超高效液相色谱-串联质谱法鉴定和分析稻米中 酚酸类化合物的组成及分布

doi:10.3864/j.issn.0578-1752.2020.03.013

中国农业科学 ›› 2020, Vol. 53 ›› Issue (3): 612-631.doi: 10.3864/j.issn.0578-1752.2020.03.013

超高效液相色谱-串联质谱法鉴定和分析稻米中酚酸类化合物的组成及分布

赵珊¹,仲伶俐¹,周虹¹,李曦¹,雷欣宇¹,黄世群¹,郑幸果¹,冯俊彦²,雷绍荣¹,郭灵安¹()

¹ 四川省农业科学院分析测试中心/农业部农产品质量安全风险评估实验室（成都）,成都 610066
² 四川省农业科学院生物技术核技术研究所, 成都 610061

收稿日期:2019-06-27 接受日期:2019-11-20 出版日期:2020-02-01 发布日期:2020-02-13
通讯作者: 郭灵安
作者简介:赵珊,Tel：028-84504142;E-mail：zhaoshan11@126.com。
基金资助:
国家农产品质量安全风险评估重大专项(GJFP201701502);四川省财政创新工程(2017QNJJ-021);四川省财政创新工程(2017QNJJ-001)

Identification and Analysis of Phenolic Acids in Rice Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry

ZHAO Shan¹,ZHONG LingLi¹,ZHOU Hong¹,LI Xi¹,LEI XinYu¹,HUANG ShiQun¹,ZHENG XingGuo¹,FENG JunYan²,LEI ShaoRong¹,GUO LingAn¹()

¹ Center of Analysis and Testing, Sichuan Academy of Agricultural Sciences/Risk Assessment Laboratory of Agricultural Products Quality and Safety (Chengdu), Ministry of Agriculture, Chengdu 610066
² Institute of Biotechnology and Nuclear Technology, Sichuan Academy of Agricultural Sciences, Chengdu 610061

Received:2019-06-27 Accepted:2019-11-20 Online:2020-02-01 Published:2020-02-13
Contact: LingAn GUO

摘要/Abstract

摘要：

【目的】水稻是世界上最重要的作物之一,也是人们饮食中酚酸类营养成分的重要来源。建立稻米中酚酸类化合物鉴定与分析的超高效液相色谱-串联质谱（UPLC-MS/MS）检测方法,以深入了解和挖掘稻米的功能性营养。【方法】采用UPLC-MS/MS法对四川收集的白米、红米、紫米和黑米等14份材料中的19种酚酸进行定性和定量分析。优化碱水解、酸水解和净化萃取方法等前处理条件,同时优化色谱柱、流动相条件和质谱条件,并采用电喷雾电离和多反应监测模式进行检测。最后利用优化的分析方法分别测定糙米样品中的游离型、可溶性酯型、可溶性糖苷型、不溶性结合型和不溶性糖苷型酚酸的含量。【结果】通过对前处理条件的比对优化,获得的最优条件为：在含1%抗坏血酸和10 mmol·L ^-1 EDTA的2 mol·L ^-1 NaOH浓度下碱水解4 h,在1 mol·L ^-1 HCl溶液下酸水解1 h;所有净化萃取都使用含0.2% BHA的乙酸乙酯;采用HSS T3色谱柱,乙腈-0.01%甲酸水溶液为流动相进行梯度洗脱;除反式肉桂酸采用正离子模式,其余均为负离子模式,各化合物峰形好、分离度和灵敏度高。19种酚酸的线性范围良好（R ²≥0.9997）,检出限在0.023—4.728 μg·L ^-1,定量限在0.076—15.759 μg·L ^-1。19种酚酸游离型酚酸提取回收率为55.3%—98.0%,18种酚酸（绿原酸除外）的碱水解和酸水解回收率分别为90.8%—103.1%、51.7%—100.3%。该方法测定的14份稻米中共鉴定出14种酚酸,定量的有12种,酚酸总含量范围为356.3—1 234.5 mg·kg ^-1,含量较高的有阿魏酸、原儿茶酸、香草酸、4-香豆酸、芥子酸和对羟基苯甲酸,其中原儿茶酸和香草酸主要存在于紫米和黑米中,主要为不溶性结合型、可溶性酯型和可溶性糖苷型酚酸。【结论】该方法准确且灵敏度高。在提取和测定过程中保护剂的加入能有效抑制酚酸的降解,增加游离型和糖苷型酚酸的鉴定与定量分析,能更精确、全面地呈现出稻米中酚酸的分布情况。

关键词: 酚酸, 超高效液相色谱, 串联质谱, 稻米

Abstract:

【Objective】 Rice is one of the most important crops in the world, and it is also an important source of phenolic acids in people’s diet. To further understand and explore the functional nutrition of rice, an ultra-high performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was established for identification and analysis of rice phenolic acids in the present study. 【Method】 The qualitative and quantitative analysis of 19 phenolic acids in 14 samples of white rice, red rice, purple rice and black rice from Sichuan province, was carried out by UPLC-MS/MS. The pretreatment conditions, including alkali hydrolysis, acid hydrolysis and purification extraction, were optimized, besides, the chromatographic column, mobile phase condition and mass spectrometry conditions were optimized too. Furthermore, all detection was carried out by electrospray ionization and multi reaction monitoring mode. Finally, the content of free ester, soluble ester, soluble glycoside, insoluble binding and insoluble glycoside phenolic acid in brown rice samples was determined by using the optimized analytical method. 【Result】 The optimal conditions were obtained through the comparison and optimization of the pre-treatment conditions. It was as follows: alkaline hydrolysis was 4 hours at the concentration of 1% ascorbic acid and 10 mmol·L ^-1 EDTA, and acid hydrolysis was 1 hour at the concentration of 1 mol·L ^-1 HCl; all purification and extraction were carried out with ethylacetate containing 0.2% BHA; HSS T3 column was used, acetonitrile-0.01% formic acid aqueous solution was used as mobile phase for gradient elution; except trans-cinnamic acid adopts positive ion mode, the rest were negative ion mode. The compounds had good peak shape, high resolution and sensitivity. The linear range of 19 phenolic acids was good (R ²≥0.9997), the detection limit was 0.023-4.728 μg·L ^-1, and the quantitative limit was 0.076-15.759 μg·L ^-1. Recoveries of 19 phenolic acids in direct extraction were 55.3%-98.0%. Recoveries of 18 phenolic acids (except chlorogenic acid) in alkali hydrolysis and acid hydrolysis were 90.8%-103.1% and 51.7%-100.3%, respectively. In total, there were 14 phenolic acids in 14 rice samples determined using this method, 12 of which were quantitative. The total content range of phenolic acids was 356.3-1 234.5 mg·kg ^-1. Ferulic acid, protocatechuic acid, vanillic acid, p-coumaric acid, sinapic acid and p-hydroxybenzoic acid had higher content. Protocatechuic acid and vanillic acid could be mainly found in purple rice and black rice, most of which were insoluble binding type, soluble ester type and soluble glycosidic phenolic acid. 【Conclusion】 The method obtained in this study was accurate and sensitive. The addition of protectors effectively inhibited the degradation of phenolic acid and increased the identification and quantitative analysis of free and glycosidic phenolic acid during extraction and determination. Therefore, distribution of phenolic acid could be presented more accurately and comprehensively in rice.

Key words: phenolic acids, ultra-high performance liquid chromatography, tandem mass spectrometry, rice

赵珊,仲伶俐,周虹,李曦,雷欣宇,黄世群,郑幸果,冯俊彦,雷绍荣,郭灵安. 超高效液相色谱-串联质谱法鉴定和分析稻米中酚酸类化合物的组成及分布[J]. 中国农业科学, 2020, 53(3): 612-631.

ZHAO Shan,ZHONG LingLi,ZHOU Hong,LI Xi,LEI XinYu,HUANG ShiQun,ZHENG XingGuo,FENG JunYan,LEI ShaoRong,GUO LingAn. Identification and Analysis of Phenolic Acids in Rice Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry[J]. Scientia Agricultura Sinica, 2020, 53(3): 612-631.

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图/表 11

化合物名称 Compounds name	英文名 English name	分子式 Molecular formula	分子量 Molecular weight	CAS登录号 CAS Number	分子结构图 Molecular structure	所属类别 Category
没食子酸 Gallic acid	3,4,5-Trihydroxybenzoic acid	C₇H₆O₅	170.1	149-91-7		羟基苯甲酸类 Hydroxybenzoic acids
2,3,4-三羟基苯甲酸 2,3,4-Trihydroxybenzoic acid	1,2,3-Benzenetriol-4-carboxylic acid	C₇H₆O₅	170.1	610-02-6
水杨酸 Salicylic acid	2-Hydroxybenzoic acid	C₇H₆O₃	138.1	69-72-7
3,5-二羟基苯甲酸 3,5-Dihydroxybenzoic acid	-	C₇H₆O₄	154.1	99-10-5
原儿茶酸 Protocatechuic acid	3,4-Dihydroxybenzoic acid	C₇H₆O₄	154.1	99-50-3
龙胆酸 Gentisic acid	2,5-Dihydroxybenzoic acid	C₇H₆O₄	154.1	490-79-9
焦儿茶酸 Pyrocatechuic acid	2,3-Dihydroxybenzoic acid	C₇H₆O₄	154.1	303-38-8
化合物名称 Compounds name	英文名 English name	分子式 Molecular formula	分子量 Molecular weight	CAS登录号 CAS Number	分子结构图 Molecular structure	所属类别 Category
对羟基苯甲酸 p-Hydroxybenzoic acid	4-Hydroxybenzoic acid	C₇H₆O₃	138.1	99-96-7
香草酸 Vanillic acid	4-Hydroxy-3-methoxybenzoic acid	C₈H₈O₄	168.1	121-34-6
丁香酸 Syringic acid	4-Hydroxy-3,5-dimethoxybenzoic acid	C₉H₁₀O₅	198.2	530-57-4
绿原酸 Chlorogenic acid	3-O-Caffeoylquinic acid	C₁₆H₁₈O₉	354.3	327-97-9		咖啡酰奎宁酸类 Caffeoylquinic acids
咖啡酸 Caffeic acid	3,4-Dihydroxycinnamic acid	C₉H₈O₄	180.2	331-39-5		羟基肉桂酸类 Hydroxycinnamic acids
4-香豆酸 p-Coumaric acid	4-Hydroxycinnamic acid	C₉H₈O₃	164.2	501-98-4
阿魏酸 Ferulic acid	4-Hydroxy-3-methoxycinnamic acid	C₁₀H₁₀O₄	194.2	1135-24-6
3-羟基肉桂酸 3-Hydroxycinnamic acid	3-Coumaric acid	C₉H₈O₃	164.2	14755-02-3
芥子酸 Sinapic acid	4-Hydroxy-3,5-dimethoxycinnamic acid	C₁₁H₁₂O₅	224.2	530-59-6
异阿魏酸 Isoferulic acid	3-Hydroxy-4-methoxycinnamic acid	C₁₀H₁₀O₄	194.2	537-73-5
2-羟基肉桂酸 2-Hydroxycinnamic acid	2-Coumaric acid	C₉H₈O₃	164.2	614-60-8
反式肉桂酸 trans-Cinnamic acid	3-Phenyl-2-propenoic acid	C₉H₈O₂	148.2	140-10-3

图1

表2

图2

表3

目标化合物的质谱分析参数"

酚酸 Phenolic acid	保留时间 Retention time (min)	质荷比Mass-to-charge ratio (m/z)		锥孔电压 Cone voltage (V)	碰撞能量Collision energy (eV)	离子扫描模式 Ion scanning mode
酚酸 Phenolic acid	保留时间 Retention time (min)	母离子 Parent ion	子离子 Daughter ion	锥孔电压 Cone voltage (V)	碰撞能量Collision energy (eV)	离子扫描模式 Ion scanning mode
没食子酸Gallic acid	1.89	168.90	124.91*、78.90	28	14,22	负离子 Negative ions
2,3,4-三羟基苯甲酸 2,3,4-Trihydroxybenzoic acid	2.87	168.90	150.94*、106.89	32	14,18	负离子Negative ions
3,5-二羟基苯甲酸 3,5-Dihydroxybenzoic acid	2.97	152.90	108.90*、64.97	14	12,12	负离子Negative ions
原儿茶酸Protocatechuic acid	3.24	152.90	108.90*、90.88	6	14,22	负离子Negative ions
龙胆酸Gentisic acid	4.64	152.90	108.90*、80.92	10	12,16	负离子Negative ions
焦儿茶酸Pyrocatechuic acid	4.65	152.90	108.90*、80.92	14	16,22	负离子Negative ions
对羟基苯甲酸 p-Hydroxybenzoic acid	4.69	136.90	92.89*、64.91	6	12,24	负离子Negative ions
绿原酸Chlorogenic acid	4.85	353.03	190.99*、84.88	18	20,40	负离子Negative ions
香草酸Vanillic acid	5.85	166.90	151.93*、107.92	8	12,22	负离子Negative ions
咖啡酸Caffeic acid	5.98	178.90	134.93*、106.88	27	16,24	负离子Negative ions
丁香酸Syringic acid	6.61	196.97	181.96*、122.89	18	14,24	负离子Negative ions
4-香豆酸p-Coumaric acid	8.97	162.97	118.92*、93.15	22	12,20	负离子Negative ions
水杨酸Salicylic acid	10.25	136.90	92.89*、64.91	16	14,22	负离子Negative ions
阿魏酸Ferulic acid	11.06	192.97	133.95*、177.95	14	18,12	负离子Negative ions
3-羟基肉桂酸 3-Hydroxycinnamic acid	11.49	162.97	118.92*、90.93	22	16,24	负离子Negative ions
芥子酸Sinapic acid	11.65	223.03	207.97*、163.93	16	14,16	负离子Negative ions
异阿魏酸Isoferulic acid	12.09	192.97	177.95*、133.96	6	12,14	负离子Negative ions
2-羟基肉桂酸 2-Hydroxycinnamic acid	13.64	162.97	119.18*、92.89	2	24,24	负离子Negative ions
反式肉桂酸 trans-Cinnamic acid	14.50	148.90	130.92*、102.94	38	10,18	正离子Positive ions

表3

表4

稻米样品在不同试验方法中添加酚酸的回收率结果（n=6）"

酚酸 Phenolic acid	游离型提取Free type extraction (%)					碱水解Alkaline hydrolysis (%)					酸水解 Acid hydrolysis (%)	RSD (%)
酚酸 Phenolic acid	HLB固相萃取法 HLB Solid-phase extraction	RSD (%)	乙酸乙酯萃取法 Ethyl acetate extraction	RSD (%)	NaOH	RSD (%)	NaOH+1%抗坏血酸 NaOH+1% ascorbic acid	RSD (%)	NaOH +1%抗坏血酸+10 mmol∙L^-1 EDTA NaOH +1% ascorbic acid+10 mmol∙L^-1 EDTA	RSD (%)	酸水解 Acid hydrolysis (%)	RSD (%)
没食子酸Gallic acid	96.3	2.95	75.7	0.83	0.0	-	87.4	4.79	92.1	2.11	73.5	2.47
2,3,4-三羟基苯甲酸 2,3,4-Trihydroxybenzoic acid	92.6	1.93	95.4	2.02	0.0	-	86.9	3.41	94.5	1.80	86.9	0.66
3,5-二羟基苯甲酸 3,5-Dihydroxybenzoic acid	102.1	0.20	86.7	4.65	95.2	2.81	97.2	1.65	97.5	0.79	96.5	0.61
原儿茶酸Protocatechuic acid	100.3	1.39	88.2	0.01	0.0	-	95.1	0.98	98.8	1.99	92.1	2.05
龙胆酸Gentisic acid	87.7	3.80	84.1	2.89	0.0	-	85.5	4.63	96.0	4.20	100.3	0.43
焦儿茶酸Pyrocatechuic acid	93.1	2.20	84.3	2.81	0.0	-	91.9	5.88	103.0	0.24	99.8	0.81
对羟基苯甲酸 p-Hydroxybenzoic acid	99.0	0.47	95.0	0.55	99.9	0.12	99.5	2.36	103.1	2.03	96.2	1.86
绿原酸Chlorogenic Acid	89.9	1.01	55.3	3.98	-	-	-	-	-	-	-	-
香草酸Vanillic acid	103.8	1.90	92.3	1.34	101.8	0.19	98.6	1.28	100.5	1.74	92.1	3.87
咖啡酸Caffeic acid	90.2	0.59	93.1	2.53	0.0	-	92.9	1.50	100.1	1.64	64.1	1.63
丁香酸Syringic acid	102.9	1.28	92.6	2.19	94.1	1.40	98.8	0.42	100.9	2.30	95.9	1.00
4-香豆酸p-Coumaric acid	93.1	2.82	94.8	1.40	90.2	0.67	104.8	2.94	100.8	2.01	51.7	3.77
水杨酸Salicylic acid	89.1	2.39	85.6	0.72	90.5	0.09	98.4	1.68	100.6	1.14	78.5	1.73
阿魏酸Ferulic acid	97.5	3.00	98.0	1.05	84.4	1.61	110.5	0.12	103.1	0.28	52.3	3.55
3-羟基肉桂酸 3-Hydroxycinnamic acid	98.1	0.95	91.8	2.49	97.8	1.18	100.0	3.15	100.9	2.42	92.5	1.64
芥子酸Sinapic acid	85.3	4.03	88.3	4.67	6.9	34.0	101.4	1.11	101.9	3.35	62.2	3.03
异阿魏酸Isoferulic acid	111.4	3.90	91.3	0.01	100.8	0.69	97.8	3.09	100.9	1.66	70.6	1.84
2-羟基肉桂酸 2-Hydroxycinnamic acid	94.4	2.88	89.9	0.01	94.4	0.70	101.1	4.28	102.1	1.60	86.9	1.64
反式肉桂酸 trans-Cinnamic acid	97.0	4.08	74.7	2.57	82.9	1.43	101.1	3.36	104.8	1.95	68.2	3.58

表4

图3

表5

表6

四川稻米样品中不同类型酚酸的含量及分布情况（n=3）"

酚酸 Phenolic acid	类型 Type	材料（品种）名称 Material (variety) name
酚酸 Phenolic acid	类型 Type	五山丝苗 Wushansimiao	德优4727 Deyou 4727	德粳6号 Dejing No.6	德香4103 Dexiang 4103	川绿优188 Chuanlvyou188	桂潮2号 Guichao No.2	川香优37 Chuanxiangyou37	螺髻山红米 Luojishan red rice	红宝石 Rubine	广汉红米 Guanghan red rice	紫米 Purple rice	黑香糯 Heixiangnuo	广汉黑米 Guanghan black rice	黑稻2号 Heidao No.2
样品水分 Sample moisture (%)		8.28	7.89	8.33	8.85	7.94	7.91	8.10	8.11	7.60	8.31	12.5	7.95	8.09	7.73
没食子酸 Gallic acid (mg∙kg^-1)	1	0.01±0.00	TD	TD	0.01±0.00	0.01±0.00	TD	0.01±0.00	0.01±0.00	0.01±0.00	0.01±0.00	0.06±0.00	0.06±0.00	0.06±0.00	0.10±0.01
	2	0.46±0.01	ND	ND	1.31±0.04	0.05±0.01	ND	0.59±0.05	0.20±0.50	ND	ND	ND	0.06±0.07	ND	0.06±0.03
	3	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
	4	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	0.26±0.02
	5	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
2,3,4-三羟基苯甲酸 2,3,4- Trihydroxybenzoic acid (mg∙kg^-1)	1	0.01±0.00	0.01±0.00	TD	TD	TD	0.01±0.00	TD	0.01±0.00	0.02±0.00	0.02±0.00	0.34±0.06	1.71±0.32	1.89±0.21	4.73±0.41
	2	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
	3	0.51±0.04	0.61±0.07	0.52±0.04	0.50±0.02	0.51±0.06	0.50±0.01	0.52±0.02	0.47±0.02	0.49±0.09	0.57±0.02	0.67±0.02	0.74±0.12	0.73±0.01	0.79±0.09
	4	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	0.06±0.06	0.20±0.03	0.08±0.03	0.45±0.04
	5	0.49±0.13	0.52±0.10	0.44±0.05	0.48±0.03	0.46±0.06	0.44±0.04	0.43±0.01	ND	ND	ND	0.49±0.01	0.40±0.04	0.47±0.06	0.46±0.02
原儿茶酸 Protocatechuic acid (mg∙kg^-1)	1	0.06±0.00	0.05±0.00	0.06±0.00	0.05±0.00	0.05±0.00	0.06±0.00	0.05±0.00	3.24±0.02	3.35±0.02	6.42±0.16	27.37±0.61	20.81±0.21	21.36±0.47	24.70±2.44
	2	ND	ND	ND	ND	ND	ND	ND	10.47±0.24	8.12±0.31	15.87±0.26	104.37±0.80	134.10±0.86	155.84±1.41	168.73±0.55
	3	ND	ND	ND	ND	ND	ND	ND	2.26±0.18	1.44±0.08	2.60±0.19	14.75±0.57	19.80±0.76	23.08±0.64	22.61±0.24
	4	ND	ND	ND	ND	ND	ND	ND	9.60±0.21	14.82±0.06	21.99±1.30	152.50±2.41	226.54±13.70	203.72±3.19	280.32±5.32
	5	ND	ND	ND	ND	ND	ND	ND	1.67±0.04	2.20±0.14	2.95±0.94	12.79±0.58	18.42±0.48	16.83±0.64	24.32±0.91
对羟基苯甲酸 p-Hydroxybenzonic acid (mg∙kg^-1)	1	0.36±0.00	0.34±0.00	0.52±0.02	0.33±0.00	0.46±0.00	0.41±0.00	0.40±0.01	0.32±0.01	0.28±0.01	0.40±0.02	1.39±0.03	0.59±0.01	0.54±0.00	0.66±0.09
	2	2.52±0.23	4.94±0.13	23.36±0.05	4.06±0.01	8.26±0.05	3.11±0.08	6.37±0.06	9.81±0.17	2.94±0.01	3.67±0.07	6.24±0.36	4.11±0.04	4.63±0.01	4.42±0.00
	3	7.75±0.50	19.13±0.06	52.23±0.64	15.41±0.19	27.03±1.05	11.21±0.44	23.08±0.51	28.27±0.22	6.91±0.24	6.98±0.46	9.63±0.22	5.72±0.30	6.57±0.07	7.31±0.24
	4	1.58±0.04	1.66±0.06	5.43±0.03	1.38±0.14	2.44±0.03	1.82±0.07	2.68±0.07	2.81±0.00	1.84±0.04	2.22±0.10	3.22±0.06	3.51±0.17	2.85±0.07	3.97±0.06
	5	1.02±0.08	1.80±0.05	6.10±0.07	1.71±0.13	2.81±0.06	1.55±0.08	2.79±0.09	4.72±0.03	1.49±0.01	1.83±0.16	2.49±0.02	0.99±0.04	1.21±0.14	1.54±0.07
香草酸 Vanillic acid (mg∙kg^-1)	1	0.42±0.01	0.40±0.00	0.45±0.03	0.39±0.00	0.43±0.01	0.46±0.01	0.45±0.00	0.27±0.01	0.33±0.02	0.50±0.04	19.38±0.18	13.45±0.37	13.96±0.25	19.63±2.72
	2	1.55±0.06	2.09±0.08	2.26±0.08	2.52±0.07	1.99±0.11	1.78±0.12	2.74±0.10	1.37±0.00	1.92±0.01	3.47±0.15	52.81±0.91	83.57±1.07	107.81±3.44	100.04±2.16
	3	2.52±0.19	3.59±0.17	3.23±0.11	4.39±0.05	3.92±0.04	3.67±0.13	4.88±0.21	2.73±0.08	2.92±0.09	3.73±0.01	13.04±0.10	21.73±0.91	23.96±0.36	21.64±0.80
	4	0.99±0.05	1.06±0.00	1.35±0.07	0.88±0.07	1.03±0.01	0.94±0.04	1.14±0.08	0.69±0.01	1.02±0.01	1.56±0.07	56.82±1.22	110.17±11.82	99.36±0.58	139.94±3.69
	5	0.81±0.02	0.86±0.03	1.01±0.01	0.90±0.05	0.96±0.10	0.88±0.01	0.97±0.01	0.85±0.02	1.02±0.02	1.27±0.07	6.97±0.04	10.39±0.62	9.89±0.21	10.72±0.10
咖啡酸 Caffeic acid (mg∙kg^-1)	1	0.73±0.00	0.98±0.04	0.66±0.01	1.00±0.01	0.33±0.01	0.30±0.00	0.44±0.02	0.32±0.05	0.43±0.00	0.43±0.02	0.50±0.01	1.18±0.01	0.85±0.02	0.67±0.02
	2	4.25±0.20	6.64±0.17	4.07±0.42	5.30±0.44	3.77±0.21	3.66±0.02	4.85±0.13	3.27±0.07	3.57±0.03	6.53±0.14	5.64±0.09	13.08±0.12	12.08±0.15	8.25±0.02
	3	2.17±0.23	3.97±0.39	2.77±0.16	4.01±0.08	2.59±0.21	2.54±0.01	2.96±0.07	1.67±0.08	2.63±0.13	2.54±0.14	2.61±0.12	4.34±0.05	3.44±0.04	3.88±0.12
	4	6.05±0.26	5.47±0.33	7.37±0.29	4.02±0.72	4.17±0.01	3.26±0.22	4.27±0.53	4.32±0.15	3.89±0.07	3.79±0.42	7.82±0.16	7.38±0.33	6.27±0.29	4.06±0.41
	5	TD	TD	TD	TD	TD	TD	TD	TD	TD	TD	0.84±0.01	0.61±0.03	0.76±0.08	0.78±0.01
酚酸 Phenolic acid	类型 Type	材料（品种）名称 Material (variety) name
酚酸 Phenolic acid	类型 Type	五山丝苗 Wushansimiao	德优4727 Deyou 4727	德粳6号 Dejing No.6	德香4103 Dexiang 4103	川绿优188 Chuanlvyou188	桂潮2号 Guichao No.2	川香优37 Chuanxiangyou37	螺髻山红米 Luojishan red rice	红宝石 Rubine	广汉红米 Guanghan red rice	紫米 Purple rice	黑香糯 Heixiangnuo	广汉黑米 Guanghan black rice	黑稻2号 Heidao No.2
丁香酸 Syringic acid (mg∙kg^-1)	1	0.11±0.00	0.12±0.00	0.13±0.01	0.14±0.00	0.15±0.00	0.18±0.01	0.16±0.00	0.14±0.01	0.10±0.00	0.15±0.01	1.57±0.01	0.23±0.01	0.22±0.00	0.20±0.03
	2	1.41±0.11	1.47±0.04	1.59±0.02	1.68±0.02	1.50±0.01	1.56±0.01	1.64±0.05	1.84±0.03	1.02±0.00	1.59±0.05	4.28±0.25	2.70±0.02	2.98±0.19	1.89±0.02
	3	0.26±0.02	0.35±0.04	0.38±0.01	0.40±0.01	0.39±0.01	0.39±0.01	0.41±0.01	0.55±0.02	0.17±0.02	0.32±0.03	0.35±0.02	0.44±0.02	0.50±0.03	0.38±0.02
	4	0.80±0.08	0.79±0.02	0.96±0.08	0.72±0.04	0.82±0.01	0.89±0.04	0.80±0.04	0.74±0.03	0.62±0.04	1.19±0.08	1.19±0.06	0.96±0.00	0.77±0.04	0.73±0.03
	5	0.18±0.02	0.19±0.01	0.22±0.01	0.17±0.01	0.18±0.02	0.23±0.01	0.19±0.02	0.17±0.00	0.15±0.01	0.22±0.08	0.20±0.00	0.17±0.02	0.15±0.01	0.13±0.00
4-香豆酸 p-Coumaric acid (mg∙kg^-1)	1	0.62±0.01	0.67±0.01	1.38±0.07	0.62±0.00	0.62±0.02	0.84±0.01	0.57±0.01	1.14±0.07	0.70±0.02	0.93±0.05	2.95±0.07	0.35±0.01	0.41±0.01	0.30±0.04
	2	3.69±0.69	3.89±0.26	11.97±2.76	3.51±0.18	4.30±0.49	5.10±0.30	3.77±0.14	13.01±1.13	8.95±0.81	6.79±0.41	9.21±0.21	5.82±0.21	6.99±0.02	4.79±0.16
	3	0.85±0.07	1.53±0.14	3.20±0.05	1.16±0.02	1.95±0.07	1.10±0.04	1.60±0.04	1.83±0.02	1.05±0.02	0.95±0.04	1.20±0.05	0.73±0.01	0.83±0.01	0.71±0.03
	4	61.26±0.21	55.60±0.16	72.13±3.97	38.24±3.31	51.68±0.03	45.91±0.20	43.15±2.90	75.53±0.83	91.74±1.48	83.21±5.40	29.68±4.17	17.71±2.68	17.92±0.19	25.50±1.93
	5	0.76±0.15	0.85±0.16	1.12±0.06	0.59±0.00	0.93±0.05	0.71±0.03	0.72±0.03	1.02±0.06	1.41±0.01	1.52±0.05	0.72±0.05	0.43±0.01	0.41±0.03	0.40±0.01
水杨酸 Salicylic acid (mg∙kg^-1)	1	0.19±0.00	0.19±0.00	0.35±0.03	0.19±0.01	0.17±0.00	0.16±0.00	0.20±0.00	0.24±0.02	0.37±0.01	0.46±0.01	1.01±0.01	0.21±0.01	0.25±0.00	0.32±0.07
	2	0.88±0.01	0.90±0.00	1.54±0.04	0.85±0.10	0.71±0.01	0.67±0.03	0.79±0.02	0.99±0.07	1.62±0.13	1.68±0.10	1.98±0.12	1.17±0.09	1.32±0.07	1.93±0.07
	3	3.96±0.26	5.72±0.08	6.25±0.03	4.43±0.06	4.73±0.31	3.31±0.02	3.68±0.10	5.36±0.13	6.53±0.50	6.86±0.15	2.95±0.07	3.84±0.21	4.29±0.23	5.84±0.33
	4	ND	ND	0.16±0.00	ND	0.12±0.08	TD	ND	0.05±0.02	0.05±0.06	0.07±0.01	0.11±0.05	ND	ND	0.01±0.00
	5	0.52±0.07	0.78±0.01	1.12±0.02	0.66±0.06	0.62±0.09	0.52±0.01	0.45±0.03	0.85±0.01	0.85±0.01	1.01±0.19	0.75±0.04	0.38±0.01	0.45±0.06	0.43±0.11
阿魏酸 Ferulic acid (mg∙kg^-1)	1	1.85±0.02	2.00±0.01	3.71±0.20	2.43±0.03	2.80±0.05	3.12±0.01	3.49±0.08	3.09±0.25	2.01±0.02	1.81±0.13	7.31±0.13	2.45±0.02	2.09±0.03	2.22±0.30
	2	17.59±2.03	20.29±2.54	36.31±7.82	19.72±0.80	29.07±0.50	33.02±4.49	23.72±0.20	48.63±1.04	24.69±1.34	29.65±1.44	35.15±0.96	36.41±1.88	49.66±5.59	30.42±2.38
	3	6.15±0.45	8.41±0.84	12.66±0.09	9.15±0.27	12.95±0.45	7.91±0.32	9.62±0.11	8.24±0.08	7.35±0.06	7.47±0.24	6.92±0.21	5.28±0.02	5.80±0.03	4.78±0.25
	4	154.49±3.27	180.16±5.45	240.69±2.93	153.75±13.16	179.00±2.17	184.74±7.25	175.56±10.56	208.43±0.63	158.46±0.25	191.68±7.32	274.44±14.66	213.68±14.68	248.27±9.31	152.52±1.60
	5	3.55±0.44	3.79±0.22	4.55±0.22	3.30±0.02	4.25±0.11	3.46±0.04	3.48±0.10	4.25±0.25	4.48±0.05	5.21±0.29	5.21±0.14	3.16±0.32	3.23±0.11	3.58±0.02
芥子酸 Sinapic acid (mg∙kg^-1)	1	0.28±0.00	0.15±0.00	0.21±0.01	0.22±0.00	0.22±0.00	0.31±0.00	0.23±0.00	0.35±0.02	0.25±0.00	0.19±0.01	1.32±0.03	0.28±0.01	0.27±0.00	0.26±0.03
	2	28.22±1.44	33.27±5.12	44.58±0.00	32.37±1.78	59.81±0.35	65.49±1.84	44.94±1.57	71.36±2.17	43.50±0.68	35.78±1.97	52.64±1.02	48.62±0.41	63.15±4.86	40.70±2.04
	3	2.03±0.23	2.60±0.41	5.94±0.44	3.21±0.15	3.82±0.16	5.04±0.23	3.14±0.00	3.35±0.02	3.45±0.18	2.15±0.14	2.58±0.11	1.92±0.01	2.27±0.07	1.79±0.01
	4	2.50±0.22	3.49±0.10	5.15±0.09	3.51±0.61	4.38±0.25	5.31±0.35	3.69±0.14	6.35±0.06	5.55±0.01	5.58±0.50	9.54±0.43	3.14±0.12	3.87±0.29	3.34±0.06
	5	0.30±0.05	0.44±0.01	0.71±0.02	0.39±0.03	0.45±0.03	0.57±0.01	0.37±0.01	0.45±0.01	0.51±0.01	0.46±0.02	0.76±0.02	0.24±0.00	0.30±0.01	0.32±0.01
反式肉桂酸 trans-Cinnamic acid (mg∙kg^-1)	1	0.05±0.00	0.01±0.00	0.07±0.01	0.01±0.01	ND	ND	0.05±0.02	0.02±0.01	0.02±0.01	0.04±0.00	ND	0.01±0.00	ND	ND
	2	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
	3	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
	4	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND
	5	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND	ND

表6

图4

图5

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编号No.	材料（品种）名称Material (variety) name	类别Category	采样地点Collected site
1	德香4103 Dexiang4103	籼稻/白米稻 Indica/white rice	绵竹 Mianzhu
2	桂朝2号 Guichao No.2	籼稻/白米稻 Indica/white rice	绵竹 Mianzhu
3	五山丝苗 Wushansimiao	籼稻/白米稻 Indica/white rice	绵竹 Mianzhu
4	德优4727 Deyou4727	籼稻/白米稻 Indica/white rice	绵竹 Mianzhu
5	德粳6号 Dejing No.6	梗稻/白米稻 Japonica/white rice	绵竹 Mianzhu
6	川香优37 Chuanxiangyou37	籼稻/白米稻 Indica/white rice	新都 Xindu
7	川绿优188 Chuanlvyou188	籼稻/白米稻 Indica/white rice	新都 Xindu
8	黑香糯 Heixiangnuo	黑米稻 Black rice	广汉 Guanghan
9	黑稻2号 Heidao No.2	黑米稻 Black rice	广汉 Guanghan
10	广汉黑米 Guanghan black rice	黑米稻 Black rice	广汉 Guanghan
11	红宝石Rubine	红米稻 Red rice	广汉 Guanghan
12	广汉红米 Guanghan red rice	红米稻 Red rice	广汉 Guanghan
13	螺髻山红米 Luojishan red rice	红米稻 Red rice	普格 Puge
14	紫米 Purple rice	紫米稻 Purple rice	遂宁 Suining

酚酸 Phenolic acid	线性范围 Linear range (μg·L^-1)	回归方程 Linear equation	相关系数（R²） Correlation coefficient	检出限 LOD (μg·L^-1)	定量限 LOQ (μg·L^-1)
没食子酸Gallic acid	1.0—500	y=4129.01x+5097.625	0.99994	0.121	0.403
2,3,4-三羟基苯甲酸2,3,4-Trihydroxybenzoic acid	1.0—500	y=1181.706x+1184.094	0.99998	0.178	0.592
3,5-二羟基苯甲酸3,5-Dihydroxybenzoic acid	1.0—500	y=4200.251x+6932.746	0.99981	0.577	1.922
原儿茶酸Protocatechuic acid	1.0—500	y=5195.678x+4966.813	0.99998	0.221	0.735
龙胆酸Gentisic acid	5.0—500	y=1143.852x-5212.479	0.99974	4.728	15.759
焦儿茶酸Pyrocatechuic acid	2.5—500	y=1578.332 x-2815.838	0.99976	1.391	4.637
对羟基苯甲酸p-Hydroxybenzoic acid	1.0—500	y=8060.058x+89591.57	0.99999	0.023	0.076
绿原酸Chlorogenic Acid	1.0—500	y=3455.433x+915.729	0.99999	0.029	0.097
香草酸Vanillic acid	1.0—250	y=791.212x+5290.2	0.99993	0.060	0.201
咖啡酸Caffeic acid	2.5—250	y=9980.757x+29851.52	0.99962	1.799	5.995
丁香酸Syringic acid	1.0—500	y=1194.07x-734.952	0.99989	0.047	0.158
4-香豆酸p-Coumaric acid	1.0—500	y=11839.49x+4169.524	0.99999	0.144	0.479
水杨酸Salicylic acid	1.0—500	y=12668.42x-8192.132	0.99989	0.126	0.420
阿魏酸Ferulic acid	1.0—500	y=3638.813x-2875.187	0.99998	0.110	0.368
3-羟基肉桂酸3-Hydroxycinnamic acid	1.0—500	y=9461.071x+10025.18	0.99998	0.122	0.408
芥子酸Sinapic acid	1.0—500	y=2006.256x-2051.911	0.99998	0.050	0.167
异阿魏酸Isoferulic acid	1.0—500	y=929.839x-1868.854	0.99966	0.227	0.756
2-羟基肉桂酸2-Hydroxycinnamic acid	1.0—500	y=2820.271x+375.238	0.99999	0.457	1.522
反式肉桂酸trans-Cinnamic acid	1.0—250	y=3065.769x+3429.845	0.99973	0.293	0.976

超高效液相色谱-串联质谱法鉴定和分析稻米中酚酸类化合物的组成及分布

Identification and Analysis of Phenolic Acids in Rice Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry

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超高效液相色谱-串联质谱法鉴定和分析稻米中 酚酸类化合物的组成及分布

Identification and Analysis of Phenolic Acids in Rice Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry

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超高效液相色谱-串联质谱法鉴定和分析稻米中酚酸类化合物的组成及分布