Screening and identification of antioxidant active ingredients from red wine via spectrum-effect relationship analysis
Main Article Content
Keywords
antioxidant activity, red wine, spectrum-effect relationship, UFLC-Q-TOF/MS
Abstract
Red wine was a prominent constituent of diets across the globe and modern pharmacological studies showed that red wine had the main function of antioxidant. However, the reported screening methods for active ingredients were inefficient and insensitive. In this research, 35 batches of red wine were used to establish the chromatography fingerprint, which were further utilized to screen and identify the antioxidant active ingredients through spectrum-effect relationship analysis. Indeed, the antioxidant capacity of red wine was evaluated by total antioxidant capacity assay kit (ABTS method). After evaluating the antioxidant capacity of samples, correlations were analyzed by Pearson correlation analysis, Spearman correlation analysis, and Gray Relational Analysis (GRA). Moreover, spectrum-effect relationships combined with ultrafast liquid chromatography/quadrupole-time-of-flight mass spectrometry (UFLC-Q-TOF/MS) revealed that the succinic acid, gallic acid, protocatechuic acid, catechin, syringic acid, salicylic acid, homogentisic acid, ellagic acid, isorhamnetin-3-O-glucoside, and trans- resveratrol show antioxidative efficacy. Collectively, the present study established the spectrum-effect relationship strategy of red wine and identified active antioxidant ingredients, which would give reasonable index components for the health function of red wine and provide reference for quick screening of bioactive compounds for food.
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References
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Svoboda Pavel, Vlčková Hana, Nováková Lucie. Development and validation of UHPLC-MS/MS method for determination of eight naturally occurring catechin derivatives in various tea samples and the role of matrix effects. J Pharm Biomed Anal. 2015;114:62–70. 10.1016/j.jpba.2015.04.026
Tkacz Karolina, Wojdyło Aneta, Turkiewicz Igor P, Ferreres Federico, Moreno Diego A, Nowicka Paulina. UPLC-PDA-Q/ TOF-MS profiling of phenolic and carotenoid compounds and their influence on anticholinergic potential for AChE and BuChE inhibition and on-line antioxidant activity of selected Hippophaë rhamnoides L. cultivars. Food Chem. 2020;309:125766. 10.1016/j.foodchem.2019.125766
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Xu Nan, Li Mingchen, Wang Ping, Wang Shuling, Shi Haiyan. Spectrum-effect relationship between antioxidant and anti-inflammatory effects of Banxia Baizhu Tianma decoction: An identification method of active substances with endothelial cell protective effect. Front Pharmacol. 2022;13:823341. 10.3389/fphar.2022.823341
Yan Linlin, Yin Peipei, Ma Chao, Liu Yujun. Method development and validation for pharmacokinetic and tissue distributions of ellagic acid using ultrahigh performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Molecules. 2014;19(11):18923–35. 10.3390/molecules191118923
Yang Lanping, Xie Xiuman, Zhang Jing, Sun Guoxiang. Microemulsion electrokinetic chromatography in combination with chemometric methods to evaluate the holistic quality consistency and predict the antioxidant activity of Ixeris sonchifolia (Bunge) Hance injection. PLoS One. 2016;11(6):e0157601. 10.1371/journal.pone.0157601
Zarubina IV, Lukk MV, Shabanov PD. Antihypoxic and antioxidant effects of exogenous succinic acid and aminothiol succinate-containing antihypoxants. Bull Exp Biol Med. 2012;153(3):336–9. 10.1007/s10517-012-1709-5
Zhang Xian-Fei, Chen Juan, Yang Jun-Li, Shi Yan-Ping. UPLC-MS/MS analysis for antioxidant components of Lycii fructus based on spectrum-effect relationship. Talanta. 2018;180:389–95. 10.1016/j.talanta.2017.12.078
Zhang Xiangyu, Wang Shilan, Wu Yujun, Liu Xiaoyi, Wang Junjun, Han Dandan. Ellagic acid alleviates diquat-induced jejunum oxidative stress in C57BL/6 mice through activating Nrf2 mediated signaling pathway. Nutrients. 2022;14(5):1103. 10.3390/nu14051103
Zhao Yun, Fang Chanlin, Jin Cuiyuan, Bao Zhiwei, Yang Guiling, Jin Yuanxiang. Catechin from green tea had the potential to decrease the chlorpyrifos induced oxidative stress in larval zebrafish (Danio rerio). Pestic Biochem Physiol. 2022;182:105028. 10.1016/j.pestbp.2021.105028
Al Khatib Maher, Costa Jessica, Spinelli Daniele, Capecchi Eliana, Saladino Raffaele, Baratto Maria Camilla, et al. Homogentisic acid and gentisic acid biosynthesized pyomelanin mimics: Structural characterization and antioxidant activity. Int J Mol Sci. 2021;22(4):1739. 10.3390/ijms22041739
Australia New Zealand Food Standards Code - Standard 4.5.1 - Wine Production Requirements (Australia Only), https://www.legislation.gov.au/Details/F2011C00249; 2004 [Accessed 24 October 2004].
Bai Zhang-Zhen, Tang Jun-Man, Ni Jing, Zheng Tian-Tian, Zhou Yang, Sun Dao-Yang, et al. Comprehensive metabolite profile of multi-bioactive extract from tree peony (Paeonia ostii and Paeonia rockii) fruits based on MS/MS molecular networking. Food Res Int. 2021;148:110609. 10.1016/j.foodres.2021.110609
Chen Wenbin, Tu Xijuan, Wu Dehui, Gao Zhaosheng, Wu Siyuan, Huang Shaokang. Comparison of the partition efficiencies of multiple phenolic compounds contained in propolis in different modes of acetonitrile–water-based homogenous liquid–liquid extraction. Molecules. 2019;24(3):442. 10.3390/molecules24030442
Du Weifeng, Zhu Weihao, Ge Weihong, Li Changyu. Research on the effect of spleen-invigorating and anti-swelling active ingredients in crude and processed coix seed based on spectrum-effects relationship combined with chemometrics. J Pharm Biomed Anal. 2021;205:114350. 10.1016/j.jpba.2021.114350
Eke Rita, Ejiofor Emmanuel, Oyedemi Sunday, Onoja Samuel, Omeh Ndukaku. Evaluation of nutritional composition of Citrullus lanatus Linn. (watermelon) seed and biochemical assessment of the seed oil in rats. J Food Biochem. 2021;45(6):e13763. 10.1111/jfbc.13763
El-Demerdash Fatma M, El-Sayed Raghda A, Abdel-Daim Mohamed M. Rosmarinus officinalis essential oil modulates renal toxicity and oxidative stress induced by potassium dichro-mate in rats. J Trace Elem Med Biol. 2021;67:126791. 10.1016/j.jtemb.2021.126791
Esteki M, Shahsavari Z, Simal-Gandara J. Food identification by high performance liquid chromatography fingerprinting and mathematical processing. Food Res Int. 2019;122: 303–17. 10.1016/j.foodres.2019.04.025
Fernández-Pachón Ma Soledad, Villaño Débora, Troncoso Ana Ma, García-Parrilla Ma Carmen. [Review of the different methods for the evaluation of the in vitro antioxidant activity of wine and study of in vivo effects]. Arch Latinoam Nutr. 2006;56(2):110–22.
Food and Drug Administration. Botanical Drug Development Guidance for Industry, https://www.fda.gov/media/93113/; 2016 [Accessed December 2016].
Gao Yuye, Yu Xie-An, Wang Bing, Yin Guo, Wang Jue, Wang Tiejie, et al. Based on multi-activity integrated strategy to screening, characterization and quantification of bioactive compounds from red wine. Molecules. 2021;26(21);6750. 10.3390/molecules26216750
Haunschild Robin, Marx Werner. 2022. On health effects of resveratrol in wine. Int J Environ Res Public Health. 2022;19(5):3110. 10.3390/ijerph19053110
Huang Yin, Tian Yuan, Zhang Zunjian, Peng Can. A HILIC-MS/ MS method for the simultaneous determination of seven organic acids in rat urine as biomarkers of exposure to realgar. J Chromatogr B Analyt Technol Biomed Life Sci. 2012;905:37–42. 10.1016/j.jchromb.2012.07.038
Kong Chang-Suk, Kim Jung-Ae, Qian Zhong-Ji, Kim You Ah, Lee Jung Im., Kim Se-Kwon, et al. Protective effect of isorhamnetin 3-O-beta-D-glucopyranoside from Salicornia herbacea against oxidation-induced cell damage. Food Chem Toxicol. 2009;47(8):1914–20. 10.1016/j.fct.2009.05.002
Lavigne Elodie Gras, Cavagnino Andrea, Steinschneider Rémy, Breton Lionel, Baraibar Martin A, Jäger Sibylle. 2022. Oxidative damage prevention in human skin and sensory neurons by a salicylic acid derivative. Free Radic Biol Med. 2022;181:98–104. 10.1016/j.freeradbiomed.2022.01.029
Ma Fengwei, Gong Xiaojian, Zhou Xin, Zhao Yang, Li Menglin. An UHPLC-MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. J Ethnopharmacol. 2015;162:377–83. 10.1016/j.jep.2014.12.044
Manjunatha S, Shaik Althaf Hussain, Maruthi Prasad E, Al Omar Suliman Yousef, Mohammad Altaf, Kodidhela Lakshmi Devi. Combined cardio-protective ability of syringic acid and resveratrol against isoproterenol induced cardio-toxicity in rats via attenuating NF-kB and TNF-α pathways. Sci Rep. 2020;10(1):3426. 10.1038/s41598-020-59925-0
Navajas-Porras Beatriz, Pérez-Burillo Sergio, Valverde-Moya Álvaro Jesús, Hinojosa-Nogueira Daniel, Pastoriza Silvia, Rufián-Henares José Ángel. Effect of cooking methods on the antioxidant capacity of plant foods submitted to in vitro digestion-fermentation. Antioxidants (Basel). 2020;9(12):1312. 10.3390/antiox9121312
Plumb Jenny, Durazzo Alessandra, Lucarini Massimo, Camilli Emanuela, Turrini Aida, Marletta Luisa, et al. Extractable and nonextractable antioxidants composition in the eBASIS database: A key tool for dietary assessment in human health and disease research. Nutrients. 2020;12(11):3405. 10.3390/nu12113405
Rao Si-Wei, Duan Yuan-Yuan, Pang Han-Qing, Xu Shao-Hua, Hu Shou-Qian, Cheng Ke-Guang, et al. Spectrum-effect relationship analysis of bioactive compounds in Zanthoxylum nitidum (Roxb.) DC by ultra-high performance liquid chromatography mass spectrometry coupled with comprehensive filtering approaches. Front Pharmacol. 2022;13:794277. 10.3389/fphar.2022.794277
Sohrabi Farzaneh, Dianat Mahin, Badavi Mohammad, Radan Maryam, Mard Seyyed Ali. Gallic acid suppresses inflammation and oxidative stress through modulating Nrf2-HO-1-NF-κB signaling pathways in elastase-induced emphysema in rats. Environ Sci Pollut Res Int. 2021;28(40):56822–34. 10.1007/s11356-021-14513-1
Somade Oluwatobi T, Adeyi Olubisi E, Ajayi Babajide O, Asunde Osiro O, Iloh Precious D, Adesanya Adedayo A, et al. Syringic and ascorbic acids prevent NDMA-induced pulmonary fibro-genesis, inflammation, apoptosis, and oxidative stress through the regulation of PI3K-Akt/PKB-mTOR-PTEN signaling pathway. Metabol Open. 2022;14:100179. 10.1016/j.metop.2022.100179
Spagnol Caroline Magnani, Assis Renata Pires, Brunetti Iguatemy Lourenço, Isaac Vera Lucia Borges, Salgado Hérida Regina Nunes, Corrêa Marcos Antonio. In vitro methods to determine the antioxidant activity of caffeic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2019;219:358–66. 10.1016/j.saa.2019.04.025
Svoboda Pavel, Vlčková Hana, Nováková Lucie. Development and validation of UHPLC-MS/MS method for determination of eight naturally occurring catechin derivatives in various tea samples and the role of matrix effects. J Pharm Biomed Anal. 2015;114:62–70. 10.1016/j.jpba.2015.04.026
Tkacz Karolina, Wojdyło Aneta, Turkiewicz Igor P, Ferreres Federico, Moreno Diego A, Nowicka Paulina. UPLC-PDA-Q/ TOF-MS profiling of phenolic and carotenoid compounds and their influence on anticholinergic potential for AChE and BuChE inhibition and on-line antioxidant activity of selected Hippophaë rhamnoides L. cultivars. Food Chem. 2020;309:125766. 10.1016/j.foodchem.2019.125766
Wang Yanan, Wu Haoshuang, Zhou Zhongyi, Maitz Manfred F, Liu Kunpeng, Zhang Bo, et al. A thrombin-triggered self-regulating anticoagulant strategy combined with anti-inflammatory capacity for blood-contacting implants. Sci Adv. 2022;8(9):eabm3378. 10.1126/sciadv.abm3378
World Health Organization. Program on traditional medicine. Guidelines for the assessment of herbal medicines. World Health Organization, https://apps.who.int/iris/handle/10665/58865; 1991 [Accessed 13 July 1991].
Xu Nan, Li Mingchen, Wang Ping, Wang Shuling, Shi Haiyan. Spectrum-effect relationship between antioxidant and anti-inflammatory effects of Banxia Baizhu Tianma decoction: An identification method of active substances with endothelial cell protective effect. Front Pharmacol. 2022;13:823341. 10.3389/fphar.2022.823341
Yan Linlin, Yin Peipei, Ma Chao, Liu Yujun. Method development and validation for pharmacokinetic and tissue distributions of ellagic acid using ultrahigh performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Molecules. 2014;19(11):18923–35. 10.3390/molecules191118923
Yang Lanping, Xie Xiuman, Zhang Jing, Sun Guoxiang. Microemulsion electrokinetic chromatography in combination with chemometric methods to evaluate the holistic quality consistency and predict the antioxidant activity of Ixeris sonchifolia (Bunge) Hance injection. PLoS One. 2016;11(6):e0157601. 10.1371/journal.pone.0157601
Zarubina IV, Lukk MV, Shabanov PD. Antihypoxic and antioxidant effects of exogenous succinic acid and aminothiol succinate-containing antihypoxants. Bull Exp Biol Med. 2012;153(3):336–9. 10.1007/s10517-012-1709-5
Zhang Xian-Fei, Chen Juan, Yang Jun-Li, Shi Yan-Ping. UPLC-MS/MS analysis for antioxidant components of Lycii fructus based on spectrum-effect relationship. Talanta. 2018;180:389–95. 10.1016/j.talanta.2017.12.078
Zhang Xiangyu, Wang Shilan, Wu Yujun, Liu Xiaoyi, Wang Junjun, Han Dandan. Ellagic acid alleviates diquat-induced jejunum oxidative stress in C57BL/6 mice through activating Nrf2 mediated signaling pathway. Nutrients. 2022;14(5):1103. 10.3390/nu14051103
Zhao Yun, Fang Chanlin, Jin Cuiyuan, Bao Zhiwei, Yang Guiling, Jin Yuanxiang. Catechin from green tea had the potential to decrease the chlorpyrifos induced oxidative stress in larval zebrafish (Danio rerio). Pestic Biochem Physiol. 2022;182:105028. 10.1016/j.pestbp.2021.105028
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