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Simultaneous Determination of Nine Bioactive Accepted Manuscript Title: Simultaneous determination of nine bioactive compounds in Yijin-tang via high-performance liquid chromatography and liquid chromatography-electrospray ionization-mass spectrometry Author: Hye Jin Yang Nam-Hui Yim Kwang Jin Lee Min Jung Gu Bohyoung Lee Youn-Hwan Hwang Jin Yeul Ma PII: S2213-4220(16)30030-0 DOI: http://dx.doi.org/doi:10.1016/j.imr.2016.04.005 Reference: IMR 200 To appear in: Received date: 14-10-2015 Revised date: 30-3-2016 Accepted date: 7-4-2016 Please cite this article as: Hye Jin YangNam-Hui YimKwang Jin LeeMin Jung GuBohyoung LeeYoun-Hwan HwangJin Yeul Ma Simultaneous determination of nine bioactive compounds in Yijin-tang via high-performance liquid chromatography and liquid chromatography-electrospray ionization-mass spectrometry (2016), http://dx.doi.org/10.1016/j.imr.2016.04.005 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. 1 Original Article 2 3 Simultaneous determination of nine bioactive compounds in Yijin-tang via high- 4 performance liquid chromatography and liquid chromatography-electrospray 5 ionization-mass spectrometry 6 7 Hye Jin Yang, Nam-Hui Yim, Kwang Jin Lee, Min Jung Gu, Bohyoung Lee, Youn-Hwan * * 8 Hwang and Jin Yeul Ma 9 10 KM Application Center, Korea Institute of Oriental Medicine, 11 70 Cheomdanro, Dong-gu, Daegu 701-300, Republic of Korea 12 13 Running title: Simultaneous determination of Yijin-tang via HPLC-DAD and LC/MS 14 * 15 Address for co-corresponding author 16 Youn-Hwan Hwang, Ph.D. 17 Senior Researcher 18 KM Application Center, 19 Korea Institute ofAccepted Oriental Medicine, Manuscript 20 70 Cheomdanro, Dong-gu, Daegu 701-300, 21 Republic of Korea 22 Tel: +82-53-940-3873 23 Fax: +82-53-940-3899 24 E-mail: [email protected] 1 Page 1 of 33 * 1 Address for co-corresponding author 2 Jin Yeul Ma, Ph.D. 3 Principal Investigator / Director 4 KM Application Center, 5 Korea Institute of Oriental Medicine, 6 70 Cheomdanro, Dong-gu, Daegu 701-300, 7 Republic of Korea 8 Tel: +82-53-940-3811 9 Fax: +82-53-940-3899 10 E-mail: [email protected] 11 Accepted Manuscript 2 Page 2 of 33 1 Original Article 2 3 Simultaneous determination of nine bioactive compounds in Yijin-tang via high- 4 performance liquid chromatography and liquid chromatography-electrospray 5 ionization-mass spectrometry 6 Accepted Manuscript 3 Page 3 of 33 1 Abstract 2 Background: Yijin-tang (YJ) has been used traditionally for the treatment of cardiovascular 3 conditions, nausea, vomiting, gastroduodenal ulcers, and chronic gastritis. In this study, a simple 4 and sensitive high-performance liquid chromatography (HPLC) method was developed for the 5 quantitation of nine bioactive compounds in YJ: homogentisic acid, liquiritin, naringin, hesperidin, 6 neohesperidin, liquiritigenin, glycyrrhizin, 6-gingerol, and pachymic acid. 7 Method: Chromatographic separation of the analytes was achieved on an RS tech C18 8 column (4.6 mm × 250 mm, 5 μm) using a mobile phase composed of water containing 0.1% (v/v) 9 trifluoroacetic acid and acetonitrile with a gradient elution at a flow rate of 1.0 mL/min. 2 10 Results: Calibration curves for all analytes showed good linearity (R ≥ 0.9995). Lower 11 limits of detection and lower limits of quantification were in the ranges of 0.03 - 0.17 μg/mL and 12 0.09 - 0.43 μg/mL, respectively. Relative standard deviations (RSDs) (%) for intra- and inter-day 13 assays were below 3%. The recovery of components ranged from 98.09% to 103.78%, with RSDs 14 (%) values ranging from 0.10% to 2.59%. 15 Conclusion: This validated HPLC method was applied to qualitative and quantitative 16 analyses of nine bioactive compounds in YJ and fermented YJ, and may be a useful tool for the 17 quality control of YJ. 18 19 Keywords: HPLC-DAD, LC/MS, Simultaneous determination, Validation, Yijin-tang 20 Accepted Manuscript 4 Page 4 of 33 1 1. Introduction 2 Yijin-tang (YJ, Erchen-tang in Chinese, Nichin-to in Japanese) is a traditional prescription 3 for the prevention and treatment of diverse diseases; it has been used widely to treat nausea, 1 4 vomiting, gastroduodenal ulcers, and chronic gastritis. YJ has also been shown to improve 5 digestive function in clinical research trials. Recently, YJ was reported to show therapeutic effects 6 on diseases of the circulatory system and protective effects against gastric mucosa in in vivo 2,3 7 experiments. YJ is composed of Pinellia ternata Breitenbach, Citrus unshiu Markovich, Poria 8 cocos Wolf, Glycyrrhiza uralensis Fisch, and Zingiber officinale Roscoe, according to the Korean 9 Herbal Pharmacopoeia. The major components of each herbal medicine in YJ are known to be 10 bioactive components, including flavonoids (e.g. liquiritin, liquiritigenin, hesperidin, rutin, naringin, 11 neohesperidin, and poncirin), triterpenoids (e.g. glycyrrhizin, pachymic acid, and eburicoic acid), 4-10 12 phenolic acids (e.g. homogentisic acid) and pungent principles (e.g. 6-gingerol and 6-shogaol). 13 These compounds, derived from each herbal medicine, have various pharmacological activities 4, 11-16 14 including anti-cancer, anti-inflammatory, anti-bacterial and anti-oxidant activities. In this 15 study, specific biomarkers were selected to evaluate the quality of YJ and its ingredients, including 16 homogentisic acid for P. ternata Breitenbach, hesperidin, naringin and neohesperidin for C. unshiu 17 Markovich, pachymic acid for P. cocos Wolf, liquiritigenin and glycyrrhizin for G. uralensis Fisch, 18 and 6-gigerol for Z. officinale Roscoe (Table 1). 19 Several analytical methods for these compounds have been developed for qualitative and 20 quantitative analysesAccepted using high-performance liquid chromatography-diode-arrayManuscript detector (HPLC- 17-25 21 DAD) and liquid chromatography/mass spectrometry (LC/MS). However, these methods cannot 22 simultaneously determine the multiple bioactive components in YJ. Although a HPLC-DAD 23 method to detect six compounds in YJ was recently developed, the identification and quantification 24 of compounds based on retention times and UV spectra are limited due to the interference of non- 26 25 target molecular components in YJ. Therefore, methods for simultaneously detecting these 5 Page 5 of 33 1 biomarkers in YJ is needed to ensure efficient quality control and pharmaceutical evaluation using 2 LC/MS. 3 In this study, a rapid, simple, and efficient analytical method for nine biomarkers in YJ was 4 developed using HPLC-DAD for quantitation and LC/MS for identification. Subsequently, the 5 method was applied to chemically profile targeted analytes in YJ and Lactobacillus-fermented YJ. Accepted Manuscript 6 Page 6 of 33 1 2. Materials and methods 2 3 2.1. Chemicals and reagents 4 Homogentisic acid, liquiritin, naringin, neohesperidin, and trifluoroacetic acid (TFA) were 5 purchased from Sigma-Aldrich Co. (St. Louis, MO, USA.). Liquiritigenin, 6-gingerol, and 6 pachymic acid were obtained from Faces Biochemical Co., Ltd. (Wuhan, China). Hesperidin and 7 glycyrrhizin were purchased from ICN Biomedicals (Santa Ana, CA, USA) and Tokyo Chemical 8 Industry Co., Ltd. (Tokyo, Japan), respectively. The purity of all standards was above 97%. All 9 herbal medicines were purchased at the Yeongcheon traditional herbal market (Yeongcheon, South 10 Korea). The chemical structures of the nine bioactive compounds are shown in Figure 1. 11 HPLC-grade acetonitrile was purchased from J.T. Baker Inc. (Philipsburg, NJ, USA). Deionized 12 water was prepared using an ultrapure water production apparatus (Millipore, Billerica, MA, USA). 13 14 2.2. Preparation and fermentation of YJ 15 All herb samples were purchased from the Yeongcheon Herbal Store (Yeongcheon, South 16 Korea) and all specimens (#50 for P. ternata Breitenbach, #22 for C. unshiu Markovich, #61 for P. 17 cocos Wolf, #3 for G. uralensis Fisch, and #6 for Z. officinale Roscoe) were stored in the herbarium 18 of the KM Application Center, Korea Institute of Oriental Medicine. Five medicinal herbs (1.95 kg, 19 Table 1) were extracted in 19.5 L of distilled water for 3 hours using a COSMOS-660 extractor 20 (Kyungseo MachineAccepted Co., Incheon, Korea). Extracts wereManuscript sieved (106 μm) to yield 15.8 L of the 21 decoction. To ferment YJ, ten bacterial strains (including L. rhamnosus KFRI 144, L. acidophillus 22 KFRI 150, L. amylophillus KFRI 161, L. acidophillus KFRI 162, L. platarum KFRI 166, L. 23 acidophillus KFRI 217, L. brevis KFRI 221, L. brevis KFRI 227, L. curvatus KFRI 231, L. 24 acidophillus KFRI 341) were obtained from the Korean Food Research Institute (Seongnam, Korea). 25 Bacterial strains were cultured in MRS broth at 37°C for 24 hours and viable cell counts of each 7 Page 7 of 33 1 strain were determined in triplicate using a pour plate method on MRS agar. Solutions of YJ 2 extracts were adjusted to pH 8 using 1 M sodium hydroxide and autoclaved for 15 min at 121°C. 9 3 Sterilized-SE solutions (500 mL) were inoculated with 5 mL of the inoculum (1% v/v, 2 × 10 4 CFU/mL). Inoculated samples were incubated at 37°C for 48 hours and a brownish powder of 5 fermented YJ extract was obtained via lypophilization. These fermented YJ (f-YJ) samples were 6 stored at 4°C before use. 7 8 2.3. Preparation of calibration standards, quality control, and analytical samples 9 Standard stock solutions of the nine bioactive standards – homogentisic acid, liquiritin, 10 naringin, hesperidin, neohesperidin, liquiritigenin, glycyrrhizin, 6-gingerol, and pachymic acid – 11 were prepared at concentrations of 200, 200, 200, 800, 200, 200, 600, 200, and 400 μg/mL, 12 respectively, by dissolving them in methanol.
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