HONG Senhui, YANG Xiuwen, HUANG Xiaoxue, et al. Improving the Hydrophobicity of Blueberry Anthocyanins through Enzymatic Acylation Modification[J]. Science and Technology of Food Industry, 2021, 42(19): 78−83. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021010208.
Citation: HONG Senhui, YANG Xiuwen, HUANG Xiaoxue, et al. Improving the Hydrophobicity of Blueberry Anthocyanins through Enzymatic Acylation Modification[J]. Science and Technology of Food Industry, 2021, 42(19): 78−83. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021010208.

Improving the Hydrophobicity of Blueberry Anthocyanins through Enzymatic Acylation Modification

More Information
  • Received Date: January 26, 2021
  • Available Online: August 01, 2021
  • In order to solve the problem of poor hydrophobicity of anthocyanins, in this paper, the blueberry anthocyanin was acylated with ferulic acid and caffeic acid, and the structure, hydrophobicity and antioxidant activity of related products were analysed. The FTIR and UV-Vis analysis indicated that ferulic acid and caffeic acid were grafted on the -OH of the glycosyl of the blueberry anthocyanins through acylation reaction, and the acylation degree of the anthocyanins acylated with ferulic acid (Fe-An) and caffeic acid (Ca-An) was 3.65% and 3.71%, respectively. Meanwhile, the total anthocyanidin content was decreased from 370.2 mg/g (Na-An) to 219.2 mg/g (Fe-An) and 222.18 mg/g (Ca-An), respectively. In addition, the hydrophobicity and antioxidant activity of blueberry anthocyanins were significantly improved after acylation with the two phenolic acids. The octanol-water partition coefficient (KOW) was increased from −0.20 (Na-An) to 0.66 (Fe-An) and 0.78 (Ca-An), DPPH clearance increased from 66.3% (Na-An) to 68.4% (Fe-An) and 74.7% (Ca-An), and inhibition ratio of β-carotene bleaching increased from 63.1% (Na - An) to 85.5% (Fe-An) and 90.3% (Ca-An). The results show that the introduction of ferulic acid and caffeic acid significantly improve the hydrophobicity and antioxidant activity of blueberry anthocyanins, which will greatly expand the application of anthocyanins in high-fat foods.
  • [1]
    陈梦雨, 黄小丹, 王钊, 等. 植物原花青素的研究进展及其应用现状[J]. 中国食物与营养,2018,24(3):54−58. [Chen M Y, Huang X D, Wang Z, et al. Research progress and application of plant proanthocyanidin[J]. Food and Nutrition in China,2018,24(3):54−58. doi: 10.3969/j.issn.1006-9577.2018.03.012
    [2]
    王静, 王瑾, 徐建峰, 等. 茶叶中花青素测定方法研究进展及分光光度测定法的优化[J]. 中国茶叶加工,2019(3):59−62, 69. [Wang J, Wang J, Xu J, et al. Advance on detection of anthocyanins in tea and improvementof spectrophotometry[J]. China Tea Processing,2019(3):59−62, 69.
    [3]
    Wang W, Hao X, Chen S, et al. pH-Responsive capsaicin@ chitosan nanocapsules for antibiofouling in marine applications[J]. Polymer,2018,158:223−230. doi: 10.1016/j.polymer.2018.10.067
    [4]
    Wang Y, Lin J, Tian J F, et al. Blueberry malvidin-3-galactoside suppresses hepatocellular carcinoma by regulating apoptosis, proliferation, and metastasis pathways in vivo and in vitro [J]. Journal of Agricultural and Food Chemistry,2019,67(2):625−363. doi: 10.1021/acs.jafc.8b06209
    [5]
    Roehrig T, Kirsch V, Schipp D, et al. Absorption of anthocyanin rutinosides after consumption of a blackcurrant (Ribes nigrum L.) extract[J]. Journal of Agricultural and Food Chemistry,2019,67(24):6792−6797. doi: 10.1021/acs.jafc.9b01567
    [6]
    蒋新龙, 蒋益花. 黑豆皮花色苷酯化修饰及其降解与抗氧化特性[J]. 中国粮油学报,2018,33(9):34−41. [Jiang X L, Jiang Y H. The black soybean peel anthocyanin process of esterification modified and its degradation and antioxidant characteristics[J]. Journal of the Chinese Cereals and Oils Association,2018,33(9):34−41. doi: 10.3969/j.issn.1003-0174.2018.09.006
    [7]
    古明辉, 陈虎, 李希羽, 等. 苹果酸酰化对黑果枸杞花青素稳定性改善的研究[J]. 食品工业科技,2017,38(23):58−63, 68. [Gu M H, Chen H, Li X Y, et al. Study of improvement on stability of anthocyanin modified by malic acid acylation from Lycium ruthenicum[J]. Science and Technology of Food Industry,2017,38(23):58−63, 68.
    [8]
    Koh J, Xu Z, Wicker L. Binding kinetics of blueberry pectin-anthocyanins and stabilization by non-covalent interactions[J]. Food Hydrocolloids,2020,99:105354. doi: 10.1016/j.foodhyd.2019.105354
    [9]
    Liu L, Ye C, Soteyome T, et al. Inhibitory effects of two types of food additives on biofilm formation by foodborne pathogens[J]. Microbiology Open,2019,8(9):e853.
    [10]
    Baron G, Altomare A, Regazzoni L, et al. Pharmacokinetic profile of bilberry anthocyanins in rats and the role of glucose transporters: LC–MS/MS and computational studies[J]. Journal of Pharmaceutical and Biomedical Analysis,2017,144:112−121. doi: 10.1016/j.jpba.2017.04.042
    [11]
    Brauch J E, Reuter L, Conrad J, et al. Characterization of anthocyanins in novel Chilean maqui berry clones by HPLC–DAD–ESI/MSn and NMR-spectroscopy[J]. Journal of Food Composition and Analysis,2017,58:16−22. doi: 10.1016/j.jfca.2017.01.003
    [12]
    Mehmood A, Zhao L, Wang Y, et al. Dietary anthocyanins as potential natural modulators for the prevention and treatment of non-alcoholic fatty liver disease: A comprehensive review[J]. Food Research International,2021,142:110180. doi: 10.1016/j.foodres.2021.110180
    [13]
    Li Y, Xu Y, Xie J, et al. Malvidin-3-O-arabinoside ameliorates ethyl carbamate-induced oxidative damage by stimulating AMPK-mediated autophagy[J]. Food & Function,2020,11(12):10317−10328.
    [14]
    张美清, 曾繁森, 叶妍琦, 等. 黑果枸杞花色苷pH和氨气敏感性及其抗氧化活性[J]. 食品工业科技,2021,42(1):22−27. [Zhang M Q, Zeng F S, Ye Y Q, et al. The pH and ammonia sensitivity and antioxidantactivity of anthocyanins from Lycium ruthenicum[J]. Science and Technology of Food Industry,2021,42(1):22−27.
    [15]
    李楠, 曾永明, 王国振, 等. 超声辅助酶法提取薰衣草花色苷及其热降解动力学[J]. 食品工业科技,2020,41(1):150−157. [Li N, Zeng Y M, Wang G Z, et al. Ultrasonic-assisted enzymatic extraction and thermal degradation kinetics of anthocyanins from lavender[J]. Science and Technology of Food Industry,2020,41(1):150−157.
    [16]
    潘颖, 梁颖, 马蓉, 等. 紫甘蓝花色昔稳定性及热降解动力学研究[J]. 食品工业科技,2021,42(5):51−59. [Pan Y, Liang Y, Ma R, et al. Stability and degradation kinetics of anthocyanins from red cabbage[J]. Science and Technology of Food Industry,2021,42(5):51−59.
    [17]
    Qin Y, Liu Y, Zhang X, et al. Development of active and intelligent packaging by incorporating betalains from red pitaya (Hylocereus polyrhizus) peel into starch/polyvinyl alcohol films[J]. Food Hydrocolloids,2020,100:105410. doi: 10.1016/j.foodhyd.2019.105410
    [18]
    Jiang G, Hou X, Zeng X, et al. Preparation and characterization of indicator films from carboxymethyl-cellulose/starch and purple sweet potato (Ipomoea batatas (L.) lam) anthocyanins for monitoring fish freshness[J]. International Journal of Biological Macromolecules,2020,143:359−372. doi: 10.1016/j.ijbiomac.2019.12.024
    [19]
    Mahdavi S A, Jafari S M, Assadpour E, et al. Storage stability of encapsulated barberry's anthocyanin and its application in jelly formulation[J]. Journal of Food Engineering,2016,181:59−66. doi: 10.1016/j.jfoodeng.2016.03.003
    [20]
    Khoo H E, Azlan A, Tang S T, et al. Anthocyanidins and anthocyanins: colored pigments as food, pharmaceutical ingredients, and the potential health benefits[J]. Food & Nutrition Research,2017,61(1):1−21.
    [21]
    Bornsek S M, Ziberna L, Polak T, et al. Bilberry and blueberry anthocyanins act as powerful intracellular antioxidants in mammalian cells[J]. Food Chemistry,2012,134(4):1878−1884. doi: 10.1016/j.foodchem.2012.03.092
    [22]
    Yan Z, Li C, Zhang L, et al. Enzymatic acylation of anthocyanin isolated from black rice with methyl aromatic acid ester as donor: Stability of the acylated derivatives[J]. Journal of Agricultural and Food Chemistry,2016,64(5):1137−1143. doi: 10.1021/acs.jafc.5b05031
    [23]
    Cai J, Zeng F, Zheng S, et al. Preparation of lipid-soluble bilberry anthocyanins through acylation with cinnamic acids and their antioxidation activities[J]. Journal of Agricultural and Food Chemistry,2020,68(28):7467−7473. doi: 10.1021/acs.jafc.0c01912
    [24]
    Yang W, Kortesniemi M, Ma X, et al. Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives[J]. Food Chemistry,2019,281:189−196. doi: 10.1016/j.foodchem.2018.12.111
    [25]
    Liu J, Zhuang Y, Hu Y, et al. Improving the color stability and antioxidation activity of blueberry anthocyanins by enzymatic acylation with p-coumaric acid and caffeic acid[J]. LWT-Food Science and Technology,2020,130:109673. doi: 10.1016/j.lwt.2020.109673
    [26]
    Pinheiro E S R, Silva I M D A, Gonzaga L V, et al. Optimization of extraction of high-ester pectin from passion fruit peel (Passiflora edulis flavicarpa) with citric acid by using response surface methodology[J]. Bioresource Technology,2008,99(3):5561−5566.
    [27]
    Bochek A, Zabivalova N, Petropavlovskii G. Determination of the esterification degree of polygalacturonic acid[J]. Russian Journal of Applied Chemistry,2001,74(5):796−799. doi: 10.1023/A:1012701219447
    [28]
    Fei P, Zeng F, Zheng S, et al. Acylation of blueberry anthocyanins with maleic acid: Improvement of the stability and its application potential in intelligent color indicator packing materials[J]. Dyes and Pigments,2021,184:108852. doi: 10.1016/j.dyepig.2020.108852
    [29]
    Keyata E O, Tola Y B, Bultosa G, et al. Phytochemical contents, antioxidant activity and functional properties of Raphanus sativus L, Eruca sativa L. and Hibiscus sabdariffa L. growing in Ethiopia[J]. Heliyon,2021,7(1):e05939. doi: 10.1016/j.heliyon.2021.e05939
    [30]
    Harborne J B. Spectral methods of characterizing anthocyanins[J]. Biochemical Journal,1958,70(1):22−28. doi: 10.1042/bj0700022
    [31]
    Harborne J B. The natural distribution in angiosperms of anthocyanins acylated with aliphatic dicarboxylic acids[J]. Phytochemistry,1986,25(8):1887−1894. doi: 10.1016/S0031-9422(00)81168-1
  • Cited by

    Periodical cited type(4)

    1. 杨体园,黄名勇,方镇洲,呙亚波,王政,邓洁红. 酶促酰化对刺葡萄锦葵啶花色苷光稳定性的影响. 中国食品添加剂. 2024(03): 96-102 .
    2. 邱小明,林良美,胡元庆. 泥蚶提取物抗氧化及抗运动性疲劳作用研究. 湖北民族大学学报(自然科学版). 2024(01): 45-50 .
    3. 王二雷,黄佳莹,段海章,徐彩娜. 花色苷稳态化技术研究进展及应用前景. 食品工业科技. 2024(18): 394-403 . 本站查看
    4. 孙晨晨,高庆超,李亚辉,张志勇,王树林,梁颖. 5种多酚类化合物提高紫甘蓝花色苷热稳定性及辅色机理初探. 现代食品科技. 2022(03): 89-96 .

    Other cited types(1)

Catalog

    Article Metrics

    Article views (312) PDF downloads (33) Cited by(5)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return