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A UPLC–MS/MS Approach for Simultaneous Determination of Eight Flavonoids in Rat Plasma, and Its Application to Pharmacokinetic

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A UPLC–MS/MS Approach for Simultaneous Determination of Eight Flavonoids in Rat Plasma, and Its Application to Pharmacokinetic Journal Code Article ID Dispatch: 22.09.16 CE: B M C 3 8 2 8 No. of Pages: 8 ME: 1 58 Received: 28 June 2016 Revised: 18 August 2016 Accepted: 24 August 2016 2 59 DOI 10.1002/bmc.3828 3 60 4 61 5 RESEARCH ARTICLE 62 6 63 7 64 8 A UPLC–MS/MS approach for simultaneous determination of 65 9 66 10 eight flavonoids in rat plasma, and its application to 67 11 ‐ ‐ ‐ 68 12 pharmacokinetic studies of Fu Zhu Jiang Tang tablet in rats 69 13 70 † † 14Q1 Yi Tao1,2* | Xi Chen1,2 | Yanhui Jiang1 | Baochang Cai1,2 71 15 72 16 73 1 School of Pharmacy, Nanjing University of 17 74 Chinese Medicine, Nanjing, China Abstract 18 2 – 75 Jiangsu Key Laboratory of Chinese Medicine The purpose of this study is to establish and validate a UPLC MS/MS approach to determine 19 Processing, Nanjing University of Chinese eight flavonoids in biological samples and apply the method to pharmacokinetic study of 76 Medicine, Nanjing, China 20 Fu‐Zhu‐Jiang‐Tang tablet. A Waters BEH C18 UPLC column was employed with methanol/ 77 21 Correspondence 0.1% formic acid–water as mobile phases. The mass analysis was carried out in a triple quadru- 78 Yi Tao, School of Pharmacy, Nanjing University 22 pole mass spectrometer using multiple reaction monitoring with negative scan mode. A one‐step 79 of Chinese Medicine, Nanjing 210023, China. 23 Email: [email protected] protein precipitation by methanol was used to extract the analytes from blood. Eight major 80 24 flavonoids were selected as markers. Our results showed that calibration curves for 81 25 3′‐hydroxypuerarin, mirificin, puerarin, 3′‐methoxypuerarin, daidzin, rutin, astragalin and 82 26 daidzein displayed good linear regression (r2 > 0.9986). The intra‐day and inter‐day precisions 83 27 (RSD) of the eight flavonoids at high, medium and low levels were <8.03% and the bias of the 84 28 accuracies ranged from −5.20 to 6.75%.The extraction recoveries of the eight flavonoids were 85 29 from 91.4 to 100.5% and the matrix effects ranged from 89.8 to 103.8%. The validated approach 86 30 was successfully applied to a pharmacokinetic study in Sprague–Dawley rats after oral adminis- 87 31 tration of FZJT tablet. Double peaks were emerged in curves of mean plasma concentration for 88 32 3′‐methoxypuerarin, which was reported for the first time. 89 33 90 34 KEYWORDS 91 35 Fu‐Zhu‐Jiang‐Tang tablet, pharmacokinetics, UPLC–MS/MS 92 36 93 37 94 38 95 39 1 | INTRODUCTION quercetin and 2‐caffeoylquinic acid isomers, which exhibit anti‐diabetic 96 40 effects through inhibition of α‐glucosidase (Zhang, Han, He, & Duan, 97 41 Fu‐Zhu‐Jiang‐Tang (FZJT) tablet, which consists of six well‐known 2008). Isoflavones, such as puerarin and daidzin, are the major constit- 98 42 traditional Chinese medicines – Pueraria lobata (PL), Morus alba (MA), uents of PL, and exert hypoglycemic and hypolipemic roles by elevating 99 43 Panax notoginseng (PN), Astragalus membranaceus (AM), Momordica insulin expression and maintaining metabolic homoeostasis (Wu et al., 100 44 charantia (MC) and Cortex lycii (CL) – has been proven to show benefi- 2013a). Ginsenosides, which belong to PN, can improve lipid profiles, 101 45 cial effects on patients with type II diabetes. A number of articles have inhibit peroxidation and increase the activity of antioxidant enzymes 102 46 been published on the traditional use of the six individual herbs for the (Xia, Sun, Zhao, & Hypolipidemic, 2011). Astragalosides, which are 103 47 treatment of diabetes (Habicht, Ludwig, Yang, & Krawinkel, 2014; Li, the major constituents of AM, show protective effects on kidney of 104 48 Wang, Xue, Gu, & Lin, 2011; Ulbricht et al., 2015; Uzayisenga, Ayeka, diabetic rats (Motomura et al., 2009). The extract of MC displays insulin 105 49 & Wang, 2014; Zhang, Pugliese, Pugliese, & Passantino, 2015). For secretagog and insulinomimetic activity, which may be ascribed to ste- 106 50 instance, the nonanthocyanin phenolics of MA known to date are rutin, roidal compounds and polypeptides (Raman and Lau, 1996). Our previ- 107 51 ous study characterized and determined the major constituents of 108 52 FZJT tablet using UPLC‐Q‐TOF/MS and HPLC‐UV (Tao et al., 2016). 109 †These two authors contributed equally. 53 Several analytical approaches have been established for pharma- 110 Abbreviations used: AM, Astragalus membranaceus; CL, Cortex lycii; FZJT, Fu‐ cokinetic determination of the above‐mentioned anti‐diabetic 54 Zhu‐Jiang‐Tang; MA, Morus alba; MC, Momordica charantia; MRM, multiple 111 55 reaction monitoring; PL, Pueraria lobata; PN, Panax notoginseng. constituents in vivo. For example, He et al. developed a sensitive 112 56 113 57 Biomedical Chromatography 2016; 1–8 wileyonlinelibrary.com/journal/bmc Copyright © 2016 John Wiley & Sons, Ltd. 1 114 1 2 TAO ET AL. 58 2 59 3 LC–MS/MS method to simultaneously determine rutin and astragalin maintained in an air‐conditioned room under the constant room 60 4 in rat plasma after oral administration of total flavonoids from mulberry temperature (23 ± 2°C), relative humidity level (50 ± 15%) and lighting 61 5 leaves (He et al., 2013). Xu, Li, and Zhang, (2015) quantified puerarin (12 h light/dark cycle) with free access to food and water for 7 days 62 6 and daidzin in rat plasma using LC‐MS/MS and applied them to a phar- before the experiment. Before the herb extract administration, the rats 63 7 macokinetic study of Gegenqinlian decoction. Furthermore, Yan et al. were fasted overnight but had access to water ad libitum. The experi- 64 8 (2014) established an LC‐MS/MS method to simultaneously quantify mental protocols were reviewed and approved by the Animal Ethics 65 9 puerarin, daidzin and daidzein in female rat plasma following oral Committee of Nanjing University of Chinese Medicine. 66 10 administration of Ge‐Gen decoction. These studies just focus on one 67 11 or two herbals. There is no report on the method for the pharmacoki- 68 2.2 | UPLC‐MS/MS conditions 12 netic study of the six‐herb preparation – FZJT tablet. The pharmacoki- 69 13 netic behavior of FZJT tablet after oral administration remains unclear. Liquid chromatography was carried out on a Shimadzu ultra perfor- 70 14 Pharmacokinetics is a branch of pharmacology dedicated to deter- mance liquid chromatography (UPLC) unit with an Acquity BEH C18 71 15 mining the fate of substances administered externally to a living organ- column (2.1 × 50 mm, 1.7 μm particle size) and inline 0.2 μm stainless 72 16 ism, which is of great importance in drug development and can explain steel frit filter. The elution solvents were optimized using methanol– 73 17 a variety of events related to the efficacy of herbal medicines (Katz, water or acetonitrile–water (with or without 0.1% formic acid) as the 74 18 Murray, Bhathena, & Sahelijo, 2008). The composition of herbal prep- mobile phase system. Finally, a gradient program was employed with 75 19 arations is complex and different constituents may have interactions. the mobile phase of solvent A (0.1% formic acid in water) and solvent 76 20 The pharmacokinetics of multi‐herbal preparations may provide valu- B (methanol) as follows: 5–30% B (0–2 min), 30% B (2.0–2.5 min), 77 21 able information for their clinical usage. In this study, our aim was to 30–100% B (2.5–6.0 min), 100% B (6.0–7.0 min). A subsequent 78 22 develop, optimize and validate a simple, sensitive and specific UPLC‐ re‐equilibration time (1 min) should be performed before next injec- 79 23 MS/MS method for the simultaneous determination of the bioactive tion. The flow rate was 0.30 mL/min and the injection volume was 80 24 compounds in rat plasma after oral administration of the FZJT total 5 μL. The column temperature was maintained at 35°C. 81 25 fraction. An AB sciex QTRAP 5500 triple quadruple mass spectrometer was 82 26 Our previous study showed that steroidal compounds and poly- employed for mass spectrometric detection. The detection was 83 27 peptides were not detected using UPLC‐Q‐TOF/MS. Therefore, only operated in the multiple reaction monitoring (MRM) mode under unit 84 28 compounds which can be detected were used for pharmacokinetic mass resolution in the mass analyzers. The mass parameters for each 85 29 analysis. Meanwhile, these eight flavonoids showed anti‐diabetic compound were optimized, including cone voltage, collision energy 86 30 effects. For instance, rutin and astragalin exhibited anti‐diabetic and so on. The MRM analysis was conducted by monitoring the 87 31 effects through inhibition of α‐glucosidase (Tao, Zhang, Cheng, & precursor ion to product ion transitions of m/z 431.0 → 311.0 for 88 32 Wang, 2013). Puerarin, daidzin and daidzein have been found to signif- 3′‐hydroxypuerarin, 415.0 → 267.0 for puerarin, 547.0 → 295.0 for 89 33 icantly decrease the baseline fasting plasma glucose and total choles- mirificin, 445.1 → 325.0 for 3′‐methoxypuerarin, 415.2 → 251.9 for 90 34 terol and increase insulin levels in several in vivo models (Liu et al., daidzin, 609.2 → 299.9 for rutin, 447.1 → 283.9 for astragalin, 91 35 2015). 3′‐Hydroxypuerarin, 3′‐methoxypuerarin, mirificin and daidzein 253.1 → 224.0 for daidzein, 405.2 → 243.0 for 2,3,5,4′‐tetrahydroxy‐ 92 36 exhibited anti‐diabetic effects by reducing oxidative stress to which stilbene‐2‐O‐β‐D‐glucoside (IS), respectively. Analyst (version 1.5.2, 93 37 the pancreatic cells were exposed (Bebrevska et al., 2010).
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