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
| Autor: | Yi Ding, Xiaoyan Chang, Xiaoming Wang, Yue Shi, Meifeng Su, Xiaomei Luo, Rong Xu, Jun Chen |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
0301 basic medicine
Antioxidant structure–activity relationship DPPH medicine.medical_treatment four phenylethanoid glycosides 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine antioxidant activities medicine Pharmacology (medical) Active metabolite Original Research Pharmacology lcsh:RM1-950 Biological activity Phenylethanoid Bioavailability intestinal microbial metabolism Metabolic pathway 030104 developmental biology lcsh:Therapeutics. Pharmacology chemistry Biochemistry 030220 oncology & carcinogenesis Echinacoside UHPLC-Q-Exactive Orbitrap HRMS |
| Zdroj: | Frontiers in Pharmacology, Vol 10 (2019) Frontiers in Pharmacology |
| ISSN: | 1663-9812 |
| DOI: | 10.3389/fphar.2019.00826/full |
| Popis: | 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 MS2 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. |
| Databáze: | OpenAIRE |
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