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Identification of the Impurities in Bopu Powder® and Sangrovit® by LC molecules Article Identification of the Impurities in Bopu Powder® and Sangrovit® by LC-MS Combined with a Screening Method Zhuang Dong 1,2,†, Mengting Liu 1,3,†, Xiaohong Zhong 2, Xiaoyong Ou 1,3, Xuan Yun 1,3, Mingcan Wang 1, Shurui Ren 1, Zhixing Qing 1,3,* and Jianguo Zeng 1,3,* 1 Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha 410128, China; [email protected] (Z.D.); [email protected] (M.L.); [email protected] (X.O.); [email protected] (X.Y.); [email protected] (M.W.); [email protected] (S.R.) 2 College of Horticulture, Hunan Agricultural University, Changsha 410128, China; [email protected] 3 College of Veterinary Medicine, Hunan Agricultural University, Changsha 410128, China * Correspondence: [email protected] (Z.Q.); [email protected] (J.Z.); Tel./Fax: +86-0731-84686560 (Z.Q. & J.Z.) † These authors contributed equally to this work. Abstract: Bopu powder® and Sangrovit® were developed from Macleaya cordata and are widely used in agriculture and animal husbandry, but their impurities have been rarely reported in the literature. Impurity analysis is of great importance to the quality and safety of veterinary drugs. In this study, high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (HPLC-Q-TOF-MS) combined with a screening method was used to screen and characterize the impurities in Bopu powder® and Sangrovit®. A total of 58 impurities were screened from Bopu Citation: Dong, Z.; Liu, M.; Zhong, powder® and Sangrovit® using the screening strategies, of which 39 were identified by their accurate X.; Ou, X.; Yun, X.; Wang, M.; Ren, S.; m/z value, characteristic MS/MS data, and fragmentation pathways of references. This established Qing, Z.; Zeng, J. Identification of the method was used for impurity analysis for the first time and proved to be a useful and rapid tool Impurities in Bopu Powder® and to screen and identify the impurities of Bopu powder® and Sangrovit®, especially for those at trace Sangrovit® by LC-MS Combined with a Screening Method. Molecules 2021, levels in a complex sample. In addition, this study marks the first comprehensive research into 26, 3851. https://doi.org/10.3390/ impurities in these two products and has great significance for the systematic detection of impurities molecules26133851 in other plant-derived drugs. ® ® Academic Editor: Míriam Keywords: impurity analysis; Bopu powder ; Sangrovit ; isoquinoline alkaloids; screening method; Pérez Trujillo LC-MS Received: 13 May 2021 Accepted: 21 June 2021 Published: 24 June 2021 1. Introduction Bopu powder® and Sangrovit®, whose main chemical compositions are isoquinoline Publisher’s Note: MDPI stays neutral alkaloids, are extracted from the natural plant Macleaya cordata, and they are widely used with regard to jurisdictional claims in in the animal breeding industry as a kind of safe, effective, and controllable Chinese published maps and institutional affil- veterinary medicine [1–5]. Bopu powder® is gray-white powder, and its main effect is anti- iations. inflammatory, which means that it can be used to treat chicken Escherichia coli diarrhea [2]. The main active components are protopine and allocryptopine, and the total content is not less than 50% [6]. Sangrovit® is an orange powder with a pungent odor, and its main effects are anti-inflammatory, thereby allowing for the maintenance of intestinal health [7]. Copyright: © 2021 by the authors. The main active components of Sangrovit® are sanguinarine and chelerythrine, with a total Licensee MDPI, Basel, Switzerland. content of not less than 60% [6]. However, as of yet, there has been no systematic study on This article is an open access article the impurities in these two products, which makes it difficult for us to correctly assess the distributed under the terms and influence of impurity composition. conditions of the Creative Commons The presence of impurities in veterinary drugs reduces their activity, affects their Attribution (CC BY) license (https:// stability, and even produces adverse reactions [8]. Impurities have an important effect on creativecommons.org/licenses/by/ the quality and safety of drugs [9,10]. Therefore, the control of impurities is an important 4.0/). Molecules 2021, 26, 3851. https://doi.org/10.3390/molecules26133851 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 3851 2 of 14 part of ensuring the quality of veterinary drugs. However, identifying the impurities from the complex matrix of plant-derived drugs remains a challenge for current analytical techniques. Many instrumental testing methods have been used in previous studies, including gas chromatography–mass spectrometry (GC-MS) [11], liquid chromatography– diode array detection (LC-DAD) [12,13], LC–mass spectrometry (LC-MS) [14,15], capillary electrophoresis–mass spectrometry, and LC–nuclear magnetic resonance (NMR) [15]. LC- MS is playing an increasingly important role in identifying impurities because of its high efficiency of separation, low level of sample consumption, excellent sensitivity, strong specificity, and the ability to provide a wealth of structural information [16,17]. However, it is time consuming to manually search for impurity signals from large amounts of raw MS data, and the signals of trace impurities are easily omitted, especially those submerged by background ions [18–20] These difficulties are considered as the bottleneck of screening impurities when using LC-MS. A robust component-mining method is needed to rapidly and efficiently screen impurities. In many early studies [21,22], the first step of identifying compounds using LC-MS is to establish the total ion chromatograms (TICs) of the samples. Through the analysis of the MS and MS/MS data of each mass spectrum peak on the TIC, the structures can be preliminarily inferred and identified. However, compounds with obvious peaks in the TICs can easily be detected and identified, while it is difficult to identify and characterize components with trace amount [23]. To solve this problem, a screening strategy including the non-target, accurate-target, and extensive-target method combined with LC-MS was employed for systematical screening impurities in the presence of Bopu powder® and Sangrovit®. The impurities were then further determined by their characteristic MS/MS data and the fragmentation pathways of isoquinoline alkaloids [24]. Finally, a total of 58 impurities were screened, and 39 of them were identified from both products (Table1). Molecules 2021, 26, 3851 3 of 14 1 Table 1. Peak number (PN), retention time (TR), molecular formula, MS , characteristic MS/MS ions, tentative identification, screening method, type, and source of impurities. Those compounds were screened by the non-target method (X), accurate-target method (Y), and extensive-target method (Z). T Molecular Screening PN R MS1 Characteristic MS/MS Ions (m/z) Tentative Identification Type Source (min) Formula Method 269.1149, 237.0797, 175.0934, 143.0482, 1 4.391 C H NO + 314.1744 N, N-dimethylisococlaurine Y Benzyltetrahydroisoquinoline Bopu powder®/Sangrovit® 19 24 3 107.0481 + ® 2 4.915 C19H24NO3 314.1752 269.1239, 207.0753, 175.0736, 107.0485 N, N-dimethylcoclaurine Y Benzyltetrahydroisoquinoline Sangrovit 324.1193, 194.0935, 177.0792, 176.0687, 3 6.945 C H NO + 342.1409 Demethylcryptopine Z Protopine Sangrovit® 19 20 5 165.0659 + ® 4 7.114 C19H24NO4 330.144 299.1172, 192.1009, 137.0616 Reticuline Y Benzyltetrahydroisoquinoline Sangrovit + ® 5 7.911 C20H22NO4 340.1258 192.1101, 149.0652 Isotetrahydroprotoberberine Z Tetrahydroptotoberberine Bopu powder 4+ ® 6 8.310 C19H18NO 324.1214 176.0779, 149.0579, 294.1161 Tetrahydrocoptisine Y Tetrahydroptotoberberine Bopu powder + ® 7 8.393 C19H16NO4 322.0909 279.0869, 294.1065, 307.0822, Isothalonil Z Protoberberine Sangrovit + ® 8 8.677 C20H22NO5 356.1395 151.0646,188.0709,189.0755,206.0777 Demethyl allocryprotopine XY Protopine Bopu powder + ® 9 9.201 C20H20NO5 354.1351 336.1232, 189.0769, 206.0803,149.0577 Protopine XY Protopine Sangrovit + ® 10 9.891 C19H14NO5 336.0862 318.0726, 308.0850, 290.0797 13-hydroxyl-coptisine Z Protoberberine Sangrovit + ® 11 10.116 C21H24NO5 370.1584 352.1580, 206.0812, 188.0728, 189.0893 Allocryprotopine YZ Protopine Sangrovit + ® 12 10.334 C20H22NO4 340.1614 192.0924, 170.9604 N-methylpyrophylline Z Tetrahydroptotoberberine Sangrovit + ® ® 13 10.824 C20H20NO4 338.1380 190.0845, 149.0669 N-methyltetrahydropalmatine Z Tetrahydroptotoberberine Bopu powder /Sangrovit + ® 14 11.373 C19H14NO4 320.0916 305.0672, 292.0863, 262.0825, 246.0860 Didemethyl chelerythrine YZ Benzophenanthridine Sangrovit + ® 15 11.414 C20H20NO4 338.1378 323.1047, 322.1029, 294.0938 7,8-dihydroberberine Z Protoberberine Sangrovit + ® 16 11.639 C20H16NO4 334.0927 319.0828, 304.0570, 291.0834, 276.0496 Demethylated chelerythrine X Benzophenanthridine Sangrovit + ® 17 11.699 C20H18NO4 336.1154 320.0759, 318.0738, 292.0937 Berberine Y Protoberberine Sangrovit 319.0836, 318.0738, 304.0545, 290.0758, 18 11.705 C H NO + 334.1021 Dihydrosanguinarine X Benzophenanthridine Sangrovit® 20 16 4 276.0665 + ® ® 19 11.722 C19H14NO4 320.0839 305.0701, 292.0909, 277.0703, 262.0830 Isodimethylchelerythrine YZ Benzophenanthridine Bopu powder /Sangrovit + ® ® 20 12.039 C20H20NO5 354.1297 206.0809, 189.0758, 188.0691, 149.0591 Isoprotopine YZ Protopine Bopu powder /Sangrovit + ® 21 12.754 C20H14NO4 332.0791 317.0701, 304.0924, 274.0836 Sanguinarine X Benzophenanthridine Bopu powder 349.0923, 348.0824, 334.0633, 320.0859, 22 13.911 C
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