食品中芳香族氨基酸的分离分析技术研究进展

doi:10.3724/SP.J.1123.2022.04011

色谱 ›› 2022, Vol. 40 ›› Issue (8): 686-693.DOI: 10.3724/SP.J.1123.2022.04011

• 特别策划:食品安全分离分析-功能性吸附材料专栏 • 上一篇下一篇

食品中芳香族氨基酸的分离分析技术研究进展

鲁晨辉¹, 张毅¹^,^*(), 苏宇杰¹, 王文龙¹, 冯永巍²^,^*()

1.江南大学食品学院, 食品科学与技术国家重点实验室, 分析食品安全学研究所, 食品安全国际合作联合实验室, 江苏无锡 214122
2.国家市场监管技术创新中心(特殊食品), 无锡市食品安全检验检测中心, 江苏无锡 214142

收稿日期:2022-04-15 出版日期:2022-08-08 发布日期:2022-07-29
通讯作者: 张毅,冯永巍
基金资助:
江苏省市场监督管理局科技计划项目(KJ204131);国家自然科学基金(21876066);河北省医学科学研究课题计划(20211856);江南大学基础科研计划(JUSRP21921);江苏省食品安全与质量控制协同创新中心项目

Advances in separation and analysis of aromatic amino acids in food

LU Chenhui¹, ZHANG Yi¹^,^*(), SU Yujie¹, WANG Wenlong¹, FENG Yongwei²^,^*()

1. State Key Laboratory of Food Science and Technology, International Joint Laboratory on Food Safety, Institute of Analytical Food Safety, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China
2. Technology Innovation Center of Special Food for State Market Regulation, Wuxi Food Safety Inspection and Test Center, Wuxi 214142, China

Received:2022-04-15 Online:2022-08-08 Published:2022-07-29
Contact: ZHANG Yi, FENG Yongwei
Supported by:
Science and Technology Project of Jiangsu Market Supervision Administration(KJ204131);National Natural Science Foundation of China(21876066);Hebei Medical Science Research Project(20211856);Jiangnan University Basic Scientific Research Plan(JUSRP21921);Program of the “Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province”

摘要/Abstract

摘要：

苯丙酮尿症等代谢病患者因基因缺陷无法正常代谢食物中的芳香族氨基酸(aromatic amino acids, AAA),常规饮食可能会造成永久性生理损伤,低AAA肽是其重要的蛋白质等同物来源。AAA分离分析技术对低AAA肽的制备和检测至关重要。该领域研究者探索了多种高效的吸附、分离材料,从复杂的蛋白质水解液中选择性吸附脱除AAA以制备符合特定氨基酸限量的低AAA肽类食品,或者建立对AAA特异性提取富集的分离分析策略。该文分析了AAA的结构特点与理化性质,总结了近年来基于活性炭、树脂等吸附材料脱除AAA的技术进展,并从样品前处理、手性分离和吸附-传感3个维度综述了二维纳米材料、分子印迹、环糊精、金属有机骨架等材料在AAA分离分析中的应用。通过探讨各类技术的优缺点,为AAA吸附脱除和分离分析技术的进步提供支撑。

关键词: 芳香族氨基酸, 吸附, 脱除, 分离, 综述

Abstract:

Amino acids are important building blocks of proteins in the human body, which are involved in many metabolic pathways. Patients with metabolic diseases such as phenylketonuria, tyrosinemia, and hepatic encephalopathy are genetically defective and cannot metabolize aromatic amino acids (AAA) in food; hence, a regular diet may lead to permanent physiological damage. For this reason, it is necessary to restrict the intake of AAA in their daily diet by limiting natural protein intake, while ensuring normal intake of low protein foods and supplementation with low-AAA protein equivalents. Sources of low-AAA protein equivalents currently rely on free amino acid complex mixtures and low-AAA peptides (also known as high-Fischer-ratio peptides), which have better absorption availability and palatability. AAA separation and analysis techniques are essential for the preparation and detection of low-AAA peptides. Researchers in this field have explored a variety of efficient adsorption materials to selectively remove AAA from complex protein hydrolysates and thus prepare low-AAA peptide foods, or to establish analysis strategies for AAA. Covering more than 70 publications on AAA removal and separation in the last decade from Web of Science Core Collection and China National Knowledge Infrastructure, this review analyzes the structural characteristics and physicochemical properties of AAA, and summarizes the technological progress of AAA removal based on adsorbents such as activated carbon and resin. The applications of two-dimensional nanomaterials, molecular imprinting, cyclodextrins, and metal-organic frameworks in AAA adsorption and analysis from three dimensions, i. e., sample pretreatment, chiral separation and adsorption sensing, are also reviewed. The mainstream adsorbents for AAA removal, such as activated carbon, still suffer from poor specificity and cause environmental pollution during post-use treatment. Existing AAA separating materials show impressive selective adsorption capability in food samples and chiral mixtures as well as high sensitivity in adsorption sensing. The development of an efficient detection technology for AAA may help in detecting trace AAA in food and in evaluating chiral AAA adulteration in food samples. By exploring the advantages and disadvantages of each type of technology, we provide support for the advancement of the removal and analysis techniques for AAA.

Key words: aromatic amino acids, adsorption, removal, separation, review

中图分类号:

O658

鲁晨辉, 张毅, 苏宇杰, 王文龙, 冯永巍. 食品中芳香族氨基酸的分离分析技术研究进展[J]. 色谱, 2022, 40(8): 686-693.

LU Chenhui, ZHANG Yi, SU Yujie, WANG Wenlong, FENG Yongwei. Advances in separation and analysis of aromatic amino acids in food[J]. Chinese Journal of Chromatography, 2022, 40(8): 686-693.

图/表 5

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Raw materials	Proteases	Adsorbents	Fischer ratio	Reference
Corn	alkaline protease, neutral protease	activated carbon	21.92	[7]
Corn	bacillus natto alkaline protease	modified activated carbon	21.80	[8]
Crude corn peptides	α-chymotrypsin, carboxypeptidase A	activated carbon (different type)	41.87	[9]
Tuna	pepsin, flavor protease	activated carbon (200 mesh)	30.33	[10]
Chlamys farreri	compound protease, flavor protease	activated carbon (200 mesh)	34.73	[11]
Antarctic krill	alkaline protease, flavor protease	activated carbon	21.12	[12]
Minced squid	pepsin, flavor protease	activated carbon (50 mesh)	/	[13,14]
Yeast	α-chymotrypsin, carboxypeptidase A	modified activated carbon	30.00-40.00	[15]
Soy protein	alkaline protease, flavor protease	activated carbon (different type)	18.90	[16]
Grass carp	pancreatin, papain	activated carbon (different type)	/	[17]
Pearl oyster	pancreatin	activated carbon	24.58	[18]
Goat milk	pepsin, flavor protease	activated carbon (200 mesh)	26.32	[19]

Raw materials	Proteases	Adsorbents	Fischer ratio	Reference
Corn	alkaline protease, neutral protease	activated carbon	21.92	[7]
Corn	bacillus natto alkaline protease	modified activated carbon	21.80	[8]
Crude corn peptides	α-chymotrypsin, carboxypeptidase A	activated carbon (different type)	41.87	[9]
Tuna	pepsin, flavor protease	activated carbon (200 mesh)	30.33	[10]
Chlamys farreri	compound protease, flavor protease	activated carbon (200 mesh)	34.73	[11]
Antarctic krill	alkaline protease, flavor protease	activated carbon	21.12	[12]
Minced squid	pepsin, flavor protease	activated carbon (50 mesh)	/	[13,14]
Yeast	α-chymotrypsin, carboxypeptidase A	modified activated carbon	30.00-40.00	[15]
Soy protein	alkaline protease, flavor protease	activated carbon (different type)	18.90	[16]
Grass carp	pancreatin, papain	activated carbon (different type)	/	[17]
Pearl oyster	pancreatin	activated carbon	24.58	[18]
Goat milk	pepsin, flavor protease	activated carbon (200 mesh)	26.32	[19]

Application	Target	Sample	Adsorbent	Analytical method	Reference
Sample	L-AAA	protein hydrolysate	MOFs	HPLC	[39]
pretreatment	AAA	lily	MWCNTs and MOFs composite	HPLC	[40]
	L-Trp	black sesame seed	GO@SiO₂	HPLC	[41]
	AAA	AAA aqueous solution	ZIF-8@β-CDPs	/	[42]
Chiral	L-Phe	D,L-Phe; D,L-Trp	L-Phe-imprinted cryogel cartridge	FPLC	[43]
separation	L-AAA	D,L-AAA mixture	surface functionalized magnetic nanoparticles	HPLC	[44]
	D-Phe	D,L-Phe mixture	D,L-Ala-CD/SiO₂	absorption spectroscopy	[45]
Adsorption-	L-Phe	artificial plasma	L-Phe imprinted SPR sensor	SPR	[46]
sensing	Phe, Tyr	standard solution	Ni@CNFs@Au	SERS	[47]
	Phe	AAA aqueous solution	pyrene@2βCD	absorption spectroscopy	[48]
	L-AAA	milk	bi-enzyme nanocomposite film-based biosensor	amperometric measurements	[49]

Application	Target	Sample	Adsorbent	Analytical method	Reference
Sample	L-AAA	protein hydrolysate	MOFs	HPLC	[39]
pretreatment	AAA	lily	MWCNTs and MOFs composite	HPLC	[40]
	L-Trp	black sesame seed	GO@SiO₂	HPLC	[41]
	AAA	AAA aqueous solution	ZIF-8@β-CDPs	/	[42]
Chiral	L-Phe	D,L-Phe; D,L-Trp	L-Phe-imprinted cryogel cartridge	FPLC	[43]
separation	L-AAA	D,L-AAA mixture	surface functionalized magnetic nanoparticles	HPLC	[44]
	D-Phe	D,L-Phe mixture	D,L-Ala-CD/SiO₂	absorption spectroscopy	[45]
Adsorption-	L-Phe	artificial plasma	L-Phe imprinted SPR sensor	SPR	[46]
sensing	Phe, Tyr	standard solution	Ni@CNFs@Au	SERS	[47]
	Phe	AAA aqueous solution	pyrene@2βCD	absorption spectroscopy	[48]
	L-AAA	milk	bi-enzyme nanocomposite film-based biosensor	amperometric measurements	[49]

食品中芳香族氨基酸的分离分析技术研究进展

Advances in separation and analysis of aromatic amino acids in food

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