دورية أكاديمية
Database-aided ultrahigh-performance liquid chromatography Q-Exactive-Orbitrap tandem mass spectrometry putatively identifies 16 unexpected compounds and three anticounterfeiting pharmacopoeia quality markers for Perillae Fructus.
| العنوان: | Database-aided ultrahigh-performance liquid chromatography Q-Exactive-Orbitrap tandem mass spectrometry putatively identifies 16 unexpected compounds and three anticounterfeiting pharmacopoeia quality markers for Perillae Fructus. |
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| المؤلفون: | Chen B; Key Laboratory of Fermentation Engineering (Ministry of Education), Cooperative Innovation Centre of Industrial Fermentation (Ministry of Education & Hubei Province), Hubei University of Technology, Wuhan, China., Liu S; Key Laboratory of Fermentation Engineering (Ministry of Education), Cooperative Innovation Centre of Industrial Fermentation (Ministry of Education & Hubei Province), Hubei University of Technology, Wuhan, China., Li X; School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China., Cai R; School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China.; College of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China., Li C; School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China., Hu Y; Key Laboratory of Fermentation Engineering (Ministry of Education), Cooperative Innovation Centre of Industrial Fermentation (Ministry of Education & Hubei Province), Hubei University of Technology, Wuhan, China., Su J; Key Laboratory of Fermentation Engineering (Ministry of Education), Cooperative Innovation Centre of Industrial Fermentation (Ministry of Education & Hubei Province), Hubei University of Technology, Wuhan, China., Lei T; School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China. |
| المصدر: | Rapid communications in mass spectrometry : RCM [Rapid Commun Mass Spectrom] 2024 Jul 15; Vol. 38 (13), pp. e9762. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: John Wiley And Sons Ltd Country of Publication: England NLM ID: 8802365 Publication Model: Print Cited Medium: Internet ISSN: 1097-0231 (Electronic) Linking ISSN: 09514198 NLM ISO Abbreviation: Rapid Commun Mass Spectrom Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Chichester : John Wiley And Sons Ltd Original Publication: London, UK : Heyden, c1987- |
| مواضيع طبية MeSH: | Tandem Mass Spectrometry*/methods , Drugs, Chinese Herbal*/chemistry , Drugs, Chinese Herbal*/analysis, Chromatography, High Pressure Liquid/methods ; Molecular Docking Simulation ; Pharmacopoeias as Topic ; Fruit/chemistry ; Scopolamine/analysis ; Depsides/analysis ; Depsides/chemistry |
| مستخلص: | Rationale: Perillae Fructus (PF) is a common traditional Chinese medicine (TCM) for the treatment of asthma. It has not been effectively characterized by rosmarinic acid (RosA), which is currently designed as the sole quality indicator in the Chinese Pharmacopoeia. Methods: This study introduced a database-aided ultrahigh-performance liquid chromatography equipped with quadrupole-Exactive-Orbitrap mass spectrometry (UHPLC/Q-Exactive-Orbitrap MS/MS) technology to putatively identify the compounds in PF, followed by literature research, quantum chemical calculation, and molecular docking to screen potential quality markers (Q-markers) of PF. Results: A total of 27 compounds were putatively identified, 16 of which had not been previously found from PF. In particular, matrine, scopolamine, and RosA showed relatively high levels of content, stability, and drug-likeness. They exhibited interactions with the asthma-related target and demonstrated the TCM properties of PF. Conclusions: The database-aided UHPLC/Q-Exactive-Orbitrap MS/MS can identify at least 27 compounds in PF. Of these, 16 compounds are unexpected, and three compounds (matrine, scopolamine, and RosA) should be considered anticounterfeiting pharmacopoeia Q-markers of PF. (© 2024 John Wiley & Sons Ltd.) |
| References: | Yu H, Qiu JF, Ma LJ, Hu YJ, Li P, Wan JB. Phytochemical and phytopharmacological review of Perilla frutescens L. (Labiatae), a traditional edible‐medicinal herb in China. Food Chem Toxicol. 2017;108(Pt B):375‐391. doi:10.1016/j.fct.2016.11.023. Ahmed HM. Ethnomedicinal, phytochemical and pharmacological investigations of Perilla frutescens (L.) Britt. Molecules. 2019;24(1):102. doi:10.3390/molecules24010102. Nguyen V, Zhang Q, Pan F, et al. Zi‐Su‐Zi decoction improves airway hyperresponsiveness in cough‐variant asthma rat model through PI3K/AKT1/mTOR, JAK2/STAT3 and HIF‐1α/NF‐κB signaling pathways. J Ethnopharmacol. 2023;314:116637. doi:10.1016/j.jep.2023.116637. Chinese Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China 2020. China Medical Science Press; 2020. (in Chinese). Zhang F, Zhang Y, Li X, et al. Research on Q‐markers of Qiliqiangxin capsule for chronic heart failure treatment based on pharmacokinetics and pharmacodynamics association. Phytomedicine. 2018;44:220‐230. doi:10.1016/j.phymed.2018.03.003. Liu CX, Liu L, Guo DA. Quality marker of TCMs: Concept and applications. Phytomedicine. 2018;44:85‐86. doi:10.1016/j.phymed.2018.05.015. Gao X, Du X, An L, et al. Wilforine, the Q‐marker and PK‐maker of Tripterygium glycosides tablet: Based on preparation quantitative analysis and PK‐PD study. Phytomedicine. 2019;54:357‐364. doi:10.1016/j.phymed.2018.03.031. Maldonado‐Reina AJ, López‐Ruiz R, Romero‐González R, Martínez Vidal JL, Garrido‐Frenich A. Assessment of co‐formulants in marketed plant protection products by LC‐Q‐Orbitrap‐MS: Application of a hybrid data treatment strategy combining suspect screening and unknown analysis. J Agric Food Chem. 2022;70(23):7302‐7313. doi:10.1021/acs.jafc.2c01152. Su J, Li D, Hu Y, et al. A novel C6‐sulfonated celastrol analog as a tyrosinase and melanin inhibitor: Design, synthesis, biological evaluation and molecular simulation. J Mol Struct. 2023;1283:135288. doi:10.1016/j.molstruc.2023.135288. Jiang Q, Li X, Tian Y, et al. Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect mesenchymal stem cells from •OH‐treated damage: Bioassay and antioxidant mechanism. BMC Complement Altern Med. 2017;17(1):242. doi:10.1186/s12906‐017‐1730‐3. Liu S, Li X, Cai R, et al. Ultra‐high‐performance liquid chromatography‐quadrupole‐Exactive‐Orbitrap‐tandem mass spectrometry‐based putative identification for Eucommiae Folium (Duzhongye) and its quality‐marker candidate for pharmacopeia. J Sep Sci. 2023;46(13):2300041. doi:10.1002/jssc.202300041. Zhang G, Chen S, Zhou W, et al. Rapid qualitative and quantitative analyses of eighteen phenolic compounds from Lycium ruthenicum Murray by UPLC‐Q‐Orbitrap MS and their antioxidant activity. Food Chem. 2018;269:150‐156. doi:10.1016/j.foodchem.2018.06.132. Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 16, Revision C. 01. 2016. Krishnan R, Binkley JS, Seeger R, Pople JA. Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys. 1980;72(1):650‐654. doi:10.1063/1.438955. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem. 1994;98(45):11623‐11627. doi:10.1021/j100096a001. Grimme S, Antony J, Ehrlich S, Krieg H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT‐D) for the 94 elements H‐Pu. J Chem Phys. 2010;132(15):154104. doi:10.1063/1.3382344. Grimme S, Ehrlich S, Goerigk L. Effect of the damping function in dispersion corrected density functional theory. J Comput Chem. 2011;32(7):1456‐1465. doi:10.1002/jcc.21759. Lu T, Chen F. Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem. 2012;33(5):580‐592. doi:10.1002/jcc.22885. Dennington R, Keith T, Millam J. GaussView, version 6. 2016. Humphrey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J Mol Graph. 1996;14(1):33‐38. doi:10.1016/0263‐7855(96)00018‐5. Xiong G, Wu Z, Yi J, et al. ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Res. 2021;49(W1):W5‐W14. doi:10.1093/nar/gkab255. Morris GM, Huey R, Olson AJ. Using AutoDock for ligand‐receptor docking. Curr Protoc Bioinformatics. 2008;24(1). doi:10.1002/0471250953.bi0814s24. Zuo Y, Chen H, Deng Y. Simultaneous determination of catechins, caffeine and gallic acids in green, oolong, black and pu‐erh teas using HPLC with a photodiode array detector. Talanta. 2002;57(2):307‐316. doi:10.1016/S0039‐9140(02)00030‐9. Liu CJ, Zhu Q. Study on HPLC characteristic fingerprint of Shenlingbaizhu powder and simultaneous determination of its five indicative components. Chin Pharmaceut. 2018;15:12‐16. (in Chinese). Deguchi Y, Ito M. Rosmarinic acid in Perilla frutescens and perilla herb analyzed by HPLC. J Nat Med. 2020;74(2):341‐352. doi:10.1007/s11418‐019‐01367‐8. Luo C, Zou L, Sun H, et al. A review of the anti‐inflammatory effects of rosmarinic acid on inflammatory diseases. Front Pharmacol. 2020;11:153. doi:10.3389/fphar.2020.00153. Liu S, Jin X, Shang Y, et al. A comprehensive review of the botany, ethnopharmacology, phytochemistry, pharmacology, toxicity and quality control of Perillae Fructus. J Ethnopharmacol. 2023;304:116022. doi:10.1016/j.jep.2022.116022. Fang S, Dong L, Liu L, et al. HERB: a high‐throughput experiment‐ and reference‐guided database of traditional Chinese medicine. Nucleic Acids Res. 2021;49(D1):D1197‐D1206. doi:10.1093/nar/gkaa1063. Fan Y, Cao X, Zhang M, et al. Quantitative comparison and chemical profile analysis of different medicinal parts of Perilla frutescens (L.) Britt. from different varieties and harvest periods. J Agric Food Chem. 2022;70(28):8838‐8853. doi:10.1021/acs.jafc.2c03104. Pereira F, Xiao K, Latino DARS, Wu C, Zhang Q, Aires‐de‐Sousa J. Machine learning methods to predict density functional theory B3LYP energies of HOMO and LUMO orbitals. J Chem Inf Model. 2017;57(1):11‐21. doi:10.1021/acs.jcim.6b00340. Li X, Chen S, Zeng J, et al. Database‐aided UHPLC‐Q‐orbitrap MS/MS strategy putatively identifies 52 compounds from Wushicha granule to propose anti‐counterfeiting quality‐markers for pharmacopoeia. Chin Med. 2023;18(1):116. doi:10.1186/s13020‐023‐00829‐2. Zhang S, Cheng M, Zhang P, et al. Insights into the stability of magnesium borate salts for rechargeable magnesium batteries from AIMD simulations. Chem Commun. 2022;58(85):11969‐11972. doi:10.1039/D2CC04357B. Zeng XT, Chen YY, Yue SJ, et al. A three‐dimensional integration strategy for Q‐markers identification: Taken Euphorbia Pekinensis Radix as an example. J Pharmaceut Biomed. 2023;224:115170. doi:10.1016/j.jpba.2022.115170. Angumeenal AR, Venkappayya D. An overview of citric acid production. LWT Food Sci Technol. 2013;50(2):367‐370. doi:10.1016/j.lwt.2012.05.016. Girawale SD, Meena SN, Nandre VS, Waghmode SB, Kodam KM. Biosynthesis of vanillic acid by Ochrobactrum anthropi and its applications. Bioorg Med Chem. 2022;72:117000. doi:10.1016/j.bmc.2022.117000. Lin Y, Yan Y. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb Cell Fact. 2012;11(1):42. doi:10.1186/1475‐2859‐11‐42. Marín L, Gutiérrez‐del‐Río I, Yagüe P, Manteca Á, Villar CJ, Lombó F. De novo biosynthesis of apigenin, luteolin, and eriodictyol in the actinomycete Streptomyces albus and production improvement by feeding and spore conditioning. Front Microbiol. 2017;8:921. doi:10.3389/fmicb.2017.00921. Ghazi‐Tehrani AK, Pontell HN. Corporate crime and state legitimacy: The 2008 Chinese melamine milk scandal. Crime Law Soc Change. 2015;63(5):247‐267. doi:10.1007/s10611‐015‐9567‐5. Mazur M, Olczak J, Olejniczak S, et al. Targeting acidic mammalian chitinase is effective in animal model of asthma. J Med Chem. 2018;61(3):695‐710. doi:10.1021/acs.jmedchem.7b01051. Chen B, Ouyang X, Cheng C, et al. Bioactive peptides derived from Radix Angelicae sinensis inhibit ferroptosis in HT22 cells through direct Keap1‐Nrf2 PPI inhibition. RSC Adv. 2023;13(32):22148‐22157. doi:10.1039/D3RA04057G. Eno EA, Cheng CR, Louis H, et al. Investigation on the molecular, electronic and spectroscopic properties of rosmarinic acid: An intuition from an experimental and computational perspective. J Biomol Struct Dyn. 2023;41(20):10287‐10301. doi:10.1080/07391102.2022.2154841. Huang WC, Chan CC, Wu SJ, et al. Matrine attenuates allergic airway inflammation and eosinophil infiltration by suppressing eotaxin and Th2 cytokine production in asthmatic mice. J Ethnopharmacol. 2014;151(1):470‐477. doi:10.1016/j.jep.2013.10.065. Demeter SL, Cordasco EM. Transdermal scopolamine in the treatment of asthma: A preliminary report. J Asthma. 1986;23(4):203‐206. doi:10.3109/02770908609073158. Yang YN, Deng YT, Zang CC, et al. The gut microbial co‐abundance gene groups (CAGs) differentially respond to the flavor (Yao‐Wei) of Chinese Materia Medica. Am J Chin Med. 2022;50(08):2223‐2244. doi:10.1142/S0192415X22500963. Liang WB, Zhao H, Zhang XM, et al. Pharmacological study on the antitussive, expectorant and antiasthmatic effects of Sanzi Yangqin decoction. Pharm Clin Chin Mater Med. 2003;2:11‐12. (in Chinese). Guo KX, Jia JH. Efficacy observation of Suzi Jiangqi decoction in the treatment of acute attack of bronchial asthma. World J Integr Tradit Western Med. 2014;3:288‐290. (in Chinese). |
| معلومات مُعتمدة: | 82304707 National Natural Science Foundation of China; 82374485 National Natural Science Foundation of China; XJ2022004001 Doctoral Research Initiation Grant of Hubei University of Technology |
| المشرفين على المادة: | 0 (Drugs, Chinese Herbal) DL48G20X8X (Scopolamine) 0 (Depsides) |
| تواريخ الأحداث: | Date Created: 20240502 Date Completed: 20240502 Latest Revision: 20240502 |
| رمز التحديث: | 20240502 |
| DOI: | 10.1002/rcm.9762 |
| PMID: | 38693787 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1097-0231 |
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| DOI: | 10.1002/rcm.9762 |