Abstract
Extraction of flavonoid glycosides and flavonoid aglycones simultaneously by enzyme-assisted micelle-mediated extraction has been proposed in this study. The discarded apple tree branches pruned during winter dormancy were selected as model materials. Extraction of phloretin (flavonoid aglycone) and phlorizin (flavonoid glycoside) from the discarded apple branches by micellar aqueous solution of nonionic surfactants with assistance of enzyme was performed to validate the method. Influencing factors like temperature, pH, time, enzyme concentration, surfactant concentration, solid to liquid ratio, and the ratio of pectinase to cellulase on the extraction yields of phloretin and phlorizin were discussed by single-factor experiments, and the main influencing factors were optimized by response surface methodology using Design-Expert 8.0.6 statistical software according to the Box-Behnken experimental design principle. The interaction of surfactants and enzymes in the extraction process was also investigated. Results indicate that the surfactants increased solubility of flavonoid glycosides and flavonoid aglycones in water simultaneously; enzymatic hydrolysis increased the diffusion rate of target components to the extraction medium and transformed flavonoid glycosides into flavonoid aglycones at the same time. Therefore, flavonoid glycosides and flavonoid aglycones were extracted simultaneously by micellar aqueous solution. The cloud point effect of nonionic surfactants separated the extracting solution into two distinct phases, which results in the concentration of the target component. In addition, the surfactant has low toxicity and volatility, making the extraction process more safe and reliable. Therefore, the process developed in this study provides an efficient and environmentally friendly technique for flavonoid glycoside and aglycone extraction simultaneously.
Similar content being viewed by others
Data Availability
The datasets generated during the current study are available in the manuscript and supplementary information.
References
Bhattacharya, S., Gupta, D., Sen, D., & Bhattacharjee, C. (2021). Process intensification on the enhancement of allicin yield from Allium sativum through ultrasound attenuated nonionic micellar extraction. Chemical Engineering and Processing-Process Intensification, 169.
Chamorro, S., Viveros, A., Alvarez, I., Vega, E., & Brenes, A. (2012). Changes in polyphenol and polysaccharide content of grape seed extract and grape pomace after enzymatic treatment. Food Chemistry, 133(2), 308–314.
Chanioti, S., Siamandoura, P., & Tzia, C. (2016). Evaluation of extracts prepared from olive oil by-products using microwave-assisted enzymatic extraction: Effect of encapsulation on the stability of final products. Waste and Biomass Valorization, 7(4), 831–842.
Coetzee, G., Joubert, E., Van Zyl, W. H., & Viljoen-Bloom, M. (2014). Improved extraction of phytochemicals from rooibos with enzyme treatment. Food and Bioproducts Processing, 92(C4), 393–401.
Cui, Q., Liu, J., Xu, W., Kang, Y.-F., Wang, X., Li, Y., & Fu, Y. (2019). Enhanced extraction and preconcentration of main target saponins from Panax notoginseng root using green and efficient formulated surfactant aqueous systems. Journal of Cleaner Production, 210, 1507–1516.
Curreri, A. M., Mitragotri, S., & Tanner, E. E. L. (2021). Recent advances in ionic liquids in biomedicine. Advanced Science, 8(17).
Do, L. D., Stevens, T. L., Kibbey, T. C. G., & Sabatini, D. A. (2014). Preliminary formulation development for aqueous surfactant-based soybean oil extraction. Industrial Crops and Products, 62, 140–146.
Ferreira, O., & Pinho, S. P. (2012). Solubility of flavonoids in pure solvents. Industrial & Engineering Chemistry Research, 51(18), 6586–6590.
Fu, Y.-J., Liu, W., Zu, Y.-G., Tong, M.-H., Li, S.-M., Yan, M.-M., Efferth, T., & Luo, H. (2008). Enzyme assisted extraction of luteolin and apigenin from pigeonpea Cajanus cajan (L.) Millsp. leaves. Food Chemistry, 111(2), 508–512.
Huang, X.-P., Ding, H., Lu, J.-D., Tang, Y.-H., Deng, B.-X., & Deng, C.-Q. (2015). Effects of the combination of the main active components of Astragalus and Panax notoginseng on inflammation and apoptosis of nerve cell after cerebral ischemia-reperfusion. American Journal of Chinese Medicine, 43(7), 1419–1438.
Jiang, Y., Ding, Y., Wang, D., Deng, Y., & Zhao, Y. (2020). Radio frequency-assisted enzymatic extraction of anthocyanins from Akebia trifoliata (Thunb.) Koidz. flowers: Process optimization, structure, and bioactivity determination. Industrial Crops and Products, 149.
Khelil, O., Choubane, S., & Cheba, B. A. (2016). Polyphenols content of spent coffee grounds subjected to physico-chemical pretreatments influences lignocellulolytic enzymes production by Bacillus sp R2. Bioresource Technology, 211, 769–773.
Mandalari, G., Bennett, R. N., Kirby, A. R., Lo Curto, R. B., Bisignano, G., Waldron, K. W., & Faulds, C. B. (2006). Enzymatic hydrolysis of flavonoids and pectic oligosaccharides from bergamot (Citrus bergamia Risso) peel. Journal of Agricultural and Food Chemistry, 54(21), 8307–8313.
Motikar, P. D., More, P. R., & Arya, S. S. (2021). A novel, green environment-friendly cloud point extraction of polyphenols from pomegranate peels: A comparative assessment with ultrasound and microwave-assisted extraction. Separation Science and Technology, 56(6), 1014–1025.
Nadar, S. S., Rao, P., & Rathod, V. K. (2018). Enzyme assisted extraction of biomolecules as an approach to novel extraction technology: A review. Food Research International, 108, 309–330.
Nakhle, L., Kfoury, M., Mallard, I., Landy, D., & Greige-Gerges, H. (2021). Microextraction of bioactive compounds using deep eutectic solvents: A review. Environmental Chemistry Letters, 19(5), 3747–3759.
Percevault, L., Limanton, E., Nicolas, P., Paquin, L., & Lagrost, C. (2021). Electrochemical determination and antioxidant capacity modulation of polyphenols in deep eutectic solvents. Acs Sustainable Chemistry & Engineering, 9(2), 776–784.
Plaza, M., & Luisa Marina, M. (2019). Pressurized hot water extraction of bioactives. Trac-Trends in Analytical Chemistry, 116, 236–247.
Purkait, M. K., DasGupta, S., & De, S. (2006). Performance of TX-100 and TX-114 for the separation of chrysoidine dye using cloud point extraction. Journal of Hazardous Materials, 137(2), 827–835.
Redha, A. A. (2021). Review on extraction of phenolic compounds from natural sources using green deep eutectic solvents. Journal of Agricultural and Food Chemistry, 69(3), 878–912.
Sheng, L., Zhu, G., & Tong, Q. (2013). Mechanism study of Tween 80 enhancing the pullulan production by Aureobasidium pullulans. Carbohydrate Polymers, 97(1), 121–123.
Sliwa, K., Sliwa, P., Sikora, E., Ogonowski, J., Oszmianski, J., & Nowicka, P. (2019). Application of polyethylene/polypropylene glycol ethers of fatty alcohols for micelle-mediated extraction of Calendula anthodium. Journal of Surfactants and Detergents, 22(3), 655–661.
Sridhar, A., Ponnuchamy, M., Kumar, P. S., Kapoor, A., Vo, D.-V.N., & Prabhakar, S. (2021). Techniques and modeling of polyphenol extraction from food: A review. Environmental Chemistry Letters, 19(4), 3409–3443.
Sun, C., Liu, W., & Zhao, P. (2014). Micelle-mediated extraction and cloud point preconcentration of chlorophylls from spinach. Separation Science and Technology, 49(18), 2921–2926.
Vatanparast, M., Hosseininaveh, V., Ghadamyari, M., & Sajjadian, S. M. (2014). Plant cell wall degrading enzymes, pectinase and cellulase, in the digestive system of the red palm weevil, Rhynchophorus ferrugineus (Coleoptera: Curculionidae). Plant Protection Science, 50(4), 190–198.
Wang, H., Ma, X., Cheng, Q., Wang, L., & Zhang, L. (2018a). Deep eutectic solvent-based ultrahigh pressure extraction of baicalin from Scutellaria baicalensis Georgi. Molecules, 23(12).
Wang, Q. F., Zhao, Y. Q., Sun, J. B., & Zhou, J. (2021). Simultaneous separation and determination of five monoterpene glycosides in Paeonia suffruticosa flower samples by ultra-high-performance liquid chromatography with a novel reinforced cloud point extraction based on ionic liquid. Microchemical Journal, 168.
Wang, S., Li, F., Wu, D., Zhang, P., Wang, H., Tao, X., Ye, J., & Nabi, M. (2018b). Enzyme pretreatment enhancing biogas yield from corn stover: Feasibility, optimization, and mechanism analysis. Journal of Agricultural and Food Chemistry, 66(38), 10026–10032.
Wang, W., Huang, G., An, C., Xin, X., Zhang, Y., & Liu, X. (2017). Transport behaviors of anionic azo dyes at interface between surfactant-modified flax shives and aqueous solution: Synchrotron infrared and adsorption studies. Applied Surface Science, 405, 119–128.
Wang, X., Peng, M.-J., Wang, Z.-H., Yang, Q.-L., & Peng, S. (2020). Ultrasound-microwave assisted extraction of flavonoid compounds from Eucommia ulmoides leaves and an evaluation of their antioxidant and antibacterial activities. Archives of Biological Sciences, 72(2), 211–221.
Wei, Y.-Q., Sun, M.-M., & Fang, H.-Y. (2019). Dienzyme-assisted salting-out extraction of flavonoids from the seeds of Cuscuta chinensis Lam. Industrial Crops and Products, 127, 232–236.
Wilkins, M. R., Widmer, W. W., Grohmann, K., & Cameron, R. G. (2007). Hydrolysis of grapefruit peel waste with cellulase and pectinase enzymes. Bioresource Technology, 98(8), 1596–1601.
Xiao, J. (2017). Dietary flavonoid aglycones and their glycosides: Which show better biological significance? Critical Reviews in Food Science and Nutrition, 57(9), 1874–1905.
Xue, K., Lue, H., Que, B., Shan, H., & Song, J. (2010). High-speed counter-current chromatography preparative separation and purification of phloretin from apple tree bark. Separation and Purification Technology, 72(3), 406–409.
Yan, M.-M., Chen, C.-Y., Zhao, B.-S., Zu, Y.-G., Fu, Y.-J., Liu, W., & Efferth, T. (2010). Enhanced extraction of astragalosides from Radix Astragali by negative pressure cavitation-accelerated enzyme pretreatment. Bioresource Technology, 101(19), 7462–7471.
Yang, J.-S., Mu, T.-H., & Ma, M.-M. (2019). Optimization of ultrasound-microwave assisted acid extraction of pectin from potato pulp by response surface methodology and its characterization. Food Chemistry, 289, 351–359.
Yang, X., Yang, Y., Zhang, Y., He, J., & Xie, Y. (2021). Enhanced exopolysaccharide production in submerged fermentation of Ganoderma lucidumby Tween 80 supplementation. Bioprocess and Biosystems Engineering, 44(1), 47–56.
Zhang, B.-B., & Cheung, P. C. K. (2011). A mechanistic study of the enhancing effect of Tween 80 on the mycelial growth and exopolysaccharide production by Pleurotus tuber-regium. Bioresource Technology, 102(17), 8323–8326.
Zhang, H.-F., Yang, X.-H., & Wang, Y. (2011). Microwave assisted extraction of secondary metabolites from plants: Current status and future directions. Trends in Food Science & Technology, 22(12), 672–688.
Zhang, H.-F., Zhang, X., Yang, X.-H., Qiu, N.-X., Wang, Y., & Wang, Z.-Z. (2013). Microwave assisted extraction of flavonoids from cultivated Epimedium sagittatum: Extraction yield and mechanism, antioxidant activity and chemical composition. Industrial Crops and Products, 50, 857–865.
Zhu, S.-C., Shi, M.-Z., Yu, Y.-L., & Cao, J. (2022). Simultaneous extraction and enrichment of alkaloids from lotus leaf by in-situ cloud point-reinforced ionic liquid assisted mechanochemical extraction technology. Industrial Crops and Products, 183.
Zhu, Z., Li, S., He, J., Thirumdas, R., Montesano, D., & Barba, F. J. (2018). Enzyme-assisted extraction of polyphenol from edible lotus (Nelumbo nucifera) rhizome knot: Ultra-filtration performance and HPLC-MS2 profile. Food Research International, 111, 291–298.
Funding
The authors gratefully acknowledge the financial supports from the Fundamental Research Funds for the Central Universities of China (2572022CG04), Heilongjiang Touyan Innovation Team Program (Tree Genetics and Breeding Innovation Team), the 111 Project (B20088), and Postdoctoral Project of Heilongjiang Province (LBH-Z21002).
Author information
Authors and Affiliations
Contributions
Yuanyuan Li: conceptualization, formal analysis, resources, validation, roles/writing — original draft, writing — review and editing. Qilei Yang: data curation, visualization. Bingxue Liu: data curation, investigation. Yanjie Liu: methodology. Qian Zhang: software. Xiuhua Zhao: formal analysis, funding acquisition, project administration, supervision. Shujun Li: writing — review and editing.
Corresponding authors
Ethics declarations
Conflict of Interest
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.
Supplementary Information
Below is the link to the electronic supplementary material.
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
Li, Y., Yang, Q., Liu, B. et al. Simultaneous Extraction of Flavonoid Glycosides and Flavonoid Aglycones from Discarded Apple Branches by Enzyme-assisted Micelle-mediated Extraction with Cloud Point Enrichment Method. Food Bioprocess Technol 16, 857–869 (2023). https://doi.org/10.1007/s11947-022-02973-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11947-022-02973-3