羧基化胶原纤维的制备及其对黄酮苷类化合物的分离特性

doi:10.19677/j.issn.1004-7964.2023.06.002

皮革科学与工程 ›› 2023, Vol. 33 ›› Issue (6): 8-16.doi: 10.19677/j.issn.1004-7964.2023.06.002

羧基化胶原纤维的制备及其对黄酮苷类化合物的分离特性

张琦弦^1,2, 孙青永¹, 石碧^1,2,*

1.四川大学轻工科学与工程学院,四川成都 610065;
2.四川大学制革清洁技术国家工程实验室,四川成都 610065

收稿日期:2023-08-06 出版日期:2023-12-01 上线日期:2023-11-14
通讯作者: *石碧(1958-),男,博士,教授,主要从事制革化学、制革清洁技术、胶原资源化利用等研究。E-mail: shibi@scu.edu.cn。
作者简介:张琦弦(1988-),女,硕士,副编审,主要从事胶原基材料功能化研究。E-mail: zhangqx@scu.edu.cn。
基金资助:
国家自然科学基金(21978176)

Preparation of Carboxyl Grafted Collagen Fiber and its Separation Performances for Flavonoid Glycosides

ZHANG Qixian^1,2, SUN Qingyong¹, SHI Bi^1,2,*

1. College of Biomass Science and Engineering, Sichuan University, Chengdu 610065, China;
2. National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, China

Received:2023-08-06 Online:2023-12-01 Published:2023-11-14

摘要/Abstract

摘要： 胶原纤维(CF)可以基于氢键和疏水作用分离黄酮类化合物,但CF对于含葡萄糖基的黄酮苷具有过强的氢键作用,黄酮苷在CF层析柱上洗脱峰拖尾、回收率低。研究利用乙醛酸(GA)将羧基(-COOH)接枝到CF上,增大CF亲水性,提高其与黄酮苷的静电斥力,削弱两者之间的氢键作用,改善黄酮苷洗脱和分离性能。水接触角、水吸收时间和等电点(pI)测定结果表明-COOH成功接枝到了CF上,使GA改性CF(GA-CF)亲水性增大,pI降低。差示扫描量热仪和扫描电镜测定结果表明GA-CF保留了胶原纤维的热稳定性和纤维结构。相比CF,GA-CF对黄芩苷和杨梅苷(黄酮苷代表物)的洗脱和分离效率增大,纯度和回收率显著提高,其分离效率高于聚酰胺,接近Sephadex LH-20,具有良好的应用潜力。

关键词: 胶原, 改性, 柱层析填料, 黄酮苷, 分离

Abstract: Collagen fiber (CF) was previously used as packing material for the separation of flavonoids based on hydrogen bond and hydrophobic interactions. However, as for flavonoid glycosides which are rich in hydroxyls in forming hydrogen bonds, CF presented excessive adsorption capacity, causing the peak tailing and low recovery in column separation. In order to weaken the hydrogen bond interaction and improve the elution rate, carboxyls (-COOHs) were grafted on CF in this work by using glyoxylic acid (GA) to enhance the hydrophilicity of CF and the electrostatic repulsion between CF and flavonoid glycosides. Results of water contact angle, absorption time of water and isoelectric point (pI) determinations proved the successful grafting of -COOHs, and the obtained GA-modified collagen fiber (GA-CF) showed significantly enhanced hydrophilicity and decreased pI. Results of differential scanning calorimetry and scanning electron microscope determinations proved that the thermal stability and special fiber structure of collagen fiber were retained after the reacting with GA. In comparison with CF, GA-CF showed higher elution rates and separation efficiency to baicalin and myricitrin (the typical flavonoid glycosides), leading to much higher purities and recoveries. In fact, the separation performance of flavonoid glycosides on GA-CF was better than that on polyamide and comparable to Sephadex LH-20.

Key words: collagen, modification, packing material, flavonoid glycosides, separation

中图分类号:

TS512
O636

张琦弦, 孙青永, 石碧. 羧基化胶原纤维的制备及其对黄酮苷类化合物的分离特性[J]. 皮革科学与工程, 2023, 33(6): 8-16.

ZHANG Qixian, SUN Qingyong, SHI Bi. Preparation of Carboxyl Grafted Collagen Fiber and its Separation Performances for Flavonoid Glycosides[J]. Leather Science and Engineering, 2023, 33(6): 8-16.

参考文献

[1] Zhang X X, Xu S C, Shen L R, et al.Factors affecting thermal stability of collagen from the aspects of extraction, processing and modification[J]. Journal of Leather Science and Engineering, 2020, 2: 19.
[2] Ke L, Wang Y P, Ye X X, et al.Collagen-based breathable, humidity-ultrastable and degradable on-skin device[J]. Journal of Materials Chemistry C, 2019, 7(9): 2548-2556.
[3] 刘文涛,白聪,沈里瑞.黑鱼胶原溶液的流变、热稳定性及化学交联改性研究[J].皮革科学与工程,2022,32(1):1-8.
[4] Tanrikulu I C,Westler W M,Ellison A J,et al.Templated collagen"double helices"maintain their structure[J].Journal of the American Chemical Society,2020,142(3):1137-1141.
[5] Nelson D M,Stanelle R D,Brown P,et al.Capillary-channeled polymer(C-CP)fibers:A novel platform for liquid-phase separations[J].American Laboratory,2005,37(13):28-32.
[6] 金杜欣,曹维,赵秀丽,等.肠道菌群对黄酮类化合物的代谢作用及生物学活性影响研究进展[J].食品与发酵工业,https://doi.org/10.13995/j.cnki.11-1802/ts.036157.
[7] 张亚楠,刘天娇,王君.植物黄酮类化合物的生理功能及在水产动物生长中的应用进展[J].饲料研究,https://link.cnki.net/urlid/11.2114.S.20230808.1038.002.
[8] 周易,杨丽,党逸云,等.淡竹叶黄酮类成分的研究[J].中成药,2023,45(1):112-118.
[9] 薄亚茹,袁艺珍,王景丽,等.三尖杉茎叶中黄酮类化合物的研究[J].中国药物化学杂志,2023,33(1):35-41.
[10] 吴萌萌,刘怡,严馨,等.苦荞麸皮黄酮提取物及有效成分的抑菌活性[J].食品与生物技术学报,2021,40(11):77-83.
[11] 杨怡萌,杨广梅,王仲明,等.荷叶黄酮自由基清除活性的量子化学研究[J].分子科学学报,2020,36(6):489-496.
[12] 刘晓艳,徐嵬,杨秀伟,等.鸡血藤黄酮类化学成分的分离与鉴定[J].中国中药杂志,2020,45(6):1384-1392.
[13] 芦宇,吕长鑫,焦天慧,等.聚酰胺纯化红树莓籽黄酮及其结合胆酸盐能力评价[J].中国食品学报. 2019,19(10):172-178.
[14] Zhang X Y,Wang R T,Zhao Y Y,et al.Separation and purification of flavonoids from polygonum cuspidatum using macroporous adsorption resin[J].Pigment and Resin Technology,2021,50:574-584.
[15] 王晓娅,苏建青,褚秀玲.大孔树脂分离纯化黄酮类化合物的研究进展[J].食品科技,2021,46(8):208-212.
[16] 徐赫,李荣华,夏岩石,等.黄酮类化合物提取、分离纯化方法研究现状及展望[J].应用化工,2021,50(6):1677-1682.
[17] 朱玉洁. 葡聚糖凝胶柱层析富集黑果枸杞总花色苷工艺及其抗氧化性研究[J].食品研究与开发,2020,41(7):12-18.
[18] Zhang Q X,Li J,Zhang W H,et al.Adsorption chromatography separation of baicalein and baicalin using collagen fiber adsorbent[J].Industrial and Engineering Chemistry Research,2013,52:2425-2433.
[19] Zhang Q X,Sun Q Y,Wang R,et al.Controllably adjusting the hydrophobicity of collagen fibers for enhancing the adsorption rate,retention capacity,and separation performance of flavonoid aglycones[J].ACS Applied Materials&Interfaces,2023,15:18516-18527.
[20] 陈丛瑾,屈丽娟,陈东.双水相萃取法分离纯化黄酮类化合物的研究进展[J].应用化工,2010,39(10):1587-1596.
[21] Maleki R,Khoshoei A,Ghasemy E,et al.Molecular insight into the smart functionalized TMC-Fullerene nanocarrier in the pH-responsive adsorption and release of anti-cancer drugs[J].Journal of Molecular Graphics and Modelling,2020,100:107660.
[22] Roman G,Noseda Grau E,Diaz Company A,et al.pH dependence of dacarbazine adsorption on activated carbon DFT study[J].EPL,2019,126:58002.
[23] Kordzadeh A,Amjad-Iranagh S,Zarif M,et al.Adsorption and encapsulation of the drug doxorubicin on covalent functionalized carbon nanotubes:A scrutinized study by using molecular dynamics simulation and quantum mechanics calculation[J].Journal of Molecular Graphics and Modelling,2019,88:11-22.
[24] Xia Y C,Yang Z L,Zhang R,et al.Enhancement of the surface hydrophobicity of low-rank coal by adsorbing DTAB:An experimental and molecular dynamics simulation study[J].Fuel,2019,239:145-152.
[25] Kim T,Kwon Y,Kwon S.Bromination effect of polybrominated diphenyl ethers on the graphyne surface on enhanced adsorption characteristics[J].AIP Advances,2020,10:075117.
[26] Liao X P,Shi B.Selective removal of tannins from medicinal plant extracts using a collagen fiber adsorbent[J].Journal of the Science of Food and Agriculture,2005,85:1285-1291.
[27] Li J,Liao X P,Liao G H,et al.Separation of flavonoid and alkaloid using collagen fiber adsorbent[J].Journal of Separation Science,2010,33(15):2230-2239.
[28] Ding P P,Liao X P,Shi B.Adsorption chromatography separation of the flavonols kaempferol,quercetin and myricetin using cross-linked collagen fibre as the stationary phase[J].Journal of the Science of Food and Agriculture,2013,93:1575-1583.
[29] 周强,刘建伟,刘智勇.离子交换法分离纯化木糖母液[J].精细石油化工,2010,27(2):32-34.
[30] Iwaki S,Fu B X,Hayakawa K.Behavior of protein aggregates via electrostatic interactions or hydrogen bonds during dough formation[J].Journal of Cereal Science,2023,111:103683.
[31] Jadhav V,Kumbhar R,Tamhankar B,et al.Volumetric and compressibility studies and phase equilibria of aqueous biphasic systems of alcohols using phase diagram[J].SN Applied Sciences,2019,1:673.
[32] Wu B,Wang N X,Shen Y,et al.Inorganic salt regulated zwitterionic nanofiltration membranes for antibiotic/monovalent salt separation[J].Journal of Membrane Science,2023,666:121144.

羧基化胶原纤维的制备及其对黄酮苷类化合物的分离特性

Preparation of Carboxyl Grafted Collagen Fiber and its Separation Performances for Flavonoid Glycosides

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