研究报告

3种氨基酸对模型葡萄酒溶液中锦葵素-3-O-葡萄糖苷辅色作用研究

  • 王静 ,
  • 刘晓蕊 ,
  • 吴静 ,
  • 李茹一
展开
  • 1(宁夏大学 食品科学与工程学院,宁夏 银川,750021)
    2(宁夏大学 葡萄酒与园艺学院,宁夏 银川,750021)
第一作者:硕士研究生(李茹一副教授为通信作者,E-mail:232183803@qq.com)

收稿日期: 2024-03-25

  修回日期: 2024-05-13

  网络出版日期: 2025-05-28

基金资助

贺兰山东麓产区风土对葡萄酒质量以及风格的影响(022104220004);高层次留学回国人员资助配套项目(022204220009)

The study of malvidin-3-O-glucoside copigmented by three amino acids in red wine model solutions

  • WANG Jing ,
  • LIU Xiaorui ,
  • WU Jing ,
  • LI Ruyi
Expand
  • 1(College of Food Science and Engineering, Ningxia University, Yinchuan 750021, China)
    2(College of Enology and Horticulture, Ningxia University, Yinchuan 750021, China)

Received date: 2024-03-25

  Revised date: 2024-05-13

  Online published: 2025-05-28

摘要

为探究芳香族氨基酸对花色苷颜色稳定性的影响,研究了3种氨基酸(L-苯丙氨酸、L-色氨酸和L-酪氨酸)与锦葵素-3-O-葡萄糖苷在红葡萄酒模型溶液中的辅色作用,以辅色效果和反应热力学参数为指标筛选最佳的辅色剂,并借助红外光谱、分子对接和分子动力学模拟分析其相互作用机制。结果表明,在最高物质的量比为1∶100时色氨酸辅色效果最佳(λmax提高了46.19%),并且ΔG°<0,为自发放热反应。傅里叶红外光谱、分子对接和分子动力学模拟结果表明,L-色氨酸可通过氢键和范德华力与锦葵素-3-O-葡萄糖苷相互作用,是提高氨基酸-锦葵素-3-O-葡萄糖苷复合物稳定性的主要驱动力。因此,在实际应用中可通过添加L-色氨酸用作辅色剂提高锦葵素-3-O-葡萄糖苷的稳定性。

本文引用格式

王静 , 刘晓蕊 , 吴静 , 李茹一 . 3种氨基酸对模型葡萄酒溶液中锦葵素-3-O-葡萄糖苷辅色作用研究[J]. 食品与发酵工业, 2025 , 51(9) : 196 -203 . DOI: 10.13995/j.cnki.11-1802/ts.039351

Abstract

In order to investigate the effect of aromatic amino acids on the colour stability of anthocyanin, the present experiments investigated the co-pigmentation of three amino acids (L-phenylalanine, L-tryptophan, and L-tyrosine) with malvidin-3-O-glucoside in a model solution of red wine, screened for the optimal co-pigment by using co-pigmentation and thermodynamic parameters of the reaction as the indexes, and analyzed the interaction using Fourier transform infrared (FT-IR) spectroscopy, molecular docking, and molecular simulation.The results showed that the best tryptophan co-pigment was achieved at the highest molar ratio of 1∶100 (λmax increased by 46.19%) and ΔG°<0, a spontaneous exothermic reaction.FT-IR.Molecular docking and molecular dynamics simulations showed that L-tryptophan can interact with malvidin-3-O-glucoside through hydrogen bonding and van der Waals forces, and is the main driving force to improve the stability of amino acid-malvidin-3-O-glucoside complexes.Therefore, the stability of malvidin-3-O-glucoside can be improved by adding L-tryptophan as a co-pigment in practical applications.

参考文献

[1] 张波. 红葡萄酒中橡木多酚辅色化机制研究[D].北京:中国农业大学, 2016.
ZHANG B.Research on the mechanism of cochromatisation of oak polyphenols in red wines [D].Beijing:China Agricultural University, 2016.
[2] 张扬, 彭晶晶, 李坤一, 等.发酵前添加有机酸对西拉红葡萄酒颜色和感官质量的影响[J].食品与发酵工业, 2023, 49(7):90-98.
ZHANG Y, PENG J J, LI K Y, et al.Effects of organic acid added before fermentation on color and sensory quality of Syrah red wine[J].Food and Fermentation Industries, 2023, 49(7):90-98.
[3] CZIBULYA Z, HORVÁTH I, KOLLÁR L, et al.The effect of temperature, pH, and ionic strength on color stability of red wine[J].Tetrahedron, 2015, 71(20):3027-3031.
[4] SUN X Y, SHOKRI S, GAO B H, et al.Improving effects of three selected co-pigments on fermentation, color stability, and anthocyanins content of blueberry wine[J].LWT, 2022, 156:113070.
[5] BOULTON R.The copigmentation of anthocyanins and its role in the color of red wine:A critical review[J].American Journal of Enology and Viticulture, 2001, 52(2):67-87.
[6] BROUILLARD R, DANGLES O.Anthocyanin molecular interactions:The first step in the formation of new pigments during wine aging?[J].Food Chemistry, 1994, 51(4):365-371.
[7] ASEN S, STEWART R N, NORRIS K H.Co-pigmentation of anthocyanins in plant tissues and its effect on color[J].Phytochemistry, 1972, 11(3):1 139-1 144.
[8] TÜRKYıLMAZ M, HAMZAOĞLU F, HANDENUR Ü, et al.Influence of amino acid addition on the thermal stability of anthocyanins in pomegranate (Punica granatum L., cv.Hicaznar) and orange (Citrus sinensis L.Osbeck, cv.Valencia) juice blend[J].Food Chemistry, 2022, 370:131061.
[9] CHUNG C, ROJANASASITHARA T, MUTILANGI W, et al.Stability improvement of natural food colors:Impact of amino acid and peptide addition on anthocyanin stability in model beverages[J].Food Chemistry, 2017, 218:277-284.
[10] ZHANG B, HE F, ZHOU P P, et al.Copigmentation between malvidin-3-O-glucoside and hydroxycinnamic acids in red wine model solutions:Investigations with experimental and theoretical methods[J].Food Research International, 2015, 78:313-320.
[11] MALAJ N, DE SIMONE B C, QUARTAROLO A D, et al.Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids[J].Food Chemistry, 2013, 141(4):3614-3620.
[12] 李伟, 席晓敏, 李辉, 等.贺兰山东麓赤霞珠干红葡萄酒陈酿过程中颜色变化研究[J].食品科学技术学报, 2020, 38(2):41-47.
LI W, XI X M, LI H, et al.Determination of color change during aging of cabernet sauvignon in eastern foothill of Helan Mountain[J].Journal of Food Science and Technology, 2020, 38(2):41-47.
[13] NIE M, WANG L, LU S M, et al.Protective effect of amino acids on the stability of bayberry anthocyanins and the interaction mechanism between L-methionine and cyanidin-3-O-glycoside[J].Food Chemistry, 2022, 396:133689.
[14] LI C X, WANG J X, LE Y, et al.Studies of bicalutamide-excipients interaction by combination of molecular docking and molecular dynamics simulation[J].Molecular Pharmaceutics, 2013, 10(6):2362-2369.
[15] STĂNCIUC N, OANCEA A M, APRODU I, et al.Investigations on binding mechanism of bioactives from elderberry (Sambucus nigra L.) by whey proteins for efficient microencapsulation[J].Journal of Food Engineering, 2018, 223:197-207.
[16] VAN DER SPOEL D, LINDAHL E, HESS B, et al.GROMACS:Fast, flexible, and free[J].Journal of Computational Chemistry, 2005, 26(16):1701-1718.
[17] DONNELLY S M, LOPEZ N A, DODIN I Y.Steepest-descent algorithm for simulating plasma-wave caustics via metaplectic geometrical optics[J].Physical Review, 2021, 104(2-2):025304.
[18] 赵磊, 潘飞, 周娜, 等.提高黑米花色苷颜色稳定性辅色剂的筛选及其作用机制[J].食品科学, 2021, 42(14):16-23.
ZHAO L, PAN F, ZHOU N, et al.Screening of co-pigments to improve color stability of black rice anthocyanins and underlying mechanism[J].Food Science, 2021, 42(14):16-23.
[19] BROUILLARD R, MAZZA G, SAAD Z, et al.The co-pigmentation reaction of anthocyanins:A microprobe for the structural study of aqueous solutions[J].Journal of the American Chemical Society, 1989, 111(7):2604-2610.
[20] CHUNG C, ROJANASASITHARA T, MUTILANGI W, et al.Enhanced stability of anthocyanin-based color in model beverage systems through whey protein isolate complexation[J].Food Research International, 2015, 76:761-768.
[21] 胡能兵, 隋益虎, 何克勤, 等.多糖、有机酸、氨基酸及其复配对紫色辣椒叶片色素辅色效果研究[J].基因组学与应用生物学, 2016, 35(3):715-720.
HU N B, SUI Y H, HE K Q, et al.Study of polysaccharides, organic acid, amino acid and its compound on copigmentation of leaf pigment in purple pepper[J].Genomics and Applied Biology, 2016, 35(3):715-720.
[22] KANHA N, SURAWANG S, PITCHAKARN P, et al.Copigmentation of cyanidin 3-O-glucoside with phenolics:Thermodynamic data and thermal stability[J].Food Bioscience, 2019, 30:100419.
[23] ACHARYA D P, SANGUANSRI L, AUGUSTIN M A.Binding of resveratrol with sodium caseinate in aqueous solutions[J].Food Chemistry, 2013, 141(2):1050-1054.
[24] 汤晓宏, 丁燕, 高德艳, 等.基于CIELab色空间法分析海底陈酿对葡萄酒色泽的影响[J].中外葡萄与葡萄酒, 2022(5):88-92.
TANG X H, DING Y, GAO D Y, et al.Effect of seafloor storage on wine colour based on CIELab colour space system[J].Sino-Overseas Grapevine & Wine, 2022(5):88-92.
[25] SOCRATES G.Infrared and Raman characteristic group frequencies:tables and charts[M].3rd ed.Chichester:Wiley, 2001.
[26] HERNÁNDEZ B, PFLÜGER F, ADENIER A, et al.Vibrational analysis of amino acids and short peptides in hydrated media.VIII.Amino acids with aromatic side chains:L-phenylalanine, L-tyrosine, and L-tryptophan[J].2010, 114(46):15319-15330.
[27] 聂铭. 氨基酸对杨梅花色苷稳定性的影响及相互作用研究[D].舟山:浙江海洋大学, 2022.
NIE M.Effects of amino acids on the stability of poplar plum anthocyanosides and the study of interactions [D].Zhoushan:Zhejiang Ocean University, 2022.
[28] AHMAD BHAT S, AHMAD S.FTIR, FT-Raman and UV-Vis spectral studies of D-tyrosine molecule[J].Journal of Molecular Structure, 2016, 1105:169-177.
[29] FAIZAN M, AHMAD S.Experimental vibrational spectroscopy (FTIR and FT-Raman) of D-tryptophan and its anharmonic theoretical studies using density functional theory[J].Journal of Molecular Structure, 2018, 1171:315-322.
[30] ZHANG B, WANG Q, ZHOU P P, et al.Copigmentation evidence of oenin with phenolic compounds:A comparative study of spectrographic, thermodynamic and theoretical data[J].Food Chemistry, 2020, 313:126163.
[31] 吴健妹, 张国文.三种糖基化中间产物与小牛胸腺DNA相互作用的多光谱和分子动力学模拟[J].南昌大学学报(理科版), 2023, 47(3):243-254.
WU J M, ZHANG G W.Multispectral and molecular dynamics simulation studies of the interaction of three glycosylation intermediates with calf Thymus DNA[J].Journal of Nanchang University (Natural Science), 2023, 47(3):243-254.
[32] XU X J, FANG S, LI Y H, et al.Effects of low acyl and high acyl gellan gum on the thermal stability of purple sweet potato anthocyanins in the presence of ascorbic acid[J].Food Hydrocolloids, 2019, 86:116-123.
[33] ZHOU R, DONG X Y, SONG L L, et al.Interaction mode and nanoparticle formation of bovine serum albumin and anthocyanin in three buffer solutions[J].Journal of Luminescence, 2014, 155:244-250.
[34] ZHAO L, PAN F, MEHMOOD A, et al.Improved color stability of anthocyanins in the presence of ascorbic acid with the combination of rosmarinic acid and xanthan gum[J].Food Chemistry, 2021, 351:129317.
[35] ZHAO L, PAN F, MEHMOOD A, et al.Protective effect and mechanism of action of xanthan gum on the color stability of black rice anthocyanins in model beverage systems[J].International Journal of Biological Macromolecules, 2020, 164:3800-3807.
文章导航

/

〈 〉