In-vivo metabolic profiling of the Natural products Emodin and Emodin-8-O-β-D-glucoside in rats using liquid chromatography quadrupole Orbitrap mass spectrometry
Junqi Bai , He Su , Baosheng Liao , Juan Huang , Danchun Zhang , Lu Gong , Xuhua Shi , Zhihai Huang , Xiaohui Qiu
{"title":"In-vivo metabolic profiling of the Natural products Emodin and Emodin-8-O-β-D-glucoside in rats using liquid chromatography quadrupole Orbitrap mass spectrometry","authors":"Junqi Bai , He Su , Baosheng Liao , Juan Huang , Danchun Zhang , Lu Gong , Xuhua Shi , Zhihai Huang , Xiaohui Qiu","doi":"10.1016/j.arabjc.2024.105905","DOIUrl":null,"url":null,"abstract":"<div><p>Emodin (EM) and emodin-8-O-<em>β</em>-D-glucoside (EG) were found in various medicinal plants such as <em>Rheum palmatum</em>, <em>Aloe vera</em>, <em>Polygonum multiflorum</em>, and <em>Polygonum cuspidatum</em>. They have different pharmacological properties and are considered potentially toxic substances. It is necessary to identify the metabolites and their distribution in the body. In this study, a comprehensive analytical strategy was developed to characterize the metabolites of EM and EG in <em>vivo</em> using UHPLC-Q-Exactive Orbitrap MS. 190 metabolites were identified in the bio-samples, in addition to the commonly reported glycoside hydrolysis, hydrogenation, hydroxylation, glucuronide conjugation, and sulfation conjugation. We also discovered new pathways such as formylation, acetylation, glycol acylation, lactation, glycerolization, malonylation, glycerol acid acylation, hydroxyvalerylation, erythrosylation, glutaric acidfication, hydroxybenzoylation, glutamylation, hydroxyglutamylation, ascorbylation, aspartylglycylation, dihydroxyphenylglycylation, trihydroxyphenylglycylation, dihydroxymethoxyphenylglycylation, and ring-opening of EM. Cluster analysis revealed that each tissue in the EM and EG groups exhibited a high degree of similarity in their metabolic pathway preferences and bodily distributions, as they clustered together. Interestingly, the presence of glycol acylation, glycerolization, and glycerol acid acylation in the liver may be related to the lipid-lowering effects of EM and EG. These findings offer valuable insights for a more comprehensive understanding of the safety and efficacy of EM and EG, as well as valuable methods for metabolic characterization.</p></div>","PeriodicalId":249,"journal":{"name":"Arabian Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":5.3000,"publicationDate":"2024-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S1878535224003071/pdfft?md5=0faeedd8f4b49ef9e1b4e7b255a4b8be&pid=1-s2.0-S1878535224003071-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Arabian Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1878535224003071","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Emodin (EM) and emodin-8-O-β-D-glucoside (EG) were found in various medicinal plants such as Rheum palmatum, Aloe vera, Polygonum multiflorum, and Polygonum cuspidatum. They have different pharmacological properties and are considered potentially toxic substances. It is necessary to identify the metabolites and their distribution in the body. In this study, a comprehensive analytical strategy was developed to characterize the metabolites of EM and EG in vivo using UHPLC-Q-Exactive Orbitrap MS. 190 metabolites were identified in the bio-samples, in addition to the commonly reported glycoside hydrolysis, hydrogenation, hydroxylation, glucuronide conjugation, and sulfation conjugation. We also discovered new pathways such as formylation, acetylation, glycol acylation, lactation, glycerolization, malonylation, glycerol acid acylation, hydroxyvalerylation, erythrosylation, glutaric acidfication, hydroxybenzoylation, glutamylation, hydroxyglutamylation, ascorbylation, aspartylglycylation, dihydroxyphenylglycylation, trihydroxyphenylglycylation, dihydroxymethoxyphenylglycylation, and ring-opening of EM. Cluster analysis revealed that each tissue in the EM and EG groups exhibited a high degree of similarity in their metabolic pathway preferences and bodily distributions, as they clustered together. Interestingly, the presence of glycol acylation, glycerolization, and glycerol acid acylation in the liver may be related to the lipid-lowering effects of EM and EG. These findings offer valuable insights for a more comprehensive understanding of the safety and efficacy of EM and EG, as well as valuable methods for metabolic characterization.
大黄素(EM)和大黄素-8-O-β-D-葡萄糖苷(EG)存在于多种药用植物中,如大黄、芦荟、何首乌和虎耳草。它们具有不同的药理特性,被认为是潜在的有毒物质。有必要对代谢物及其在体内的分布进行鉴定。本研究采用 UHPLC-Q-Exactive Orbitrap MS 开发了一种全面的分析策略,以确定 EM 和 EG 体内代谢物的特征。除了常见的糖苷水解、氢化、羟基化、葡萄糖醛酸共轭和硫化共轭外,还在生物样本中鉴定出 190 种代谢物。我们还发现了新的途径,如甲酰化、乙酰化、乙二醇酰化、乳酸化、甘油化、丙二酰化、甘油酸酰化、羟基戊酰化、赤藓酰化、戊二酸化、羟基苯甲酰化、羟基苯甲酰化、羟基苯甲酰基化、羟基苯甲酰基化等、羟基苯甲酰化、谷氨酰化、羟基谷氨酰化、抗坏血酸化、天冬氨酰甘氨酰化、二羟苯基甘氨酰化、三羟苯基甘氨酰化、二羟甲氧基苯基甘氨酰化和 EM 开环。聚类分析显示,EM 组和 EG 组中的每个组织在代谢途径偏好和体内分布方面都表现出高度的相似性,因为它们聚集在一起。有趣的是,肝脏中存在的乙二醇酰化、甘油化和甘油酸酰化可能与 EM 和 EG 的降脂作用有关。这些发现为更全面地了解 EM 和 EG 的安全性和有效性提供了宝贵的见解,同时也为代谢特征描述提供了宝贵的方法。
期刊介绍:
The Arabian Journal of Chemistry is an English language, peer-reviewed scholarly publication in the area of chemistry. The Arabian Journal of Chemistry publishes original papers, reviews and short reports on, but not limited to: inorganic, physical, organic, analytical and biochemistry.
The Arabian Journal of Chemistry is issued by the Arab Union of Chemists and is published by King Saud University together with the Saudi Chemical Society in collaboration with Elsevier and is edited by an international group of eminent researchers.