Abstract
To take better advantage of buckwheat polyphenols, processings including extrusion, steam explosion, microwave, roasting, superheated steam, ultrasound and enzymolysis treatment were applied to buckwheat bran to release more bioactive polyphenols. Polyphenols were extracted and characterized, and rutin was identified as the predominant compound. To further improve the properties of buckwheat polyphenols, rutin was selected as the target polyphenol and a formation of its ionic cross-linking complex was proposed. Rutin was loaded on chitooligosaccharide as Rutin-COS with tripolyphosphate (TPP) as crosslinking agent, whose molecular structure and properties were investigated. Results showed that all processing significantly increased (p < 0.05) the content of buckwheat polyphenols, up to 1.83-fold increase. The composition of polyphenols was altered, and their antioxidant (up to 15% increase) and antibacterial activities were significantly enhanced (p < 0.05). Among all the processings, extrusion and superheated steam showed the best effect. For Rutin-COS complex, the encapsulation efficiency was as high as 74.77% with the mass ratio of rutin and COS at 1:8. The structure of Rutin-COS was stabilized by hydrogen bonding between aromatic rings of rutin and amino and hydroxy groups of COS in the network formed by COS and TPP. Compared to free rutin, Rutin-COS presented better thermal stability and water solubility. The antioxidant and antibacterial activities of Rutin-COS were also significantly improved (p < 0.05) due to the molecular interaction between rutin and COS. The combination of processing and complexation strategy for buckwheat polyphenols in this work provided new approaches to take better advantages of polyphenols of cereal foods.
Graphical Abstract
Similar content being viewed by others
Availability of Data and Materials
The authors confirm that the data supporting the findings of this study are available within the article.
References
Belkacem, N., Khettal, B., Hudaib, M., Bustanji, Y., Abu-Irmaileh, B., & Amrine, C. S. (2021). Antioxidant, antibacterial, and cytotoxic activities of Cedrus atlantica organic extracts and essential oil. European Journal of Integrative Medicine, 42, 101292. https://doi.org/10.1016/j.eujim.2021.101292
Blaszczak, W., Zielinska, D., Zielinski, H., Szawara-Nowak, D., & Fornal, J. (2013). Antioxidant properties and rutin content of high pressure-treated raw and roasted buckwheat groats. Food and Bioprocess Technology, 6, 92–100. https://doi.org/10.1007/s11947-011-0669-5
Bockuviene, A., & Sereikaite, J. (2019). Preparation and characterisation of novel water-soluble carotene-chitooligosaccharides complexes. Carbohydrate Polymers, 225, 115226. https://doi.org/10.1016/j.carbpol.2019.115226
Brand-Williams, W., Cuvelier, M. E., & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. LWT-Food Science and Technology, 28, 25–30. https://doi.org/10.1016/S0023-6438(95)80008-5
Calinoiu, L. F., & Vodnar, D. C. (2020). Thermal processing for the release of polyphenols compounds from wheat and oat bran. Biomolecules, 10, 21. https://doi.org/10.3390/biom10010021
Cao, R. G., Liu, X. R., Zhai, X. Q., Wang, L. L., & Zhou, Z. K. (2021). Preparation, investigation and storage application of thymol-chitooligosaccharide complex with enhanced antioxidant and antibacterial properties. Journal of the Science of Food and Agriculture, 102, 1561–1568. https://doi.org/10.1002/jsfa.11492
Cao, R. G., Ma, Q. C., Fu, Y., Zhou, Z. K., & Zhao, X. Y. (2019). Preparation, evaluation and characterization of rutin-chitooligosaccharide complex. Plant Foods for Human Nutrition, 74, 328–333. https://doi.org/10.1007/s11130-019-00740-y
Cao, R. G., Zhao, Y. L., Zhou, Z. K., & Zhao, X. Y. (2018). Enhancement of the water solubility and antioxidant activity of hesperidin by chitooligosaccharide. Journal of the Science of Food and Agriculture, 98, 2422–2427. https://doi.org/10.1002/jsfa.8734
Celebioglu, A., Yildiz, Z. I., & Uyar, T. (2017). Thymol/cyclodextrin inclusion complex nanofibrous webs: Enhanced water solubility, high thermal stability and antioxidant property of thymol. Food Research International, 106, 280–290. https://doi.org/10.1016/j.foodres.2017.12.062
Chen, N., Gao, H. Z., He, Q., Yu, Z. L., & Zeng, W. C. (2022). Influence of structure complexity of polyphenols compounds on their binding with maize starch. Food Structure, 33, 100286. https://doi.org/10.1016/j.foostr.2022.100286
Germ, M., Arvay, J., Vollmannova, A., Toth, T., Golob, A., Luthar, Z., et al. (2019). The temperature threshold for the transformation of rutin to quercetin in Tartary buckwheat dough. Food Chemistry, 283, 28–31. https://doi.org/10.1016/j.foodchem.2019.01.038
Gullon, B., Pintado, M. E., Fernandez-Lopez, J., Perez-Alvarez, J. A., & Viuda-Martos, M. (2015). In vitro gastrointestinal digestion of pomegranate peel (Punica granatum) flour obtained from co-products: Changes in the antioxidant potential and bioactive compounds stability. Journal of Functional Foods, 19, 617–628. https://doi.org/10.1016/j.jff.2015.09.056
Hu, Q. B., & Luo, Y. C. (2016). Polyphenol-chitosan conjugates: Synthesis, characterization, and applications. Carbohydrate Polymers, 151, 624–639. https://doi.org/10.1016/j.carbpol.2016.05.109
Hu, Z. Q., Tang, X. Z., Zhang, M., Hu, X. Q., Yu, C., Zhu, Z. W., et al. (2018). Effects of different extrusion temperatures on extrusion behavior, polyphenols acids, antioxidant activity, anthocyanins and phytosterols of black rice. RSC Advances, 8, 7123–7132. https://doi.org/10.1039/c7ra13329d
Kutlu, N., Isci, A., Sakiyan, O., & Yilmaz, A. E. (2021). Extraction of phenolic compounds from cornelian cherry (cornus mas l.) using microwave and ohmic heating assisted microwave methods. Food and Bioprocess Technology, 14, 650–664. https://doi.org/10.1007/s11947-021-02588-0
Li, S. Y., Zhang, R., Lei, D., Huang, Y. Q., Cheng, S. Y., Zhu, Z. Z., et al. (2021). Impact of ultrasound, microwaves and high-pressure processing on food components and their interactions. Trends in Food Science & Technology, 109, 1–15. https://doi.org/10.1016/j.tifs.2021.01.017
Liu, L., Wen, W., Zhang, R. F., Wei, Z. C., Deng, Y. Y., Xiao, J., et al. (2017). Complex enzyme hydrolysis releases antioxidative polyphenolss from rice bran. Food Chemistry, 214, 1–8. https://doi.org/10.1016/j.foodchem.2016.07.038
Lu, C. R., Chen, B., & Shen, Y. H. (2018). Composition and antioxidant, antibacterial, and anti-HepG2 cell activities of polyphenols from seed coat of amygdalus pedunculata pall. Food Chemistry, 265, 111–119. https://doi.org/10.1016/j.foodchem.2018.05.091
Ma, Q., Zhao, Y., Wang, H. L., Li, J., Yang, Q. H., Gao, L. C., et al. (2020). Comparative study on the effects of buckwheat by roasting: Antioxidant properties, nutrients, pasting, and thermal properties. Journal of Cereal Science, 95, 103041. https://doi.org/10.1016/j.jcs.2020.103041
Mehta, D., Yadav, K., Chaturvedi, K., et al. (2022). Impact of cold plasma on extraction of polyphenol from de-oiled rice and corn bran: Improvement in extraction efficiency, in vitro digestibility, antioxidant activity, cytotoxicity and anti-inflammatory responses. Food and Bioprocess Technology, 15, 1142–1156. https://doi.org/10.1007/s11947-022-02801-8
Mittal, A., Singh, A., Bin, Z., Visessanguan, W., & Benjakul, S. (2022). Chitooligosaccharide conjugates prepared using several phenolic compounds via ascorbic acid/H2O2 free radical grafting: Characteristics, antioxidant, antidiabetic, and antimicrobial activities. Foods, 11, 920. https://doi.org/10.3390/foods11070920
Narasagoudr, S. S., Hegde, V. G., Chougale, R. B., Masti, S. P., Vootla, S., & Malabadi, R. B. (2020). Physico-chemical and functional properties of rutin induced chitosan/poly (vinyl alcohol) bioactive films for food packaging applications. Food Hydrocolloids, 109, 106096. https://doi.org/10.1016/j.foodhyd.2020.106096
Osete-Alcaraz, A., Bautista-Ortin, A. B., Ortega-Regules, A. E., & Gomez-Plaza, E. (2019). Combined use of pectolytic enzymes and ultrasounds for improving the extraction of phenolic compounds during vinification. Food and Bioprocess Technology, 12, 1330–1339. https://doi.org/10.1007/s11947-019-02303-0
Peng, G., Gan, J. P., Dong, R. H., Chen, Y., Xie, J. H., Huang, Z. Y., et al. (2021). Combined microwave and enzymatic treatment improve the release of insoluble bound polyphenols compounds from the grapefruit peel insoluble dietary fiber. LWT-Food Science and Technology, 149, 111905. https://doi.org/10.1016/j.lwt.2021.111905
Remanan, M. K., & Zhu, F. (2021). Encapsulation of rutin using quinoa and maize starch nanoparticles. Food Chemistry, 353, 128534. https://doi.org/10.1016/j.foodchem.2020.128534
Saji, N., Schwarz, L. J., Santhakumar, A. B., & Blanchard, C. L. (2020). Stabilization treatment of rice bran alters polyphenols content and antioxidant activity. Cereal Chemistry, 97, 281–292. https://doi.org/10.1002/cche.10243
Sorita, G. D., Leimann, F. V., & Ferreira, S. R. S. (2022). Phenolic fraction from peanut (arachis hypogaea l.) by-product: innovative extraction techniques and new encapsulation trends for its valorization. Food and Bioprocess Technology. https://doi.org/10.1007/s11947-022-02901-5
Souza, M. P., Vaz, A. F. M., Correia, M. T. S., Cerqueira, M. A., Vicente, A. A., & Carneiro-da-Cunha, M. G. (2014). Quercetin-loaded lecithin/chitosan nanoparticles for functional food applications. Food and Bioprocess Technology, 7, 1149–1159. https://doi.org/10.1007/s11947-013-1160-2
Sun-Waterhouse, D., Wadhwa, S. S., & Waterhouse, G. I. N. (2013). Spray-drying microencapsulation of polyphenol bioactives: A comparative study using different natural fibre polymers as encapsulants. Food and Bioprocess Technology, 6, 2376–2388. https://doi.org/10.1007/s11947-012-0946-y
Tang, Y., Li, X. H., Zhang, B., Chen, P. X., Liu, R. H., & Tsao, R. (2015). Characterisation of polyphenolss, betanins and antioxidant activities in seeds of three Chenopodium quinoa Willd. genotypes. Food Chemistry, 166, 380–388. https://doi.org/10.1016/j.foodchem.2014.06.018
Tchabo, W., Ma, Y. K., Kwaw, E., Zhang, H. N., Li, X., & Afoakwah, N. A. (2017). Effects of ultrasound, high pressure, and manosonication processes on polyphenols profile and antioxidant properties of a sulfur dioxide-free mulberry (morus nigra) wine. Food and Bioprocess Technology, 10, 1210–1223. https://doi.org/10.1007/s11947-017-1892-5
Wang, Y. Y., Xie, M. H., Ma, G. X., Fang, Y., Yang, W. J., Ma, N., et al. (2019). The antioxidant and antimicrobial activities of different polyphenols acids grafted onto chitosan. Carbohydrate Polymers, 225, 115238. https://doi.org/10.1016/j.carbpol.2019.115238
Wu, J., Wang, Y. P., Yang, H., Liu, X. Y., & Lu, Z. (2017). Preparation and biological activity studies of resveratrol loaded ionically cross-linked chitosan-TPP nanoparticles. Carbohydrate Polymers, 175, 170–177. https://doi.org/10.1016/j.carbpol.2017.07.058
Wu, Y. P., Yang, Y., Zhang, Z. J., Wang, Z. H., Zhao, Y. B., & Sun, L. (2018). A facile method to prepare size-tunable silver nanoparticles and its antibacterial mechanism. Advanced Powder Technology, 29, 407–415. https://doi.org/10.1016/j.apt.2017.11.028
Yasmin, A., Zeb, A., Khalil, A. W., et al. (2008). Effect of processing on anti-nutritional factors of red kidney bean (phaseolus vulgaris) grains. Food and Bioprocess Technology, 1, 415–419. https://doi.org/10.1007/s11947-008-0125-3
Ye, G. D., Wu, Y. N., Wang, L. P., Tan, B., Shen, W. Y., Li, X. N., et al. (2021). Comparison of six modification methods on the chemical composition, functional properties and antioxidant capacity of wheat bran. LWT-Food Science and Technology, 149, 111996. https://doi.org/10.1016/j.lwt.2021.111996
Zhang, C., Yu, X., Diao, Y., et al. (2020). Free radical grafting of epigallocatechin gallate onto carboxymethyl chitosan: Preparation, characterization, and application on the preservation of grape juice. Food and Bioprocess Technology, 13, 807–817. https://doi.org/10.1007/s11947-020-02442-9
Zhang, W. N., Zhu, Y. Y., Liu, Q. Q., Bao, J. S., & Liu, Q. (2017). Identification and quantification of polyphenols in hull, bran and endosperm of common buckwheat (Fagopyrum esculentum) seeds. Journal of Functional Foods, 38, 363–369. https://doi.org/10.1016/j.jff.2017.09.024
Zhu, B., He, H., Guo, D., Zhao, M., & Hou, T. (2019). Two novel calcium delivery systems fabricated by casein phosphopeptides and chitosan oligosaccharides: Preparation, characterization, and bioactive studies. Food Hydrocolloids, 102, 105567. https://doi.org/10.1016/j.foodhyd.2019.105567
Funding
This work was supported by the Program of Beijing Advanced Innovation Center for Food Nutrition and Human Health (20181037) and the National Natural Science Foundation of China (31601477, 32001706).
Author information
Authors and Affiliations
Contributions
Xinru Liu: Conceptualization, methodology, data curation, writing-original draft. Qianwei Ma: Methodology, visualization, data curation, writing-original draft. Yongjun Sun: Resources. Wenming Ju: Resources. Thanutchaporn Kumrungsee: Writing-review and editing. Zhongkai Zhou: Resources. Lijuan Wang: Review. Ruge Cao: Project administration, funding acquisition, supervision, writing-review and editing.
Corresponding authors
Ethics declarations
Competing Interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Liu, X., Ma, Q., Sun, Y. et al. Effects of Processings and Complexation on Solubility, Antioxidant and Antibacterial Properties of Buckwheat Polyphenols. Food Bioprocess Technol (2023). https://doi.org/10.1007/s11947-023-03217-8
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11947-023-03217-8