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Simultaneous Determination of Aesculin, Aesculetin, Fraxetin

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Simultaneous Determination of Aesculin, Aesculetin, Fraxetin molecules Article Simultaneous Determination of Aesculin, Aesculetin, Fraxetin, Fraxin and Polydatin in Beagle Dog Plasma by UPLC-ESI-MS/MS and Its Application in a Pharmacokinetic Study after Oral Administration Extracts of Ledum palustre L. Zhibin Wang 1, Wenbo Zhu 1, Hua Liu 1, Gaosong Wu 1, Mengmeng Song 1, Bingyou Yang 1, Deqiang Yang 1, Qiuhong Wang 1,2 and Haixue Kuang 1,2,* 1 Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, 24 Heping Road, Xiangfang District, Harbin 150040, China; [email protected] (Z.W.); [email protected] (W.Z.); [email protected] (H.L.); [email protected] (G.W.); [email protected] (M.S.); [email protected] (B.Y.); [email protected] (D.Y.); [email protected] (Q.W.) 2 School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, 232 Outer Ring Road, University Town, Guangzhou 510006, China * Correspondence: [email protected]; Tel.: +86-451-87267188 Received: 20 August 2018; Accepted: 5 September 2018; Published: 7 September 2018 Abstract: A rapid, simple and sensitive ultra-performance liquid chromatography-electrospray- ionization-tandem mass spectrometry (UPLC-ESI-MS/MS) method was developed and validated for the simultaneous determination of aesculin, aesculetin, fraxetin, fraxin and polydatin in beagle dog plasma for the first time. Plasma samples were pretreated by protein precipitation with methanol. Chromatographic separation was performed on an Acquity UPLC HSS T3 C18 column (2.1 mm × 100 mm, 1.8 µm) with gradient elution at a flow rate of 0.4 mL/min, using a mobile phase consisting of 0.1% formic acid (A) and acetonitrile (B). The analytes and IS were detected by multiple reaction monitoring (MRM) via negative ion mode with ion transitions of m/z 339.1–m/z 176.8 for aesculin, m/z 176.8–m/z 88.9 for aesculetin, m/z 206.8–m/z 192.1 for fraxetin, m/z 369.1–m/z 206.9 for fraxin, m/z 389.1–m/z 227.0 for polydatin and m/z 415.2–m/z 295.1 for puerarin. This method was validated according to the FDA guidelines and the results met the requirements of analysis. The calibration curves of analytes were linear with correlation coefficients more than 0.9980. The intra- and inter-day precisions were less than 15% and the accuracy was within ±15%. The maximum plasma concentration (Cmax) of aesculin, aesculetin, fraxetin, fraxin and polydatin was 46.75 ± 7.46, 209.9 ± 57.65, 369.7 ± 48.87, 67.04 ± 12.09 and 47.14 ± 12.04 ng/mL, respectively. The time to reach the maximum plasma concentration (Tmax) was 1.32 ± 0.38 h for aesculin, 1.03 ± 0.27 h for aesculetin, 0.94 ± 0.23 h for fraxetin, 0.83 ± 0.18 h for fraxin and 1.15 ± 0.15 h for polydatin. The results indicated that the absorption of aesculin might be slow in beagle dog plasma. This method was successfully applied for pharmacokinetics in beagle dog plasma after oral administration of the extracts of Ledum palustre L. at a dosage of 0.27 g/kg. Keywords: Ledum palustre L.; UPLC-ESI-MS/MS; pharmacokinetics 1. Introduction Ledum palustre L. is an evergreen low shrub, which belongs to the Ericaceae family and is widely distributed in northern Europe, central Europe, northern Asia, America and the northeast of China. The ointment and decoction of L. palustre have been used to treat menxenia, infertility and gastric Molecules 2018, 23, 2285; doi:10.3390/molecules23092285 www.mdpi.com/journal/molecules Molecules 2018, 23, 2285 2 of 12 ulcers in folk for a long time. Not only that, it also plays an important role in treating insect bites, arthrosis, and rheumatism [1–3]. Previous studies have reported that L. palustre contains various types of components, such as coumarins, flavonoids, triterpenes, volatile oils and hydroxycinnamic acids [4]. The aesculin, aesculetin, fraxetin and fraxin belong to coumarins, and polydatin is an active stilbene compound. The five components isolated from L. palustre are the main active ingredients in natural herbs [5,6]. Pharmacological studies have revealed that the five components have several similar pharmacological activities, including anti-inflammatory, anti-oxidant, anti-tumor, anti-viral, and so on [7–12]. In particular, polydatin possesses extensive cardiovascular pharmacological activity, such as cardio-myocyte protection, vascular smooth muscle dilation, anti-thrombosis, etc. [13,14]. To investigate the pharmacokinetic characteristics of aesculin, aesculetin, fraxetin, fraxin and polydatin, several analytical methods based on chromatographic techniques for single or simultaneous quantification of analytes have been reported in recent years. High-performance liquid chromatography with ultraviolet (HPLC-UV), high-performance liquid chromatography quadrupole time of flight tandem mass (HPLC-QTQF-MS/MS), high-performance liquid chromatography with fluorescence detection (HPLC-FD), liquid chromatography tandem mass spectrometry (LC-MS/MS) and high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) methods were implemented for the determination and quantitation of aesculin, aesculetin, fraxetin, fraxin and polydatin in rat plasma and rabbit plasma [15–21]. In addition, only a single report was retrieved online which described the pharmacokinetics of polydatin in beagle dog plasma [22]. The gastric emptying time and pH value of gastric fluid in beagle dogs was similar to humans under a fasting state. The detection results of drug in beagle dog can be used to analyze change regulation in the human body. Therefore, it is important to develop a method for simultaneous determination of the five components in beagle dog plasma. A rapid, sensitive and simple ultra-performance liquid chromatography-electrospray-ionization- tandem mass spectrometry (UPLC-ESI-MS/MS) method for the simultaneous determination of aesculin, aesculetin, fraxetin, fraxin and polydatin was developed and validated in this paper. This method was successfully applied to pharmacokinetics of the five components above after oral administration of extracts of L. palustre in beagle dog for the first time. The results of this study will provide useful information for further experimental research and clinical application. 2. Results and Discussion 2.1. Optimization of UPLC-ESI-MS/MS Conditions The mobile phase was a decisive factor in the chromatographic analysis, which could affect the separation and ionization. Different solvent combinations, including water-acetonitrile and water-methanol with formic acid, were required to be tested for perfect peak shape, high response and stable retention time. It was found that the water-acetonitrile system possessed good separation efficiency with lower noise, and the retention time of the analytes was more stable than the water-methanol system. Higher signal response and sharp peaks of analytes were observed after addition of 0.1% formic acid into the mobile phase, and the sensitivity of detecting was improved. Therefore, 0.1% formic acid-acetonitrile was employed as the final mobile phase with gradient elution. The total test time was 5 min. The analytes and IS were determined in both negative and positive ion mode, the signal sensitivity and reproducibility were better in negative ionization mode than in positive mode. Therefore, the negative ion mode was selected for the quantification. On the basis of the full-scan spectra shown in Figure1, the deprotonated molecular ions [M − H]− were selected as parent ions because of their high response. The declustering potential (DP) and collision energy (CE) of analytes and IS were optimized in order to obtain product ion. In the process of optimization, the most abundant and stable fragment was m/z 176.8 for aesculin, m/z 88.9 for aesculetin, m/z 192.1 for fraxetin, m/z 206.9 for fraxin, m/z 227.0 for polydatin, and m/z 295.1 for puerarin. Therefore, the ion transitions of the analytes Molecules 2018, 23, x FOR PEER REVIEW 3 of 13 and IS were optimized in order to obtain product ion. In the process of optimization, the most Moleculesabundant2018 and, 23 ,stable 2285 fragment was m/z 176.8 for aesculin, m/z 88.9 for aesculetin, m/z 192.1 for fraxetin,3 of 12 m/z 206.9 for fraxin, m/z 227.0 for polydatin, and m/z 295.1 for puerarin. Therefore, the ion transitions wereof them analytes/z 339.1– werem/z m176.8/z 339.1– for aesculin,m/z 176.8 mfor/ zaesculin,176.8–m /mz/z88.9 176.8– form aesculetin,/z 88.9 for aesculetin,m/z 206.8– mm//zz 206.8–192.1m for/z fraxetin,192.1 for mfraxetin,/z 369.1– mm/z/ 369.1–z 206.9m for/z 206.9 fraxin, form fraxin,/z 389.1– m/zm 389.1–/z 227.0m/z for 227.0 polydatin for polydatin and m/ andz 415.2– m/z 415.2–m/z 295.1m/z for295.1 puerarin. for puerarin. The optimized The optimized parameters parameters and MRM and MRM transitions transitions of the of analytes the analytes and IS and can IS be can found be infound Table in1 .Table 1. Figure 1. ChemicalChemical structures structures and and product product ion ion mass mass spectra spectra of analytes of analytes and andIS. ( IS.A): (aesculin;A): aesculin; (B): (aesculetin;B): aesculetin; (C): (fraxetin;C): fraxetin; (D): (fraxin;D): fraxin; (E): (polydatin;E): polydatin; (F): (puerarin.F): puerarin. Table 1. Optimized mass spectrometric parameters for analytes and IS. Table 1. Optimized mass spectrometric parameters for analytes and IS. Precursor Ion Product Ion Declustering Collision Analytes Precursor Product Collision Polarity Analytes (m/z) (mDeclustering/z) Potential Potential (V) (V) Energy (V) Polarity Ion (m/z) Ion (m/z) Energy (V) aesculinaesculin 339.1 339.1176.8 176.8103.1 103.1 40.740.7 negativenegative aesculetin 176.8 88.9 69.3 34.9 negative aesculetinfraxetin 176.8 206.888.9 192.169.3 64.9 22.634.9 negativenegative fraxetinfraxin 206.8 369.1192.1 206.964.9 75.8 30.822.6 negativenegative fraxinpolydatin 369.1 389.1206.9 227.075.8 85.6 22.030.8 negativenegative polydatinpuerarin 389.1 415.2227.0 295.185.6 92.9 34.422.0 negativenegative puerarin 415.2 295.1 92.9 34.4 negative 2.2.
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