Abstract
[Objective] To purify and enrich the distiller's grain polyphenols (DGPs ) with good antioxidant activity.[Methods] Organic solvent extraction combined with macroporous adsorption resin was used to enrich and recover DGPs from the distiller's grains deep eutectic solvent (DES ) extraction solution.The purity and antioxidant activity of the purified products were determined.Extraction solvents and resin types were screened,and adsorption kinetics,isotherms,and thermodynamics were used to explain the adsorption mechanism.The optimal process conditions were determined.The in vitro antioxidant activity of the polyphenols was evaluated by measuring their ability to scavenge 1,1-diphenyl -2-trinitrophenylhydrazine (DPPH ) free radicals and 2,2'-azino -bis(3-ethylbenzothiazoline -6-sulfonic acid ) diammonium salt (ABTS ) free radicals.[Results]] Dichloromethane was the most suitable extraction solvent,with a polyphenol recovery rate of 90.83% when the ratio of dichloromethane to DES was 2∶1.The best resin for purifying DGPs was DM 130,with an adsorption rate of 78.70%.The adsorption of DGPs by DM 130 resin conformed to pseudo -second -order kinetics and the Langmuir adsorption model,indicating that the process is spontaneous and exothermic.The optimal purification conditions with DM 130 resin were a sample solution pH of 5,a sample concentration of 0.8 mg/mL,a flow rate of 2 BV/h,a sample volume of 3.4 BV,and elution with 60% ethanol at a flow rate of 引用格式:晏俊玲,郑佳,张伟建,等.酒糟多酚类物质纯化及体外抗氧化活性研究 [J].食品与机械,2025,41(3):161-170.C itation:YAN Junling,ZHENG Jia,ZHANG Weijian,et al.Purification of polyphenols from distiller's grains and its antioxidant activity in vitro [J].Food & Machinery,2025,41(3):161-170.3 BV/h and an elution volume of 6.9 BV.The overall recovery rate of DGPs from the distiller's grains DES extraction solution after dichloromethane extraction and DM 130 resin adsorption was 88.90%,with polyphenol purity increasing from 2.11% to 16.05%.Seven phenolic compounds were detected in the purified product,with ferulic acid being the most abundant.The IC50 values for scavenging DPPH and ABTS+ free radicals were 0.080 4 mg/mL and 0.185 0 mg/mL,respectively.[Conclusion] The purification method for the DGPs established in this study is effective and feasible,and the enriched DGPs exhibit good antioxidant activity.
Publication Date
4-25-2025
First Page
161
Last Page
170
DOI
10.13652/j.spjx.1003.5788.2024.80701
Recommended Citation
Junling, YAN; Jia, ZHENG; Weijian, ZHANG; Mao, LI; Jiawei, ZHAO; and fengyang, QIN
(2025)
"Purification of polyphenols from distiller's grains and its antioxidant activity in vitro,"
Food and Machinery: Vol. 41:
Iss.
3, Article 23.
DOI: 10.13652/j.spjx.1003.5788.2024.80701
Available at:
https://www.ifoodmm.cn/journal/vol41/iss3/23
References
[1] 钟江,黄永光,周蝶,等.酱香型和清香型白酒糟多酚类物质解析及对短链脂肪酸调节作用研究 [J].食品与发酵工业,2024,50(3):110-121.ZHONG J,HUANG Y G,ZHOU D,et al.Analysis of polyphenols in sauce-flavor and light-flavor Baijiu distiller's grain and their effects on the regulation of short-chain fatty acids[J].Food and Fermentation Industries,2024,50(3):110-121.
[2] 尹艳艳,张健,陆伦维,等.刺梨多酚类物质研究进展 [J].食品与机械,2024,40(1):234-240.YIN Y Y,ZHANG J,LU L W,et al.Research progress on polyphenols in chestnut rose fruit [J].Food & Machinery,2024,40(1):234-240.
[3] CHEN J H,ZHAO C L,LI Y S,et al.Moutai distiller's grains polyphenol extracts and rutin alleviate DSS-induced colitis in mice:modulation of gut microbiota and intestinal barrier function (R2) [J].Heliyon,2023,9(11):e22186.
[4] 汤夕瑶,刘宇佳,朱杰,等.酒糟结合多酚的抗氧化活性及对α-淀粉酶荧光特性的影响 [J].食品安全质量检测学报,2023,14(17):36-44.TANG X Y,LIU Y J,ZHU J,et al.Antioxidant activity of bound polyphenols from distiller's grains and the effects on fluorescence characteristics of α-amylase [J].Journal of Food Safety & Quality,2023,14(17):36-44.
[5] 钟江,黄永光,胡鹏刚,等.清酱香型白酒糟酚类物质鉴定及其活性功能解析 [J].中国酿造,2024,43(1):69-76.ZHONG J,HUANG Y G,HU P G,et al.Identification of phenolics and functional analysis of their activity in light/sauce-flavor Baijiu distiller's grain [J].China Brewing,2024,43(1):69-76.
[6] USMANI Z,SHARMA M,TRIPATHI M,et al.Biobased natural deep eutectic system as versatile solvents:structure,interaction and advanced applications [J].Science of the Total Environment,2023,881:163002.
[7] 晏俊玲,李茂,张伟建,等.深共熔溶剂提取酒糟多酚类物质及其体外抗氧化、降血糖活性研究 [J].食品与发酵工业,2024,50(18):265-272.YAN J L,LI M,ZHANG W J,et al.Deep eutectic solvent extraction of distiller's grains polyphenols and its antioxidant and hypoglycemic abilities in vitro [J].Food and Fermentation Industries,2024,50(18):265-272.
[8] 盛倩茹,王娟.大孔树脂纯化香蕉皮缩合单宁的吸附特性分析与工艺优化 [J].农业工程学报,2024,40(13):302-310.SHENG Q R,WANG J.Optimizing the adsorption and purification of banana peel condensed tannins by macroporous resin [J].Transactions of the Chinese Society of Agricultural Engineering,2024,40(13):302-310.
[9] ZHANG X,SU X Y,YU X Y,et al.Preparative separation of iridoid glucosides and crocins from Gardeniae Fructus using sequential macroporous resin column chromatography and evaluation of their anti-inflammatory and antioxidant activities[J].Journal of Chromatography B,2023,1 229:123887.
[10] 孙立兰,王坤,张友良,等.芸豆皮多酚制备、纯化、鉴定及抗油脂氧化作用研究 [J].食品工业科技,2025,46(2):292-300.SUN L L,WANG K,ZHANG Y L,et al.Preparation,purification,identification and anti-lipid oxidation of kidney bean skin polyphenols [J].Science and Technology of Food Industry,2025,46(2):292-300.
[11] 叶先青,席俊,朱晓艾,等.金莲花多酚的提取、纯化工艺优化及其抗氧化活性研究 [J].河南工业大学学报 (自然科学字母不同表示差异显著 (P<0.05)版),2024,45(5):72-80.YE X Q,XI J,ZHU X A,et al.Optimization of extraction,purification process and antioxidation activity of polyphenols from Flos trollii [J].Journal of Henan University of Technology (Natural Science Edition ),2024,45(5):72-80.
[12] 谢倩,王威,陈清西.橄榄多酚含量测定方法的比较 [J].食品科学,2014,35(8):204-207.XIE Q,WANG W,CHEN Q X.Comparative study on three different methods for the determination of total phenolics in Chinese olive [J].Food Science,2014,35(8):204-207.
[13] CHEN X M,WANG H,HUANG X J,et al.Efficient enrichment of total flavonoids from kale (Brassica oleracea L.var.acephala L.) extracts by NKA- 9 resin and antioxidant activities of flavonoids extract in vitro [J].Food Chemistry,2022,374:131508.
[14] CAO D,BU F J,CHENG X X,et al.Purification of phenolics from Plantago depressa by macroporous resin:adsorption/desorption characteristics,chromatographic process development and UPLC-TQ-MS/MS quantitative analysis [J].LWT,2024,203:116405.
[15] ZHANG Z W,WANG F,YANG W B,et al.A comparative study on the adsorption of 8-amino- 1-naphthol- 3,6-disulfonic acid by a macroporous amination resin [J].Chemical Engineering Journal,2016,283:1 522-1 533.
[16] 雷嘉昕,李政,莫嘉玮,等.管萼山豆根总黄酮的提取工艺优化及其抗氧化活性研究 [J].林产化学与工业,2024,44(3):87-96.LEI J X,LI Z,MO J W,et al.Extraction process optimization of total flavonoids from Euchresta tubulosa Dunn and antioxidant activity [J].Chemistry and Industry of Forest Products,2024,44(3):87-96.
[17] 翟晓娜,胡龙彪,李媛媛,等.菜籽饼超微粉酶解制备抗氧化活性肽 [J].农业工程学报,2024,40(4):284-291.ZHAI X N,HU L B,LI Y Y,et al.Preparing antioxidant peptides from ultra-fine powder of rapeseed meal [J].Transactions of the Chinese Society of Agricultural Engineering,2024,40(4):284-291.
[18] LIU X Y,YAN S,ZHOU H,et al.Separation and purification of glabridin from a deep eutectic solvent extract of Glycyrrhiza glabra residue by macroporous resin and its mechanism [J].Separation and Purification Technology,2023,315:123731.
[19] 许伟,刘军利,孙康,等.颗粒活性炭对亚甲基蓝的吸附与再生研究 [J].林产化学与工业,2024,44(3):69-77.XU W,LIU J L,SUN K,et al.Adsorption and regeneration properties of granular activitied carbon for methylene blue [J].Chemistry and Industry of Forest Products,2024,44(3):69-77.
[20] KE C R,REN Y,GAO P,et al.Separation and purification of pyrroloquinoline quinone from fermentation broth by pretreatment coupled with macroporous resin adsorption [J].Separation and Purification Technology,2021,257:117962.
[21] CHANG X L,WANG D,CHEN B Y,et al.Adsorption and desorption properties of macroporous resins for anthocyanins from the calyx extract of Roselle (Hibiscus sabdariffa L.) [J].Journal of Agricultural and Food Chemistry,2012,60(9):2 368-2 376.
[22] 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.
[23] XI L S,MU T H,SUN H N.Preparative purification of polyphenols from sweet potato (Ipomoea batatas L.) leaves by AB-8 macroporous resins [J].Food Chemistry,2015,172:166-174.
[24] BOPARAI H K,JOSEPH M,O'CARROLL D M.Kinetics and thermodynamics of cadmium ion removal by adsorption onto nano zerovalent iron particles [J].Journal of Hazardous Materials,2011,186(1):458-465.
[25] 寇亮,刘越敏,柳娜,等.大孔吸附树脂分离纯化湿生扁蕾总(口山 )酮[J].中药新药与临床药理,2022,33(4):522-530.KOU L,LIU Y M,LIU N,et al.Separation and purification of total xanthones from Gentianopsis paludosa using macroporous adsorption resin [J].Traditional Chinese Drug Research and Clinical,2022,33(4):522-530.
[26] GONG L Z,WU Y Z,QIU X H,et al.Adsorption characteristics and enrichment of emodin from marine-derived Aspergillus flavipes HN 4-13 extract by macroporous resin XAD- 16[J].Marine Drugs,2022,20(4):231.
[27] YANG Y H,LIANG Q M,ZHANG B,et al.Adsorption and desorption characteristics of flavonoids from white tea using macroporous adsorption resin [J].Journal of Chromatography A,2024,1 715:464621.
[28] 吴萍香,魏明,丁凯莉,等.大孔树脂纯化艾草多酚及其对α-葡萄糖苷酶活性抑制作用 [J].食品与机械,2023,39(7):13-19.WU P X,WEI M,DING K L,et al.Purification of polyphenols from wormwood by macroporous resin and inhibitory activity of its against α-glucosidase [J].Food & Machinery,2023,39(7):13-19.
[29] 马燕,魏媛,王冕,等.谷物酚酸合成途径及代谢调控研究进展[J].食品科学,2019,40(15):269-276.MA Y,WEI Y,WANG M,et al.A review of process in understand biosynthesis pathway and metabolic regulation of phenolic acids in cereals [J].Food Science,2019,40(15):269-276.