Evaluating the Effects of Different Drying Methods on the Bioactive Components and Antioxidant Activities of Ziziphi Spinosae Semen Based on <sup>1</sup>H NMR and GC-MS Approach

XIE Yujun; YAN Yan; LI Ze; PEI Xiangping; WANG Rui; DU Chenhui

doi:10.13386/j.issn1002-0306.2021120334

Volume 43 Issue 21

Oct. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(21): 282-293. > DOI: 10.13386/j.issn1002-0306.2021120334

XIE Yujun, YAN Yan, LI Ze, et al. Evaluating the Effects of Different Drying Methods on the Bioactive Components and Antioxidant Activities of Ziziphi Spinosae Semen Based on ¹H NMR and GC-MS Approach[J]. Science and Technology of Food Industry, 2022, 43(21): 282−293. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021120334.

Citation:

PDF (4077 KB)

Evaluating the Effects of Different Drying Methods on the Bioactive Components and Antioxidant Activities of Ziziphi Spinosae Semen Based on ¹H NMR and GC-MS Approach

1.
College of Traditional Chinese Medicine and Food Engineering, Shanxi University of Chinese Medicine, Taiyuan 030619, China
2.
Modern Research Center for Traditional Chinese Medicine, Shanxi University, Taiyuan 030006, China

More Information

Received Date: January 03, 2022
Available Online: August 20, 2022

Graphical Abstract

Abstract

Abstract

The drying is an important part of the processing of Ziziphi Spinosae Semen (ZSS) in the producing area and has an important effect on the quality of ZSS. In this study, an integrated ¹H nuclear magnetic resonance and gas chromatography-mass spectrometry method was developed to reveal the effects of vacuum drying (VD), freeze-drying (FD), and hot air drying (HAD) method on the chemical composition and antioxidant activity of ZSS. Then the effects of different drying methods on the quality of ZSS were investigated. The results showed that the VD produced high contents of 6 fatty acids (palmitic acid, linoleic acid, oleinic acid, stearic acid, squalene, and γ-tocopherol), 7 amino acids (leucine, isoleucine, valine, alanine, γ-aminobutyric acid, glutamine, and threonine), and 2 carbohydrates (α-glucose and β-glucose), but exhibited weak DPPH radical scavenging activity, ABTS cation radical scavenging activity and FRAP antioxidant activity (FD>VD>HAD). However, FD gave an improved secondary metabolite profile retention, such as jujuboside A, betulinic acid, magnoflorine, and 6ʹʹʹ-feruloylspinosin, thereby resulting in a superior DPPH radical scavenging activity (IC₅₀: 2.82±0.15 mg/mL), ABTS cation radical scavenging activity (IC₅₀: 0.86±0.02 mg/mL) and FRAP antioxidant activity (58.91±2.87 mg V_C/g). Thus, FD was a suitable drying method to maximize the product quality retention of ZSS. This study can provide a scientific reference for the establishment of reasonable processing technical specifications of ZSS and provide an experimental basis for improving the quality of ZSS.

FullText(HTML)

References (42)

References

[1]	国家药典委员会. 中华人民共和国药典: 一部[S]. 北京: 中国医药科技出版社, 2020: 366 National Pharmacopoeia Commission. Chinese pharmacopoeia: 1[S]. Beijing: China Medical Science Press, 2020: 366.
[2]	SUN S, LIU H, XU S, et al. Quality analysis of commercial samples of Ziziphi Spinosae Semen (suanzaoren) by means of chromatographic fingerprinting assisted by principal component analysis[J]. Journal of Pharmaceutical Analysis,2014,4(3):217−222. doi: 10.1016/j.jpha.2014.01.003
[3]	SHI S, FENG J, AN G, et al. Dynamics of heat transfer and moisture in beef jerky during hot air drying[J]. Meat Science,2021,182:108638. doi: 10.1016/j.meatsci.2021.108638
[4]	SĘCZYK Ł, OZDEMIR F A, KOŁODZIEJ B. In vitro bioaccessibility and activity of basil (Ocimum basilicum L.) phytochemicals as affected by cultivar and postharvest preservation method-Convection drying, freezing, and freeze-drying[J]. Food Chemstry,2022,382:132363. doi: 10.1016/j.foodchem.2022.132363
[5]	XU P, PENG X Y, YUAN T J, et al. Effect of vacuum drying on drying kinetics and quality of the aqueous extracts of Callicarpa nudiflora Hook[J]. LWT-Food Science and Technology,2021,152:112305. doi: 10.1016/j.lwt.2021.112305
[6]	张毅航, 方东路, 仲磊, 等. 热风干燥和真空冷冻干燥对猴头菇不同部位风味物质的影响[J]. 食品工业科技,2022,43(8):58−67. [ZHANG Y H, FANG D L, ZHONG L, et al. Effects of hot air-drying and vacuum freeze-drying on flavor components in different parts of Hericium erinaceus[J]. Science and Technology of Food Industry,2022,43(8):58−67.
[7]	MFN A, AP A, NAK A, et al. Metabolic variations in seaweed, Sargassum polycystum samples subjected to different drying methods via ¹H NMR-based metabolomics and their bioactivity in diverse solvent extracts[J]. Arabian Journal of Chemistry,2020,13(11):7652−7664. doi: 10.1016/j.arabjc.2020.09.002
[8]	杜晨晖, 解玉军, 申晨曦, 等. 干燥方式对酸枣果肉活性物质及抗氧化能力的影响[J]. 食品科学,2020,41(15):140−147. [DU C H, XIE Y J, SHEN C X, et al. Effects of different drying methods on bioactive compounds and antioxidant capacity of Ziziphi Spinosae sarcocarp[J]. Food Science,2020,41(15):140−147. doi: 10.7506/spkx1002-6630-20190701-012
[9]	国家药典委员会. 中华人民共和国药典: 四部[S]. 北京: 中国医药科技出版社, 2020: 103 National Pharmacopoeia Commission. Chinese pharmacopoeia: 4[S]. Beijing: China Medical Science Press, 2020: 103.
[10]	YAN Y, SHEN C, PEI X, et al. Compare the chemical profiling of Ziziphi Spinosae Semen and Ziziphi Mauritianae Semen using untargeted metabolomics[J]. Journal of Food Composition and Analysis,2020,94:103635. doi: 10.1016/j.jfca.2020.103635
[11]	YAN Y, FU C, CUI X, et al. Metabolic profile and underlying antioxidant improvement of Ziziphi Spinosae Folium by human intestinal bacteria[J]. Food Chemistry,2020,320:126651. doi: 10.1016/j.foodchem.2020.126651
[12]	ZHENG M, XIA Q, LU S. Study on drying methods and their influences on effective components of loquat flower tea[J]. LWT-Food Science and Technology,2015,63(1):14−20. doi: 10.1016/j.lwt.2015.03.090
[13]	杜晨晖, 闫艳, 朱羽尧, 等. 山西不同产地酸枣仁中脂肪酸类成分的GC-MS分析[J]. 中国实验方剂学杂志,2018,24(24):19−25. [DU C H, YAN Y, ZHU Y Y, et al. Analysis of fatty acid components in Ziziphi Spinosae Semen from different growing areas in Shanxi Province by GC-MS[J]. Chinese Journal of Experimental Traditional Medical Formulae,2018,24(24):19−25. doi: 10.13422/j.cnki.syfjx.20182103
[14]	孙明哲, 张闪闪, 闫琳, 等. 酸枣仁油的研究与开发进展[J]. 粮油食品科技,2020,28(4):119−125. [SUN M Z, ZHANG S S, YAN L, et al. Research and development progress of Semen Ziziphi Spinosae oil[J]. Science and Technology of Cereals, Oils and Foods,2020,28(4):119−125.
[15]	WANG F, LIU X, CHEN Y, et al. Characterization of fatty oil of Zizyphi Spinosi Semen obtained by supercritical fluid extraction[J]. Journal of the American Oil Chemists Society,2011,88(4):467−472. doi: 10.1007/s11746-010-1700-0
[16]	李颂, 刘洋, 王春玲. 角鲨烯的健康功效及应用[J]. 食品研究与开发,2016,37(14):206−209. [LI S, LIU Y, WANG C L. The health benefits and application of squalene[J]. Food Research and Development,2016,37(14):206−209. doi: 10.3969/j.issn.1005-6521.2016.14.050
[17]	王红, 吴启南, 伍城颖, 等. 高效液相色谱法测定芡实中不同构型维生素E的含量[J]. 食品工业科技,2014,35(8):74−78. [WANG H, WU Q N, WU C Y, et al. Determination of different configuration of vitamin E in euryale semen by HPLC[J]. Science and Technology of Food Industry,2014,35(8):74−78.
[18]	ARAYA J, RODRIGO R, VIDELA LA, et al. Increase in long-chain polyunsaturated fatty acid n-6/n-3 ratio in relation to hepatic steatosis in patients with non-alcoholic fatty liver disease[J]. Clinical Science,2004,106(6):635−643. doi: 10.1042/CS20030326
[19]	CAI J, ZHANG J, TIAN Y, et al. Orthogonal comparison of GC-MS and ¹H NMR spectroscopy for short chain fatty acid quantitation[J]. Analytical Chemistry,2017,89(15):7900−7906. doi: 10.1021/acs.analchem.7b00848
[20]	YUAN Q, HE Y, XIANG P, et al. Influences of different drying methods on the structural characteristics and multiple bioactivities of polysaccharides from okra (Abelmoschus esculentus)[J]. International Journal of Biological Macromolecules,2020,147:1053−1063. doi: 10.1016/j.ijbiomac.2019.10.073
[21]	MEDIANI A, ABAS F, KHATIB A, et al. ¹H NMR based metabolomics approach to understanding the drying effects on the phytochemicals in Cosmos caudatus[J]. Food Research International,2012,49(2):763−770. doi: 10.1016/j.foodres.2012.09.022
[22]	谢其亮, 陈重, 潘岩, 等. 不同干燥方法对商陆总皂苷和皂苷甲含量的影响[J]. 湖北农业科学,2019,58(8):126−128. [XIE Q L, CHEN Z, PAN Y, et al. Different dry means on the contents of total saponins and esculentoside A of Phytolacca americana[J]. Hubei Agricultural Sciences,2019,58(8):126−128.
[23]	谭亚杰, 濮宗进, 唐于平, 等. 基于UPLC-QTRAP(R)/MS²方法评价不同干燥方式对益母草中化学成分的影响[J]. 中草药,2019,50(7):1576−1586. [TAN Y J, PU Z J, TANG Y P, et al. Effects of different drying methods on multiple chemical components in Leonurus japonicus based on UPLC-QTRAP^®/MS²[J]. Chinese Traditional and Herbal Drugs,2019,50(7):1576−1586. doi: 10.7501/j.issn.0253-2670.2019.07.013
[24]	李雪营, 林先燕, 孙晓惠, 等. 杜仲不同“发汗”加工方法制品中总黄酮含量的比较[J]. 时珍国医国药,2019,30(3):597−599. [LI X Y, LIN X Y, SUN X H, et al. Comparison on the contents of total flavone in Eucommiae ulmoides processed by different sweating methods[J]. Lishizhen Medicine and Materia Medica Research,2019,30(3):597−599.
[25]	DENG Y, LUO Y, WANG Y, et al. Effect of different drying methods on the myosin structure, amino acid composition, protein digestibility and volatile profile of squid fillets[J]. Food Che-mistry,2015,171:168−176. doi: 10.1016/j.foodchem.2014.09.002
[26]	ZHANG M, TANG J, MUJUMDAR A S, et al. Trends in microwave-related drying of fruits and vegetables[J]. Trends In Food Science & Technology,2006,17(10):524−534.
[27]	FARAHMANDFAR R, TIRGARIAN B, DEHGHAN B, et al. Changes in chemical composition and biological activity of essential oil from Thomson navel orange (Citrus sinensis L. Osbeck) peel under freezing, convective, vacuum, and microwave drying methods[J]. Food Science & Nutrition,2020,8(1):124−138.
[28]	KRUMREICH F D, BORGES C D, MENDONCA C R B, et al. Bioactive compounds and quality parameters of avocado oil obtained by different processes[J]. Food Chemistry,2018,257:376−381. doi: 10.1016/j.foodchem.2018.03.048
[29]	HAYAT K, ABAS S, HUSSAIN S, et al. Effect of microwave and conventional oven heating on phenolic constituents, fatty acids, minerals and antioxidant potential of fennel seed[J]. Industrial Crops and Products,2019,140:111610. doi: 10.1016/j.indcrop.2019.111610
[30]	LASISI D. A comparative study of effects of drying methods on quality of cocoa beans[J]. International Journal of Coal Science & Technology,2014,3(1):991−996.
[31]	GUEHI T S, ZAHOULI I B, BAN-KOFFI L, et al. Performance of different drying methods and their effects on the chemical quality attributes of raw cocoa material[J]. International Journal of Food Science and Technology,2010,45(8):1564−1571. doi: 10.1111/j.1365-2621.2010.02302.x
[32]	李泽, 解玉军, 段慧竹, 等. 酸枣仁-茯苓共发酵的抗氧化活性增强机制研究[J]. 中国中药杂志,2021,46(3):620−629. [LI Z, XIE Y J, DUAN H Z, et al. Study on mechanism of enhancing antioxidant activity in fermented Ziziphi Spinosae Semen with Poria cocos[J]. China Journal of Chinese Matera Medica,2021,46(3):620−629.
[33]	谢光璟, 刘源才, 胡辉, 等. 基于Trx系统介导的抗氧化应激探讨天王补心方对失眠模型大鼠的干预作用[J]. 时珍国医国药,2019,30(4):805−808. [XIE G J, LIU Y C, HU H, et al. To explore the intervention effect of Tianwang Buxin Prescription on insomnia model rats based on Trx system mediated antioxidant stress[J]. Lishizhen Medicine and Materia Medica Research,2019,30(4):805−808.
[34]	孙燕. 酸枣仁生物碱和皂苷部位配伍指纹图谱及解郁安神作用机制的研究[D]. 天津: 天津医科大学, 2014 SUN Y. Study on the finger-print and depression-relieving and spirit-quieting effect of them compatibility alkaloids with saponins from SZS[D]. Tianjin: Tianjin Medicical University, 2014.
[35]	丁轲, 马崟松, 韩涛, 等. 酸枣仁抗氧化成分的分离及其相互作用研究[J]. 高校化学工程学报,2013,27(5):842−853. [DING K, MA Y S, HAN T, et al. Separation and interaction of the ingredients of antioxidant activities in Zizyphi Spinosi Semen[J]. Journal of Chemical Engineering of Chinese Universities,2013,27(5):842−853. doi: 10.3969/j.issn.1003-9015.2013.05.019
[36]	ADESANWO J K, MAKINDE O O, OBAFEMI C A. Phytochemical analysis and antioxidant activity of methanol extract and betulinic acid isolated from the roots of Tetracera potatoria[J]. Journal of Pharmacy Research,2013,6(9):903−907. doi: 10.1016/j.jopr.2013.09.003
[37]	李冰洁, 张睿, 李庆林. 酸枣仁皂苷A对脂多糖诱导星形胶质细胞C6氧化损伤的保护作用[J]. 安徽中医药大学学报,2018,37(2):71−76. [LI B J, ZHANG R, LI Q L. Protective effect of Jujuboside A against lipopolysaccharide-induced oxidative damage in C6 astrocytes[J]. Journal of Anhui University of Chinese Medicine,2018,37(2):71−76. doi: 10.3969/j.issn.2095-7246.2018.02.021
[38]	NASEER S, LONE S H, LONE J A, et al. LC-MS guided isolation, quantification and antioxidant evaluation of bioactive principles from Epimedium elatum[J]. Journal of Chromatography B,2015,989:62−70. doi: 10.1016/j.jchromb.2015.02.046
[39]	沈雁, 陈卫军, 张涛, 等. 吲哚丁酸的体外抗氧化活性研究[J]. 热带作物学报,2014,35(6):1153−1156. [SHEN Y, CHEN W J, ZHANG T, et al. Antioxidant activity of indole-3-butyric acid[J]. Chinese Journal of Tropical Crops,2014,35(6):1153−1156. doi: 10.3969/j.issn.1000-2561.2014.06.019
[40]	NENGROO Z R, RAUF A. Fatty acid composition and antioxidant activities of five medicinal plants from Kashmir[J]. Industrial Crops and Products,2019,140:111596. doi: 10.1016/j.indcrop.2019.111596
[41]	MARTÍNEZ-TOMÉ M, GARCÍA-CARMONA F, MURCIA M A. Comparison of the antioxidant and pro-oxidant activities of broccoli amino acids with those of common food additives[J]. Journal of the Science of Food and Agriculture,2001,81(10):1019−1026. doi: 10.1002/jsfa.889
[42]	LEE S Y, ABAS F, KHATIB A, et al. Metabolite profiling of Neptunia oleracea and correlation with antioxidant and α-glucosidase inhibitory activities using ¹H NMR-based metabolomics[J]. Phytochemistry Letters,2016,16:23−33. doi: 10.1016/j.phytol.2016.02.014