resulted in a total decrease in anthocyanins, bound phenolic acids, and most free phenolics. Therefore, this technology cannot be applied to functional bread. The results can help develop a breadmaking technology for purple wheat varieties.

Keywords

Triticum aestivum L., purple wheat, whole-wheat flour, bread, phenolic compounds, anthocyanins, phenolic acids, antioxidant activity

FUNDING

The study was funded by the Ministry of Science and Higher Education of the Russian Federation (Minobrnauki) as part of the state assignments completed by Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS (Topic 122011800137-0).

REFERENCES

1. Rosell CM. Trends in science of doughs and bread quality. In: Preedy VR, Watson RR, editors. Flour and breads and their fortification in health and disease prevention. Academic Press; 2019. p. 333–343. https://doi.org/10.1016/B978-0-12-814639-2.00026-5
2. Ma D, Wang C, Feng J, Xu B. Wheat grain phenolics: a review on composition, bioactivity, and influencing factors. Journal of the Science of Food and Agriculture. 2021;101(15):6167–6185. https://doi.org/10.1002/jsfa.11428
3. Shabunina MV, Andreeva A, Pavlova AS. Use of animal origin protein concentrates in bread baking. Foods and Raw Materials. 2023;11(2):338–346. https://doi.org/10.21603/2308-4057-2023-2-570
4. Ciudad-Mulero M, Barros L, Fernandes Â, Ferreira ICFR, Callejo MJ, Matallana-González MC, et al. Potential health claims of durum and bread wheat flours as functional ingredients. Nutrients. 2020;12(2). https://doi.org/10.3390/nu12020504
5. Di Cairano M, Tolve R, Cela N, Sportiello L, Scarpa T, Galgano F. Functional cereal-based bakery products, breakfast cereals, and pasta products. In: Punia Bangar S, Kumar Siroha A, editors. Functional cereals and cereal foods. Properties, functionality and applications. Cham: Springer; 2022. pp. 215–249. https://doi.org/10.1007/978-3-031-05611-6_9
6. Reynolds A, Mann J, Cummings J, Winter N, Mete E, Te Morenga L. Carbohydrate quality and human health: A series of systematic reviews and meta-analyses. The Lancet. 2019;393(10170):434–445. https://doi.org/10.1016/S0140-6736(18)31809-9
7. Tian W, Zheng Y, Wang W, Wang D, Tilley M, Zhang G, et al. A comprehensive review of wheat phytochemicals: From farm to fork and beyond. Comprehensive Reviews in Food Science and Food Safety. 2022;21(3):2274–2308. https://doi.org/10.1111/1541-4337.12960
8. Iametti S, Abbasi Parizad PA, Bonomi F, Marengo M. Pigmented grains as a source of bioactives. In: Ferranti P, Berry EM, Anderson JR, editors. Encyclopedia of food security and sustainability. Vol. 1. Elsevier; 2019. pp. 261–270. https://doi.org/10.1016/B978-0-08-100596-5.22385-8
9. Mattioli R, Francioso A, Mosca L, Silva P. Anthocyanins: A comprehensive review of their chemical properties and health effects on cardiovascular and neurodegenerative diseases. Molecules. 2020;25(17). https://doi.org/10.3390/molecules25173809
10. Francavilla A, Joye IJ. Anthocyanins in whole grain cereals and their potential effect on health. Nutrients. 2020;12(10). https://doi.org/10.3390/nu12102922
11. Garg M, Kaur S, Sharma A, Kumari A, Tiwari V, Sharma S, et al. Rising demand for healthy foods-anthocyanin biofortified colored wheat is a new research trend. Frontiers in Nutrition. 2022;9. https://doi.org/10.3389/fnut.2022.878221
12. Tian S, Sun Y, Chen Z, Yang Y, Wang Y. Functional properties of polyphenols in grains and effects of physicochemical processing on polyphenols. Journal of Food Quality. 2019;2019. https://doi.org/10.1155/2019/2793973
13. Beta T, Li W, Apea-Bah FB. Flour and bread from black, purple, and blue-colored wheats. In: Preedy VR, Watson RR, editors. Flour and breads and their fortification in health and disease prevention. Academic Press; 2019. pp. 75–88. https://doi.org/10.1016/B978-0-12-814639-2.00006-X
14. Calderaro A, Barreca D, Bellocco E, Smeriglio A, Trombetta D, Laganà G. Colored phytonutrients: Role and applications in the functional foods of anthocyanins. In: Nabavi SM, Suntar I, Barreca D, Khan H, editors. Phytonutrients in food. From traditional to rational usage. Woodhead Publishing; 2020. pp. 177–195. https://doi.org/10.1016/B978-0-12-815354-3.00011-3
15. Gamel TH, Wright AJ, Pickard M, Abdel‐Aal E-SM. Characterization of anthocyanin‐containing purple wheat prototype products as functional foods with potential health benefits. Cereal Chemistry. 2019;97(1):34–38. https://doi.org/10.1002/cche.10190
16. Bartl P, Albreht A, Skrt M, Tremlová B, Ošťádalová M, Šmejkal K, et al. Anthocyanins in purple and blue wheat grains and in resulting bread: Quantity, composition, and thermal stability. International Journal of Food Sciences and Nutrition. 2015;66(5):514–519. https://doi.org/10.3109/09637486.2015.1056108
17. Eliášová M, Kotíková Z, Lachman J, Orsák M, Martinek P. Influence of baking on anthocyanin content in coloured-grain wheat bread. Plant, Soil and Environment. 2020;66(8):381–386. https://doi.org/10.17221/210/2020-PSE
18. Gordeeva E, Shamanin V, Shoeva O, Kukoeva T, Morgounov A, Khlestkina E. The strategy for marker-assisted breeding of anthocyanin-rich spring bread wheat (Triticum aestivum L.) cultivars in Western Siberia. Agronomy. 2020;10(10). https://doi.org/10.3390/agronomy10101603
19. Vasilova NZ, Askhadullin DF, Askhadullin DF, Bagavieva EZ, Tazutdinova MR, Khusainova II. Violet-green variety of spring soft wheat Nadira. Legumes and Groat Crops. 2021;40(4):66–75. (In Russ.) https://doi.org/10.24412/2309-348X-2021-4-66-75
20. Belyavskaya IG. Improvement of the assortment of diet bakery products. Modern Applications of Bioequivalence and Bioavailability. 2017;2(4). https://doi.org/10.19080/MABB.2017.02.555591
21. Khlebova LP, Melnikova YuV, Barysheva NV, Suharkova NV, Vistovskaya VP. The quality and content of anthocyanins in purple- and blue-grained wheat in the south of Western Siberia. IOP Conference Series: Earth and Environmental Science. 2021;723. https://doi.org/10.1088/1755-1315/723/2/022099
22. Usenko NI, Khlestkina EK, Asavasanti S, Gordeeva EI, Yudina RS, Otmakhova YuS. Possibilities of enriching food products with anthocyanins by using new forms of cereals. Foods and Raw Materials. 2018;6(1):128–135. https://doi.org/10.21603/2308-4057-2018-1-128-135
23. Askhadullin DF, Askhadullin DF, Bagavieva EZ, Vasilova NZ, Kirillova ES, Tazutdinova MR. Patent for breeding achievement No. 11624. Soft spring wheat: NADIRA. 2021. (In Russ.)
24. Angelino D, Cossu M, Marti A, Zanoletti M, Chiavaroli L, Brighenti F, et al. Bioaccessibility and bioavailability of phenolic compounds in bread: A review. Food and Function. 2017;8(7):2368–2393. https://doi.org/10.1039/C7FO00574A
25. Francavilla A, Joye IJ. Anthocyanin content of crackers and bread made with purple and blue wheat varieties. Molecules. 2022;27(21). https://doi.org/10.3390/molecules27217180
26. Abdel-Aal E-SM, Rabalski I. Effect of baking on free and bound phenolic acids in wholegrain bakery products. Journal of Cereal Science. 2013;57(3):312–318. https://doi.org/10.1016/j.jcs.2012.12.001
27. Rumyantseva NI, Valieva AI, Akulov AN, Askhadullin DF, Askhadullin DF, Vasilova NZ. Drought and high temperatures effect on yield and grain quality of purple-grain lines of spring soft wheat. Biomics. 2021;13(3):254–273. (In Russ.) https://doi.org/10.31301/2221-6197.bmcs.2021-17
28. Martini D, Taddei F, Ciccoritti R, Pasquini M, Nicoletti I, Corradini D, et al. Variation of total antioxidant activity and of phenolic acid, total phenolics and yellow coloured pigments in durum wheat (Triticum turgidum L. var. durum) as a function of genotype, crop year and growing area. Journal of Cereal Science. 2015;65:175–185. https://doi.org/10.1016/j.jcs.2015.06.012
29. Laddomada B, Blanco A, Mita G, D’Amico L, Singh RP, Ammar K, et al. Drought and heat stress impacts on phenolic acids accumulation in durum wheat cultivars. Foods. 2021;10(9). https://doi.org/10.3390/foods10092142
30. Folin O, Ciocalteu V. On tyrosine and tryptophane determinations in proteins. Journal of Biological Chemistry. 1927;73(2):627–650. https://doi.org/10.1016/S0021-9258(18)84277-6
31. Kim K-H, Tsao R, Yang R, Cui SW. Phenolic acid profiles and antioxidant activities of wheat bran extracts and the effect of hydrolysis conditions. Food Chemistry. 2006;95(3):466–473. https://doi.org/10.1016/j.foodchem.2005.01.032
32. Beta T, Qiu Y, Liu Q, Borgen A, Apea-Bah FB. Purple wheat (Triticum sp.) seeds: Phenolic composition and antioxidant properties. In: Preedy VR, Watson RR, editors. Nuts and seeds in health and disease prevention. Academic Press; 2020. pp. 103–125. https://doi.org/10.1016/B978-0-12-818553-7.00010-3
33. Sadilova E, Stintzing FC, Carle R. Thermal degradation of acylated and nonacylated anthocyanins. Journal of Food Science. 2006;71(8):C504–C512. https://doi.org/10.1111/j.1750-3841.2006.00148.x
34. Buanafina MMO, Morris P. The impact of cell wall feruloylation on plant growth, responses to environmental stress, plant pathogens and cell wall degradability. Agronomy. 2022;12(8). https://doi.org/10.3390/agronomy12081847
35. Santos NA, Cordeiro AMTM, Damasceno SS, Aguiar RT, Rosenhaim R, Carvalho Filho JR, et al. Commercial antioxidants and thermal stability evaluations. Fuel. 2012;97:638–643. https://doi.org/10.1016/j.fuel.2012.01.074
36. Cheng Y, Xu Q, Liu J, Zhao C, Xue F, Zhao Y. Decomposition of five phenolic compounds in high temperature water. Journal of the Brazilian Chemical Society. 2014;25:2102–2107. https://doi.org/10.5935/0103-5053.20140201
37. Paznocht L, Kotíková Z, Burešová B, Lachman J, Martinek P. Phenolic acids in kernels of different coloured-grain wheat genotypes. Plant, Soil and Environment. 2020;66(2):57–64. https://doi.org/10.17221/380/2019-PSE
38. Shamanin VP, Tekin-Cakmak ZH, Gordeeva EI, Karasu S, Pototskaya I, Chursin AS, et al. Antioxidant capacity and profiles of phenolic acids in various genotypes of purple wheat. Foods. 2022;11(16). https://doi.org/10.3390/foods11162515
39. Leváková L, Lacko-Bartošová M. Phenolic acids and antioxidant activity of wheat species: A review. Agriculture (Pol’nohospodárstvo). 2017;63(3):92–101. https://doi.org/10.1515/agri-2017-0009
40. Boz H. p -Coumaric acid in cereals: Presence, antioxidant and antimicrobial effects. International Journal of Food Science and Technology. 2015;50(11):2323–2328. https://doi.org/10.1111/ijfs.12898
41. Mehaya FM, Mohammad AA. Thermostability of bioactive compounds during roasting process of coffee beans. Heliyon. 2020;6(11). https://doi.org/10.1016/j.heliyon.2020.e05508
42. Ma D, Xu B, Feng J, Hu H, Tang J, Yin G, et al. Dynamic metabolomics and transcriptomics analyses for characterization of phenolic compounds and their biosynthetic characteristics in wheat grain. Frontiers in Nutrition. 2022;9. https://doi.org/10.3389/fnut.2022.844337
43. Leonard W, Zhang P, Ying D, Adhikari B, Fang Z. Fermentation transforms the phenolic profiles and bioactivities of plant-based foods. Biotechnology Advances. 2021;49. https://doi.org/10.1016/j.biotechadv.2021.107763