The macroporous adsorption resins were used to enrich the walnut pellicle polyphenols and the separation process conditions were optimized, the phenolic compounds were then identified. The results showed that the AB-8 resin was the ideal resin for enriching crude walnut pellicle polyphenols. The ideal enrichment parameters were as follows: sample concentration was 2.00 mg/mL at pH 3.0 with the static adsorption time for 3 h, meanwhile 70% ethanol was used as the eluent solvent. Dynamic adsorption study showed that the maximum loading amount was 14 BV and the amount of eluent was 4 BV. Under above conditions, the purity of walnut pellicle polyphenols was increased from 24.24% to 70.52%. The walnut pellicle polyphenols were identified using the Ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC-TOF-MS/MS). There were more than 30 kinds of polyphenols compounds were tentatively identified including ellagic acid, HHDP-glucose isomer, Di-HHDP-glucose, trigalloyl-HHDP glucose, teragalloyl-glucose, casuarinin/casuarinin isomer, glansrin C isomer, ellagic acid hexose isomer, ellagic acid pentose isomer, glansreginin A. This research indicates that macroporous adsorption resin could act as a preliminary separation media for refined walnut polyphenols containing mainly ellagic acid and its derivatives.
[1] 陈勤, 李磊珂, 吴耀.核桃仁的成分与药理研究进展[J].安徽大学学报(自然科学版), 2005, 29(1):86-89.
CHEN Q, LI L K, WU Y.Progress of research on the chemical components and pharmaceutical action of walnut kernel[J].Journal of Anhui University (Natural Sciences), 2005, 29(1):86-89.
[2] REGUEIRO J, SÁNCHEZ-GONZÁLEZ C, VALLVERDÚ-QUERALT A, et al.Comprehensive identification of walnut polyphenols by liquid chromatography coupled to linear ion trap-Orbitrap mass spectrometry[J].Food Chemistry, 2014, 152:340-348.
[3] LABUCKAS D O, MAESTRI D M, PERELLÓ M, et al.Phenolics from walnut (Juglans regia L.) kernels:Antioxidant activity and interactions with proteins[J].Food Chemistry, 2008, 107(2):607-612.
[4] 王克建, 齐建勋, 胡小松, 等.多酚对核桃仁食用品质影响的初步研究[J].食品科学, 2006, 27(5):95-97.
WANG K J, QI J X, HU X S, et al.Study on effect of polyphenols on astringency quality of walnut kernel[J].Food Science, 2006, 27(5):95-97.
[5] BOULEKBACHE-MAKHLOUF L, MEUDEC E, MAZAURIC J P, et al.Qualitative and semi-quantitative analysis of phenolics in Eucalyptus globulus leaves by high-performance liquid chromatography coupled with diode array detection and electrospray ionisation mass spectrometry[J].Phytochemical Analysis, 2013, 24(2):162-170.
[6] VINSON J A, CAI Y X.Nuts, especially walnuts, have both antioxidant quantity and efficacy and exhibit significant potential health benefits[J].Food & Function, 2012, 3(2):134-140.
[7] 刘旻昊, 齐娜, 邓红, 等.新疆红肉苹果多酚的纯化、组成分析与抗氧化活性[J].食品工业科技, 2019, 40(12):38-44;50.
LIU M H, QI N, DENG H, et al.Purification, composition analysis and its antioxidant activity of polyphenols from red-flesh apple of Xinjiang[J].Science and Technology of Food Industry, 2019, 40(12):38-44;50.
[8] GUO C X, QIAO J P, ZHANG S W, et al.Purification of polyphenols from kiwi fruit peel extracts using macroporous resins and high-performance liquid chromatography analysis[J].International Journal of Food Science & Technology, 2018, 53(6):1 486-1 493.
[9] 张旭, 陈丹, 曹丽娟, 等.5种大孔树脂纯化鲜核桃青皮汁多酚工艺的比较[J].中成药, 2016, 38(8):1 852-1 855.
ZHANG X, CHEN D, CAO L J, et al.Comparison of five kinds of Macroporous resins for purification of polyphenols in walnut green husk peel juice[J].Chinese Traditional Patent Medicine, 2016, 38(8):1 852-1 855.
[10] 徐佳. 核桃外果皮多酚提取纯化及抗氧化活性研究[D].乌鲁木齐:新疆农业大学, 2012.
XU J.Study on the extraction, identification and antioxidant activity of polyphenols from walnut husk[D].Urumqi:Xingjiang Agricultural University, 2012.
[11] 赵聪. 核桃种皮多酚的提纯鉴定及抗氧化活性研究[D].天津:天津科技大学, 2016.
ZHAO C.Purifocation, identification and antioxidant activity of polyphenols from walnut kernel pellicle[D].Tianjin:Tianjin University of Science & Technology, 2016.
[12] LIU P Z, LI L L, SONG L J, et al.Characterisation of phenolics in fruit septum of Juglans regia Linn.by ultra performance liquid chromatography coupled with Orbitrap mass spectrometer[J].Food Chemistry, 2019, 286:669-677.
[13] ZHANG Y G, KAN H, CHEN S X, et al.Comparison of phenolic compounds extracted from Diaphragma juglandis fructus, walnut pellicle, and flowers of Juglans regia using methanol, ultrasonic wave, and enzyme assisted-extraction[J].Food Chemistry, 2020, 321:126672.
[14] 李笑笑. 核桃内种皮多酚的提取及核桃油与核桃蛋白粉的稳定性研究[D].无锡:江南大学, 2017.
LI X X.Study on polyphenol extration from walnut kernel skin and stability of walnut oil and walnut protein powder[D].Wuxi:Jiangnan University, 2017.
[15] 甘芝霖, 倪元颖, 郭悦, 等.大孔树脂分离纯化玫瑰果多酚及其抗氧化性[J].农业工程学报, 2015, 31(24):298-306.
GAN Z L, NI Y Y, GUO Y, et al.Separation and purification of rosehip polyphenols by macroporous resin and its antioxidant activity[J].Transactions of the Chinese Society of Agricultural Engineering, 2015, 31(24):298-306.
[16] 王克建, 杜明, 胡小松, 等.核桃仁中多酚类物质的液相/电喷雾质谱分析[J].分析化学, 2009(6):867-872.
WANG K J, DU M, HU X S, et al.Identification of phenolic compounds in walnut (Juglans regia L) seeds by high performance liquid chromatography electrospray ionization mass spectrometry[J].Chinese Journal of Analytical Chemistry, 2009(6):867-872.
[17] WANG X Q, CONTRERAS M D M, XU D M, et al.New insights into free and bound phenolic compounds as antioxidant cluster in tea seed oil:Distribution and contribution[J].LWT, 2021, 136:110315.
[18] LIU R X, ZHAO Z Y, DAI S J, et al.Identification and quantification of bioactive compounds in Diaphragma juglandis fructus by UHPLC-Q-orbitrap HRMS and UHPLC-MS/MS[J].Journal of Agricultural and Food Chemistry, 2019, 67(13):3 811-3 825.
[19] SLATNAR A, MIKULIC-PETKOVSEK M, STAMPAR F, et al.Identification and quantification of phenolic compounds in kernels, oil and bagasse pellets of common walnut (Juglans regia L.)[J].Food Research International, 2015, 67:255-263.
[20] GRACE M H, YOUSEF G G, GUSTAFSON S J, et al.Phytochemical changes in phenolics, anthocyanins, ascorbic acid, and carotenoids associated with sweetpotato storage and impacts on bioactive properties[J].Food Chemistry, 2014, 145:717-724.
[21] KAFKAS E, ATTAR S H, GUNDESLI M A, et al.Phenolic and fatty acid profile, and protein content of different walnut cultivars and genotypes (Juglans regia L.) grown in the USA[J].International Journal of Fruit Science, 2020, 20(sup3):S1711-S1720.