Identification of Metabolites in Human Plasma and Urine after Consumption of a Polyphenol-Rich Juice DrinkClick to copy article linkArticle link copied!
Abstract
A polyphenol-rich (P-R) juice drink was developed as a potential approach to increase intake of dietary polyphenols. Analysis of the beverage by HPLC with PDA, fluorescence, and MS detection facilitated the identification/partial identification of 40 flavonoids and related phenolic compounds. The main constituents were (−)-epigallocatechin and other green tea flavan-3-ols, phloretin-2′-O-glucoside, gallic acid, hesperetin-7-O-rutinoside, 5-O-caffeoylquinic acid, and procyanidins, with trace levels of several flavonols and purple grape juice anthocyanins also being present. Healthy human subjects (n = 10) consumed 350 mL of the P-R juice drink, after which plasma and urine samples were collected over a 0−24 h period. HPLC-MS analysis identified 13 metabolites in plasma and a further 20 in urine. Qualitatively, the profiles of the glucuronide, sulfated, and methylated metabolites were very similar to those detected in earlier investigations when the main components in the juice drink were consumed separately in feeding studies with coffee, green tea, orange juice, and apple cider.
Cited By
This article is cited by 42 publications.
- Shuhan Feng, Jianyong Yi, Xuan Li, Xinye Wu, Yuanyuan Zhao, Youchuan Ma, Jinfeng Bi. Systematic Review of Phenolic Compounds in Apple Fruits: Compositions, Distribution, Absorption, Metabolism, and Processing Stability. Journal of Agricultural and Food Chemistry 2021, 69
(1)
, 7-27. https://doi.org/10.1021/acs.jafc.0c05481
- Anna Kårlund, Kati Hanhineva, Marko Lehtonen, Reijo O. Karjalainen, and Mari Sandell . Nontargeted Metabolite Profiles and Sensory Properties of Strawberry Cultivars Grown both Organically and Conventionally. Journal of Agricultural and Food Chemistry 2015, 63
(3)
, 1010-1019. https://doi.org/10.1021/jf505183j
- Gordon J. McDougall, Sean Conner, Gema Pereira-Caro, Rocio Gonzalez-Barrio, Emma M. Brown, Susan Verrall, Derek Stewart, Tanya Moffet, Maria Ibars, Roger Lawther, Gloria O’Connor, Ian Rowland, Alan Crozier, and Chris I. R. Gill . Tracking (Poly)phenol Components from Raspberries in Ileal Fluid. Journal of Agricultural and Food Chemistry 2014, 62
(30)
, 7631-7641. https://doi.org/10.1021/jf502259j
- W. Mullen, J. Gonzalez, J. Siwy, J. Franke, N. Sattar, A. Mullan, S. Roberts, C. Delles, H. Mischak, and A. Albalat . A Pilot Study on the Effect of Short-Term Consumption of a Polyphenol Rich Drink on Biomarkers of Coronary Artery Disease Defined by Urinary Proteomics. Journal of Agricultural and Food Chemistry 2011, 59
(24)
, 12850-12857. https://doi.org/10.1021/jf203369r
- Gary Williamson, Michael N. Clifford. A critical examination of human data for the biological activity of quercetin and its phase-2 conjugates. Critical Reviews in Food Science and Nutrition 2024, 41 , 1-37. https://doi.org/10.1080/10408398.2023.2299329
- Ana Reis, Sara Rocha, Irundika HK. Dias, Raquel Costa, Raquel Soares, José Luis Sánchez-Quesada, Antonio Perez, Victor de Freitas. Type 2 Diabetes mellitus alters the cargo of (poly)phenol metabolome and the oxidative status in circulating lipoproteins. Redox Biology 2023, 59 , 102572. https://doi.org/10.1016/j.redox.2022.102572
- Malgorzata Rogozinska, Kamil Lisiecki, Zbigniew Czarnocki, Magdalena Biesaga. Antioxidant Activity of Sulfate Metabolites of Chlorogenic Acid. Applied Sciences 2023, 13
(4)
, 2192. https://doi.org/10.3390/app13042192
- Adriana Trifan, Simon Vlad Luca. Phloretin: Advances on Resources, Biosynthesis Pathway, Bioavailability, Bioactivity, and Pharmacology. 2023, 1-31. https://doi.org/10.1007/978-3-030-94753-8_26-1
- Christo J. F. Muller, Elizabeth Joubert, Nireshni Chellan, Yutaka Miura, Kazumi Yagasaki. New Insights into the Efficacy of Aspalathin and Other Related Phytochemicals in Type 2 Diabetes—A Review. International Journal of Molecular Sciences 2022, 23
(1)
, 356. https://doi.org/10.3390/ijms23010356
- Ana Reis, Rosa Perez-Gregorio, Nuno Mateus, Victor de Freitas. Interactions of dietary polyphenols with epithelial lipids: advances from membrane and cell models in the study of polyphenol absorption, transport and delivery to the epithelium. Critical Reviews in Food Science and Nutrition 2021, 61
(18)
, 3007-3030. https://doi.org/10.1080/10408398.2020.1791794
- Sara Rocha, Olga Oskolkova, Victor de Freitas, Ana Reis. (Poly)phenol‐Rich Diets in the Management of Endothelial Dysfunction in Diabetes Mellitus: Biological Properties in Cultured Endothelial Cells. Molecular Nutrition & Food Research 2021, 65
(15)
https://doi.org/10.1002/mnfr.202001130
- Anallely López-Yerena, Inés Domínguez-López, Anna Vallverdú-Queralt, Maria Pérez, Olga Jáuregui, Elvira Escribano-Ferrer, Rosa M. Lamuela-Raventós. Metabolomics Technologies for the Identification and Quantification of Dietary Phenolic Compound Metabolites: An Overview. Antioxidants 2021, 10
(6)
, 846. https://doi.org/10.3390/antiox10060846
- Jeprianto Manurung, Jonas Kappen, Jan Schnitzler, Andrej Frolov, Ludger A. Wessjohann, Andria Agusta, Alexandra N. Muellner-Riehl, Katrin Franke. Analysis of Unusual Sulfated Constituents and Anti-infective Properties of Two Indonesian Mangroves, Lumnitzera littorea and Lumnitzera racemosa (Combretaceae). Separations 2021, 8
(6)
, 82. https://doi.org/10.3390/separations8060082
- Ana Reis, Sara Rocha, Victor de Freitas. Going “Green” in the Prevention and Management of Atherothrombotic Diseases: The Role of Dietary Polyphenols. Journal of Clinical Medicine 2021, 10
(7)
, 1490. https://doi.org/10.3390/jcm10071490
- Ibrahim M. Abu-Reidah, David Arráez-Román, Mohammed Al-Nuri, Ismail Warad, Antonio Segura-Carretero. Untargeted metabolite profiling and phytochemical analysis of Micromeria fruticosa L. (Lamiaceae) leaves. Food Chemistry 2019, 279 , 128-143. https://doi.org/10.1016/j.foodchem.2018.11.144
- Monica L. Castro-Acosta, Thomas A. B. Sanders, Dianne P. Reidlinger, Julia Darzi, Wendy L. Hall. Adherence to UK dietary guidelines is associated with higher dietary intake of total and specific polyphenols compared with a traditional UK diet: further analysis of data from the Cardiovascular risk REduction Study: Supported by an Integrated Dietary Approach (CRESSIDA) randomised controlled trial. British Journal of Nutrition 2019, 121
(4)
, 402-415. https://doi.org/10.1017/S0007114518003409
- Fabio Castello, Giuseppina Costabile, Letizia Bresciani, Michele Tassotti, Daniele Naviglio, Delia Luongo, Paola Ciciola, Marilena Vitale, Claudia Vetrani, Gianni Galaverna, Furio Brighenti, Rosalba Giacco, Daniele Del Rio, Pedro Mena. Bioavailability and pharmacokinetic profile of grape pomace phenolic compounds in humans. Archives of Biochemistry and Biophysics 2018, 646 , 1-9. https://doi.org/10.1016/j.abb.2018.03.021
- Xuan Zeng, Weiwei Su, Yuying Zheng, Hong Liu, Panlin Li, Weijian Zhang, Yuting Liang, Yang Bai, Wei Peng, Hongliang Yao. UFLC-Q-TOF-MS/MS-Based Screening and Identification of Flavonoids and Derived Metabolites in Human Urine after Oral Administration of Exocarpium Citri Grandis Extract. Molecules 2018, 23
(4)
, 895. https://doi.org/10.3390/molecules23040895
- Gemma Sasot, Miriam Martínez-Huélamo, Anna Vallverdú-Queralt, Mercè Mercader-Martí, Ramon Estruch, Rosa M. Lamuela-Raventós. Identification of phenolic metabolites in human urine after the intake of a functional food made from grape extract by a high resolution LTQ-Orbitrap-MS approach. Food Research International 2017, 100 , 435-444. https://doi.org/10.1016/j.foodres.2017.01.020
- Xuan Zeng, Weiwei Su, Yang Bai, Taobin Chen, Zenghao Yan, Jiawei Wang, Minmin Su, Yuying Zheng, Wei Peng, Hongliang Yao. Urinary metabolite profiling of flavonoids in Chinese volunteers after consumption of orange juice by UFLC-Q-TOF-MS/MS. Journal of Chromatography B 2017, 1061-1062 , 79-88. https://doi.org/10.1016/j.jchromb.2017.07.015
- Silvia Lima Costa, Victor Diogenes Amaral Silva, Cleide dos Santos Souza, Cleonice Creusa Santos, Irmgard Paris, Patricia Muñoz, Juan Segura-Aguilar. Impact of Plant-Derived Flavonoids on Neurodegenerative Diseases. Neurotoxicity Research 2016, 30
(1)
, 41-52. https://doi.org/10.1007/s12640-016-9600-1
- Marcos Roberto de Oliveira. Phloretin‐induced cytoprotective effects on mammalian cells: A mechanistic view and future directions. BioFactors 2016, 42
(1)
, 13-40. https://doi.org/10.1002/biof.1256
- Paul F. Cancalon. Citrus Juices Health Benefits. 2016, 115-127. https://doi.org/10.1007/978-3-319-23672-8_8
- Kayleigh A. Clarke, Tristan P. Dew, Rachel E.B. Watson, Mark D. Farrar, Joanne E. Osman, Anna Nicolaou, Lesley E. Rhodes, Gary Williamson. Green tea catechins and their metabolites in human skin before and after exposure to ultraviolet radiation. The Journal of Nutritional Biochemistry 2016, 27 , 203-210. https://doi.org/10.1016/j.jnutbio.2015.09.001
- Yu-Lin Kao, Yi-Ming Kuo, Yi-Ru Lee, Shun-Fa Yang, Wen-Rong Chen, Huei-Jane Lee. Apple polyphenol induces cell apoptosis, cell cycle arrest at G2/M phase, and mitotic catastrophe in human bladder transitional carcinoma cells. Journal of Functional Foods 2015, 14 , 384-394. https://doi.org/10.1016/j.jff.2015.02.002
- Kayleigh A. Clarke, Tristan P. Dew, Rachel E.B. Watson, Mark D. Farrar, Susan Bennett, Anna Nicolaou, Lesley E. Rhodes, Gary Williamson. High performance liquid chromatography tandem mass spectrometry dual extraction method for identification of green tea catechin metabolites excreted in human urine. Journal of Chromatography B 2014, 972 , 29-37. https://doi.org/10.1016/j.jchromb.2014.09.035
- Hiroyuki Sakakibara, Yoko Ichikawa, Sanae Tajima, Yoshie Makino, Yusuke Wakasugi, Kayoko Shimoi, Saori Kobayashi, Shigenori Kumazawa, Toshinao Goda. Practical application of flavonoid-poor menu meals to the study of the bioavailability of bilberry anthocyanins in human subjects. Bioscience, Biotechnology, and Biochemistry 2014, 78
(10)
, 1748-1752. https://doi.org/10.1080/09168451.2014.932667
- Anurag Singh, Audrey Demont, Lucas Actis-Goretta, Sébastien Holvoet, Antoine Lévêques, Melissa Lepage, Sophie Nutten, Annick Mercenier. Identification of epicatechin as one of the key bioactive constituents of polyphenol-enriched extracts that demonstrate an anti-allergic effect in a murine model of food allergy. British Journal of Nutrition 2014, 112
(3)
, 358-368. https://doi.org/10.1017/S0007114514000877
- Ana Faria, Manuela Meireles, Iva Fernandes, Celestino Santos-Buelga, Susana Gonzalez-Manzano, Montserrat Dueñas, Victor de Freitas, Nuno Mateus, Conceição Calhau. Flavonoid metabolites transport across a human BBB model. Food Chemistry 2014, 149 , 190-196. https://doi.org/10.1016/j.foodchem.2013.10.095
- Cristiana Miglio, Ilaria Peluso, Anna Raguzzini, Deborah V. Villaño, Eleonora Cesqui, Giovina Catasta, Elisabetta Toti, Mauro Serafini. Fruit juice drinks prevent endogenous antioxidant response to high-fat meal ingestion. British Journal of Nutrition 2014, 111
(2)
, 294-300. https://doi.org/10.1017/S0007114513002407
- Kua Hu, Jia-yu Zhang, Ke Zan, Jun Li, Peng-fei Tu. Qualitative and quantitative evaluation of Microctis Folium (the leaves of Microcos paniculata L.) by high performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry. Analytical Methods 2014, 6
(17)
, 6850. https://doi.org/10.1039/C4AY00196F
- Giuseppina Pace Pereira Lima, Fabio Vianello, Camila Renata Corrêa, Renê Arnoux da Silva Campos, Milena Galhardo Borguini. Polyphenols in Fruits and Vegetables and Its Effect on Human Health. Food and Nutrition Sciences 2014, 05
(11)
, 1065-1082. https://doi.org/10.4236/fns.2014.511117
- Clara Ibáñez, Carolina Simó, Virginia García-Cañas, Alejandro Cifuentes, María Castro-Puyana. Metabolomics, peptidomics and proteomics applications of capillary electrophoresis-mass spectrometry in Foodomics: A review. Analytica Chimica Acta 2013, 802 , 1-13. https://doi.org/10.1016/j.aca.2013.07.042
- Rong Tsao, Hongyan Li. Analytical techniques for phytochemicals. 2013, 434-451. https://doi.org/10.1002/9781118464717.ch19
- Hannah Deußer, Dorothee Rogoll, Wolfgang Scheppach, Antje Volk, Ralph Melcher, Elke Richling. Gastrointestinal absorption and metabolism of apple polyphenols ex vivo by the pig intestinal mucosa in the Ussing chamber. Biotechnology Journal 2013, 8
(3)
, 363-370. https://doi.org/10.1002/biot.201200303
- Gina Borges, Michael E. J. Lean, Susan A. Roberts, Alan Crozier. Bioavailability of dietary (poly)phenols: a study with ileostomists to discriminate between absorption in small and large intestine. Food & Function 2013, 4
(5)
, 754. https://doi.org/10.1039/c3fo60024f
- Riitta Törrönen, Gordon J. McDougall, Gary Dobson, Derek Stewart, Jarkko Hellström, Pirjo Mattila, Juha-Matti Pihlava, Ali Koskela, Reijo Karjalainen. Fortification of blackcurrant juice with crowberry: Impact on polyphenol composition, urinary phenolic metabolites, and postprandial glycemic response in healthy subjects. Journal of Functional Foods 2012, 4
(4)
, 746-756. https://doi.org/10.1016/j.jff.2012.05.001
- Celestino Santos‐Buelga, Susana González‐Manzano, Montserrat Dueñas, Ana M. González‐Paramás. Analysis and Characterisation of Flavonoid Phase II Metabolites. 2012, 249-286. https://doi.org/10.1002/9781118299753.ch11
- Carlos-Eduardo Narváez-Cuenca, Jean-Paul Vincken, Harry Gruppen. Identification and quantification of (dihydro) hydroxycinnamic acids and their conjugates in potato by UHPLC–DAD–ESI-MSn. Food Chemistry 2012, 130
(3)
, 730-738. https://doi.org/10.1016/j.foodchem.2011.04.050
- Hiroyuki Sakakibara, Yoko Ichikawa, Sanae Tajima, Yoshie Makino, Yusuke Wakasugi, Shigenori Kumazawa, Satoshi Sasaki, Kayoko Shimoi, Toshinao Goda. Protocols for Preparation of a Flavonoid-poor Menu Satisfying the Dietary Reference Intakes for Japanese, 2005. Nippon Eiyo Shokuryo Gakkaishi 2012, 65
(5)
, 229-235. https://doi.org/10.4327/jsnfs.65.229
- Navamayooran Thavanesan. The putative effects of green tea on body fat: an evaluation of the evidence and a review of the potential mechanisms. British Journal of Nutrition 2011, 106
(9)
, 1297-1309. https://doi.org/10.1017/S0007114511003849
- Gina Borges, William Mullen, Adam Mullan, Michael E. J. Lean, Susan A. Roberts, Alan Crozier. Bioavailability of multiple components following acute ingestion of a polyphenol‐rich juice drink. Molecular Nutrition & Food Research 2010, 54
(S2)
https://doi.org/10.1002/mnfr.200900611
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.