UPLC-FLD determination and antioxidant activity of polyphenols in virgin olive oil

doi:10.3969/j.issn.1004-1524.2021.05.16

Acta Agriculturae Zhejiangensis ›› 2021, Vol. 33 ›› Issue (5): 907-915.DOI: 10.3969/j.issn.1004-1524.2021.05.16

• Quality and Safety of Agricultural Products • Previous Articles Next Articles

UPLC-FLD determination and antioxidant activity of polyphenols in virgin olive oil

LI Xue¹^,²^,³(), ZHANG Yu¹^,²^,³, WANG Junhong¹^,³, ZHU Zuoyi¹^,³, SUN Suling¹, LIU Zhi¹^,⁴, ZHU Shenlong³, SHEN Guoxin³, Agusti ROMERO⁵, WANG Wei¹^,³^,^*()

1. Institue of Agro-Product Safety and Nutrition, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China
2. Key Laboratory of Information Traceability for Agricultural Products, Ministry of Agriculture and Rural Affairs of China, Hangzhou 310021, China
3. International Joint Laboratory for Quality and Nutrition of Woody Oils, Hangzhou 310021, China
4. College of Agriculture and Biotechnology, Hunan University of Humanities, Science and Technology, Loudi 417000, China
5. Institute of Agriculture and Food Research and Technology, Catalonia 08140, Spain

Received:2020-07-07 Online:2021-05-25 Published:2021-05-25
Contact: WANG Wei

Abstract

Abstract:

An ultra high performance liquid chromatography (UPLC) coupled with fluorescence detector (FLD) was used to determine the contents of 6 selected phenolic compounds in different samples of virgin olive oil. The total polyphenols content and antioxidant activity of these samples were also detected. The chromatographic column used was Cadenza (150 mm×4.6 mm, 5 μm) and the mobile phase was composed of 0.1% formate-water (A) and acetonitrile (B). Column temperature was at 35℃. The excitation wavelength and emission wavelength were 278 nm and 339 nm. Under the conditions, 6 phenolic compounds in virgin olive oil could be separated well within 17 min, with a wider range of concentration, good linear relationship (R²≥ 0.999 5), high precision with the relative standard deviation (RSD) of intra-day precision≤ 4.91%, RSD of inter-day precision ≤ 5.41%, and reliable recovery with the average recovery rate of 93.42%-119.86%, RSD≤6.26%. The contents of hydroxytyrosol, tyrosol, vanillic acid, pinoresinol and total polyphenols in different virgin olive oil samples were significantly different, while the contents of oleuropein and ligstroside were the lowest and the differences between samples were relatively small. Polyphenols extracts of virgin olive oil have good antioxidant activity, but significant differences between different samples were detected. The total antioxidant capacities of the samples were from 0.95 to 2.71 mmol·L^-1 Trolox determined by ABTS method. DPPH free radical scavenging activities of samples were 7.22%-66.23%. Hydroxyl free radical clearance capabilities of samples were 13.24-136.06 U·mL^-1. Coratina showed the strongest antioxidant activity among samples. The content of total polyphenols was significantly correlated to total antioxidant capacity of the extracts of virgin olive oil.

Key words: virgin olive oil, polyphenol, UPLC-FLD, antioxidant activity

CLC Number:

S509

LI Xue, ZHANG Yu, WANG Junhong, ZHU Zuoyi, SUN Suling, LIU Zhi, ZHU Shenlong, SHEN Guoxin, Agusti ROMERO, WANG Wei. UPLC-FLD determination and antioxidant activity of polyphenols in virgin olive oil[J]. Acta Agriculturae Zhejiangensis, 2021, 33(5): 907-915.

Figures/Tables 5

References 24

[1]	GAVAHIAN M, MOUSAVI KHANEGHAH A, LORENZO J M, et al. Health benefits of olive oil and its components: Impacts on gut microbiota antioxidant activities, and prevention of noncommunicable diseases[J]. Trends in Food Science & Technology, 2019,88:220-227.
[2]	戚欢阳, 李强. 初榨橄榄油抗动脉粥样硬化药效物质分析[J]. 海峡药学, 2019,31(6):49-51.
	QI H Y, LI Q. Analysis of substance with antiatherogenic effect in extra virgin olive oil[J]. Strait Pharmaceutical Journal, 2019,31(6):49-51.(in Chinese with English abstract)
[3]	向春蓉, 徐洲, 王寒冬, 等. 3个引进油橄榄品种初榨油多酚类化合物含量及抗氧化活性研究[J]. 中国粮油学报, 2017,32(9):94-98.
	XIANG C R, XU Z, WANG H D, et al. The content of polyphenol and antioxidant property of three vatieties virgin olive oil[J]. Journal of the Chinese Cereals and Oils Association, 2017,32(9):94-98.(in Chinese with English abstract)
[4]	王玲平, 周生茂, 戴丹丽, 等. 植物酚类物质研究进展[J]. 浙江农业学报, 2010,22(5):696-701.
	WANG L P, ZHOU S M, DAI D L, et al. Progress in plant phenolic compounds[J]. Acta Agriculturae Zhejiangensis, 2010,22(5):696-701.(in Chinese with English abstract)
[5]	张东, 薛雅琳, 朱琳, 等. 我国陇南地区初榨橄榄油多酚类化合物组成研究[J]. 中国油脂, 2016,41(4):37-40.
	ZHANG D, XUE Y L, ZHU L, et al. Polyphenols composition of virgin olive oils in Longnan district in China[J]. China Oils and Fats, 2016,41(4):37-40.(in Chinese with English abstract)
[6]	李雪, 张玉, 王君虹, 等. 特级初榨橄榄油中酚类化合物不同提取方法对比研究[J]. 中国油脂, 2020,45(1):102-107, 131.
	LI X, ZHANG Y, WANG J H, et al. Comparison of different extraction methods of phenolic compounds in extra virgin olive oil[J]. China Oils and Fats, 2020,45(1):102-107, 131.(in Chinese with English abstract)
[7]	白云慧, 温海超, 张磊, 等. 基于酚类化合物组成差异的7类植物油脂识别[J]. 食品科学, 2018,39(22):207-212.
	BAI Y H, WEN H C, ZHANG L, et al. Phenolic compositions and discrimination of seven vegetable oils[J]. Food Science, 2018,39(22):207-212.(in Chinese with English abstract)
[8]	CONDELLI N, CARUSO M C, GALGANO F, et al. Prediction of the antioxidant activity of extra virgin olive oils produced in the Mediterranean area[J]. Food Chemistry, 2015,177:233-239. DOI URL
[9]	BEAUCHAMP G K, KEAST R S J, MOREL D, et al. Ibuprofen-like activity in extra-virgin olive oil[J]. Nature, 2005,437(7055):45-46. DOI URL
[10]	ABDALLAH M, MARZOCCO S, ADESSO S, et al. Olive oil polyphenols extracts inhibit inflammatory markers in J774A.1 murine macrophages and scavenge free radicals[J]. Acta Histochemica, 2018,120(1):1-10. DOI URL
[11]	LAURETTI E, NENOV M, DINCER O, et al. Extra virgin olive oil improves synaptic activity, short-term plasticity, memory, and neuropathology in a tauopathy model[J]. Aging Cell, 2020,19(1):e13076.
[12]	MIHO H, MORAL J, LÓPEZ-GONZÁLEZ M A, et al. The phenolic profile of virgin olive oil is influenced by malaxation conditions and determines the oxidative stability[J]. Food Chemistry, 2020,314:126183. DOI URL
[13]	BAJOUB A, MEDINA-RODRÍGUEZ S, GÓMEZ-ROMERO M, et al. Assessing the varietal origin of extra-virgin olive oil using liquid chromatography fingerprints of phenolic compound, data fusion and chemometrics[J]. Food Chemistry, 2017,215:245-255. DOI URL
[14]	FUENTES E, PAUCAR F, TAPIA F, et al. Effect of the composition of extra virgin olive oils on the differentiation and antioxidant capacities of twelve monovarietals[J]. Food Chemistry, 2018,243:285-294. DOI URL
[15]	BAJOUB A, PACCHIAROTTA T, HURTADO-FERNÁNDEZ E, et al. Comparing two metabolic profiling approaches (liquid chromatography and gas chromatography coupled to mass spectrometry) for extra-virgin olive oil phenolic compounds analysis: a botanical classification perspective[J]. Journal of Chromatography A, 2016,1428:267-279. DOI URL
[16]	ALARCÓN FLORES M I, ROMERO-GONZÁLEZ R, GARRIDO FRENICH A, et al. Analysis of phenolic compounds in olive oil by solid-phase extraction and ultra high performance liquid chromatography-tandem mass spectrometry[J]. Food Chemistry, 2012,134(4):2465-2472. DOI URL
[17]	SELVAGGINI R, SERVILI M, URBANI S, et al. Evaluation of phenolic compounds in virgin olive oil by direct injection in high-performance liquid chromatography with fluorometric detection[J]. Journal of Agricultural and Food Chemistry, 2006,54(8):2832-2838. DOI URL
[18]	GODOY-CABALLERO M P, ACEDO-VALENZUELA M I, GALEANO-DÍAZ T. Simple quantification of phenolic compounds present in the minor fraction of virgin olive oil by LC-DAD-FLD[J]. Talanta, 2012,101:479-487. DOI URL
[19]	王强, 王锴, 黄梅桂, 等. LLE-UPLC-FLD法测定橄榄油中羟基酪醇和酪醇的含量[J]. 食品工业科技, 2018,39(9):233-238.
	WANG Q, WANG K, HUANG M G, et al. Determination of the contents of tyrosol and hydroxytyrosol in olive oil by liquid-liquid extraction and UPLC-FLD[J]. Science and Technology of Food Industry, 2018,39(9):233-238.(in Chinese with English abstract)
[20]	GHISONI S, LUCINI L, ANGILLETTA F, et al. Discrimination of extra-virgin-olive oils from different cultivars and geographical origins by untargeted metabolomics[J]. Food Research International, 2019,121:746-753. DOI URL
[21]	SÁNCHEZ DE MEDINA V, PRIEGO-CAPOTE F, DE CASTRO M D L. Characterization of monovarietal virgin olive oils by phenols profiling[J]. Talanta, 2015,132:424-432. DOI URL
[22]	DEIANA P, SANTONA M, DETTORI S, et al. Multivariate approach to assess the chemical composition of Italian virgin olive oils as a function of variety and harvest period[J]. Food Chemistry, 2019,300:125243. DOI URL
[23]	BARBOSA M L, DE MENESES A A P M, DE AGUIAR R P S, et al. Oxidative stress, antioxidant defense and depressive disorders: a systematic review of biochemical and molecular markers[J]. Neurology, Psychiatry and Brain Research, 2020,36:65-72. DOI URL
[24]	柯琼华, 王广, 田瑞, 等. 薇菜多糖结构及清除ABTS⁺·的反应动力学分析[J]. 西北农林科技大学学报(自然科学版), 2020,48(11):1-9.
	KE Q H, WANG G, TIAN R, et al. Structure and antioxidant kinetics on ABTS⁺·free radical of polysaccharides from Osmunda japonica Thunb[J]. Journal of Northwest A&F University, 2020,48(11):1-9. (in Chinese with English abstract)

多酚化合物 Polyphenols	荧光检测器FLD					紫外检测器UV
多酚化合物 Polyphenols	回归方程 Regress equation	相关系数 R²	线性范围 Linear range/ (μg·mL^-1)	定量限 LOQ/(μg· mL^-1)	检出限 LOD/(μg· mL^-1)	回归方程 Regress equation	相关系数 R²	线性范围 Linear range/ (μg·mL^-1)	定量限 LOQ/(μg· mL^-1)	检出限 LOD/(μg· mL^-1)
羟基酪醇 Hydroxytyrosol	y=2394141.98x -26214.42	1.0000	0.026-12.8	0.003	0.001	y=9007.84x -219.50	1.0000	0.128-12.8	0.128	0.039
酪醇 Tyrosol	y=2737496.85x -30373.56	1.0000	0.005-10.2	0.004	0.001	y=7006.96x -284.44	1.0000	0.102-10.2	0.102	0.034
香草酸 Vanillic acid	y=2638811.24x -21127.88	1.0000	0.022-11.0	0.006	0.002	y=12618.85x -485.26	1.0000	0.110-11.0	0.110	0.033
橄榄苦苷 Oleuropein	y=283557.60x -78095.20	0.9995	0.098-29.4	0.066	0.020	y=2634.68x -728.51	0.9999	0.490-29.4	0.490	0.148
女贞苷 Ligstroside	y=120011.15x -30187.66	0.9996	0.170-51.0	0.170	0.052	y=1503.57x -813.65	0.9998	0.850-51.0	0.850	0.258
松脂酚 Pinoresinol	y=6008326.90x -2178721.02	0.9995	0.0860-25.8	0.003	0.001	y=8179.26x -4051.88	0.9997	0.430-25.8	0.430	0.130

多酚化合物 Polyphenols	荧光检测器FLD					紫外检测器UV
多酚化合物 Polyphenols	回归方程 Regress equation	相关系数 R²	线性范围 Linear range/ (μg·mL^-1)	定量限 LOQ/(μg· mL^-1)	检出限 LOD/(μg· mL^-1)	回归方程 Regress equation	相关系数 R²	线性范围 Linear range/ (μg·mL^-1)	定量限 LOQ/(μg· mL^-1)	检出限 LOD/(μg· mL^-1)
羟基酪醇 Hydroxytyrosol	y=2394141.98x -26214.42	1.0000	0.026-12.8	0.003	0.001	y=9007.84x -219.50	1.0000	0.128-12.8	0.128	0.039
酪醇 Tyrosol	y=2737496.85x -30373.56	1.0000	0.005-10.2	0.004	0.001	y=7006.96x -284.44	1.0000	0.102-10.2	0.102	0.034
香草酸 Vanillic acid	y=2638811.24x -21127.88	1.0000	0.022-11.0	0.006	0.002	y=12618.85x -485.26	1.0000	0.110-11.0	0.110	0.033
橄榄苦苷 Oleuropein	y=283557.60x -78095.20	0.9995	0.098-29.4	0.066	0.020	y=2634.68x -728.51	0.9999	0.490-29.4	0.490	0.148
女贞苷 Ligstroside	y=120011.15x -30187.66	0.9996	0.170-51.0	0.170	0.052	y=1503.57x -813.65	0.9998	0.850-51.0	0.850	0.258
松脂酚 Pinoresinol	y=6008326.90x -2178721.02	0.9995	0.0860-25.8	0.003	0.001	y=8179.26x -4051.88	0.9997	0.430-25.8	0.430	0.130

多酚化合物 Polyphenols	样品含量 Concentration/ μg	低浓度Low concentration		高浓度High concentration
多酚化合物 Polyphenols	样品含量 Concentration/ μg	加标量 Concentration of addition standard/(μg·g^-1)	回收率 Recovery rates/%	加标量 Concentration of addition standard/(μg·g^-1)	回收率 Recovery rates/%
羟基酪醇Hydroxytyrosol	0	1.26	119.2±1.09	12.59	110.99±0.33
酪醇Tyrosol	0	1.00	99.75±0.39	10.03	106.53±0.62
香草酸Vanillic acid	0	0.96	93.42±0.31	9.64	116.68±0.34
橄榄苦苷Oleuropein	0	1.08	110.51±2.48	10.82	100.67±6.26
女贞苷Ligstroside	0	1.67	119.50±3.12	16.72	100.30±2.33
松脂酚Pinoresinol	0	0.85	119.86±1.10	8.46	101.69±0.67

多酚化合物 Polyphenols	样品含量 Concentration/ μg	低浓度Low concentration		高浓度High concentration
多酚化合物 Polyphenols	样品含量 Concentration/ μg	加标量 Concentration of addition standard/(μg·g^-1)	回收率 Recovery rates/%	加标量 Concentration of addition standard/(μg·g^-1)	回收率 Recovery rates/%
羟基酪醇Hydroxytyrosol	0	1.26	119.2±1.09	12.59	110.99±0.33
酪醇Tyrosol	0	1.00	99.75±0.39	10.03	106.53±0.62
香草酸Vanillic acid	0	0.96	93.42±0.31	9.64	116.68±0.34
橄榄苦苷Oleuropein	0	1.08	110.51±2.48	10.82	100.67±6.26
女贞苷Ligstroside	0	1.67	119.50±3.12	16.72	100.30±2.33
松脂酚Pinoresinol	0	0.85	119.86±1.10	8.46	101.69±0.67

品种 Variety	化合物含量 Content/(μg·g^-1)						总多酚含量 Total polyphenol content/ (μg·g^-1)	DPPH/%	ABTS/ (mmol· L^-1)	抑制羟自由基能力 Hydroxyl radical clearance capacity/ (U·mL^-1)
品种 Variety	羟基酪醇 Hydroxy- tyrosol	酪醇 Tyrosol	香草酸 Vanillic acid	橄榄苦苷 Oleuro- pein	女贞苷 Ligstro- side	松脂醇 Pinoresinol	总多酚含量 Total polyphenol content/ (μg·g^-1)	DPPH/%	ABTS/ (mmol· L^-1)	抑制羟自由基能力 Hydroxyl radical clearance capacity/ (U·mL^-1)
Coratina 科拉蒂	6.26± 0.16Ba	8.73± 0.17Aa	1.19± 1.23Dc	0.97± 0.94Ea	—	3.20± 1.85Cd	160.36± 4.26a	66.23± 3.11 a	2.71± 0.37 a	136.06± 16.52 a
Picual 皮瓜尔	4.13± 0.75 Bb	5.65± 0.37 Ac	1.58± 1.14 Da	0.96± 0.26Eb	—	4.05± 0.55Cb	70.99± 0.53c	11.47± 13.21 d	1.13± 3.19 c	44.19± 14.72 b
Arbosana 阿尔波萨纳	0.75± 3.53 Ed	3.45± 0.16 Bd	1.46± 0.30 Cb	0.96± 0.46Db	—	4.15± 0.45Aa	71.14± 1.31c	24.47± 6.44 b	1.38± 0.84 b	13.24± 4.49 c
Koroneiki 柯基	3.91± 1.56 Bc	6.63± 0.07 Ab	0.99± 0.87 De	0.95± 0.44 Db	—	3.12± 0.39 Cd	92.28± 0.82b	7.22± 7.64 d	1.40± 0.41 b	27.47± 6.46 bc
Arbequina 豆果	0.56± 2.17 Ee	2.83± 0.27 Be	1.12± 0.74 Cd	0.95± 0.19 Db	—	3.52± 0.46 Ac	45.82± 1.24d	19.54± 3.98 c	0.95± 4.76 d	39.59± 5.72 b

UPLC-FLD determination and antioxidant activity of polyphenols in virgin olive oil

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 5

References 24

Related Articles 11

Recommended Articles

Metrics

Comments

[1]	LI Yuancheng, SUN Hong, WU Yifei, YAO Xiaohong, SHEN Qi, TANG Jiangwu. Nutritional components and antioxidant activity of solid-state fermented cottonseed kernel [J]. , 2020, 32(4): 610-615.
[2]	YANG Zhi, LI Wenyi, GAO Yuntao, XIONG Huabin, CHEN Yijian, YANG Huijuan. Optimization of extraction process of total flavonoids from Acerola cherry by response surface methodology and their antioxidant activities [J]. , 2020, 32(10): 1866-1872.
[3]	ZHANG Hanqing, LIU Ruiling, WU Weijie, DENG Shanggui, GAO Haiyan, CHEN Hangjun. Effect of apple polyphenols on quality and browning of fresh-cut lotus root [J]. , 2019, 31(9): 1549-1554.
[4]	QIN Yi, LYU Guoying, ZHANG Zuofa. Studies on immunomodulatory and antioxidant activities in vitro of recombinant human lactoferrin from transgenic rice [J]. , 2018, 30(1): 1-6.
[5]	SU Bo, JIANG Hubiao, QIAO Jianli, PAN Jie, XU Wei, WU Anning, DING Ting. Resistance mechanism of bio-control strain DZSY21 against maize sheath blight [J]. , 2017, 29(3): 450-459.
[6]	CHAI Xinyi, NI Zanpeng, YU Shijun, ZHANG Weiwei, YIN Peifeng. Optimization of Se-rich liquid fermentation conditions and antioxidant activity of polysaccharide from Auricularia auricula mycelia [J]. , 2017, 29(11): 1903-1911.
[7]	JIN Qunli， ZHANG Zuofa， FAN Lijun， CAI Weiming*. Comparison of antioxidant activity of the extracts from the fruiting body of brown Agaricus bisporus at different growth stages [J]. , 2016, 28(5): 797-.
[8]	YIN Na1， LIN Xiao\\|qing2， YANG Yue\\|wei1， XU Hai\\|sheng2，*. Separation， purification and in vitro activity of antioxidant peptides from Whitmania pigra [J]. , 2015, 27(3): 348-.
[9]	WANG Jun\\|hong;GAO Hai\\|yan*;GE Lin\\|mei;CHEN Hang\\|jun;FANG Xiang\\|jun. Technological study on microwave\\|assisted extraction of polyphenols from Sargassum fusiforme [J]. , 2013, 25(6): 0-1372.
[10]	SHAO Jin-hua;LI Tao;YANG Jia . Study on microwave-assisted extraction of garlic polysaccharide and its antioxidant activity [J]. , 2013, 25(4): 0-872.
[11]	RU Yi;CHENG Anwei;*;WANG Wenliang;JIN Qiong;GONG Zhiqing;WANG Shoujing;. Study on the content of extractable and non\\|extractable polyphenols in onions [J]. , 2013, 25(1): 0-191.