In this study, neohesperidin in peony seed meal was isolated and purified by AB-8 resin combined with C18, and its biological activity was explored, which provided a basis for the development of related products.Six macroporous resins (AB-8, X-5, DM301, CAD-40, D101, and NKA) were screened by the adsorption kinetics model, and the adsorption/analytical capacity of AB-8 resin was superior to the other five.The optimal separation conditions for AB-8 were that the loading rate was 8 BV/h, the loading volume was 60 mL, the eluent was 60% (volume fraction) ethanol-aqueous solution, and the elution flow rate was 5 mL/min.The antioxidant activity of 1 mg/mL neohesperidin was 83.23%, 81.05%, and 72.03% for DPPH free radicals, ·O2-, and ABTScationic radicals, respectively.250 mg/mL of new hesperidin can improve the antioxidant activity in the cell activity to reduce intracellular reactive oxygen species content.Experiments showed that the inhibition rate of 2 000 mg/mL of new hesperidin on K562 was 92.49%, and 500 mg/mL of new hesperidin could effectively inhibit the K562 G1 phase of division.Molecular dynamics simulation results showed that neohesperidin inhibited the proliferation of K562 through hydrogen bonding with B-cell lymphoma-2 and cyclin-dependent kinase 2. In this study, the active substance neohesperidin was isolated from peony seed meal, which provided a theoretical basis for scientific understanding of peony seed meal waste.
[1] DENG R X, GAO J Y, YI J P, et al.Peony seeds oil by-products:Chemistry and bioactivity[J].Industrial Crops and Products, 2022, 187:115333.
[2] HUANG Y, OHNO O, SUENAGA K, et al.Apoptosis-inducing activity and antiproliferative effect of Paeoniflorigenone from moutan cortex[J].Bioscience, Biotechnology, and Biochemistry, 2017, 81(6):1106-1113.
[3] XIANG J L, YANG C B, BETA T, et al.Phenolic profile and antioxidant activity of the edible tree peony flower and underlying mechanisms of preventive effect on H2O2-induced oxidative damage in caco-2 cells[J].Foods, 2019, 8(10):471.
[4] SHI J J, ZHANG J G, SUN Y H, et al.Physicochemical properties and antioxidant activities of polysaccharides sequentially extracted from peony seed dreg[J].International Journal of Biological Macromolecules, 2016, 91:23-30.
[5] GÓRNIAK I, BARTOSZEWSKI R, KRÓLICZEWSKI J.Comprehensive review of antimicrobial activities of plant flavonoids[J].Phytochemistry Reviews, 2019, 18(1):241-272.
[6] SUN Z G, LI Z N, ZHANG J M, et al.Recent developments of flavonoids with various activities[J].Current Topics in Medicinal Chemistry, 2022, 22(4):305-329.
[7] XU F, ZANG J, CHEN D Z, et al.Neohesperidin induces cellular apoptosis in human breast adenocarcinoma MDA-MB-231 cells via activating the Bcl-2/Bax-mediated signaling pathway[J].Natural Product Communications, 2012, 7(11):1475-1478.
[8] JIA S, HU Y, ZHANG W N, et al.Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L.in diabetic KK-a(y) mice[J].Food & Function, 2015, 6(3):878-886.
[9] CHEN L, ZHU S M, WANG C Q, et al.Development of a HPLC-UV method for the separation and quantification of hesperidin, neohesperidin, neohesperidin dihydrochalcone and hesperetin[J].Natural Product Research, 2023, 37(10):1714-1718.
[10] UCHIYAMA N, KIM I H, KIKURA-HANAJIRI R, et al.HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines[J].Journal of Pharmaceutical and Biomedical Analysis, 2008, 46(5):864-869.
[11] WANG S S, QIN Z K, WANG Y C, et al.A novel ethanolic two-phase system based on deep eutectic solvents and amphiphilic copolymer for the extraction of neohesperidin and naringin from the pomelo peel[J].Foods, 2022, 11(17):2590.
[12] DALMAU E, ROSSELLÓ C, EIM V, et al.Ultrasound-assisted aqueous extraction of biocompounds from orange byproduct:Experimental kinetics and modeling[J].Antioxidants, 2020, 9(4):352.
[13] WANG S B, LI Z G, LIU W, et al.Neohesperidin induces cell cycle arrest, apoptosis, and autophagy via the ROS/JNK signaling pathway in human osteosarcoma cells[J].The American Journal of Chinese Medicine, 2021, 49(5):1251-1274.
[14] ORTIZ A C, FIDELES S O M, REIS C H B, et al.Therapeutic effects of citrus flavonoids neohesperidin, hesperidin and its aglycone, hesperetin on bone health[J].Biomolecules, 2022, 12(5):626.
[15] ZHANG J S, FU X D, YANG L, et al.Neohesperidin inhibits cardiac remodeling induced by Ang II in vivo and in vitro[J].Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 2020, 129:110364.
[16] 邹平, 徐莹, 陈文涛, 等.牡丹籽粕中黄酮类化合物的提取工艺优化及膜法分离纯化[J].食品工业科技, 2023, 44(18):258-267.
ZOU P, XU Y, CHEN W T, et al.Optimization of extraction process and purification of flavonoids from peony seed meal by membrane method[J].Science and Technology of Food Industry, 2023, 44(18):258-267.
[17] SHEN D B, LABRECHE F, WU C E, et al.Ultrasound-assisted adsorption/desorption of jujube peel flavonoids using macroporous resins[J].Food Chemistry, 2022, 368:130800.
[18] LYU C, YANG J, LIU R, et al.A comparative study on the adsorption and desorption characteristics of flavonoids from honey by six resins[J].Food Chemistry, 2018, 268:424-430.
[19] LIMWACHIRANON J, HUANG H, LI L, et al.Recovery of lotus (Nelumbo nucifera Gaertn.) seedpod flavonoids using polar macroporous resins:The updated understanding on adsorption/desorption mechanisms and the involved intermolecular attractions and bonding[J].Food Chemistry, 2019, 299:125108.
[20] WANG Y, LIU X J, CHEN J B, et al.Citrus flavonoids and their antioxidant evaluation[J].Critical Reviews in Food Science and Nutrition, 2022, 62(14):3833-3854.
[21] WEI G W.Protein structure prediction beyond AlphaFold[J].Nature Machine Intelligence, 2019, 1:336-337.
[22] KIM S, THIESSEN P A, BOLTON E E, et al.PubChem substance and compound databases[J].Nucleic Acids Research, 2016, 44(D1):D1202-D1213.
[23] GENHEDEN S, RYDE U.The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities[J].Expert Opinion on Drug Discovery, 2015, 10(5):449-461.
[24] NGUYEN H, ROE D R, SIMMERLING C.Improved generalized born solvent model parameters for protein simulations[J].Journal of Chemical Theory and Computation, 2013, 9(4):2020-2034.
[25] CHANG T T, BI Y J, JING L L, et al.Simultaneous adsorption of acid and flavonoids from hawthorn juice onto resins[J].Journal of Food Engineering, 2021, 291:110195.
[26] DONG Y, ZHAO M M, SUN-WATERHOUSE D, et al.Absorption and desorption behaviour of the flavonoids from Glycyrrhiza glabra L.leaf on macroporous adsorption resins[J].Food Chemistry, 2015, 168:538-545.
[27] YANG D, LI M M, WANG W J, et al.Separation and purification of anthocyanins from Roselle by macroporous resins[J].LWT, 2022, 161:113371.
[28] NAEIMI A F, ALIZADEH M.Antioxidant properties of the flavonoid fisetin:An updated review of in vivo and in vitro studies[J].Trends in Food Science & Technology, 2017, 70:34-44.
