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Identification of Multiple Constituents in Shuganjieyu Capsule and Rat Original Research Paper Identification of Multiple Constituents in Shuganjieyu Capsule and Rat Plasma after Oral Administration by Ultra-Performance Liquid Chromatography Coupled with Electrospray Ionization and Ion Trap Mass Spectrometry Y. C. Xiao, L. T. Liu, J. J. Bian, C. Q. Yan, L. Ye, M. X. Zhao, Q. S. Huang, W. Wang, K. Liang, Z. F. Shi and X. Ke* Chengdu Kanghong Pharmaceutical Co. Ltd., Chengdu, Sichuan 610036, P.R. China Received: 06 August 2016; accepted: 18 October 2016 Shuganjieyu (SGJY) capsule is a classical formula widely used in Chinese clinical application. In this paper, an ultra- performance liquid chromatography coupled with electrospray ionization and ion trap mass spectrometry has been established to separate and identify the chemical constituents of SGJY and the multiple constituents of SGJY in rats. The chromatographic separation was performed on a C18 RRHD column (150 × 2.1 mm, 1.8 μm), while 0.1% formic acid–water and 0.1% formic acid–acetonitrile was used as mobile phase. Mass spectral data were acquired in both positive and negative modes. On the basis of the characteristic retention time (Rt) and mass spectral data with those of reference standards and relevant references, 73 constituents from the SGJY and 15 ingredients including 10 original constituents and 5 metabolites from the rat plasma after oral administration of SGJY were identified or tentatively characterized. This study provided helpful chemical information for further pharmacology and active mechanism re- search on SGJY. Keywords: Constituents, rat plasma, UHPLC–ESI–MS/MS, Shuganjieyu capsule 1. Introduction S150102) were offered by Chengdu Kanghong Pharmaceutical Co. Ltd. (Chengdu, China). The reference standards of rutin, Shuganjieyu (SGJY) capsule, which contains two medicinal hyperoside, quercetin, isofraxidin, epicatechin, chlorogenic acid, materials, including the dried herbs of Hypericum perforatum L. and eleutheroside E were purchased from National Institutes for and the dried roots and rhizomes or stems of Acanthopanax Food and Drug Control (Beijing, P.R. China), hypericin was senticosus (Rupr. et Maxim) Harms, is the first approved Chinese purchased from Chengdu Munster biotechnology company herbal medicine for mild to moderate monopolar depression in (Chengdu, China), and hyperforin was purchased from Chinese. Currently, the research of the chemical components in ChromaDex Corporate (California, USA). (6S,7E,9R)-Roseoside SGJY has been mainly based on identification of chemical con- was isolated in our laboratory (purity, >98%), and its chemical stituents respectively and systematically from individual herb ex- structure was identified by spectral analysis. HPLC-grade tracts. The constituents of SGJY are numerous and diverse. acetonitrile and methanol were purchased from Honeywell However, until now, like most traditional Chinese medicine Burdick & Jackson (Ulsan, Korea). Ultrapure water for the (TCM), there have been few reports on the absorption and effi- preparation of samples and mobile phase was prepared with cacy after oral administration of SGJY, which is valuable for fur- Milli-Q Biocel water system (Millipore, Massachusetts, USA). ther studies on the pharmaceutical effect and mechanism of the Other reagents were of analytical grade. SGJY formula. As tandem mass spectrometry (MS/MS) has been 2.2. Instrumentation and Analytical Conditions. The proven to be efficient tool for the rapid on-line analysis for the Agilent 1290 Infinity UHPLC system (Agilent Technologies known compounds and elucidation of unknown compounds in Inc., California, USA) was equipped with quaternary pump, complex matrices, in this study, a high-speed and sensitive tech- vacuum degasser, a cooling autosampler, and a diode-array nique ultrahigh-performance liquid chromatography (UHPLC)– detector. An Agilent Eclipse Plus C RRHD column (150 × electrospray ionization (ESI)–MS/MS system was adopted to 18 2.1 mm, 1.8 μm) was utilized for separation with the column characterize the constituents of SGJY capsule and the metabolic temperature at 30 °C. A binary gradient elution was adopted with profile in rat plasma after oral administration of SGJY. Moreover, mobile phase consisting of (A) 0.1% formic acid in water and the result of this study was expected to provide helpful chemical (B)0.1%formicacidinacetonitrile:0–3min,B5%;3–15 min, information for further pharmacology and active mechanism re- B5–10%; 15–25 min, B 10–20%; 25–40 min, B 20–40%; search on SGJY formula. 40–45 min, B 40–100%; 45–50 min, B 100%; 50–51 min, B 100–5%; and 51–60 min, B 5%. The flow rate was set at 0.20 mL/min. The autosampler was conditioned at 4 °C, and the 2. Experimental injection volume was 10 μL. 2.1. Materials and Reagents. Shuganjieyu capsule (batch ThermoQuest Finnigan LTQ system equipped with an electro- number 150314), the extract of H. perforatum L. (batch number spray ionization source (ThermoQuest LC/MS Division, San Jose, S150402), and the extract of A. senticosus Harms (batch number CA, USA) was used for mass spectrometric measurements. The ESI–MSn spectra were acquired in both positive and negative ion * Author for correspondence: [email protected] modes. The mass spectrometry detector (MSD) parameters were This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International License (https://creativecommons.org/licenses/by-nc/4.0/), which permits unrestricted use, distribution, and reproduction in any medium for non-commercial purposes, provided the original author and source are credited, a link to the CC License is provided, and changes - if any - are indicated. DOI: 10.1556/1326.2017.00094 Acta Chromatographica 30(2018)2, 95–102 © 2017 The Author(s) First published online: 21 June 2017 Unauthenticated | Downloaded 09/27/21 10:12 PM UTC Identification of Multiple Constituents in SGJY as follows: in (+) ESI, spray voltage, 3500 V (sheath gas, 15 arb; 3. Results and Discussions auxiliary gas, 5 arb; purge gas, 0 arb); capillary temperature, 275 °C; capillary voltage, 10 V; lens voltage, 80 V; in (−)ESI, 3.1. UPLC–MS/MS Analysis and Identification the spray voltage, 5000 V (sheath gas, 15 arb; auxiliary gas, 5 arb; Constituents of SGJY. Figures 1 and 2 show the ion chromato- purge gas, 0 arb); capillary temperature, 275 °C; capillary voltage, gram of SGJY in both positive and negative ion modes. A total −10 V; lens voltage, −100V. Tandem mass spectrometry of 73 peaks were identified or tentatively characterized including (MS/MS) was collected with data-dependent mode, and the 14 organic acids, 37 flavonoids, 8 prenylated phloroglucinols, three highest intensity peaks in full-scan spectra were ac- 2 naphthodianthrones, 5 lignans, 3 phenylpropanoids, and 4 other quired for MS/MS analysis. Helium was used as collision compounds, on the basis of the ultraviolet (UV) spectra, MS gas (collision energy, 35 eV). The full-scan range was from spectra, and MS/MS spectra with fragmentation patterns of refer- 100 to 1000 m/z. ence standards or literature data. All the detailed data are shown in 2.3. Animals, Drug Administration, and Blood Sampling. Table 1. Ten male Sprague-Dawley (SD) rats (160–220 g) were 3.1.1. Identification of Components by Standards. Com- obtained from Chengdu Dashuo Laboratory Animal Co., Ltd. pounds 5, 9, 13, 20, 29, 30, 31, 59, 71,and72 were respectively (Sichuan, China). The animals were acclimatized to the attributed to chlorogenic acid, (6S,7E,9R)-roseoside, epicatechin, facilities for 5 days, and then fasted, with free access to water eleutheroside E, rutin, isofraxidin, hyperoside, quercetin, hyperi- for 12 h prior to the experiment. All procedures were in cin, and hyperforin, by comparison with the retention times and accordance with the Guidelines on the Care and Use of mass spectral data of the reference standards. Animals for Scientific Purposes 2004. 3.1.2. Identification of Components through Investigating 2.4. Sample Preparation Literatures 2.4.1. Preparation of SGJY Extract Samples. SGJY cap- 3.1.2.1. Organic acids identification. Organic acids are vital sule was ground into fine powder. A total of 100 mg was accu- compounds found in both H. perforatum L. and A. senticosus rately weighed, and 10 mL distilled water was added. Each Harms. Chlorogenic acid (5) was identified for certain by com- extract of medicinal material contained in SGJY was 50 mg ac- parison with the reference standards. Chlorogenic acid, one of curately weighed and dissolved in 10 mL distilled water. All themainorganicacidsinSGJY,couldbeusedtocharacterize the samples were ultrasonically extracted for 10 min and then the fragmentation pathways. It gave diagnostic ions at m/z 372 + + + filtered through a syringe filter (0.45 μm). Filtrate (10 μL) was [M + NH4] , 355 [M + H] , and 163 [M + H − 192] in positive subjected to UPLC–ESI–MS/MS analysis. mode and at m/z 353 [M − H]− and 191 [M − H − Caffe]− in 2.4.2. Preparation of Plasma Samples. Capsule contents of negative mode. Based on these fragmentation patterns, com- SGJY were dispersed with distilled water as stock solution pounds 1–4, 6, 7, 11, 15, 16, 19, 22, 37,and43 were identified. (0.5 g/mL). The above suspension was orally administered to Compounds 1 and 7 gave precursor ions at m/z 355 [M + H]+ five rats (1.0 mL/100 g body weight). An equal volume of and 353 [M − H]− and fragment ions at m/z 163 in positive mode distilled water was orally administered to the other five rats as and 191 in negative mode, which, with the same diagnostic ions control; 60 min after drug administration, the animals were of chlorogenic acid (5), were assigned as neochlorogenic acid anesthetized by the injection of 7% chloral hydrate. The blood and 1-O-caffeoylquinic acid [1]. Compounds 4, 11,and19 gave was collected from the abdominal aorta and then centrifuged diagnostic ions 16 Da less than 5, were assigned as p-coumaroyl- at 10,000 rpm for 10 min at 4 °C.
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