Research progress on isolation and purification of peptides from Huangjiu and their functions

  • FANG Shiqi ,
  • REN Qingxi ,
  • ZHOU Zhilei ,
  • JI Zhongwei ,
  • ZHOU Jiandi ,
  • XU Yuezheng ,
  • MAO Jian
Expand
  • 1(School of Food Sciences and Technology, Jiangnan University, Wuxi 214000, China)
    2(Jiangnan University (Shaoxing) Industrial Technology Research Institute, Shaoxing 312000, China)
    3(Zhejiang Guyuelongshan Shaoxing Wine Co.Ltd., Shaoxing 312000, China)

Received date: 2024-08-12

  Revised date: 2024-09-23

  Online published: 2025-05-28

Abstract

Huangjiu, widely distributed in various regions of China, is one of the fermented alcoholic beverages with the richest peptide content.Peptides, as important functional ingredients in Huangjiu, contribute to its distinctive flavor profiles and diverse biological activities.In the paper, the common methods for the separation and purification methods of peptides in Huangjiu were systematically reviewed, and some potential novel technologies, including molecularly imprinted membranes and magnetic nanoparticles, were introduced in detail.In addition, the identification of Huangjiu peptides was also outlined from the two aspects of database-driven comparison and de novo sequencing, and its flavor sensory and biological functionalities were summarized, aiming to offer a theoretical framework and practical guidance for enhancing the healthcare benefits and the high-quality development of Huangjiu.

Cite this article

FANG Shiqi , REN Qingxi , ZHOU Zhilei , JI Zhongwei , ZHOU Jiandi , XU Yuezheng , MAO Jian . Research progress on isolation and purification of peptides from Huangjiu and their functions[J]. Food and Fermentation Industries, 2025 , 51(8) : 341 -350 . DOI: 10.13995/j.cnki.11-1802/ts.040716

References

[1] 于抗非, 毛青钟, 裘哲灵, 等.小米黄酒酿造工艺及体外抗氧化活性研究[J].酿酒, 2024, 51(1):87-94.
YU K F, MAO Q Z, QIU Z L, et al.Study on brewing technology and antioxidant activity in vitro of millet Huangjiu[J].Liquor Making, 2024, 51(1):87-94.
[2] 阮凤喜. 半干型客家黄酒工艺优化及风味物质的研究[D].广州:仲恺农业工程学院, 2022.
RUAN F X.Research on process optimization and flavor compounds of semi-dry Hakka Huangjiu[D].Guangzhou:Zhongkai University of Agriculture and Engineering, 2022.
[3] 汪江波, 王浩, 孔博, 等.黄酒酿造技术研究进展[J].酿酒, 2020, 47(6):26-30.
WANG J B, WANG H, KONG B, et al.Recent advances in Huangjiu fermentation technology[J].Liquor Making, 2020, 47(6):26-30.
[4] 毛青钟, 宣贤尧.绍兴黄酒的酿造特点[J].中国酿造, 2006,25(4):5-8.
MAO Q Z, XUAN X Y.Brewing characteristics of Shaoxing Huangjiu[J].China Brewing, 2006,25(4):5-8.
[5] 罗浩怡, 曾林, 张雅琦, 等.黄酒中多肽的研究进展[J].现代食品, 2021, 27(2):85-88.
LUO H Y, ZENG L, ZHANG Y Q, et al.Research progress of peptides in Huangjiu[J].Modern Food, 2021, 27(2):85-88.
[6] LU Q Y, LEE R P, HUANG J J, et al.Quantification of bioactive constituents and antioxidant activity of Chinese yellow wine[J].Journal of Food Composition and Analysis, 2015, 44:86-92.
[7] 周梦洁. 黄酒肽的分离纯化、结构鉴定及其降血糖活性研究[D].杭州:浙江大学, 2021.
ZHOU M J.Studies on the purification, identification, and hypoglycemic activity of peptides from Chinese rice wine[D].Hangzhou:Zhejiang University, 2021.
[8] 谢广发, 戴军, 赵光鳌, 等.科学认识黄酒的保健养生功能[J].中国酿造, 2004,23(1):30-31.
XIE G F, DAI J, ZHAO G A, et al.Understanding scientifically the health-protect function of rice wine[J].China Brewing, 2004,23(1):30-31.
[9] CHANG R, ZHOU Z L, DONG Y, et al.Ion-exchange purification, nano-HPLC-MS/MS identification and molecular dynamics simulation of novel umami peptides from fermented grain wine (Huangjiu)[J].Journal of Food Composition and Analysis, 2024, 125:105822.
[10] HAN F L, XU Y.Identification of low molecular weight peptides in Chinese rice wine (Huang Jiu) by UPLC-ESI-MS/MS[J].Journal of the Institute of Brewing, 2011, 117(2):238-250.
[11] 王正元. 黍米黄酒生物活性肽的分离鉴定及功能性研究[D].郑州:河南工业大学, 2015.
WANG Z Y. Isolation, identification and functional study of bioactive peptides from millet rice wine[D]. Zhengzhou: Henan University of Technology, 2015.
[12] GUO J B, LU A C, SUN Y N, et al.Purification and identification of antioxidant and angiotensin converting enzyme-inhibitory peptides from Guangdong glutinous rice wine[J].LWT, 2022, 169:113953.
[13] YU H Y, WANG X Y, XIE J R, et al.Isolation and identification of bitter-tasting peptides in Shaoxing rice wine using ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry combined with taste orientation strategy[J].Journal of Chromatography A, 2022, 1676:463193.
[14] SHI Y, FENG R X, MAO J Q, et al.Structural characterization of peptides from Huangjiu and their regulation of hepatic steatosis and gut microbiota dysbiosis in hyperlipidemia mice[J].Frontiers in Pharmacology, 2021, 12:689092
[15] 戴军, 谢广发, 陈尚卫, 等.绍兴黄酒中一种ACE活性抑制肽的分离和鉴定[J].食品与发酵工业, 2005, 31(5):98-101.
DAI J, XIE G F, CHEN S W, et al.Isolation and identification of inhibitory peptides for angiotensin converting enzyme in Shaoxing rice wine[J].Food and Fermentation Industries, 2005, 31(5):98-101.
[16] 李燕, 陆丽利, 郑校先, 等.大孔树脂吸附黄酒中活性肽的研究[J].化学研究与应用, 2010, 22(10):1272-1277.
LI Y, LU L L, ZHENG X X, et al.Study on the separation of peptides from Chinese rice wine by macroporous resin[J].Chemical Research and Application, 2010, 22(10):1272-1277.
[17] CHANG R, ZHOU Z L, DONG Y, et al.Sensory-guided isolation, identification, and active site calculation of novel umami peptides from ethanol precipitation fractions of fermented grain wine (Huangjiu)[J].Foods, 2023, 12(18):3398.
[18] ZHANG B, GUAN Z B, CAO Y, et al.Secretome of aspergillus oryzae in Shaoxing rice wine koji[J].International Journal of Food Microbiology, 2012, 155(3):113-119.
[19] ZHENG X Q, CHI H, MA S, et al.Identification of novel α-glucosidase inhibitory peptides in rice wine and their antioxidant activities using in silico and in vitro analyses[J].LWT-Food Science and Technology, 2023, 178:114629.
[20] 孟如杰. 黄酒中抗氧化活性物质的研究[D].无锡:江南大学, 2008.
MENG R J. Study on antioxidant active substances in yellow rice wine[D]. Wuxi: Jiangnan University, 2008.
[21] LU Z D, XIE G F, WU D H, et al.Isolation and identification of the bitter compound from Huangjiu[J].Food Chemistry, 2021, 349:129133.
[22] YANG H, LIU H B, TANG Z S, et al.Synthesis, performance, and application of molecularly imprinted membranes:A review[J].Journal of Environmental Chemical Engineering, 2021, 9(6):106352.
[23] SUN G L, LU Y.A novel one-pot strategy of preparation of N-phenylacrylamide-styrene co-polymer open tubular capillary column for peptides separation[J].Journal of Separation Science, 2020, 43(24):4461-4468.
[24] FENG X Z, LIAO D K, SUN L X, et al.Affinity purification of angiotensin converting enzyme inhibitory peptides from wakame (Undaria Pinnatifida) using immobilized ACE on magnetic metal organic frameworks[J].Marine Drugs, 2021, 19(3):177.
[25] CAI H Y, ZHANG Q, SHEN L Z, et al.Phenolic profile and antioxidant activity of Chinese rice wine fermented with different rice materials and starters[J].LWT-Food Science and Technology, 2019, 111:226-234.
[26] WANG H, LIU R R, LIU Y F, et al.Investigation on adsorption mechanism of peptides with surface-modified super-macroporous resins[J].Langmuir, 2019, 35(13):4471-4480.
[27] ULBRICHT M.Membrane separations using molecularly imprinted polymers[J].Journal of Chromatography B, 2004, 804(1):113-125.
[28] OKUTUCU B, ZIHNIOGLU F.Different approaches to synthesize carnosine selective imprinted polymers[J].Materials Science and Engineering:C, 2012, 32(5):1174-1178.
[29] BUI B T S, MIER A, HAUPT K.Molecularly imprinted polymers as synthetic antibodies for protein recognition:The next generation[J].Small, 2023, 19(13):2206453.
[30] ZHANG M Y, WANG Y F, HU K L, et al.Molecularly imprinted polymer with high capacity and selectivity for separation of bovine serum albumin[J].ACS Applied Polymer Materials, 2023, 5(12):9751-9760.
[31] GUMMADI S, KANDULA V N.A review on electrophoresis, capillary electrophoresis and hyphenations[J].International Journal of Pharmaceutical Sciences and Research, 2020, 11(12):6038-6056.
[32] ALI F, ALOTHMAN Z A, AL-SHAALAN N H.Mixed-mode open tubular column for peptide separations by capillary electrochromatography[J].Journal of Separation Science, 2021, 44(13):2602-2611.
[33] NAITHANI V, CHEDDAH S, YANG K G, et al.Preparation of open tubular capillary column covalently coated with polystyrene sulfonate with 4,4′-Azobis(4-cyanopentanoyl chloride) as polymerization initiator for electrochromatographic separation of alkaloids, sulfonamides, and peptides[J].Journal of Separation Science, 2023, 46(10):2200711.
[34] MITTAL A, ROY I, GANDHI S.Magnetic nanoparticles:an overview for biomedical applications[J].Magnetochemistry, 2022, 8(9):107.
[35] EIVAZZADEH-KEIHAN R, BAHREINIZAD H, AMIRI Z, et al.Functionalized magnetic nanoparticles for the separation and purification of proteins and peptides[J].TrAC Trends in Analytical Chemistry, 2021, 141:116291.
[36] WANG J D, HAN Q, WANG K, et al.Recent advances in development of functional magnetic adsorbents for selective separation of proteins/peptides[J].Talanta, 2023, 253:123919.
[37] LU Y, WU Y J, HOU X H, et al.Separation and identification of ACE inhibitory peptides from lizard fish proteins hydrolysates by metal affinity-immobilized magnetic liposome[J].Protein Expression and Purification, 2022, 191:106027.
[38] ZHANG Y Y, LIU L H, ZHANG M, et al.The research progress of bioactive peptides derived from traditional natural products in China[J].Molecules, 2023, 28(17):6421.
[39] MUTH T, HARTKOPF F, VAUDEL M, et al.A potential golden age to come: Current tools, recent use cases, and future avenues for de novo sequencing in proteomics[J].Proteomics, 2018, 18(18):e1700150.
[40] NG C C A, ZHOU Y, YAO Z P.Algorithms for de-novo sequencing of peptides by tandem mass spectrometry:A review[J].Analytica Chimica Acta, 2023, 1268:341330.
[41] MEDZIHRADSZKY K F, CHALKLEY R J.Lessons in de novo peptide sequencing by tandem mass spectrometry[J].Mass Spectrometry Reviews, 2015, 34(1):43-63.
[42] ALLMER J.Algorithms for the de novo sequencing of peptides from tandem mass spectra[J].Expert Review of Proteomics, 2011, 8(5):645-657.
[43] ZHANG S, SHAN Y C, ZHANG S R, et al.NIPTL-Novo:Non-isobaric peptide termini labeling assisted peptide de novo sequencing[J].Journal of Proteomics, 2017, 154:40-48.
[44] ASHBY M, PETKOVA A, GANI J, et al.Use of peptide libraries for identification and optimization of novel antimicrobial peptides[J].Current Topics in Medicinal Chemistry, 2017, 17(5):537-553.
[45] AGYEI D, TSOPMO A, UDENIGWE C C.Bioinformatics and peptidomics approaches to the discovery and analysis of food-derived bioactive peptides[J].Analytical and Bioanalytical Chemistry, 2018, 410(15):3463-3472.
[46] DU Z J, COMER J, LI Y H.Bioinformatics approaches to discovering food-derived bioactive peptides:Reviews and perspectives[J].TrAC Trends in Analytical Chemistry, 2023, 162:117051.
[47] LÓPEZ-MARTÍNEZ R, LIZBETH RAMÍREZ-SALINAS G, CORREA-BASURTO J, et al. Inhibition of influenza A virus infection in vitro by peptides designed in silico[J]. PLoS One, 2013, 8(10): e76876.
[48] ZHUANG M Z, ZHAO M M, LIN L Z, et al.Macroporous resin purification of peptides with umami taste from soy sauce[J].Food Chemistry, 2016, 190:338-344.
[49] 黄岩, 史伊格, 梁莉, 等.食品中苦味物质的感知与调控研究进展[J].食品科学, 2023, 44(11):185-195.
HUANG Y, SHI Y G, LIANG L, et al.Research progress on perception and regulation of bitter compounds in foods[J].Food Science, 2023, 44(11):185-195.
[50] 徐亚光, 杜传来.鲜味和鲜味肽的研究进展[J].赤峰学院学报(自然科学版), 2024, 40(2):6-13.
XU Y G, DU C L.Research progress of umami taste and umami peptides[J].Journal of Chifeng University (Natural Science Edition), 2024, 40(2):6-13.
[51] GURDA D, KIETRYS A M, SZOPA A, et al.Life with oxidative stress[J].Chemical and Process Engineering, 2012, 33(4):509-528.
[52] GULCIN I·.Antioxidants and antioxidant methods:An updated overview[J].Archives of Toxicology, 2020, 94(3):651-715.
[53] 张红玉, 李会珍, 张天伟, 等.抗氧化肽作用机制研究进展[J].食品安全质量检测学报, 2022, 13(12):3981-3988.
ZHANG H Y, LI H Z, ZHANG T W, et al.Research progress on the mechanism of antioxidant peptides[J].Journal of Food Safety and Quality, 2022, 13(12):3981-3988.
[54] NORAMBUENA-SOTO I, LOPEZ-CRISOSTO C, MARTINEZ-BILBAO J, et al.Angiotensin-(1-9) in hypertension[J].Biochemical Pharmacology, 2022, 203:115183.
[55] ZIAJA M, URBANEK K A, KOWALSKA K, et al.Angiotensin II and angiotensin receptors 1 and 2-multifunctional system in cells biology, what do we know?[J].Cells, 2021, 10(2):381.
[56] MARTYNIAK A, TOMASIK P J.A new perspective on the renin-angiotensin system[J].Diagnostics, 2022, 13(1):16.
[57] GIANI J F, VEIRAS L C, SHEN J Z Y, et al.Novel roles of the renal angiotensin-converting enzyme[J].Molecular and Cellular Endocrinology, 2021, 529:111257.
[58] 王宝贝, 张慧, 刘宇松, 等.食源性多肽的降血压作用及其机制研究进展[J].食品与机械, 2024, 40(3):217-224.
WANG B B, ZHANG H, LIU Y S, et al.Research progress on the mechanism of food-derived antihypertensive peptides[J].Food and Machinery, 2024, 40(3):217-224.
[59] 张钰. 柽柳提取物对小鼠酒精性肝损伤的保护作用及其作用机制研究[D].济南:济南大学, 2017.
ZHANG Y.Study on the protective effect and mechanism of tamarisk extract on alcoholic liver injury in mice[D] Jinan:Jinan University, 2017.
[60] YAN Y H, LI Y Z, ZHANG Z W, et al.Advances of peptides for antibacterial applications[J].Colloids and Surfaces B:Biointerfaces, 2021, 202:111682.
[61] CIULLA M G, GELAIN F.Structure-activity relationships of antibacterial peptides[J].Microbial Biotechnology, 2023, 16(4):757-777.
[62] DI SOMMA A, MORETTA A, CANè C, et al.Antimicrobial and antibiofilm peptides[J].Biomolecules, 2020, 10(4):652.
[63] 杨慧.黄酒对大肠杆菌的抗菌活性研究[D].洛阳:河南科技大学, 2011.
YANG H.Study on the antibacterial activity of Huangjiu against Escherichia coli[D] Luoyang:Henan University of Science and Technology, 2011.
[64] 杨晨远, 于子川, 秦迪, 等.抗菌肽的结构分析、抗菌机制及改造应用的研究进展[J].微生物学报, 2024, 64(7):2242-2259.
YANG C Y, YU Z C, QIN D, et al.Research progress in structures, mechanisms, and modification of antimicrobial peptides[J].Acta Microbiologica Sinica, 2024, 64(7):2242-2259.
[65] 冯瑞雪, 史瑛, 姬中伟, 等.黄酒多肽的多级分离纯化及其对小鼠巨噬细胞免疫调节的影响[J].食品工业科技, 2020, 41(13):289-295.
FENG R X, SHI Y, JI Z W, et al.Multistep separation and purification of Huangjiu peptides and its effects on the immune regulation of macrophage in mice[J].Science and Technology of Food Industry, 2020, 41(13):289-295.
Outlines

/

〈 〉