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An Integrated Approach for Studying Exposure, Metabolism and Disposition of Multiple Component Herbal Medicines Using High Resolution

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An Integrated Approach for Studying Exposure, Metabolism and Disposition of Multiple Component Herbal Medicines Using High Resolution DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 An integrated approach for studying exposure, metabolism and disposition of multiple component herbal medicines using high resolution mass spectrometry and multiple data processing tools Caisheng Wu, Haiying Zhang, Caihong Wang, Hailin Qin, Mingshe Zhu and Jinlan Zhang Downloaded from State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences& Peking Union Medical College, Beijing, China (C.W., C.W., H.Q., J.Z.), and Department of Biotransformation, Bristol-Myers Squibb Company, Princeton, USA (H.Z., M.Z.) dmd.aspetjournals.org at ASPET Journals on September 27, 2021 1 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 Running Title Study ADME of multiple TCM components using HRMS technology Corresponding author: Mingshe Zhu Department of Biotransformation, Bristol-Myers Squibb Company, Princeton, NJ 08540, USA; Tel (609) 252-3324; E-mail: [email protected] Jinlan Zhang State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Downloaded from Materia Medica, Chinese Academy of Medical Sciences& Peking Union Medical College, 2 Nanwei Road，Beijing 100050, China; Tel & Fax: 086 10 83154880; E-mail: [email protected] dmd.aspetjournals.org # Text pages : 38 # Tables: 1 at ASPET Journals on September 27, 2021 # Figures: 6 #References: 45 # Words in Abstract: 250 # Words in Introduction: 748 #Words in Discussion: 1502 ABBREVIATIONS: Absorption, metabolism, distribution and elimination, ADME; active fraction of Xiao-Xu-Ming Decoction, AF-XXMD; extracted ion chromatography, EIC; high resolution mass spectrometry, HRMS; isotope pattern filer, IPF; mass defect filter, MDF; mass spectral trees similarity filter, MTSF: neutral loss filter, NLF; precise and thorough background subtraction, PATBS; traditional Chinese medicine, TCM; Yin-Chen-Hao-Tang ,YCHT. 2 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 Downloaded from dmd.aspetjournals.org at ASPET Journals on September 27, 2021 3 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 Abstract A typical prescription of traditional Chinese medicine (TCM) contains up to a few hundreds of prototype components. Studying their absorption, metabolism, distribution and elimination (ADME) represents great challenges. The objective of this study was to develop a practical approach for investigating ADME of individual prototypes in TCM. An active fraction of Xiao-Xu-Ming Decoction (AF-XXMD) as a Downloaded from model TCM prescription was orally administered to rats. AF-XXMD-related components in plasma, urine, bile and feces were detected using high resolution mass dmd.aspetjournals.org spectrometry and background subtraction, an untargeted data-mining tool, and structurally characterized based on MSn spectral data. Connection of detected AF-XXMD metabolites to their precursor species, either prototypes or upstream at ASPET Journals on September 27, 2021 metabolites, were determined based on mass spectral similarity and the matching of biotransformation reactions. As a result, 247 AF-XXMD-related components were detected and structurally characterized in rats, 134 of which were metabolites. Among 198 AF-XXMD prototypes dosed, 65 were fully or partially absorbed and 13 prototypes and 34 metabolites were found in the circulation. Glucuronidation, isomerization and deglycosylation followed by biliary and urinary excretions and direct elimination of prototypes via kidney and liver were major clearance pathways of AF-XXMD prototypes. As an example, the ADME profile of H56, the single major AF-XXMD component in rat plasma, was elucidated based on profiles of H56-related components in plasma and excreta. The results demonstrate that the new analytical approach is a useful tool for rapid and comprehensive detection and characterization 4 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 of TCM components in biological matrix and study of ADME of a TCM prescription in vivo. Downloaded from dmd.aspetjournals.org at ASPET Journals on September 27, 2021 5 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 Introduction Understanding of bioactive substances of Traditional Chinese medicine (TCM) and their action mechanisms is of great interest to drug discovery scientists and clinicians. The effectiveness of TCM is generally recognized to be associated with chemical constituents of TCM in the circulation (Wang et al., 2011; Zhang et al., 2011; Zhang et al., 2013). Concentrations and duration of individual TCM components in Downloaded from the circulation depend on its absorption, distribution, metabolism and excretion (ADME) processes that are often mediated by metabolizing enzymes and transporters. dmd.aspetjournals.org Inhibition or induction of the involved enzymes or transporters by a co-administered TCM component or a pharmaceutical drug could significantly change exposure levels of bioactive plasma components, leading to drug-drug interactions (DDI) among at ASPET Journals on September 27, 2021 herbal components and between an herbal component and a pharmaceutical drug (Cheng et al., 2014; Jia et al., 2015; Ma et al., 2014; Posadzki et al., 2013). In addition, the study of ADME of herbal medicines is very important for the elucidation of mechanisms of TCM-induced toxicity. Herbal medicine-mediated organ toxicity is often related to high exposure and accumulation of certain toxic components in the organs (Xiong et al., 2014, Qiu et al., 2000; Hu et al., 2004, Yue et al., 2009; Su et al., 2004, Yuan et al., 2011; Ding et al., 2012, Zhu, 2002). An ADME study of a drug in human and animal is often carried out using radioactivity profiling after dosing a radiolabeled drug. However, it is not practical to use multiple radiolabeled TCM prototype compounds in a TCM ADME study. Therefore, the success of ADME study of a TCM prescription relies on LC/MS 6 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 technology (Song et al., 2014). In the past ten years, many TCM research groups have made significant efforts in the development and application of a variety of LC/MS approaches for detection and characterization of TCM components in the circulation and excrete (Yang et al., 2012; Wu et al., 2012; Geng et al., 2014; Zuo et al., 2015; Yan et al., 2013). The first analytical challenge faced in studying the ADME of herbal medicines using HRMS is to sensitively and comprehensively detect TCM Downloaded from components in plasma, urine, feces and bile samples. The task is often accomplished by processing accurate MS and MS/MS datasets using targeted data-mining tools dmd.aspetjournals.org (Yang et al., 2011; Wu et al., 2012), including mass defect filter (MDF), extracted ion chromatography (EIC), product ion filter (PIF), neutral loss filter (NLF) and isotope pattern filter (IPF). These high resolution mass spectrometry (HRMS)-based at ASPET Journals on September 27, 2021 data-mining technologies are originally developed for the detection and identification of drug metabolites in complex biological systems (Bateman et al., 2007; Geng et al., 2014; Du et al., 2015; Ma et al., 2012; Ma and Zhu 2009; Zhu et al., 2011). In addition, mass spectral trees similarity filter (MTSF) technology (Jin et al., 2013) is employed for the detection and identification of TCM metabolite based on similarity of product ion spectra of metabolites to those of their precursor species. These targeted data-mining approaches are capable of searching for metabolites based on their predicted mass defects (MDF), fragmentation patterns (NLF and PIF) or molecular weights (EIC) from individual TCM prototypes. However, since an herbal medicine can contain up to a few hundred parent components, searching for their metabolite components based on their masses, mass defects or product ion spectra 7 DMD Fast Forward. Published on March 24, 2016 as DOI: 10.1124/dmd.115.068189 This article has not been copyedited and formatted. The final version may differ from this version. DMD # 68189 predicted from individual TCM prototypes is truly time-consuming and labor-intensive. More importantly, many major TCM metabolite components in plasma or excretes are formed via multiple steps of biotransformation so that their detection by targeted data-mining tools may fail. The second analytical challenge faced in a TCM ADME study is the determination of metabolic pathways of individual TCM parent components, especially when dealing with a few hundreds of Downloaded from in vivo TCM components. The main objective of the current study was to develop a practical and integrated dmd.aspetjournals.org approach for study of in vivo ADME of TCM medicine. To evaluate the utility and effectiveness of this approach, metabolism and disposition of a model TCM prescription, an active fraction of Xiao-Xu-Ming Decoction (AF-XXMD), in rats at ASPET Journals on September 27, 2021 were determined. The prescription of Xiao-Xu-Ming decoction is used for the treatment of theoplegia and the sequela of theoplegia. The formula of XXMD consists of 14 crude herbal medicines (Supplemental Table 1). AF-XXMD is previously characterized and isolated from XXMD (Wang et al.
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