Preparation, Structure Identification of ACE Inhibitory Glycopeptide from Quinoa and Its Stability <i>in Vitro</i>

YU Yuyuan; ZHOU Qingqing; ZHOU Liusha; HU Xianglian; XU Haixing; SHI Yongqing

doi:10.13386/j.issn1002-0306.2022080166

Volume 44 Issue 12

Jun. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(12): 18-28. > DOI: 10.13386/j.issn1002-0306.2022080166

YU Yuyuan, ZHOU Qingqing, ZHOU Liusha, et al. Preparation, Structure Identification of ACE Inhibitory Glycopeptide from Quinoa and Its Stability in Vitro[J]. Science and Technology of Food Industry, 2023, 44(12): 18−28. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022080166.

Citation:

PDF (3139 KB)

Preparation, Structure Identification of ACE Inhibitory Glycopeptide from Quinoa and Its Stability in Vitro

College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310018, China

More Information

Received Date: August 17, 2022
Available Online: April 18, 2023

Graphical Abstract

Abstract

Abstract

The aim of this study was to purify angiotensin I-converting enzyme (ACE) inhibitory glycopeptide from quinoa fermented by Mucor wutungkiao and Rhizopus oryzae. The fermentation process conditions were optimized by a single factor experiment and a response surface experiment. The fermentation liquid was separated and purified by vacuum concentration, alcohol precipitation, Sephadex G-15 and reverse-phase high performance liquid chromatography. Fourier infrared spectroscopy was used to determine the composition of functional groups and β-elimination method to determine the glycopeptide bonding type. The effects of temperature, pH, metal ions, and in vitro simulated digestion on the activity were analyzed. The results showed that the optimal fermentation parameters were as follows: 8.7 d of fermentation time, 2.8% (φ) of total inoculum size containing Mucor wutungkiao to Rhizopus oryzae in a volume ratio of 1:1, and 1:18 g/mL of a solid-liquid ratio. The ACE inhibition rate was 64.22%±4.57%. A novel glycopeptides F₃b, was isolated and purified by ethanol precipitation, Sephadex G-15, and reverse-phase high performance liquid chromatography. Fourier-transform infrared spectroscopy proved the presence of polypeptides and polysaccharides in F₃b, and β-elimination reaction further demonstrated that the glycoprotein was an O-linked type. In vitro stability results indicate that the ACE inhibitory activity of glycopeptides was hardly changed under heating conditions from 25 to 55 ℃, and was 86.23%±3.47% of the original activity at 100 °C. Conversely, pH (from 2 to 12) had no significant effect (P>0.05) on the ACE inhibitory activity of glycopeptides. 4 mmol/L of Zn²⁺ and Fe³⁺ increased the ACE inhibitory activity of F₃b to 109.91%±8.12% and 117.43%±6.78% of the control, respectively. While same concentration of K⁺ and Ca²⁺ reduced the ACE inhibitory activity to 78.94%±2.18% and 85.31%±4.99% of the control, respectively. After simulated gastrointestinal digestion, the ACE inhibitory activity of F₃b decreased to 70.00%±3.30% of the control. In summary, this study could enrich the variety of ACE inhibitory peptides and provide technical reference for high-value utilization of quinoa.
- quinoa,
- glycopeptides,
- angiotensin I-converting enzyme (ACE) inhibitory activity,
- structure,
- stability

FullText(HTML)

References (58)

References

[1]	马丽媛, 吴亚哲, 陈伟伟. 《中国心血管病报告2018》要点介绍[J]. 中华高血压杂志,2019,27(83):712−716. [MA Liyuan, WU Yazhe, CHEN Weiwei. Key points of China Cardiovascular Disease Report 2018[J]. Chin J Hypertension,2019,27(83):712−716. MA Liyuan, WU Yazhe, CHEN Weiwei. Key points of China Cardiovascular Disease Report 2018[J]. Chin J Hypertension, 2019, 27(83): 712-716.
[2]	ZHANG Biying, LIU Jingbo, WEN Hedi, et al. Structural requirements and interaction mechanisms of ACE inhibitory peptides: Molecular simulation and thermodynamics studies on LAPYK and its modified peptides[J]. Food Science and Human Wellness,2022,11(6):1623−1630. doi: 10.1016/j.fshw.2022.06.021
[3]	NINGRUM S, SUTRISNO A, HSU J L. An exploration of angiotensin-converting enzyme (ACE) inhibitory peptides derived from gastrointestinal protease hydrolysate of milk using a modified bioassay-guided fractionation approach coupled with in silico analysis[J]. Journal of Dairy Science, 2022, 105(3): 1913-1928.
[4]	GU Yuchen, WU Jianping. LC-MS/MS coupled with QSAR modeling in characterising of angiotensin I-converting enzyme inhibitory peptides from soybean proteins[J]. Food Chemistry,2013,141(3):2682−2690. doi: 10.1016/j.foodchem.2013.04.064
[5]	ABEDIN M M, CHOURASIA R, PHUKON L C, et al. Characterization of ACE inhibitory and antioxidant peptides in yak and cow milk hard chhurpi cheese of the Sikkim Himalayan region[J]. Food Chemistry,2022,13:100231.
[6]	薛张芝, 张洪超, 丁源, 等. 墨鱼缠卵腺糖蛋白的抗氧化及抑菌活性研究[J]. 核农学报,2019,33(97):1544−1550. [XUE Zhangzhi, ZHANG Hongchao, DING Yuan, et al. Antioxidative and antibacterial activities of glycoprotein from cuttlefish oviposita[J]. Chinese Journal of Nuclear Agronomy,2019,33(97):1544−1550. doi: 10.11869/j.issn.100-8551.2019.08.1544 XUE Zhangzhi, ZHANG Hongchao, DING Yuan, et al. Antioxidative and antibacterial activities of glycoprotein from cuttlefish oviposita[J]. Chinese Journal of Nuclear Agronomy, 2019, 33(97): 1544-1550. doi: 10.11869/j.issn.100-8551.2019.08.1544
[7]	QIN Gaoyixin, XU Wu, LIU Junping, et al. Purification, characterization and hypoglycemic activity of glycoproteins obtained from pea (Pisum sativum L.)[J]. Food Science and Human Wellness,2021,10(3):297−307. doi: 10.1016/j.fshw.2021.02.021
[8]	LI Shanshan, TAO Lingchen, YU Xinyu, et al. Royal jelly proteins and their derived peptides: Preparation, properties, and biological activities[J]. Journal of Agricultural and Food Chemistry,2021,69(48):14415−14427. doi: 10.1021/acs.jafc.1c05942
[9]	张宏玲. 生姜糖蛋白提取纯化及活性研究[D]. 锦州: 渤海大学, 2019 ZHANG Hongling. Extraction, purification and activity of ginger glycoprotein[D]. Jinzhou: Bohai University, 2019.
[10]	KARAMI Z, PEIGHAMBARDOUST S H, HESARI J, et al. Antioxidant, anticancer and ACE-inhibitory activities of bioactive peptides from wheat germ protein hydrolysates[J]. Food Bioscience,2019,32:100450.
[11]	刘文. 牡蛎加工下脚料综合利用的关键技术研究[D]. 宁波: 宁波大学, 2013 LIU Wen. Research on the key technology of comprehensive utilization of oyster processing waste[D]. Ningbo: Ningbo University, 2013.
[12]	AONDONA M M, IKYA J K, UKEYIMA M T, et al. In vitro antioxidant and antihypertensive properties of sesame seed enzymatic protein hydrolysate and ultrafiltration peptide fractions[J]. Journal of Food Biochemistry,2021,45(1):e13587.
[13]	齐天明, 李志坚, 秦培友, 等. 藜麦栽培技术研究与应用展望[J]. 中国农业科技导报,2022,24(84):157−165. [QI Tianming, LI Zhijian, QIN Peiyou, et al. Research and application prospects of quinoa cultivation technology[J]. China Agricultural Science and Technology Herald,2022,24(84):157−165. doi: 10.13304/j.nykjdb.2021.0190 QI Tianming, LI Zhijian, QIN Peiyou, et al. Research and application prospects of quinoa cultivation technology[J]. China Agricultural Science and Technology Herald, 2022, 24(84): 157-165. doi: 10.13304/j.nykjdb.2021.0190
[14]	DAKHILI S, ABDOLALIZADEH L, HOSSEINI S M, et al. Quinoa protein: Composition, structure and functional properties[J]. Food Chemistry,2019,299:125161.
[15]	MIR N A, RIAR C S, SINGH S. Effect of pH and holding time on the characteristics of protein isolates from Chenopodium seeds and study of their amino acid profile and scoring[J]. Food Chemistry,2018,272(Jan.30):165−173.
[16]	SHARMA R, GARG P, KUMAR P, et al. Microbial fermentation and its role in quality improvement of fermented foods[J]. Fermentation,2020,6(4):106. doi: 10.3390/fermentation6040106
[17]	CHANGYU Zhou, QIANG Xia, LIHUI Du, et al. Recent developments in off-odor formation mechanism and the potential regulation by starter cultures in dry-cured ham[J]. Critical Reviews in Food Science and Nutrition, 2022: 1−15.
[18]	SUZUKI S, OHMORI H, HAYASHIDA S, et al. Lipase and protease activities in Koji cheeses surface-ripened with Aspergillus strains[J]. Food Science and Technology Research,2021,27(3):543−549. doi: 10.3136/fstr.27.543
[19]	LAI C Y, HOU C Y, CHUANG P T, et al. Microbiota and mycobiota of soy sauce-supplied lactic acid bacteria treated with high pressure[J]. Fermentation,2022,8(7):338. doi: 10.3390/fermentation8070338
[20]	ANNA S J, BOŻENA S, ANA M C, et al. Mould starter selection for extended solid-state fermentation of quinoa[J]. LWT,2019,99:231−237. doi: 10.1016/j.lwt.2018.09.055
[21]	WEI Guanmian, REGENSTEIN J M, LIU Xiaoming, et al. Comparative aroma and taste profiles of oil furu (soybean curd) fermented with different mucor strains[J]. Journal of Food Science,2020,85(11):1−9.
[22]	赵新淮, 冯志彪. 蛋白质水解物水解度的测定[J]. 食品科学,1994,11(23):65−67. [ZHAO Xinhuai, FENG Zhibiao. Determination of the degree of hydrolysis of protein hydrolyzates[J]. Food Science,1994,11(23):65−67. ZHAO Xinhuai, FENG Zhibiao. Determination of the degree of hydrolysis of protein hydrolyzates[J]. Food Science, 1994, 11(23): 65-67.
[23]	刘璇璇, 武莹敏, 朱振宝, 等. 水酶法联产核桃油和核桃多肽工艺优化及油脂脂肪酸分析[J]. 食品工业科技,2022,43(18):217−224. [LIU Xuanxuan, WU Yingmin, ZHU Zhenbao, et al. Optimization of synchronous extraction process of oil and polypeptide from walnut by aqueous enzymatic method and the fatty acid composition analysis of its oil[J]. Science and Technology of Food Industry,2022,43(18):217−224. LIU Xuanxuan, WU Yingmin, ZHU Zhenbao, et al. Optimization of synchronous extraction process of oil and polypeptide from walnut by aqueous enzymatic method and the fatty acid composition analysis of its oil[J]. Science and Technology of Food Industry, 2022, 43(18): 217−224.
[24]	LI Fengjuan, YIN Lijun, XIN Xin, et al. Changes in angiotensin I-converting enzyme inhibitory activities during the ripening of douchi (a Chinese traditional soybean product) fermented by various starter cultures[J]. International Journal of Food Properties,2010,13(3):512−524. doi: 10.1080/10942910802688176
[25]	向媛嫄, 王文林, 宋海云, 等. 去糖基化对水溶澳洲坚果糖肽结构和抗氧化性的影响[J]. 食品与发酵工业,2021,47(11):98−103. [XIANG Yuanyuan, WANG Wenlin, SONG Haiyun, et al. Effect of deglycosylation on the structure and antioxidant activity of water-soluble macadamia glycopeptide[J]. Food and Fermentation Industries,2021,47(11):98−103. XIANG Yuanyuan, WANG Wenlin, SONG Haiyun, et al. Effect of deglycosylation on the structure and antioxidant activity of water-soluble macadamia glycopeptide[J]. Food and Fermentation Industries, 2021, 47(11): 98-103.
[26]	WEN Chaoting, ZHANG Jixian, FENG Yuqin, et al. Purification and identification of novel antioxidant peptides from watermelon seed protein hydrolysates and their cytoprotective effects on H₂O₂-induced oxidative stress[J]. Food Chemistry,2020,327:127059. doi: 10.1016/j.foodchem.2020.127059
[27]	YANG Jing, HUANG Jichao, DONG Xiaoli, et al. Purification and identification of antioxidant peptides from duck plasma proteins[J]. Food Chemistry,2020,319:126534. doi: 10.1016/j.foodchem.2020.126534
[28]	曲金萍, 陈金玉, 张坤生, 等. 响应面法优化鸡胸肉肌原纤维蛋白抗氧化肽的制备及其二级结构研究[J]. 食品研究与开发,2020,41(20):1−8. [QU Jingping, CHEN Jingyu, ZHANG Kunsheng, et al. Response surface methodology to optimize the preparation of chicken breast myofibrillar protein antioxidant peptide and its secondary structure research[J]. Food Research and Development,2020,41(20):1−8. QU Jingping, CHEN Jingyu, ZHANG Kunsheng, et al. Response surface methodology to optimize the preparation of chicken breast myofibrillar protein antioxidant peptide and its secondary structure research[J]. Food Research and Development, 2020, 41(20): 1- 8.
[29]	沈柱英, 黄占旺, 肖建辉, 等. 纳豆糖蛋白的分离纯化、结构表征及其免疫活性研究[J]. 食品科学,2015,36(82):215−222. [SHEN Zhuying, HUANG Zhanwang, XIAO Jianhui, et al. Isolation, purification, structural characterization and immune activity of Natto glycoprotein[J]. Food Science,2015,36(82):215−222. SHEN Zhuying, HUANG Zhanwang, XIAO Jianhui, et al. Isolation, purification, structural characterization and immune activity of Natto glycoprotein [J]. Food Science, 2015, 36(82): 215-222.
[30]	姬中伟. 小米醇溶蛋白肽的制备及其抗氧化与抗炎活性研究[D]. 无锡: 江南大学, 2020 Ji Zhongwei. Preparation and antioxidant and anti-inflammatory activities of millet gliadin peptide[D]. Wuxi: Jiangnan University, 2020.
[31]	ZHENG Yajun, SHI Panqi, LI Yan, et al. A novel ACE-inhibitory hexapeptide from camellia glutelin-2 hydrolysates: Identification, characterization and stability profiles under different food processing conditions[J]. LWT,2021,147:111682. doi: 10.1016/j.lwt.2021.111682
[32]	CHAI T T, XIAO J B, DASS S M, et al. Identification of antioxidant peptides derived from tropical jackfruit seed and investigation of the stability profiles[J]. Food Chemistry,2021,340:127876. doi: 10.1016/j.foodchem.2020.127876
[33]	PEBRIANTI S A, CAHYANTO M N, INDRATI R. Angiotensin I-converting enzyme (ACE) inhibitory activity of ace inhibitory peptides produced during the fermentation of pigeon pea (Cajanus cajan) tempe[J]. Indonesian Food and Nutrition Progress,2020,16(2):47. doi: 10.22146/ifnp.46921
[34]	王婕娉, 刘睿, 丁士勇, 等. 响应面优化混菌发酵蜂王幼虫制备抗氧化肽及其结构鉴定[J]. 食品与发酵工业,2022,48(6):210−217. [WANG Jieping, LIU Rui, DING Shiyong, et al. Preparation of antioxidant peptides by response surface optimization of mixed fermentation from queen bee larvae and its structure identification[J]. Food and Fermentation Industries,2022,48(6):210−217. WANG Jieping, LIU Rui, DING Shiyong, et al. Preparation of antioxidant peptides by response surface optimization of mixed fermentation from queen bee larvae and its structure identification[J]. Food and Fermentation Industries, 2022, 48(6): 210-217.
[35]	李景, 陈定刚. 响应面优化米曲霉固态发酵豆粕制备ACE抑制肽条件[J]. 食品研究与开发,2018,39(196):120−125. [LI Jing, CHEN Dinggang. Preparation of ACE inhibitory peptide from soybean meal fermented by Aspergillus oryzae by response surface optimization[J]. Food Research and Development,2018,39(196):120−125. LI Jing, CHEN Dinggang. Preparation of ACE inhibitory peptide from soybean meal fermented by Aspergillus oryzae by response surface optimization [J]. Food Research and Development, 2018, 39(196): 120-125.
[36]	李雨霖, 倪婕, 薛璐瑜, 等. 解淀粉芽孢杆菌YA289降解虾头蛋白的发酵工艺优化[J]. 现代食品科技,2022,165(165):1−10. [LI Yulin, NI Jie, XUE Luyu, et al. Optimization of fermentation technology for degradation of shrimp head protein by Bacillus amyloliticus YA289[J]. Modern Food Science and Technology,2022,165(165):1−10. doi: 10.13982/j.mfst.1673-9078.2022.10.1399 LI Yulin, NI Jie, XUE Luyu, et al. Optimization of fermentation technology for degradation of shrimp head protein by Bacillus amyloliticus YA289[J]. Modern Food Science and Technology, 2022, 165 (165): 1-10. doi: 10.13982/j.mfst.1673-9078.2022.10.1399
[37]	李顺. 总状毛霉和米根霉混合发酵腐乳研究[D]. 合肥: 合肥工业大学, 2017 LI Shun. Study on fermented beancurd mixed with Mucor racemose and Rhizopus oryzae[D]. Hefei: Hefei University of Technology, 2017.
[38]	王銮, 包怡红, 康宁. 混菌固态发酵榛仁粕制备降血压肽工艺优化研究[J]. 中国粮油学报,2018,33(164):35−41. [Wang Luan, BAO Yihong, Kang Ning. Optimization of preparation of blood pressure peptide from hazelnut meal by solid-state fermentation with mixed bacteria[J]. Journal of the China Cereals and Oils Society,2018,33(164):35−41. doi: 10.3969/j.issn.1003-0174.2018.12.007 Wang Luan, BAO Yihong, Kang Ning. Optimization of preparation of blood pressure peptide from hazelnut meal by solid-state fermentation with mixed bacteria[J]. Journal of the China Cereals and Oils Society, 2018, 33(164): 35-41 doi: 10.3969/j.issn.1003-0174.2018.12.007
[39]	高洁, 高翔, 于佳, 等. 纳豆菌发酵扇贝裙边制备ACE抑制肽的工艺优化[J]. 现代食品科技,2018,34(168):165−175. [GAO Jie, GAO Xiang, YU Jia, et al. Optimization of process for preparation of ACE inhibitory peptide from scallop skirt fermented by natto[J]. Modern Food Science and Technology,2018,34(168):165−175. doi: 10.13982/j.mfst.1673-9078.2018.11.026 GAO Jie, GAO Xiang, YU Jia, et al. Optimization of process for preparation of ACE inhibitory peptide from scallop skirt fermented by natto[J]. Modern Food Science and Technology, 2018, 34(168): 165-175. doi: 10.13982/j.mfst.1673-9078.2018.11.026
[40]	SUN Runan, LIU Xiaofang, YU Yuan, et al. Preparation process optimization, structural characterization and in vitro digestion stability analysis of Antarctic krill (Euphausia superba) peptides-zinc chelate[J]. Food Chemistry,2021,340:128056. doi: 10.1016/j.foodchem.2020.128056
[41]	VIDAL A R, DUARTE L P, SCHMIDT M M, et al. Extraction and characterization of collagen from sheep slaughter by-products[J]. Waste Management,2020,102(1):838−846.
[42]	KARAMI M, SHAHRAKY M K, RANJBAR M, et al. Preparation, purification, and characterization of low-molecular-weight hyaluronic acid[J]. Biotechnology Letters,2021,43(1):133−142. doi: 10.1007/s10529-020-03035-4
[43]	TUVAANJAV S, KOMATA M, MA C, et al. Isolation and antiviral activity of water-soluble Cynomorium songaricum Rupr. polysaccharides[J]. Journal of Asian Natural Products Research,2016,18(2):159−171. doi: 10.1080/10286020.2015.1082547
[44]	ZENG Fanke, CHEN Wenbo, HE Ping, et al. Structural characterization of polysaccharides with potential antioxidant and immunomodulatory activities from Chinese water chestnut peels[J]. Carbohydrate Polymers,2020,246:116551. doi: 10.1016/j.carbpol.2020.116551
[45]	ALBERT S B, ROBERT G. Structure of the O-linked oligosaccharides from a major thyroid cell surface glycoprotein[J]. Archives of Biochemistry & Biophysics,1997,343(1):73−80.
[46]	ZHANG Haiqiang, HAN Luanwei, SUN Xiaomei, et al. A glycoprotein from mountain cultivated ginseng: Insights into their chemical characteristics and intracellular antioxidant activity[J]. International Journal of Biological Macromolecules,2022,217:761−774. doi: 10.1016/j.ijbiomac.2022.07.023
[47]	LIU K, DU R, CHEN F. Stability of the antioxidant peptide SeMet-Pro-Ser identified from selenized brown rice protein hydrolysates[J]. Food Chem,2020,319:126540. doi: 10.1016/j.foodchem.2020.126540
[48]	LI Meiqing, XIA Shanwei, ZHANG Yijun, et al. Optimization of ACE inhibitory peptides from black soybean by microwave-assisted enzymatic method and study on its stability[J]. LWT,2018,98:358−365. doi: 10.1016/j.lwt.2018.08.045
[49]	UNNIKRISHNAN P, KIZHAKKETHIL B P, GEORGE J C, et al. Antioxidant peptides from dark meat of yellowfin tuna (Thunnus albacares): Process optimization and characterization[J]. Waste and Biomass Valorization,2021,12(4):1845−1860. doi: 10.1007/s12649-020-01129-8
[50]	WANG Rui, YUN Jianmin, WU Shujuan, et al. Optimisation and characterisation of novel angiotensin-converting enzyme inhibitory peptides prepared by double enzymatic hydrolysis from Agaricus bisporus scraps[J]. Foods,2022,11(3):394. doi: 10.3390/foods11030394
[51]	WANG Kai, LUO Qinwen, HONG Hui, et al. Novel antioxidant and ACE inhibitory peptide identified from Arthrospira platensis protein and stability against thermal/pH treatments and simulated gastrointestinal digestion[J]. Food Research International,2020,139(1):109908.
[52]	SOVAGO I, KALLAY C, VARNAGY K. Peptides as complexing agents: Factors influencing the structure and thermodynamic stability of peptide complexes[J]. Coordination Chemistry Reviews,2012,256(19−20):2225−2233. doi: 10.1016/j.ccr.2012.02.026
[53]	LAI Xingfei, PAN Shunshun, ZHANG Wenji, et al. Properties of ACE inhibitory peptide prepared from protein in green tea residue and evaluation of its anti-hypertensive activity[J]. Process Biochemistry,2020,92:277−287. doi: 10.1016/j.procbio.2020.01.021
[54]	高泽汝. 玉米胚芽ACE抑制肽的制备及作用机制和稳定性研究[D]. 郑州: 河南工业大学, 2021 GAO Zheru. Preparation, mechanism and stability of ACE-inhibiting peptide from maize germ[D]. Zhengzhou: Henan University of Technology, 2021.
[55]	沈嘉森, 苏永昌, 陈晓婷, 等. 龙须菜ACE抑制肽的体外稳定性和抗氧化活性研究[J]. 食品工业科技,2022,43(7):384−392. [SHEN Jiasen, SU Yongchang, CHEN Xiaoting, et al. Study on in vitro stability and antioxidant activity of ACE inhibitory peptide from Gracilaria lemaneiformis[J]. Science and Technology of Food Industry,2022,43(7):384−392. doi: 10.13386/j.issn1002-0306.2021080345 SHEN Jiasen, SU Yongchang, CHEN Xiaoting, et al. Study on in vitro stability and antioxidant activity of ACE inhibitory peptide from Gracilaria lemaneiformis[J]. Science and Technology of Food Industry, 2022, 43(7): 384−392. doi: 10.13386/j.issn1002-0306.2021080345
[56]	WONG F C, JIANBO X, ONG M G L, et al. Identification and characterization of antioxidant peptides from hydrolysate of blue-spotted stingray and their stability against thermal, pH and simulated gastrointestinal digestion treatments[J]. Food Chemistry,2019,271:614−622. doi: 10.1016/j.foodchem.2018.07.206
[57]	MIRZAEI M, MIRDAMADI S, SAFAVI M, et al. The stability of antioxidant and ACE-inhibitory peptides as influenced by peptide sequences[J]. LWT- Food Science and Technology,2020,130:109710. doi: 10.1016/j.lwt.2020.109710
[58]	李烨彤, 苏志光, 张惠, 等. 糖基化大豆蛋白酶解物的分离纯化及耐消化稳定性的研究[J]. 大豆科学,2015,34(61):474−479. [LI Yatong, SU Zhiguang, ZHANG Hui, et al. Isolation and purification of glycated soybean protease hydrolysate and its stability in digestion[J]. Soybean Science,2015,34(61):474−479. LI Yatong, SU Zhiguang, ZHANG Hui, et al. Isolation and purification of glycated soybean protease hydrolysate and its stability in digestion[J]. Soybean Science, 2015, 34(61): 474-479.