研究报告

羟基红花黄色素A对晚期糖基化终末产物形成的抑制作用

  • 王佳敏 ,
  • 张博辉 ,
  • 王来忠 ,
  • 过利敏 ,
  • 包晓玮
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  • 1(新疆农业大学 食品科学与药学学院,新疆 乌鲁木齐,830052)
    2(新疆维吾尔自治区农业科学院 农产品加工研究所,新疆 乌鲁木齐,830091)
    3(新疆宏展特色农业科技开发有限公司,新疆 塔城,834800)
第一作者:硕士研究生(过利敏副研究员和包晓玮教授为共同通信作者,E-mail:guolm_xj@163.com;408531623@qq.com)

收稿日期: 2025-09-03

  修回日期: 2025-10-30

  网络出版日期: 2026-07-17

基金资助

新疆红花综合利用技术研究及产品创制(2023B02005-3);自治区杰出青年基金项目(2024D01E11);国家科技部外国专家引进项目(G2023046003L)

Inhibitory effect of hydroxysafflor yellow A on formation of advanced glycation end products

  • WANG Jiamin ,
  • ZHANG Bohui ,
  • WANG Laizhong ,
  • GUO Limin ,
  • BAO Xiaowei
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  • 1(School of Food Science and Pharmacy, Xinjiang Agricultural University, Urumqi 830052, China)
    2(Institute of Agro-Products Storage and Processing, Xinjiang Academy of Agricultural Sciences, Urumqi 830091, China)
    3(Xinjiang Hongzhan Characteristic Agricultural Technology Development Co.Ltd., Tacheng 834800, China)

Received date: 2025-09-03

  Revised date: 2025-10-30

  Online published: 2026-07-17

摘要

该研究旨在探讨羟基红花黄色素A(hydroxysafflor yellow A,HSYA)对晚期糖基化终末产物(advanced glycation end products,AGEs)形成的影响。通过构建牛血清白蛋白(bovine serum protein,BSA)-甲基乙二醛(methylglyoxal,MGO)糖基化模拟体系,结合光谱法、分子对接和SDS-PAGE等方法,检测体系中荧光性AGEs、蛋白质氧化产物(二酪氨酸、犬尿氨酸、N-甲酰犬尿氨酸),并研究HSYA与BSA的结合特征。结果表明,300 μmol/L的HSYA对荧光性AGEs、二酪氨酸、犬尿氨酸及N-甲酰犬尿氨酸的抑制率分别达到70.07%、51.71%、68.34%和80.37%。荧光光谱结果表明,HSYA与BSA之间有1类结合位点,猝灭机制为静态猝灭,且二者之间主要作用力为氢键和范德华力。SDS-PAGE结果表明,HSYA能够抑制BSA-MGO体系中BSA交联结构的形成。分子对接结果表明,HSYA可结合到BSA的TRP-213残基与BSA形成复合物,同时与BSA的ARG残基之间存在氢键和范德华力,阻碍BSA糖基化位点与MGO结合,从而抑制AGEs的产生。因此,HSYA具有开发为AGEs天然抑制剂的潜力。

本文引用格式

王佳敏 , 张博辉 , 王来忠 , 过利敏 , 包晓玮 . 羟基红花黄色素A对晚期糖基化终末产物形成的抑制作用[J]. 食品与发酵工业, 2026 , 52(12) : 161 -167 . DOI: 10.13995/j.cnki.11-1802/ts.044397

Abstract

This study aimed to explore the effect of hydroxysafflor yellow A (HSYA) on the formation of advanced glycation end products (AGEs).By establishing a simulated glycation system using bovine serum protein (BSA) and methylglyoxal (MGO), combined with spectroscopic analysis, molecular docking, and sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), this study quantitatively measured fluorescent AGEs, protein oxidation products (dityrosine, kynurenine, N-formylkynurenine) in the system to investigate the binding characteristics of HSYA with BSA.Results showed that HSYA at 300 μmol/L achieved inhibition rates of 70.07%, 51.71%, 68.34% and 80.37% on fluorescent AGEs, dityrosine, kynurenine and N-formylkynurenine, respectively.Fluorescence spectroscopy results showed that the existence of a binding site between HSYA and BSA.The quenching mechanism was static quenching and the main forces were hydrogen bonds and van der Waals forces.SDS-PAGE results showed that HSYA could inhibit the formation of BSA cross-linked structures in the BSA-MGO system.Molecular docking results showed that HSYA can bind to the TRP-213 residue of BSA to form a complex with BSA, and at the same time there is a hydrogen bond and van der Waals force between the ARG residue of BSA, which hinders the binding of BSA glycosylation sites to MGO, thereby inhibiting the production of AGEs.Therefore, HSYA has the potential to be developed as a natural inhibitor of AGEs.

参考文献

[1] LIANG Z L, CHEN X, LI L, et al.The fate of dietary advanced glycation end products in the body:From oral intake to excretion[J].Critical Reviews in Food Science and Nutrition, 2020, 60(20):3475-3491.
[2] YUAN X J, FENG S Q, LI J N, et al.Generation of advanced glycation end products from glycated protein or fructose/glyoxal-protein adducts under in vitro simulated gastrointestinal digestion[J].Food Chemistry, 2025, 463:141175.
[3] ZHANG C Y, GUO Y R, HOU T Y, et al.Formation of advanced glycation end products in glucose-amino acid models of Maillard reaction under dry- and wet- heating conditions[J].Journal of the Science of Food and Agriculture, 2025, 105(4):2342-2351.
[4] THORNALLEY P J.Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation endproducts[J].Archives of Biochemistry and Biophysics, 2003, 419(1):31-40.
[5] 王婉婷, 陈婉冰, 朱从一, 等.茶枝柑果皮类黄酮抑制AGEs的效果及作用机制[J].食品工业科技, 2025, 46(9):153-164.
WANG W T, CHEN W B, ZHU C Y, et al.Inhibitory effects of flavonoids from Citrus reticulata ‘Chachi’ peel on the formation of advanced glycation end-products[J].Science and Technology of Food Industry, 2025, 46(9):153-164.
[6] 张玉静. 矢车菊素-3-O-葡萄糖苷共价/非共价结合牛血清白蛋白抑制晚期糖基化终产物形成及其应用[D].南昌:南昌大学, 2022.
ZHANG Y J.Covalent / noncovalent binding of Gyanidin-3-O-Glucoside to bovine serum albumin inhibits the formation of advanced glycation end products and its application[D].Nanchang:Nanchang University, 2022.
[7] 郭芳瑜, 张南海, 邹晴如, 等.鸢尾苷对晚期糖基化终末产物形成的抑制作用[J].食品工业科技, 2024, 45(24):98-106.
GUO F Y, ZHANG N H, ZOU Q R, et al.Inhibitory effect of tectoridin on the formation of advanced glycation end products[J].Science and Technology of Food Industry, 2024, 45(24):98-106.
[8] 马新毅, 王梦娜, 曹彦刚, 等.红花中芳香苷类化学成分研究[J].中药材, 2024, 47(2):352-356.
MA X Y, WANG M N, CAO Y G, et al.Chemical constituents of aromatic glycosides from Carthamus tinctorius[J].Journal of Chinese Medicinal Materials, 2024, 47(2):352-356.
[9] ZHANG L L, TIAN K, TANG Z H, et al.Phytochemistry and pharmacology of Carthamus tinctorius L.[J].The American Journal of Chinese Medicine, 2016, 44(2):197-226.
[10] 白启荣, 郭姣洁, 吴娇.红花的化学成分及药理作用研究进展[J].新乡医学院学报, 2024, 41(1):88-94;100.
BAI Q R, GUO J J, WU J.Research progress on chemical constituents and pharmacological effects of safflower[J].Journal of Xinxiang Medical University, 2024, 41(1):88-94;100.
[11] SALEM N, MSAADA K, HAMDAOUI G, et al.Variation in phenolic composition and antioxidant activity during flower development of safflower (Carthamus tinctorius L.)[J].Journal of Agricultural and Food Chemistry, 2011, 59(9):4455-4463.
[12] 吴美云. 羟基红花黄色素A保护皮肤抵抗UVA及UVB诱导的氧化损伤的分子机制研究[D].上海:华东师范大学, 2018.
WU M Y.The mechanism of hydroxysafflor yellow A protecting the skin from UVA and UVB damage[D].Shanghai:East China Normal University, 2018.
[13] 张懿铭. 二氢槲皮素对晚期糖基化终末产物的抑制作用及机制研究[D].南昌:江西中医药大学, 2023.
ZHANG Y M.Study on the inhibitory effect and mechanism of taxifolin on the formation of advanced glycation end products[D].Nanchang:Jiangxi University of Chinese Medicine, 2023.
[14] WU X Q, ZHANG G W, HU M M, et al.Molecular characteristics of gallocatechin gallate affecting protein glycation[J].Food Hydrocolloids, 2020, 105:105782.
[15] TANG X D, CAI A, LI D L, et al.Jasmine (Jasminum officinale L.var.grandiflorum) flower extracts inhibit the formation of methylglyoxal induced advanced glycation endproducts[J].The FASEB Journal, 2019, 33(S1):471.21.
[16] DEZHAMPANAH H, MOHAMMADI A, MIANDEHI O R.Exploring binding characteristics of two azo disperse dyes with bovine serum albumin by spectroscopic and molecular docking techniques[J].Russian Journal of Physical Chemistry B, 2023, 17(2):251-261.
[17] QIN C, LI Y Q, ZHANG Y Z, et al.Insights into oat polyphenols constituent against advanced glycation end products mechanism by spectroscopy and molecular interaction[J].Food Bioscience, 2021, 43:101313.
[18] 于湛, 张微, 吴迪, 等.柚皮素、柚皮苷与牛血清白蛋白相互作用的机理分析[J].沈阳师范大学学报:自然科学版, 2023, 41(2):108-113.
YU Z, ZHANG W, WU D, et al.Mechanistic analysis the binding interactions of naringenin and naringin with bovine serum albumin[J].Journal of Shenyang Normal University(Natural Science Edition), 2023, 41(2):108-113.
[19] HUANG L Q, YANG X, PENG A L, et al.Inhibitory effect of leonurine on the formation of advanced glycation end products[J].Food & Function, 2015, 6(2):584-589.
[20] 罗娇依, 曹晨阳, 孙姗姗, 等.热加工食品中晚期糖基化终产物及其检测技术研究进展[J].食品安全质量检测学报, 2024, 15(24):77-85.
LUO J Y, CAO C Y, SUN S S, et al.Research progress on advanced glycosylation end products and detection method in thermal processed foods[J].Journal of Food Safety and Quality, 2024, 15(24):77-85.
[21] NI M T, SONG X, PAN J H, et al.Vitexin inhibits protein glycation through structural protection, methylglyoxal trapping, and alteration of glycation site[J].Journal of Agricultural and Food Chemistry, 2021, 69(8):2462-2476.
[22] SOBHY R, ZHAN F C, MEKAWI E, et al.The noncovalent conjugations of bovine serum albumin with three structurally different phytosterols exerted antiglycation effects:A study with AGEs-inhibition, multispectral, and docking investigations[J].Bioorganic Chemistry, 2020, 94:103478.
[23] JANA G, SING S, DAS A, et al.Interaction of food colorant indigo carmine with human and bovine serum albumins:A multispectroscopic, calorimetric, and theoretical investigation[J].International Journal of Biological Macromolecules, 2024, 259:129143.
[24] 闫焕, 康柱, 张炎, 等.多光谱法结合分子对接探究4种黄酮与β-乳球蛋白的相互作用[J].食品安全质量检测学报, 2024, 15(13):77-88.
YAN H, KANG Z, ZHANG Y, et al.Exploration on interaction between 4 kinds of flavonoids and β-lactoglobulin by multi-spectroscopy analysis and molecular docking[J].Journal of Food Safety and Quality, 2024, 15(13):77-88.
[25] 葛珍珍, 赵玉翔, 胡乔乔, 等.基于荧光光谱法探究柿原花青素与黏蛋白的相互作用机制[J].食品工业科技, 2025, 46(1):130-137.
GE Z Z, ZHAO Y X, HU Q Q, et al.Exploring the interaction mechanism between persimmon proanthocyanidins and mucin based on fluorescence spectroscopy[J].Science and Technology of Food Industry, 2025, 46(1):130-137.
[26] 谢格格, 张昊, 吴远杰, 等.基于荧光光谱法研究酪蛋白与茶黄素类的相互作用[J].茶叶, 2024, 50(2):83-87.
XIE G G, ZHANG H, WU Y J, et al.A study on interaction mechanism of casein and theaflavins using fluorescence spectrometry[J].Journal of Tea, 2024, 50(2):83-87.
[27] KOUR H D, PATHANIA A, PATHANIA A R.Insights into the binding of metadoxine with bovine serum albumin:A multi-spectroscopic investigation combined with molecular docking[J].Current Protein & Peptide Science, 2025, 26(3):213-225.
[28] LV Y F, LIANG Q Q, LI Y, et al.Study of the binding mechanism between hydroxytyrosol and bovine serum albumin using multispectral and molecular docking[J].Food Hydrocolloids, 2022, 122:107072.
[29] EL GAMMAL R N, ELMANSI H, EL-EMAM A A, et al.Exploring the molecular interaction of mebendazole with bovine serum albumin using multi-spectroscopic approaches and molecular docking[J].Scientific Reports, 2022, 12:11582.
[30] 王晓萌. 四种植物活性成分与血清蛋白相互作用机理研究[D].杭州:浙江农林大学, 2016.
WANG X M.The study of binding mechanism between four plant active ingredients of ecotope and serum albumin[D].Hangzhou:Zhejiang A&F University, 2016.
[31] MA T X, ZHANG L, XU L, et al.Mitigation of isoquercitrin on β-lactoglobulin glycation:Insight into the mechanisms by mass spectrometry and interaction analysis[J].International Journal of Biological Macromolecules, 2020, 155:1133-1141.
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