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      An Integrated Approach to Characterize Intestinal Metabolites of Four Phenylethanoid Glycosides and Intestinal Microbe-Mediated Antioxidant Activity Evaluation In Vitro Using UHPLC-Q-Exactive High-Resolution Mass Spectrometry and a 1,1-Diphenyl-2-picrylhydrazyl-Based Assay

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          Abstract

          Intestinal bacteria have a significant role in metabolism and the pharmacologic actions of traditional Chinese medicine active ingredients. Phenylethanoid glycosides (PhGs), as typical phenolic natural products, possess wide bioactivities, but low oral bioavailability. The aim of this work was to elucidate the metabolic mechanism underlying PhGs in the intestinal tract and screen for more active metabolites. In this study, a rapid and reliable method using an effective post-acquisition approach based on advanced ultra-high-performance liquid chromatography (UHPLC) coupled with hybrid Quadrupole-Orbitrap high resolution mass spectrometry (Q-Exactive-HRMS) provided full MS and HCD MS 2 data. Thermo Scientific™ Compound Discoverer™ software with a Fragment Ion Search (FISh) function in one single workflow was developed to investigate the intestinal microbial metabolism of four typical PhGs. Furthermore, antioxidant activity evaluation of PhGs and their related metabolites was simultaneously carried out in combination with a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay to understand how intestinal microbiota transformations modulate biological activity and explore structure–activity relationships (SARs). As a result, 26 metabolites of poliumoside, 42 metabolites of echinacoside, 42 metabolites of tubuloside, and 46 metabolites of 2′-acetylacteoside were identified. Degradation, reduction, hydroxylation, acetylation, hydration, methylation, and sulfate conjugation were the major metabolic pathways of PhGs. Furthermore, the degraded metabolites with better bioavailability had potent antioxidant activity that could be attributed to the phenolic hydroxyl groups. These findings may enhance our understanding of the metabolism, pharmacologic actions, and real active forms of PhGs.

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          Interaction between phenolics and gut microbiota: role in human health.

          Dietary phenolic compounds are often transformed before absorption. This transformation modulates their biological activity. Different studies have been carried out to understand gut microbiota transformations of particular polyphenol types and identify the responsible microorganisms. Although there are potentially thousands of different phenolic compounds in the diet, they are typically transformed to a much smaller number of metabolites. The aim of this review was to discuss the current information about the microbial degradation metabolites obtained from different phenolics and their formation pathways, identifying their differences and similarities. The modulation of gut microbial population by phenolics was also reviewed in order to understand the two-way phenolic-microbiota interaction. Clostridium and Eubacterium genera, which are phylogenetically associated, are other common elements involved in the metabolism of many phenolics. The health benefits from phenolic consumption should be attributed to their bioactive metabolites and also to the modulation of the intestinal bacterial population.
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            Understanding the Molecular Mechanisms of the Interplay Between Herbal Medicines and Gut Microbiota

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              Bioactivities of Phenolics by Focusing on Suppression of Chronic Diseases: A Review

              Phenolics, which are secondary metabolites of plants, exhibit remarkable bioactivities. In this contribution, we have focused on their protective effect against chronic diseases rather than their antioxidant activities, which have been widely discussed in the literature. A large body of epidemiological studies has proven the bioactivities of phenolics in both standard compounds and natural extracts: namely, anticancer, anti-inflammatory, and antibacterial activities as well as reducing diabetes, cardiovascular disease, and neurodegenerative disease. Phenolics also display anti-analgesic, anti-allergic, and anti-Alzheimer’s properties. Thus, this review provides crucial information for better understanding the bioactivities of phenolics in foods and fills a gap in the existing collective and overall knowledge in the field.
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                Author and article information

                Contributors
                Journal
                Front Pharmacol
                Front Pharmacol
                Front. Pharmacol.
                Frontiers in Pharmacology
                Frontiers Media S.A.
                1663-9812
                25 July 2019
                2019
                : 10
                : 826
                Affiliations
                [1] 1Institute of Medicinal Plant Development, Chinese Academy of Medical Science and Peking Union Medical College , Beijing, China
                [2] 2Beijing University of Chinese Medicine , Beijing, China
                [3] 3School of Pharmaceutical Sciences, Tsinghua University , Beijing, China
                Author notes

                Edited by: Syed Nasir Abbas Bukhari, Al Jouf University, Saudi Arabia

                Reviewed by: Ya-nan Yang, Institute of Materia Medica (IMM), China; Yi Dai, Jinan University, China

                *Correspondence: Yue Shi, shiyue1029@ 123456126.com

                This article was submitted to Experimental Pharmacology and Drug Discovery, a section of the journal Frontiers in Pharmacology

                Article
                10.3389/fphar.2019.00826
                6669795
                31402862
                b28379ab-5bc4-472e-a9d9-220f24856e04
                Copyright © 2019 Wang, Chang, Luo, Su, Xu, Chen, Ding and Shi

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 29 March 2019
                : 26 June 2019
                Page count
                Figures: 7, Tables: 1, Equations: 0, References: 48, Pages: 18, Words: 12552
                Funding
                Funded by: National Natural Science Foundation of China 10.13039/501100001809
                Categories
                Pharmacology
                Original Research

                Pharmacology & Pharmaceutical medicine
                intestinal microbial metabolism,four phenylethanoid glycosides,uhplc-q-exactive orbitrap hrms,antioxidant activities,structure–activity relationship

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