Study on Carboxymethylation Modification and Antioxidant Activity of Polysaccharides from <i>Zizyphus jujuba</i>

FU Yuxia; GUO Xin; WEI Yabo; DENG Xiaorong; LEI Yongdong; LIU Pingping; ZHANG Jian

doi:10.13386/j.issn1002-0306.2021120127

Volume 43 Issue 17

Aug. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(17): 104-113. > DOI: 10.13386/j.issn1002-0306.2021120127

FU Yuxia, GUO Xin, WEI Yabo, et al. Study on Carboxymethylation Modification and Antioxidant Activity of Polysaccharides from Zizyphus jujuba[J]. Science and Technology of Food Industry, 2022, 43(17): 104−113. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021120127.

Citation:

PDF (9785 KB)

Study on Carboxymethylation Modification and Antioxidant Activity of Polysaccharides from Zizyphus jujuba

College of Food Science, Shihezi University, Shihezi 832000, China

More Information

Received Date: December 12, 2021
Available Online: July 02, 2022

Graphical Abstract

Abstract

Abstract

To investigate the changes of structural characteristics and antioxidant activity of carboxymethylated jujube polysaccharides, this study was carried out on the Zizyphus jujuba polysaccharide carboxymethylated modification. The crude polysaccharides of jujube were used as raw materials, deproteinization by Sevage method and decolorization by macroporous resin AB-8, then the polysaccharide was modified by carboxymethylation. With carboxymethyl substitution degree as the index, the concentration of NaOH, the addition amount of monochloroacetic acid and the temperature were optimized by single factor and response surface test. The scavenging ability of DPPH and hydroxyl radical and its reducing power and chelating ability to Fe²⁺ were taken as indexes before and after modification to explore the effect of antioxidant activity of carboxymethylated jujube polysaccharide. The results showed that the optimal process of carboxymethylation modification was as follows: Reaction temperature was 70 ℃, the addition amount of chloroacetic acid was 3.5%, and the concentration of NaOH was 3 mol/L. Under these conditions, carboxymethylated Zizyphus jujuba polysaccharides had the best molecular modification effect, and the degree of substitution up to 1.157. When the concentration was 5 mg/mL, the scavenging rates of DPPH and hydroxyl radical were 93.83% and 44.7%, and the reducing power and chelating capacity of Fe²⁺ were 0.462 and 44.05%. The significant improvement of antioxidant activity of Zizyphus jujuba polysaccharides indicated that carboxymethylation modification could improve antioxidant activity of polysaccharides, which could provide theoretical basis for further study of Zizyphus jujuba polysaccharides.
- Zizyphus jujuba polysaccharide,
- carboxymethylation,
- degree of substitution,
- antioxidant

FullText(HTML)

References (41)

References

[1]	LIU M, WANG J, WANG L, et al. The historical and current research progress on jujube–a superfruit for the future[J]. Horticulture Research,2020,7(1):17. doi: 10.1038/s41438-020-0239-y
[2]	CHEN J, TSIM K. A Review of edible jujube, the Ziziphus jujuba fruit: A heath food supplement for anemia prevalence[J]. Frontiers in Pharmacology,2020,11:593655. doi: 10.3389/fphar.2020.593655
[3]	冀晓龙, 尹明松, 侯春彦, 等. 红枣多糖提取、分离纯化及生物活性研究进展[J]. 食品工业科技,2020,41(23):346−353, 358. [JI X L, YIN M S, HOU C Y, et al. Rencent advances in jujube (Ziziphus jujuba Mill.) polysaccharides: Extraction, isolation and purification and bioactivities[J]. Science and Technology of Food Industry,2020,41(23):346−353, 358. JI X L, YIN M S, HOU C Y, et al. Rencent advances in jujube (Ziziphus jujuba Mill. ) polysaccharides: extraction, isolation and purification and bioactivities[J]. Science and Technology of Food Industry, 2020, 41(23): 346-353, 358.
[4]	ZHENG Y, WANG B, CHEN X, The research on the influence of jujube polysaccharide on anti-fatigue in endurance training [C]// REN P, LI Y, SONG H. International conference on applied engineering and management. Beijing, 2015: 1381−1386.
[5]	CHAN P H, CHEN J P, LAM C T W, et al. Fruit of Ziziphus jujuba (Jujube) at two stages of maturity: Distinction by metabolic profiling and biological assessment[J]. Journal of Agricultural and Food Chemistry,2015,63(2):739−744. doi: 10.1021/jf5041564
[6]	LI Z, LIU X, WANG Y, et al. In vitro antioxidative and immunological activities of polysaccharides from Zizyphus jujuba cv. Muzao[J]. International Journal of Biological Macromolecules,2017,95:1119−1125. doi: 10.1016/j.ijbiomac.2016.10.102
[7]	周际松, 汪芷玥, 汤凯, 等. 羧甲基化茯苓多糖的抗氧化性分析[J]. 中国食品添加剂,2020,31(7):120−125. [ZHOU J S, WANG Z Y, TANG K, et al. Antioxidant activity of carboxymethylated poria cocos polysaccharide[J]. China Food Additives,2020,31(7):120−125. ZHOU J S, WANG Z Y, TANG K, et al. Antioxidant activity of carboxymethylated poria cocos polysaccharide [J]. China Food Additives, 2020, 31(07): 120-125.
[8]	陈胜军, 刘先进, 杨贤庆, 等. 鲍鱼内脏多糖分离纯化与抗氧化活性评价[J]. 南方农业学报,2019,50(2):372−377. [CHEN S J, LIU X J, YANG X Q, et al. Isolation, purification and antioxidant activity evaluation of polysaccharides from abalone viscera[J]. Journal of Southern Agriculture,2019,50(2):372−377. doi: 10.3969/j.issn.2095-1191.2019.02.22 CHEN S J, LIU X J, YANG X Q, et al. Isolation, purification and antioxidant activity evaluation of polysaccharides from abalone viscera [J]. Journal of Southern Agriculture, 2019, 50(2): 372-377. doi: 10.3969/j.issn.2095-1191.2019.02.22
[9]	李小蓉, 郭惠, 龙旭, 等. 倒卵叶五加多糖脱蛋白工艺研究[J]. 化学与生物工程,2018,35(8):53−56, 68. [LI X R, GUO H, LONG X, et al. Deproteinization process of polysaccharide from Acanthopanax obovatus Hoo[J]. Chemistry & Bioengineering,2018,35(8):53−56, 68. doi: 10.3969/j.issn.1672-5425.2018.08.011 LI X R, GUO H, LONG X, et al. Deproteinization process of polysaccharide from Acanthopanax obovatus Hoo[J]. Chemistry & Bioengineering, 2018, 35(8): 53-56, 68 doi: 10.3969/j.issn.1672-5425.2018.08.011
[10]	刘佳维, 周君, 高亚杰, 等. 红参多糖脱蛋白的研究[J]. 食品科技,2018,43(7):188−192. [LIU W J, ZHOU J, GAO Y J, et al. Deproteinization of polysaccharide from red ginseng[J]. Food Science and Technology,2018,43(7):188−192. LIU W J, ZHOU J, GAO Y J, et al. Deproteinization of polysaccharide from red ginseng[J]. Food Science and Technology, 2018, 43(7): 188-192.
[11]	韩伟, 陈静雯. 应用大孔树脂提纯蛹虫草多糖的工艺研究[J]. 徐州工程学院学报(自然科学版),2021,36(2):7−14. [HAN W, CHEN J W. Study on purification of cordyceps militaris polysaccharides by macroporous resin[J]. Journal of Xuzhou Institute of Technology (Natural Sciences Edition),2021,36(2):7−14. HAN W, CHEN J W. Study on purification of cordyceps militaris polysaccharides by macroporous resin[J]. Journal of Xuzhou Institute of Technology(Natural Sciences Edition), 2021, 36(2): 7-14.
[12]	艾拉旦·麦麦提艾力, 李洋, 姚军, 等. 管花肉苁蓉多糖水提物的分离及免疫活性研究[J]. 中国药房,2021,32(12):1479−1484. [AILADAN-Maimaitiailli, LI Y, YAO J, et al. Study on separation and immunocompetence of water extract of polysaccharide from Cistanche tubulosa[J]. China Pharmacy,2021,32(12):1479−1484. doi: 10.6039/j.issn.1001-0408.2021.12.12 AILADAN-Maimaitiailli LI Y, YAO J, et al. Study on separation and immunocompetence of water extract of polysaccharide from Cistanche tubulosa[J]. China Pharmacy, 2021, 32(12): 1479-1484. doi: 10.6039/j.issn.1001-0408.2021.12.12
[13]	王迎香, 唐子惟, 彭腾, 等. 苯酚-硫酸法测定酒蒸多花黄精多糖含量的优化[J]. 食品工业科技,2021,42(18):308−316. [WANG Y X, TANG Z W, PENG T, et al. Optimization of phenol sulfuric acid method for the polysaccharide content of wine-steamed Polygonatum cyrtonema Hua[J]. Science and Technology of Food Industry,2021,42(18):308−316. WANG Y X, TANG Z W, PENG T, et al. Optimization of phenol sulfuric acid method for the polysaccharide content of wine-steamed Polygonatum cyrtonema Hua[J]. Science and Technology of Food Industry, 2021, 42(18): 308−316.
[14]	KONDO M, MULIANDA R, MATAMURA M, et al. Validation of a phenol: Ulfuric acid method in a microplate format for the quantification of soluble sugars in ruminant feeds[J]. Animal Science Journal,2021,92:e13530.
[15]	曹泽虹, 董玉玮, 李超, 等. 骏枣的多糖提取及其蛋白脱除研究[J]. 食品科学技术学报,2020,38(6):121−126. [CAO Z H, DONG Y W, LI C, et al. Study on polysaccharide extraction and protein removal from Ziziphus jujuba Mill. cv Junzao[J]. Journal of Food Science and Technology,2020,38(6):121−126. doi: 10.3969/j.issn.2095-6002.2020.06.015 CAO Z H, DONG Y W, LI C, et al. Study on polysaccharide extraction and protein removal from Ziziphus jujuba Mill. cv Junzao[J]. Journal of Food Science and Technology, 2020, 38(6): 121 - 126. doi: 10.3969/j.issn.2095-6002.2020.06.015
[16]	杨静, 白冰, 王宁, 等. 考马斯亮蓝法对烟草薄片涂布液中蛋白质含量的测定[J]. 湖北农业科学,2017,56(5):946−947, 950. [YANG J, BAl B, WANG N, et al. Determination of protein content in reconstituted tobacco coating liquid by coomassie brilliant blue method[J]. Hubei Agricultural Sciences,2017,56(5):946−947, 950. YANG J, BAl B, WANG N, et al. Determination of protein content in reconstituted tobacco coating liquid by coomassie brilliant blue method[J]. Hubei Agricultural Sciences, 2017, 56(5): 946-947, 950.
[17]	陈栅. 枣和酸枣多糖羧甲基化修饰工艺及活性研究[D]. 保定: 河北农业大学, 2021. CHEN Z. Carboxymethylation modification processes and activity of jujube and wild jujube polysaccharide[D]. Baoding: Hebei Agricultural University, 2021.
[18]	程浩. 大蒜多糖衍生物的制备及抗氧化活性研究[D]. 重庆: 重庆师范大学, 2020. CHENG H. Preparation and antioxidant activity of garlic polysaccharide derivatives[D]. Chongqing: Chongqing Normal University, 2020.
[19]	张洋婷, 韩丽琴, 郗艳丽, 等. 红景天多糖羧甲基化修饰及其抗氧化活性[J]. 中国公共卫生,2017,33(10):4. [ZHANG Y T, HAN L Q, XI Y L, et al. Carboxymethylation modification and antioxidant activity of rhodiola polysaccharide[J]. Chinese Journal of Public Health,2017,33(10):4. doi: 10.11847/zgggws2017-33-10-11 ZHANG Y T, HAN L Q, XI Y L, et al. Carboxymethylation modification and antioxidant activity of rhodiola polysaccharide [J]. Chinese Journal of Public Health, 2017, 33(10): 4. doi: 10.11847/zgggws2017-33-10-11
[20]	房斐, 陈雪峰, 刘宁, 等. 羧甲基化苹果渣多糖的制备及其表征[J]. 食品科技,2019,44(9):289−294, 302. [FANG P, CHEN X F, LIU N, et al. Preparation and characterization of carboxymethylated apple pomace polysaccharide[J]. Food Science and Technology,2019,44(9):289−294, 302. FANG P, CHEN X F, LIU N, et al. Preparation and characterization of carboxymethylated apple pomace polysaccharide[J]. Food Science and Technology, [19] 2019, 44(9): 289-294, 302.
[21]	邓威, 孙晓楠, 张润泽, 等. 寒葱精油挥发性成分及抗氧化活性研究[J]. 中国调味品,2021,46(10):59−64. [DENG W, SUN X N, ZHANG R Z, et al. Study on the volatile components and antioxidant activity of essential oil from Allium victorialis L[J]. China Condiment,2021,46(10):59−64. doi: 10.3969/j.issn.1000-9973.2021.10.011 DENG W, SUN X N, ZHANG R Z, et al. Study on the volatile components and antioxidant activity of essential oil from Allium victorialis L[J]. China Condiment, 2021, 46(10): 59-64. doi: 10.3969/j.issn.1000-9973.2021.10.011
[22]	KOU X H, CHEN Q, L X H, et al. Quantitative assessment of bioactive compounds and the antioxidant activity of 15 jujube cultivars[J]. Food Chemistry,2015,173:1037−1044. doi: 10.1016/j.foodchem.2014.10.110
[23]	ZHANG Y, SUN X, VIDYARTHI S K, et al. Active components and antioxidant activity of thirty-seven varieties of Chinese jujube fruits (Ziziphus jujuba Mill.)[J]. International Journal of Food Properties,2021,24(1):1479−1494. doi: 10.1080/10942912.2021.1977656
[24]	PRASAD K N, CHEW L Y, KHOO H E, et al. Antioxidant capacities of peel, pulp, and seed fractions of Canarium odontophyllum Miq. fruit[J]. Journal of Biomedicine and Biotechnology, 2010, 2010(11).
[25]	QIN Y, YUAN Q, ZHANG Y, et al. Enzyme-assisted extraction optimization, characterization and antioxidant activity of polysaccharides from sea cucumber Phyllophorus proteus[J]. Molecules,2018,23(3):590. doi: 10.3390/molecules23030590
[26]	和英, 顾婷, 杨永寿, 等. 美洲大蠊提取物抗氧化活性研究[J]. 大理大学学报,2021,6(2):10−14. [HENG Y, GU T, YANG Y S, et al. Study on the antioxidant activity of different Periplaneta Americana extracts[J]. Journal of Dali University,2021,6(2):10−14. doi: 10.3969/j.issn.2096-2266.2021.02.002 HENG Y, GU T, YANG Y S, et al. Study on the antioxidant activity of different Periplaneta Americana extracts[J]. Journal of Dali University, 2021, 6(2): 10-14. doi: 10.3969/j.issn.2096-2266.2021.02.002
[27]	王婧, 陶爱恩, 杨燕, 等. 滇黄精中多糖的分离与抗氧化活性研究[J]. 中草药,2021,52(16):4789−4796. [WANG J, TAO A E, YANG Y, et al. Separation, physicochemical properties and anti-oxidant activities of three polysaccharides from Polygonatum kingianum[J]. Chinese Traditional and Herbal Drugs,2021,52(16):4789−4796. doi: 10.7501/j.issn.0253-2670.2021.16.004 WANG J, TAO A E, YANG Y, et al. Separation, physicochemical properties and anti-oxidant activities of three polysaccharides from Polygonatum kingianum[J]. Chinese Traditional and Herbal Drugs, 2021, 52(16): 4789-4796. doi: 10.7501/j.issn.0253-2670.2021.16.004
[28]	李霞, 胡楠, 赵启迪, 等. 肠浒苔多糖的羧甲基化修饰及其抗氧化活性研究[J]. 广西植物,2019,39(11):1519−1526. [LI X, HU N, ZHAO Q D, et al. Study on carboxymethylation modification and antioxidant activity of Enteromorpha prolifera polysaccharides[J]. Guangxi Botany,2019,39(11):1519−1526. doi: 10.11931/guihaia.gxzw201807003 LI X, HU N, ZHAO Q D, et al. Study on carboxymethylation modification and antioxidant activity of Enteromorpha prolifera polysaccharides [J]. Guangxi botany, 2019, 39(11): 1519-1526. doi: 10.11931/guihaia.gxzw201807003
[29]	谢建华. 青钱柳多糖的分子修饰及其生物活性研究[D]. 南昌: 南昌大学, 2014. XIE J H. Modification of polysaccharides from Cyclocarya paliurus and their biological activities[D]. Nanchang: Nanchang University, 2014.
[30]	步营, 吕月月, 朱文慧, 等. 基于模糊数学与响应面分析法开发味噌风味鲅鱼罐头[J]. 中国调味品,2021,46(9):90−94. [BU Y, LÜ Y Y, ZHU W H, et al. Development of canned miso-flavor spanish mackerel based on fuzzy mathematics and response surface analysis[J]. China Condiment,2021,46(9):90−94. doi: 10.3969/j.issn.1000-9973.2021.09.017 BU Y, LÜ Y Y, ZHU W H, et al. Development of canned miso-flavor spanish mackerel based on fuzzy mathematics and response surface analysis[J]. China Condiment, 2021, 46(9): 90-94. doi: 10.3969/j.issn.1000-9973.2021.09.017
[31]	FENG R F, KOU J J, CHEN S, et al. Preparation optimization, characterization, and antioxidant and prebiotic activities of carboxymethylated polysaccharides from jujube[J/OL]. Journal of Food Quality, 2021, https://doi.org/10.1155/2021/3268149.
[32]	陈阳, 孙代华, 江丹, 等. 响应面分析法优化艾叶药渣中白坚木皮醇乙醇提取工艺[J]. 中国食品添加剂,2021,32(9):90−96. [CHEN Y, SUN D H, JIANG D, et al. Optimization of quebrachitol ethanol extraction from Folium Artemisiae Argyi extraction dregs by response surface methodology (RSM)[J]. Chinese Food Additives,2021,32(9):90−96. CHEN Y, SUN D H, JIANG D, et al. Optimization of quebrachitol ethanol extraction from Folium Artemisiae Argyi extraction dregs by response surface methodology(RSM) [J]. Chinese food additives, 2021, 32(9): 90-96.
[33]	曹阔, 吴兴雨, 孙凯杨, 等. 响应面分析法优化酶法提取小米谷糠蛋白工艺[J]. 江苏农业科学,2021,49(18):169−173. [CAO K, WU X Y, SUN K Y, et al. Optimization of enzymatic extraction process of millet G protein by response surface methodology[J]. Jiangsu Agricultural Sciences,2021,49(18):169−173. CAO K, WU X Y, SUN K Y, et al. Optimization of enzymatic extraction process of millet G protein by response surface methodology[J]. Jiangsu Agricultural Sciences, 2021, 49(18): 169-173.
[34]	王银平. 玉木耳多糖的制备、结构表征及其与乳清蛋白相互作用研究[D] 长春: 吉林大学, 2020. WANG Y P. Preparation, structure characterization and interaction with whey protein of polysaccharides from Auricularia auriculata [D]. Changchun: Jilin University, 2020.
[35]	SUN L, MENG Y, SUN J, et al. Characterization, antioxidant activities and hepatoprotective effects of polysaccharides from pre-pressing separation Fuji apple peel[J]. Cyta Journal of Food,2017,15(2):307−319. doi: 10.1080/19476337.2016.1263241
[36]	LIN X, LIU K, YIN S, et al. A novel pectic polysaccharide of jujube pomace: structural analysis and intracellular antioxidant activities[J]. Antioxidants,2020,9(2):127. doi: 10.3390/antiox9020127
[37]	JI X, HOU C, YAN Y, et al. Comparison of structural characterization and antioxidant activity of polysaccharides from jujube (Ziziphus jujuba Mill.) fruit[J]. International Journal of Biological Macromolecules,2020,149:1008−1018. doi: 10.1016/j.ijbiomac.2020.02.018
[38]	何培新, 吴双双, 郑凯, 等. 杨树桑黄胞外多糖的分子结构及抗氧化活性[J]. 食品与生物技术学报,2018,37(9):939−947. [HE P X, WU S S, ZHENG K, et al. Molecular structure and antioxidant activity of polysaccharides from Phellinus vaninii Ljup[J]. Journal of Food Science and Biotechnology,2018,37(9):939−947. doi: 10.3969/j.issn.1673-1689.2018.09.007 HE P X, WU S S, ZHENG K, et al. Molecular structure and antioxidant activity of polysaccharides from Phellinus vaninii Ljup[J]. Journal of Food Science and Biotechnology, 2018, 37(9): 939-947. doi: 10.3969/j.issn.1673-1689.2018.09.007
[39]	陈义勇, 张阳. 杏鲍菇多糖羧甲基化修饰工艺及其抗氧化活性[J]. 食品与发酵工业,2016,42(7):119−127. [CHEN Y Y, ZHANG Y. Carboxymethylation modification and antioxidant activity of Pleurotus eryngii polysaccharides[J]. Food and Fermentation Industries,2016,42(7):119−127. CHEN Y Y, ZHANG Y. Carboxymethylation modification and antioxidant activity of Pleurotus eryngii polysaccharides[J]. Food and Fermentation Industries, 2016, 42(7): 119-127.
[40]	马诣欣. 橡木根皮多糖硫酸酯的制备、结构表征及抗氧化活性研究[D]. 兰州: 西北师范大学. MA Y X. Preparation, structure characterization and antioxidant activity of polysaccharide sulfate ester from oak root bark[D]. Lanzhou: Northwest Normal University.
[41]	白家峰, 姚延超, 郑毅, 等. 罗汉果多糖的羧甲基化修饰及抗氧化性能影响研究[J]. 湖北农业科学,2021,60(15):107−111. [BAI J F, YAO Y C, ZHENG Y, et al. Study on the effect of carboxymethylation of Siraitia grosvenorii polysaccharide on its antioxidant[J]. Hubei Agricultural Sciences,2021,60(15):107−111. BAI J F, YAO Y C, ZHENG Y, et al. Study on the effect of carboxymethylation of Siraitia grosvenorii polysaccharide on its antioxidant[J]. Hubei Agricultural Sciences, 2021, 60(15): 107-111.

Supplements (0)

Cited By

Cited by

Periodical cited type(2)

1.	赵志程，赵巍，张爱霞，刘敬科，生庆海，李朋亮. 脂质热解形成的挥发性成分及途径研究进展. 粮食与油脂. 2024(08): 12-18 .
2.	刘颖，黄小波. 食品中活泼羰基化合物研究进展. 中外食品工业. 2024(11): 43-45 .