采用QuEChERS结合UHPLC-MS/MS定量分析热加工肉制品中的三种胺类物质

秦志伟; 叶博; 刘玲

doi:10.13386/j.issn1002-0306.2021120176

采用QuEChERS结合UHPLC-MS/MS定量分析热加工肉制品中的三种胺类物质

doi: 10.13386/j.issn1002-0306.2021120176

秦志伟^1,,
叶博^{1, 2},
刘玲^1, ,

1.
沈阳农业大学食品学院，辽宁沈阳 110000
2.
辽宁现代农业工程中心，辽宁沈阳 110000

基金项目: 沈阳市科学计划项目：肉制品常见热加工方式中有毒有害化学因子的筛查和数据库的建立（20-206-4-22）；辽宁省教育厅科学研究经费项目：肉制品热加工过程中形成有毒化学物质的风险评估（LSNJC202011）。

详细信息

作者简介:
秦志伟（1997−），男，硕士研究生，研究方向：食品加工与安全，E-mail：q1594301871@163.com

通讯作者:
刘玲（1973−），女，博士，教授，研究方向：食品化学与分析，E-mail：liuling4568@sina.com

中图分类号: TS251.6
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- 文章访问数: 34
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- 被引次数: 0
出版历程
- 收稿日期: 2021-12-20
- 网络出版日期: 2022-08-04

Quantitative Analysis of Three Amines in Thermally Processed Meat Products Using QuEChERS Combined with UHPLC-MS/MS

QIN Zhiwei^1
,,
YE BO^{1, 2},
LIU Ling^{1
, ,}

1.
College of Food Science, Shenyang Agricultural University, Shenyang 110000, China
2.
Liaoning Modern Agricultural Engineering Center, Shenyang 110000, China

摘要

摘要: 肉制品加热中产生的胺类物质对人体健康存在危害，检测方法不够简便。本文采用QuEChERS技术结合超高效液相色谱-串联质谱（UHPLC-MS/MS）技术建立同时检测丙烯酰胺（AA）、亚硝胺（NAs）和杂环胺（HAAs）含量的方法，用于分析热加工肉制品中产生的胺类物质。结果表明：该方法检测出的三类成分20种胺类物质在相应浓度范围内显示出良好的线性（R²>0.991），检测限和定量限分别为0.01~1.6 ng/g和0.03~4.8 ng/g，日内回收率介于66.3%~116.5%之间，日内精密度介于0.78%~9.0%之间。每个胺类物的5×LOQ加标水平计算的日间精度范围为3.4%~9.4%。该方法应用于煎烤的四种肉制品中AA、NAs和HAAs的分析，共检测出9种胺类物质，浓度范围为0.08~31.26 ng/g。
- 丙烯酰胺 /
- 杂环胺 /
- 亚硝胺 /
- 热加工肉制品
Abstract: The amines produced in heating meat products are harmful to human health, but the current detection method is not simple enough. In this study, QuEChERS technology combined with ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was used to establish a method for the simultaneous detection of acrylamide (AA), nitrosamines (NAs) and heterocyclic amines (HAAs) in processed meat products. The results showed that the analytic methods of 20 amines in the three components showed good linearity (R²>0.991) in the corresponding concentration range, and the detection limit and quantification limit were 0.01~1.6 ng/g and 0.03~4.8 ng/g, respectively. The average daily recovery rate was between 66.3%~111.5%, and the intraday precision was between 0.78%~9.0%. The daily accuracy range of the 5×LOQ spiked level calculation for each amine was 3.4%~9.4%. The method was applied to the analysis of AA, NAs and HAAs in four meat products for grilling, in them 9 amines were detected with the concentration range of 0.08~31.26 ng/g.
- acrylamide /
- heterocyclic amines /
- nitrosamines /
- thermally processed meat products

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图 1 流动相中不同乙酸铵添加条件下20种胺类物质的色谱图

Figure 1. Chromatograms of 20 amines under different ammonium acetate addition conditions in mobile phase

注：A、B、C、D、E分别为20 mmol/L、10 mmol/L、5 mmol/L、1 mmol/L、0.5 mmol/L。

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图 2 流动相为1 mmol/L乙酸铵0.06%甲酸条件下20种胺类物质混合标准溶液色谱图

Figure 2. Chromatogram of a mixed standard solution of 20 amines with the mobile phase 1 mmol/L ammonium acetate and 0.06% formic acid

（1.AA;2.NPYR；3;DMIP；4.IQ；5.MeIQ；6.IQx；7.MeIQx；8. 4,8-DiMeIQx，7,8-DiMeIQx；9. Norharman；10.4,7,8-DiMeIQx；11.Harman；12.NPIP；13.PHIP；14. TRP-P-1，TRP-P-2；15.AaC；16.NDPA；17.NDBA；18.NDPHA）

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图 3 流动相为1mmol/L乙酸铵0.06%甲酸条件下20种胺类物质提取离子流图

Figure 3. Ion flow diagram of 20 kinds of amines extracted with the mobile phase 1mmol/L ammonium acetate and 0.06% formic acid

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图 4 20种胺类物质在不同提取剂中的回收率

Figure 4. Extraction recoveries of 20 amines in different extractants

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图 5 20种胺类物质在不同吸附剂中的回收率

Figure 5. Extraction recoveries of 20 amines in different adsorbents

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表 1 AA、NAs、HAAs的质谱条件

Table 1. MS conditions of AA, NAs and HAAs

化合物	保留时间（min）	锥孔电压（V）	MRM离子对（m/z）	碰撞电压（V）
AA	0.84	35	72.13/55.27^* 72.13/43.93	10 10
DMIP	2.34	48	162.96/148.05^* 162.96/105.203	22 32
IQx	3.02	58	199.98/185.08^* 199.98/131.12	26 38
IQ	2.51	56	198.90/184.07 198.90/130.00	28 40
MeIQ	2.86	52	212.97/198.01^* 212.97/116.87	24 50
MeIQx	3.38	54	213.97/130.97^* 213.97/199.02	38 26
7,8-DiMeIQx	3.65	60	228.00/213.06^* 228.00/131.03	26 38
4,8-DiMeIQx	3.65	54	227.94/212.94^* 227.94/144.83	22 38
Norharman	3.76	60	168.95/141.99^* 168.95/89.01	26 42
Harman	3.93	58	182.90/114.97^* 182.90/167.94	32 26
TRP-P-2	4.13	56	197.97/127.59^* 197.97/77.09	28 48
PHIP	4.15	58	224.97/210.03^* 224.97/114.71	28 48
TRP-P-1	4.28	56	211.98/179.19^* 211.98/115.04	38 44
AaC	4.42	46	183.91/157.003^* 183.91/88.95	20 46
NPYR	2.22	4	100.85/55.12^* 100.85/40.00	25 15
NDPA	5.77	24	130.97/89.08^* 130.97/42.85	8 13
NDPHA	7.12	28	199.09/169.10^* 199.09/74.10	10 12
NDBA	6.98	28	158.97/102.99^* 158.97/56.95	10 13
NMOR	1.72	30	117/45^* 117/87	18 18
NPIP	4.07	30	115/41^* 115/69	16 12
4,7,8-TriMeIQx	3.87	54	241.87/145.01	40
Norharman-d7	3.73	62	176.03/120.37	30
注：*为定量离子。

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表 2 20种目标化合物的标准曲线、定量限、检测线和基质效应

Table 2. Standard curves, quantification limits, detection lines and matrix effects of 20 target compounds

化合物	线性范围（ng/mL）	校准曲线	R²	LOD（ug/kg）	LOQ（ug/kg）	ME
AA	1~100	y=174.061x+74.1202	0.997	0.75	2.25	0.93
DMIP	0.1~100	y=0.0102x+0.017	0.998	0.1	0.3	0.67
IQx	0.1~100	y=0.009x+0.0064	0.999	0.06	0.18	0.83
IQ	0.1~100	y=0.0069x+0.0172	0.994	0.06	0.18	0.41
MeIQ	0.1~100	y=0.0157x+0.0093	0.991	0.1	0.3	1.17
MeIQx	0.1~100	y=0.0105x+0.0048	0.998	0.02	0.06	1.17
7,8-DiMeIQx	0.1~100	y=0.032x−0.0093	0.996	0.01	0.03	1.09
4,8-DiMeIQx	0.1~100	y=0.0231x−0.0006	0.997	0.02	0.06	0.97
Norharman	0.1~100	y=0.0467x−0.0185	0.999	0.06	0.18	1.15
Harman	0.1~100	y=0.9079x−0.9526	0.998	0.02	0.06	1.17
TRP-P-2	1~100	y=0.0059x−0.0548	0.995	0.75	2.25	0.47
PhIP	0.1~100	y=0.4951x−0.4404	0.994	0.01	0.03	1.15
TRP-P-1	0.1~100	y=0.0448x−0.07	0.997	0.01	0.03	1.23
AaC	0.5~100	y=0.0127x+0.0015	0.996	0.4	1.2	0.95
NPYR	2~100	y=565.381x−62.9893	0.995	1.5	4.5	0.63
NDPA	1~100	y=272.29x−6.82813	0.997	0.8	2.4	0.80
NDPHA	0.1~100	y=187.967x+280.38	0.999	0.06	0.18	0.79
NDBA	0.1~100	y=666.164x+440.269	0.997	0.01	0.03	0.80
NMOR	2~100	y=41.4562x−23.3852	0.996	1.6	4.8	1.01
NPIP	0.5~100	y=436.673x−552.953	0.998	0.5	1.5	1.10

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表 3 20种胺类物质的加标回收率

Table 3. Standard recovery rates of 20 amines

化合物	本底量（ng/g）	添加量（ng/g）	回收率%
化合物	本底量（ng/g）	添加量（ng/g）	1×LOQ	5×LOQ	10×LOQ
AA	3	3.0、15.0、30.0	89.4±3.7	96.4±6.4	97.8±7.8
DMIP	ND	0.3、1.5、3.0	89.1±4.9	92.3±4.3	94.4±5.5
IQx	ND	0.2、1.0、2.0	86.2±5.8	84.2±6.4	90.5±7.2
IQ	ND	0.2、1.0、2.0	71.2±2.9	83.1±5.9	77.8±4.5
MeIQ	ND	0.3、1.5、3.0	111.5±9.2	103.5±7.3	115.2±7.0
MeIQx	ND	0.1、0.5、1.0	87.2±6.7	82.7±5.7	81.5±4.8
7,8-DiMeIQx	ND	0.1、0.5、1.0	90.4±3.0	92.5±3.9	83.7±4.4
4,8-DiMeIQx	ND	0.1、0.5、1.0	96.6±4.5	99.1±6.8	95.1±5.9
Norharman	1.7	0.2、1.0、2.0	116.5±3.6	104.3±4.0	104.6±6.1
Harman	1.4	0.1、0.5、1.0	88.0±4.6	82.9±5.3	90.0±3.8
TRP-P-2	ND	3.0、15.0、30.0	66.3±2.9	71.4±3.4	72.9±4.1
PHIP	ND	0.1、0.5、1.0	96.3±5.8	110.3±6.7	109.3±8.5
TRP-P-1	ND	0.1、0.5、1.0	97.1±3.5	105.1±8.4	100.8±2.1
AaC	ND	1.0、5.0、10.0	98.5±9.5	90.2±8.3	107.3±8.8
NPYR	ND	5.0、25.0、50.0	81.2±5.2	77.8±6.4	74.7±5.7
NDPA	ND	3.0、15.0、30.0	109.4±7.6	96.4±6.4	97.9±7.8
NDPHA	ND	0.2、1.0、2.0	85.7±7.1	97.7±4.7	96.3±5.9
NDBA	ND	0.1、0.5、1.0	81.7±4.3	82.7±8.2	88.5±5.1
NMOR	ND	5.0、25.0、50.0	86.4±4.7	80.1±5.6	77.3±3.6
NPIP	ND	2.0、10.0、20.0	86.3±3.1	92.3±7.0	86.3±5.5
注：ND表示未检出。

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表 4 20种胺类物质的精密度

Table 4. Precisions of 20 amines

化合物	本底量（ng/g）	日间精密度（%）	日内精密度（%，n=5）
化合物	本底量（ng/g）	日间精密度（%）	1×LOQ	5×LOQ	10×LOQ
AA	3	4.3±2.5	6.1±2.1	5.8±0.4	6.5±1.1
DMIP	ND	6.9±2.6	5.7±0.8	3.3±1.1	7.8±1.3
IQx	ND	8.0±2.4	5.1±0.8	5.5±1.3	7.7±1.5
IQ	ND	8.9±1.8	7.3±1.6	7.2±3.0	3.1±0.7
MeIQ	ND	7.0±2.1	5.9±1.7	7.8±1.3	6.4±2.6
MeIQx	ND	5.2±2.1	4.8±2.5	5.9±1.1	7.1±1.3
7,8-DiMeIQx	ND	5.4±2.3	5.4±1.6	2.9±1.2	4.0±0.7
4,8-DiMeIQx	ND	3.4±0.2	5.1±1.5	5.2±1.5	5.5±1.6
Norharman	1.7	7.1±3.1	5.2±1.1	7.8±3.5	5.9±2.5
Harman	1.4	7.9±1.1	4.5±1.1	0.78±0.4	6.2±1.2
TRP-P-2	ND	5.8±2.9	6.6±1.3	6.2±1.9	8.1±1.6
PHIP	ND	7.0±2.4	6.7±2.2	5.3±1.6	5.3±1.3
TRP-P-1	ND	8.5±2.4	8.2±3.3	4.1±0.8	3.9±1.6
AaC	ND	6.9±3.1	8.3±3.2	6.9±2.8	6.8±1.4
NPYR	ND	6.6±1.8	8.8±1.4	7.8±3.3	3.9±0.6
NDPA	ND	8.7±2.0	4.1±1.1	3.8±0.7	5.3±1.2
NDPHA	ND	9.4±2.6	5.3±1.5	7.2±2.9	3.8±0.8
NDBA	ND	5.4±2.3	9.0±2.1	4.3±1.5	6.6±1.6
NMOR	ND	6.1±1.9	6.9±1.5	6.9±2.3	8.1±1.5
NPIP	ND	8.1±1.7	6.2±1.1	5.1±1.5	5.7±1.4
注：ND表示未检出。

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表 5 煎烤3、5、7 min四种肉品中胺类物质的含量

Table 5. Amines contents in four types of meat products at grilling for 3, 5, and 7 minutes

有害物种类	加工时间（min）	肉制品胺类物质含量（ng/g）
有害物种类	加工时间（min）	牛肉	鸡肉	猪肉	羊肉
NDPHA	3	9.06±0.01^a	2.53±0.41^b	−	1.29±0.10^c
	5	11.47±0.76^a	5.53±1.46^b	−	1.09±0.13^c
	7	11.83±0.25^a	6.56±0.11^b	−	1.28±0.34^c
4,8-DiMeIQx	3	0.07±0.01^d	0.26±0.04^a	0.2±0.01^b	0.13±0.02^c
	5	0.29±0.04^b	0.28±0.04^b	0.58±0.22^a	0.11±0.01^c
	7	0.22±0.07^c	0.40±0.02^b	1.44±0.24^a	0.22±0.08^c
7,8-DiMeIQx	3	0.03±0.02^c	0.17±0.05^a	0.13±0.06^b	0.16±0.05^a
	5	0.22±0.11^c	0.25±0.10^b	0.99±0.07^a	0.12±0.06^d
	7	0.46±0.19^b	0.30±0.12^d	1.76±0.08^a	0.41±0.05^c
PHIP	3	−	0.08±0.02^a	0.06±0.02^b	−
	5	−	0.14±0.03^b	0.68±0.36^a	−
	7	−	0.14±0.02^b	1.89±0.39^a	0.14±0.02^b
Norharman	3	15.48±2.68^a	6.68±0.40^b	6.48±1.00^c	5.37±0.44^d
	5	17.8±6.89^a	5.45±0.23^d	7.59±2.95^c	9.07±0.68^b
	7	22.69±2.02^a	7.69±0.84^d	8.75±1.24^c	15.18±3.96^b
Harman	3	3.21±0.19^a	1.69±0.06^c	1.53±0.20^d	2.16±0.02^b
	5	3.28±1.44^b	1.79±0.07^d	3.19±1.20^c	9.74±0.11a
	7	4.53±0.33^b	2.07±0.09^d	3.12±0.21^c	10.22±0.31^a
NDBA	3	0.08±0.02^c	0.13±0.01^b	0.15±0.02^a	0.09±0.01^c
	5	0.13±0.01^d	0.15±0.07^c	0.17±0.02^b	0.19±0.06^a
	7	0.16±0.03^c	0.23±0.02^b	0.23±0.03^b	0.25±0.05^a
NPIP	3	18.41±3.06^a	8.24±0.78^b	6.45±0.78^c	4.96±0.95^d
	5	28.89±1.57^a	13.03±0.10^b	11.95±0.49^c	6.89±1.02^d
	7	31.26±1.79^a	14.27±1.01^b	13.45±1.59^c	7.78±1.15^d
AA	3	11.90±3.29^b	5.61±3.75^d	8.37±0.77^c	12.58±2.94^a
	5	19.20±6.42^a	18.58±3.81^b	14.64±2.09^c	10.38±0.77^d
	7	28.31±2.96^a	18.83±3.27^b	22.60±1.74^c	18.20±4.08^d
注：−表示未检出；同行数据间不同字母表示差异显著（P<0.05）。

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