Optimization of bioactive compound mixtures: Polyphenol content, antioxidant activity, and synergistic effect Optimization of bioactive compound mixtures
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Abstract
The rapid expansion of the food industry has significantly increased the generation of by-products rich in bioactive compounds with untapped potential. This study aims to optimise the mixtures of bioactive compound by evaluation of the polyphenol content, antioxidant and synergistic effects. The Simplex-Centroid design and response surface methodology (RSM) combined with correlation analysis were used for this purpose. Each of the three investigated bioactive substances Sodium L-ascorbate (SLA); Dihydroquercetin isolate from Larix sibirica Ledeb (DHQ), and freeze-dried (30% w/v) ethanol extract from distilled rose (Rosa damascena Mill.) petals (FDRPE) contribute uniquely to redox reactions. Although FDRPE exhibited the lowest total polyphenol content (TPC) and weakest antioxidant activity, its combinations with SLA and DHQ demonstrated enhanced radical scavenging and metal-chelating activities. Response surface methodology indicated that dihydroquercetin (DHQ) alone could achieve the strongest antioxidant activity but requires higher concentrations. The results suggest that the combined use of SLA, DHQ, and FDRPE positively impacts radical scavenging activity, as well as transition metal-chelating activity (FRAP and CUPRAC). The optimum is achieved by combining a 6.11962E-7 SLA + 88.5131 DHQ + 11.4869 FDRPE mg.L-1. The optimized mixture have the potential to be incorporated into various food matrices at lower concentrations compared to their individual use, enhancing the practical application in the food industry.
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Birsa M.L., Sarbu L.G. A Structure-Activity Relationship Study on the Antioxidant Properties of Dithiocarbamic Flavanones. Antioxidants, 2024, 13(8): 963. https://doi.org/10.3390/antiox13080963
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Constantin O.E., Stoica F., Rațu R.N., Stănciuc N., Bahrim G.E., Râpeanu G. Bioactive Components, Applications, Extractions, and Health Benefits of Winery By-Products from a Circular Bioeconomy Perspective: A Review. Antioxidants, 2024, 13(1): 100. https://doi.org/10.3390/antiox13010100
Dinkova R., Heffels P., Shikov V., Weber F., Schieber A., Mihalev K. Effect of enzyme-assisted extraction on the chilled storage stability of bilberry (Vaccinium myrtillus L.) anthocyanins in skin extracts and freshly pressed juices. Food research international, 2014, 65(11:А): 35-41. https://doi.org/10.1016/j.foodres.2014.05.066
Dinkova R., Vardakas A., Dimitrova E., Weber F., Passon M., Shikov V., Schieber A., Mihalev K. Valorization of rose (Rosa damascena Mill.) by-product: polyphenolic characterization and potential food application. European Food Research and Technology, 2022, 248(7): 2351-2358 https://doi.org/10.1007/s00217-022-04051-6
Dragoev S., Vlahova-Vangelova D., Balev D., Bozhilov D., Dagnon S. Valorization of waste by-products of rose oil production as feedstuff phytonutrients. Bulgarian Journal of Agricultural Science, 2021, 27(1): 209-219. Available at: https://www.agrojournal.org/27/01-29.pdf
Ebrahimi P., Lante A. Environmentally friendly techniques for the recovery of polyphenols from food by-products and their impact on polyphenol oxidase: a critical review. Applied Sciences, 2022, 12(4): 1923. https://doi.org/10.3390/app12041923
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Fomichev Y., Nikanova L., Lashin A. The effectiveness of using Dihydroquercetin (taxifolin) in animal husbandry, poultry and apiculture for prevention of metabolic disorders, higher antioxidative capacity, better resistence and realisation of a productive potential of organism. Journal of International Scientific Publications: Agriculture & Food, 2016, 4(1): 140-159. Available at: https://www.scientific-publications.net/get/1000020/1465221212710716.pdf
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Gulcin İ., Alwasel S.H. DPPH radical scavenging assay. Processes, 2023, 11(8): 2248. https://doi.org/10.3390/pr11082248
Kobyalko V.O., Mirzoyev E.B., Gubina O.A., Florova N.A., Melnik A.D. Impact of dihydroquercetin and ascorbic acid on the content of malonic dialdehyde and metallothioneins in rat's organism exposed to a chronic effect of cadmium.The Journal “Toksikologicheskiy vestnik”, 2009, 17(4): 16-19. [in Russian]
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Liu W.Y., Chen L.Y., Huang Y.Y., Fu L., Song L.Y., Wang Y.Y., Bi Y.F. Antioxidation and active constituents analysis of flower residue of Rosa damascena. Chinese Herbal Medicines, 2020, 12(3): 336-341. https://10.1016/j.chmed.2020.05.005
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Önder D. Variation in antioxidant capacity, antioxidant activity and mineral composition during flower development of oil-bearing rose (Rosa damascena Mill.). Scientific Reports, 2023, 13(1): 17255. https://doi.org/10.1038/s41598-023-44461-4
Perron N.R., Wang H.C., DeGuire S.N., Jenkins M., Lawson M., Brumaghim J.L. Kinetics of iron oxidation upon polyphenol binding. Dalton Transactions, 2010, 39(41): 9982-9987. https://doi.org/10.1039/c0dt00752h
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Rokaityte A., Zaborskiene G., Gunstiene S., Raudonis R., Janulis V., Garmiene G., Stimbirys A. Effect of taxifolin on physicochemical and microbiological parameters of dry-cured pork sausage. Czech Journal of Food Sciences, 2019, 37(5): 366-373. https://doi.org/10.17221/57/2018-cjfs
Rokaitytė A., Zaborskienė G., Orentaitė-Gustienė S. Antioxidant and antimicrobial activity of mixtures of taxifolin and ascorbic acid as alternative to the added nitrite in dry-cured sausages. In Foodbalt 2017: 11th Baltic Conference on Food Science and Technology" Food Science And Technology in a Changing World", Jelgava, April 27-28, 2017. Available at: https://lsmu.lt/cris/entities/publication/2e891d8a-c10b-40ce-835a-e1e7b9ccfc92
Şahin S., Kurtulbaş E. Green Extraction and Valorization of By-Products from Food Processing, Foods, 2024, 13(10): 1589. https://doi.org/10.3390/foods13101589
Schauss A.G., Tselyico S.S., Kuznetsova V.A., Yegorova I. Toxicological and genotoxicity assessment of a dihydroquercetin-rich Dahurian larch tree (Larix gmelinii Rupr) extract (Lavitol). International Journal of Toxicology, 2015, 34(2): 162-181. https://doi.org/10.1177/1091581815576975
Schieber A., Mihalev K., Berardini N., Mollov P., Carle R. Flavonol glycosides from distilled petals of Rosa damascena Mill. Zeitschrift für Naturforschung C, 2005, 60(5-6): 379-384. https://doi.org/10.1515/znc-2005-5-602
Shikov V., Kammerer D.R., Mihalev K., Mollov P., Carle R. Antioxidant capacity and colour stability of texture-improved canned strawberries as affected by the addition of rose (Rosa damascena Mill.) petal extracts. Food research international, 2012, 46(2): 552-556. https://doi.org/10.1016/j.foodres.2011.04.004
Shikov V., Kammerer D.R., Mihalev K., Mollov P., Carle R. Heat stability of strawberry anthocyanins in model solutions containing natural copigments extracted from rose (Rosa damascena Mill.) petals. Journal of agricultural and food chemistry, 2008, 56(18): 8521-8526. https://doi.org/10.1021/jf801946g
Shopska V., Teneva D., Denkova-Kostova R., Ivanova K., Denev P., Kostov G. Modelling of malt mixture for the production of wort with increased biological value. Beverages, 2022, 8(3): 44. https://doi.org/10.3390/beverages8030044
Slavov A., Spasov H., Dinkova R., Denev P., Dincheva I., Topuzova M. G., Chalova V. Aromatized Wine-Type Beverages with Added Byproducts of Essential Rose Oil Industry. Applied Sciences, 2023, 13(18): 10417. https://doi.org/10.3390/app131810417
Slavov A., Vasileva I., Denev P., Dinkova R., Teneva D., Ognyanov M., Georgiev Y. Polyphenol-rich extracts from essential oil industry wastes. Bulgarian Chemical Communications, 2020, 52 (Special Issue D): 78-83. Available at: http://bcc.bas.bg/BCC_Volumes/Volume_52_Special_D_2020/BCC-52-D-2020-78-83-Slavov-B10.pdf
Slavov A., Vasileva I., Stefanov L., Stoyanova A. Valorization of wastes from the rose oil industry. Reviews in Environmental Science and Bio/Technology, 2017, 16(2): 309-325. https://doi.org/10.1007/s11157-017-9430-5
Staykov A.S., Dragoev S.G., Balev D.K., Vlahova-Vangelova D.B., Pavlova M.R. Preserving the quality and prolongation the shelf-life of beef packed under vacuum or modified atmosphere using ternary antioxidant blend. Journal of Microbiology, Biotechnology and Food Sciences, 2016, 5(6): 617-622. https://doi.org/10.15414/jmbfs.2016.5.6.617-622
Topal F., Nar M., Gocer H., Kalin P., Kocyigit U.M., Gülçin İ., Alwasel S.H. Antioxidant activity of taxifolin: an activity–structure relationship. Journal of enzyme inhibition and medicinal chemistry, 2016, 31(4): 674-683. https://doi.org/10.3109/14756366.2015.1057723
Vardakas A., Kechagias A., Penov N., Giannakas A.E. Optimization of Enzymatic Assisted Extraction of Bioactive Compounds from Olea europaea Leaves. Biomass, 2024, 4(3): 647-657. htps://doi.org/10.3390/biomass4030035
Vilimanovich U., Jevremovic, S.A. Dihydroquercetin: a novel potent flavonoid antioxidant as an adjuvant for effective cancer treatment. EC Nutrition, 2019, 14(9): 660-674. Available at: https://ecronicon.net/assets/ecnu/pdf/ECNU-14-00640.pdf
Wang T.C., Chang P.C. Measurement and correlation for the solid solubility of antioxidants sodium L-ascorbate and sodium erythorbate monohydrate in supercritical carbon dioxide. Journal of Chemical & Engineering Data, 2015, 60(3): 790-794. https://doi.org/10.1021/je5009153
Zahra M., Abrahamse H., George B.P. Flavonoids: Antioxidant powerhouses and their role in nanomedicine. Antioxidants, 13(8): 922. https://doi.org/10.3390/antiox13080922
Aleixandre-Tudo J.L., Buica A., Nieuwoudt H., Aleixandre J.L., du Toit W. Spectrophotometric analysis of phenolic compounds in grapes and wines. Journal of agricultural and food chemistry, 2017, 65(20): 4009-4026. https://doi.org/10.1021/acs.jafc.7b01724
Baydar N.G, Baydar H. Phenolic compounds, antiradical activity and antioxidant capacity of oil-bearing rose (Rosa damascena Mill.) extracts. Industrial Crops and Products, 2013, 41(1): 375-380. https://doi.org/10.1016/j.indcrop.2012.04.045
Bayram I., Decker E.A. Underlying mechanisms of synergistic antioxidant interactions during lipid oxidation. Trends in food science & technology, 2023, 133(3): 219-230. https://doi.org/10.1016/j.tifs.2023.02.003
Benzie I.F., Strain J.J. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical biochemistry, 1996, 239(1): 70-76. https://doi.org/10.1006/abio.1996.0292
Birsa M.L., Sarbu L.G. A Structure-Activity Relationship Study on the Antioxidant Properties of Dithiocarbamic Flavanones. Antioxidants, 2024, 13(8): 963. https://doi.org/10.3390/antiox13080963
Bobolaki N., Photiades A., Grigorakis S., Makris D.P. Empirical kinetic modelling of the effect of L-ascorbic acid on the Cu (II)-induced oxidation of quercetin. ChemEngineering, 2018, 2(4): 46. https://doi.org/10.3390/chemengineering2040046
Brand-Williams W., Cuvelier M.E., Berset C.L.W.T. Use of a free radical method to evaluate antioxidant activity. LWT-Food science and Technology, 1995, 28(1): 25-30. https://doi.org/10.1016/S0023-6438(95)80008-5
Constantin O.E., Stoica F., Rațu R.N., Stănciuc N., Bahrim G.E., Râpeanu G. Bioactive Components, Applications, Extractions, and Health Benefits of Winery By-Products from a Circular Bioeconomy Perspective: A Review. Antioxidants, 2024, 13(1): 100. https://doi.org/10.3390/antiox13010100
Dinkova R., Heffels P., Shikov V., Weber F., Schieber A., Mihalev K. Effect of enzyme-assisted extraction on the chilled storage stability of bilberry (Vaccinium myrtillus L.) anthocyanins in skin extracts and freshly pressed juices. Food research international, 2014, 65(11:А): 35-41. https://doi.org/10.1016/j.foodres.2014.05.066
Dinkova R., Vardakas A., Dimitrova E., Weber F., Passon M., Shikov V., Schieber A., Mihalev K. Valorization of rose (Rosa damascena Mill.) by-product: polyphenolic characterization and potential food application. European Food Research and Technology, 2022, 248(7): 2351-2358 https://doi.org/10.1007/s00217-022-04051-6
Dragoev S., Vlahova-Vangelova D., Balev D., Bozhilov D., Dagnon S. Valorization of waste by-products of rose oil production as feedstuff phytonutrients. Bulgarian Journal of Agricultural Science, 2021, 27(1): 209-219. Available at: https://www.agrojournal.org/27/01-29.pdf
Ebrahimi P., Lante A. Environmentally friendly techniques for the recovery of polyphenols from food by-products and their impact on polyphenol oxidase: a critical review. Applied Sciences, 2022, 12(4): 1923. https://doi.org/10.3390/app12041923
Efenberger-Szmechtyk M., Nowak A., Czyzowska A. Plant extracts rich in polyphenols: Antibacterial agents and natural preservatives for meat and meat products. Critical reviews in food science and nutrition, 2021, 61(1): 149-178. https://doi.org/10.1080/10408398.2020.1722060
Fomichev Y., Nikanova L., Lashin A. The effectiveness of using Dihydroquercetin (taxifolin) in animal husbandry, poultry and apiculture for prevention of metabolic disorders, higher antioxidative capacity, better resistence and realisation of a productive potential of organism. Journal of International Scientific Publications: Agriculture & Food, 2016, 4(1): 140-159. Available at: https://www.scientific-publications.net/get/1000020/1465221212710716.pdf
Gulcin İ. Antioxidants and antioxidant methods: An updated overview. Archives of toxicology, 2020, 94(3): 651-715. https://doi.org/10.1007/s00204-020-02689-3
Gulcin İ., Alwasel S.H. DPPH radical scavenging assay. Processes, 2023, 11(8): 2248. https://doi.org/10.3390/pr11082248
Kobyalko V.O., Mirzoyev E.B., Gubina O.A., Florova N.A., Melnik A.D. Impact of dihydroquercetin and ascorbic acid on the content of malonic dialdehyde and metallothioneins in rat's organism exposed to a chronic effect of cadmium.The Journal “Toksikologicheskiy vestnik”, 2009, 17(4): 16-19. [in Russian]
Kolev N., Vlahova-Vangelova D., Balev D., Dragoev S. Stabilization of oxidative processes in cooked sausages by optimization of incorporated biologically active substances. Carpathian Journal of Food Science and Technology, 2022, 14(4): 180-188. https://doi.org/10.34302/crpjfst/2022.14.4.14
Liu W.Y., Chen L.Y., Huang Y.Y., Fu L., Song L.Y., Wang Y.Y., Bi Y.F. Antioxidation and active constituents analysis of flower residue of Rosa damascena. Chinese Herbal Medicines, 2020, 12(3): 336-341. https://10.1016/j.chmed.2020.05.005
Ministry of Agriculture, Food and Forestry (MAFF), "Agrostatistics" department. Yields from field crops - harvest 2019. No. 375 – June 2020; harvest 2020. No. 391 – June 2021; harvest 2021. No. 407 – June 2022; harvest 2022. No. 427 – June 2023. [in Bulgarian] Available at: https://www.mzh.government.bg/bg/statistika-i-analizi/
Önder D. Variation in antioxidant capacity, antioxidant activity and mineral composition during flower development of oil-bearing rose (Rosa damascena Mill.). Scientific Reports, 2023, 13(1): 17255. https://doi.org/10.1038/s41598-023-44461-4
Perron N.R., Wang H.C., DeGuire S.N., Jenkins M., Lawson M., Brumaghim J.L. Kinetics of iron oxidation upon polyphenol binding. Dalton Transactions, 2010, 39(41): 9982-9987. https://doi.org/10.1039/c0dt00752h
Petkova N., Todorova M., Grozeva, N., Gerdzhikova M. Phenolic content and antioxidant activity of water extracts from Rosa damascena petals grown in Kazanlak valley, Bulgaria. Scientific Papers. Series B. Horticulture, 2020, 64(2): 345-352. Online ISSN: 2286-1580. Available at: https://horticulturejournal.usamv.ro/pdf/2020/issue_2/Art47.pdf
Rokaityte A., Zaborskiene G., Gunstiene S., Raudonis R., Janulis V., Garmiene G., Stimbirys A. Effect of taxifolin on physicochemical and microbiological parameters of dry-cured pork sausage. Czech Journal of Food Sciences, 2019, 37(5): 366-373. https://doi.org/10.17221/57/2018-cjfs
Rokaitytė A., Zaborskienė G., Orentaitė-Gustienė S. Antioxidant and antimicrobial activity of mixtures of taxifolin and ascorbic acid as alternative to the added nitrite in dry-cured sausages. In Foodbalt 2017: 11th Baltic Conference on Food Science and Technology" Food Science And Technology in a Changing World", Jelgava, April 27-28, 2017. Available at: https://lsmu.lt/cris/entities/publication/2e891d8a-c10b-40ce-835a-e1e7b9ccfc92
Şahin S., Kurtulbaş E. Green Extraction and Valorization of By-Products from Food Processing, Foods, 2024, 13(10): 1589. https://doi.org/10.3390/foods13101589
Schauss A.G., Tselyico S.S., Kuznetsova V.A., Yegorova I. Toxicological and genotoxicity assessment of a dihydroquercetin-rich Dahurian larch tree (Larix gmelinii Rupr) extract (Lavitol). International Journal of Toxicology, 2015, 34(2): 162-181. https://doi.org/10.1177/1091581815576975
Schieber A., Mihalev K., Berardini N., Mollov P., Carle R. Flavonol glycosides from distilled petals of Rosa damascena Mill. Zeitschrift für Naturforschung C, 2005, 60(5-6): 379-384. https://doi.org/10.1515/znc-2005-5-602
Shikov V., Kammerer D.R., Mihalev K., Mollov P., Carle R. Antioxidant capacity and colour stability of texture-improved canned strawberries as affected by the addition of rose (Rosa damascena Mill.) petal extracts. Food research international, 2012, 46(2): 552-556. https://doi.org/10.1016/j.foodres.2011.04.004
Shikov V., Kammerer D.R., Mihalev K., Mollov P., Carle R. Heat stability of strawberry anthocyanins in model solutions containing natural copigments extracted from rose (Rosa damascena Mill.) petals. Journal of agricultural and food chemistry, 2008, 56(18): 8521-8526. https://doi.org/10.1021/jf801946g
Shopska V., Teneva D., Denkova-Kostova R., Ivanova K., Denev P., Kostov G. Modelling of malt mixture for the production of wort with increased biological value. Beverages, 2022, 8(3): 44. https://doi.org/10.3390/beverages8030044
Slavov A., Spasov H., Dinkova R., Denev P., Dincheva I., Topuzova M. G., Chalova V. Aromatized Wine-Type Beverages with Added Byproducts of Essential Rose Oil Industry. Applied Sciences, 2023, 13(18): 10417. https://doi.org/10.3390/app131810417
Slavov A., Vasileva I., Denev P., Dinkova R., Teneva D., Ognyanov M., Georgiev Y. Polyphenol-rich extracts from essential oil industry wastes. Bulgarian Chemical Communications, 2020, 52 (Special Issue D): 78-83. Available at: http://bcc.bas.bg/BCC_Volumes/Volume_52_Special_D_2020/BCC-52-D-2020-78-83-Slavov-B10.pdf
Slavov A., Vasileva I., Stefanov L., Stoyanova A. Valorization of wastes from the rose oil industry. Reviews in Environmental Science and Bio/Technology, 2017, 16(2): 309-325. https://doi.org/10.1007/s11157-017-9430-5
Staykov A.S., Dragoev S.G., Balev D.K., Vlahova-Vangelova D.B., Pavlova M.R. Preserving the quality and prolongation the shelf-life of beef packed under vacuum or modified atmosphere using ternary antioxidant blend. Journal of Microbiology, Biotechnology and Food Sciences, 2016, 5(6): 617-622. https://doi.org/10.15414/jmbfs.2016.5.6.617-622
Topal F., Nar M., Gocer H., Kalin P., Kocyigit U.M., Gülçin İ., Alwasel S.H. Antioxidant activity of taxifolin: an activity–structure relationship. Journal of enzyme inhibition and medicinal chemistry, 2016, 31(4): 674-683. https://doi.org/10.3109/14756366.2015.1057723
Vardakas A., Kechagias A., Penov N., Giannakas A.E. Optimization of Enzymatic Assisted Extraction of Bioactive Compounds from Olea europaea Leaves. Biomass, 2024, 4(3): 647-657. htps://doi.org/10.3390/biomass4030035
Vilimanovich U., Jevremovic, S.A. Dihydroquercetin: a novel potent flavonoid antioxidant as an adjuvant for effective cancer treatment. EC Nutrition, 2019, 14(9): 660-674. Available at: https://ecronicon.net/assets/ecnu/pdf/ECNU-14-00640.pdf
Wang T.C., Chang P.C. Measurement and correlation for the solid solubility of antioxidants sodium L-ascorbate and sodium erythorbate monohydrate in supercritical carbon dioxide. Journal of Chemical & Engineering Data, 2015, 60(3): 790-794. https://doi.org/10.1021/je5009153
Zahra M., Abrahamse H., George B.P. Flavonoids: Antioxidant powerhouses and their role in nanomedicine. Antioxidants, 13(8): 922. https://doi.org/10.3390/antiox13080922
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How to Cite
VLAHOVA-VANGELOVA, Desislava Borislavova et al.
Optimization of bioactive compound mixtures: Polyphenol content, antioxidant activity, and synergistic effect.
Food Science and Applied Biotechnology, [S.l.], v. 8, n. 1, p. 99-111, mar. 2025.
ISSN 2603-3380.
Available at: <https://www.ijfsab.com/index.php/fsab/article/view/466>. Date accessed: 20 apr. 2025.
doi: https://doi.org/10.30721/fsab2025.v8.i1.466.