Microwave-assisted ionic liquid microextraction combined with high performance liquid chromatography for the determination of naphthoquinones from Arnebia euchroma (Royle) Johnst

References

• Shen, C. C.; Syu, W. J.; Li, S. Y.; Lin, C. H.; Lee, G. H.; Sun, C. M. Antimicrobial Activities of Naphthazarins from Arnebia euchroma. J. Nat. Prod. 2002, 65, 1857–1862. DOI: 10.1021/np010599w.
   PubMed Web of Science ®Google Scholar
• Bimal, P. S.; Mukesh, K. S.; Purkha, R. M.; Pooran, M. S.; Swaroop, S. Anti-Inflammatory Activity of Shikonin Derivatives from Arnebia hispidissima. Phytomedicine. 2003, 10, 375–380. DOI: 10.1078/0944-7113-00262.
   PubMed Web of Science ®Google Scholar
• He, Y.; Li, Q.; Su, M.; Huang, W.; Zhu, B. Acetylshikonin from Zicao Exerts Antifertility Effects at High Dose in Rats by Suppressing the Secretion of GTH. Biochem. Biophys. Res. Commun. 2016, 476, 560–565. DOI: 10.1016/j.bbrc.2016.05.162.
   PubMed Web of Science ®Google Scholar
• Fan, H. Y.; Yang, M. Y.; Che, X.; Zhang, Z. L.; Xu, H.; Liu, K.; Meng, Q. G. Activity Study of a Hydroxynaphthoquinone Fraction from Arnebia euchroma in Experimental Arthritis. Fitoterapia. 2012, 83, 1226–1237. DOI: 10.1016/j.fitote.2012.06.011.
   PubMed Web of Science ®Google Scholar
• Yen, C. Y.; Chiang, W. D.; Liu, S. Y.; Wang, K. T.; Liao, E. C.; Hsieh, C. L. Lithospermum Erythrorhizon Extract Inhibits Der p2-Induced Inflammatory Response through Alleviation of Thymic Stromal Lymphopoietin, Nuclear Factor Kappa B, and Inflammasome Expression in Human Bronchial Epithelial Cells. J. Ethnopharmacol. 2017, 201, 1–8. DOI: 10.1016/j.jep.2017.02.038.
   PubMed Web of Science ®Google Scholar
• Seetharaman, R.; Da, J. P.; Cheol, P.; Sejin, P.; Young, H. P.; Sun, T. K.; Yung, H. C.; Young, W. C. In Vitro and in Vivo Anticancer Effects of Lithospermum erythrorhizon Extract on B16F10 Murine Melanoma. J. Ethnopharmacol. 2012, 144, 335–345. DOI: 10.1016/j.jep.2012.09.017.
   PubMed Web of Science ®Google Scholar
• Li, Q. S.; Zeng, J. C.; Su, M. L.; He, Y.; Zhu, B. H. Acetylshikonin from Zicao Attenuates Cognitive Impairment and Hippocampus Senescence in D-Galactose-Induced Aging Mouse Model via Upregulating the Expression of SIRT1. Brain Res. Bull. 2018, 137, 311–318. DOI: 10.1016/j.brainresbull.2018.01.007.
   PubMed Web of Science ®Google Scholar
• Agata, S.; Natalia, P.; Anna, Z.; Andrzej, P.; Katarzyna, S. B.; Katarzyna, P.; N. J. Antigenotoxic, G. Anti-Photogenotoxic and Antioxidant Activities of Natural Naphthoquinone Shikonin and Acetylshikonin and Arnebia euchroma Callus Extracts Evaluated by the Umu-Test and EPR Method. Toxicol. In Vitro 2015, 30, 364–372. DOI: 10.1016/j.tiv.2015.09.029.
   PubMed Web of Science ®Google Scholar
• Wang, X.; Hayashi, S.; Umezaki, M.; Yamamoto, T.; Kageyama-Yahara, N.; Kondo, T.; Kadowaki, M. Shikonin, a Constituent of Lithospermum erythrorhizon Exhibits anti-Allergic Effects by Suppressing Orphan Nuclear Receptor Nr4a Family Gene Expression as a New Prototype of Calcineurin Inhibitors in Mast Cells. Chem. Biol. Interact. 2014, 224, 117–127. DOI: 10.1016/j.cbi.2014.10.021.
   PubMed Web of Science ®Google Scholar
• Ahmed, B.; Ellen, H.; Samah, C.; Ahlam, A.; Heidi, R. K.; Nilesh, W. G.; Fawaz, G. H. Decreased Adiposity and Enhanced Glucose Tolerance in Shikonin Treated Mice. Obesity 2015, 23, 2269–2277. DOI: 10.1002/oby.21263.
   PubMed Web of Science ®Google Scholar
• Guan, L.; Luo, Q.; Shi, J.; Yu, W. Application of Ionic-Liquid-Magnetized Stirring Bar Liquid-Phase Microextraction Coupled with HPLC for the Determination of Naphthoquinones in Zicao. J. Sep. Sci. 2018, 41, 868–876. DOI: 10.1002/jssc.201700970.
   PubMed Web of Science ®Google Scholar
• Pharmacopoeia Committee of China (Ed.). Chinese Pharmacopoeia; Chemical Industry Publishing House: Beijing, 2015; pp. 340–341.
   Google Scholar
• Bozan, B.; Baser, K.; Kara, S. Quantitative Determination of Naphthoquinones of Arnebia densiflora by TLC-Densitometry. Fitoterapia. 1999, 70, 402–406. DOI: 10.1016/S0367-326X(99)00066-0.
   Web of Science ®Google Scholar
• He, J. M.; Zhang, S. Y.; Mu, Q. Online-Storage Recycling Counter-Current Chromatography for Preparative Isolation of Naphthaquinones from Arnebia euchroma (Royle) Johnst. J. Chromatogr. A 2016, 1464, 79–86. DOI: 10.1016/j.chroma.2016.08.022.
   PubMed Web of Science ®Google Scholar
• Meng, J.; Yang, Z.; Liang, J.; Guo, M.; Wu, S. Multi-Channel Recycling Counter-Current Chromatography for Natural Product Isolation: Tanshinones as Examples. J. Chromatogr. A 2014, 1327, 27–38. DOI: 10.1016/j.chroma.2013.12.069.
   PubMed Web of Science ®Google Scholar
• Lü, H.; Wang, J.; Wang, X.; Lin, X.; Wu, X.; Xie, Z. Rapid Separation and Determination of Structurally Related Anthraquinones in Rhubarb by Pressurized Capillary Electrochromatography. J. Pharm. Biomed. Anal. 2007, 43, 352–357. DOI: 10.1016/j.jpba.2006.06.023.
   PubMed Web of Science ®Google Scholar
• Koyama, J.; Morita, I.; Kobayashi, N. Simultaneous Determination of Anthraquinones in Rhubarb by High-Performance Liquid Chromatography and Capillary Electrophoresis. J. Chromatogr. A 2007, 1145, 183–189. DOI: 10.1016/j.chroma.2007.01.076.
   PubMed Web of Science ®Google Scholar
• Kumazawa, T.; Seno, H.; Urakami, T.; Matsumoto, T.; Suzuki, O. Trace Levels of Pyrroloquinoline Quinone in Human and Rat Samples Detected by Gas Chromatography/Mass Spectrometry. Biochim. Biophys. Acta. 1992, 1156, 62–66. DOI: 10.1016/0304-4165(92)90096-D.
   PubMed Web of Science ®Google Scholar
• Liao, M.; Li, A.; Chen, C.; Ouyang, H.; Zhang, Y.; Xu, Y.; Feng, Y.; Jiang, H. Systematic Identification of Shikonins and Shikonofurans in Medicinal Zicao Species Using Ultra-High Performance Liquid Chromatography Quadrupole Time of Flight Tandem Mass Spectrometry Combined with a Data Mining Strategy. J. Chromatogr. A. 2015, 1425, 158–172. DOI: 10.1016/j.chroma.2015.11.028.
   PubMed Web of Science ®Google Scholar
• Dorothea, A.; Markus, G. Analysis of Anthraquinones in Rhubarb (Rheum palmatum and Rheum officinale) by Supercritical Fluid Chromatography. Talanta. 2015, 144, 1239–1244. DOI: 10.1016/j.talanta.2015.08.011.
   PubMed Web of Science ®Google Scholar
• Zhang, H. F.; Shi, Y. P. Temperature-Assisted Ionic Liquid Dispersive Liquid-Liquid Microextraction Combined with High Performance Liquid Chromatography for the Determination of Anthraquinones in Radix et Rhizoma Rhei Samples. Talanta. 2010, 82, 1010–1016. DOI: 10.1016/j.talanta.2010.06.008.
   PubMed Web of Science ®Google Scholar
• Shi, Z.; Zhu, X.; Cheng, Q.; Zhang, H. Micellar Extraction and Preconcentration of Anthraquinone Derivatives from Rhubarb Prior to Their HPLC-DAD Determination. J. Liq. Chromatogr. Relat. Technol. 2007, 30, 255–271. DOI: 10.1080/10826070601064474.
   Web of Science ®Google Scholar
• Zhang, L. S.; Hu, S.; Chen, X.; Bai, X. H.; Li, Q. S. A New Ionic Liquid-Water-Organic Solvent Three Phase Microextraction for Simultaneous Preconcentration Flavonoids and Anthraquinones from Traditional Chinese Prescription. J. Pharm. Biomed. Anal. 2013, 86, 36–39. DOI: 10.1016/j.jpba.2013.07.007.
   PubMed Web of Science ®Google Scholar
• Roberto, M.; Laura, M.; Anna, F.; Salvatore, F.; Maria, A. R. Determination of Aloe Emodin in Aloe vera Extracts and Commercial Formulations by HPLC with Tandem UV Absorption and Fluorescence Detection. Food Chem. 2011, 126, 387–393. DOI: 10.1016/j.foodchem.2010.10.112.
   Web of Science ®Google Scholar
• Tian, J.; Chen, X.; Bai, X. Comparison of Dispersive Liquid-Liquid Microextraction Based on Organic Solvent and Ionic Liquid Combined with High Performance Liquid Chromatography for the Analysis of Emodin and Its Metabolites in Urine Samples. J. Sep. Sci. 2012, 35, 145–152. DOI: 10.1002/jssc.201100729.
   PubMed Web of Science ®Google Scholar
• Boryana, T.; Dorina, T.; Vassya, B. Different Extraction Methods of Biologically Active Components from Propolis: A Preliminary Study. Chem. Cent. J. 2007, 1, 1–4. DOI: 10.1186/1752-153X-1-13.
   PubMedGoogle Scholar
• Maria Dolores, L. C.; Feliciano Priego, P. C. Soxhlet Extraction: Past and Present Panacea. J. Chromatogr. A 2010, 1217, 2383–2389. DOI: 10.1016/j.chroma.2009.11.027.
   PubMed Web of Science ®Google Scholar
• Romanik, G.; Gilgenast, E.; Przyjazny, A.; Kamiński, M. Techniques of Preparing Plant Material for Chromatographic Separation and Analysis. J. Biochem. Biophys. Methods. 2007, 70, 253–261. DOI: 10.1016/j.jbbm.2006.09.012.
   PubMedGoogle Scholar
• Jiao, Y.; Zuo, Y. Ultrasonic Extraction and HPLC Determination of Anthraquinones, Aloe-Emodine, Emodine, Rheine, Chrysophanol and Physcione, in Roots of Polygoni multiflori. Phytochem. Anal. 2009, 20, 272–278. DOI: 10.1002/pca.1124.
   PubMed Web of Science ®Google Scholar
• Xiao, Y.; Wang, Y.; Gao, S.; Zhang, R.; Ren, R.; Li, N.; Zhang, H. Determination of the Active Constituents in Arnebia euchroma (Royle) Johnst. by Ionic Liquid-Based Ultrasonic-Assisted Extraction High-Performance Liquid Chromatography. J. Chromatogr. A 2011, 879, 1833–1838. DOI: 10.1016/j.jchromb.2011.05.009.
   Web of Science ®Google Scholar
• Iwalewa, E. O.; Iwalewa, O. J.; Adeboye, J. O. Analgesic, Antipyretic, anti-Inflammatory Effects of Methanol, Chloroform and Ether Extracts of Vernonia Cinerea Less Leaf. J. Ethnopharmacol. 2003, 86, 229–234. DOI: 10.1016/S0378-8741(03)00081-3.
   PubMed Web of Science ®Google Scholar
• Verma, C.; Ebenso, E. E.; Quraishi, M. A. Ionic Liquids as Green and Sustainable Corrosion Inhibitors for Metals and Alloys: An Overview. J. Mol. Liq. 2017, 233, 403–414. DOI: 10.1016/j.molliq.2017.02.111.
   Web of Science ®Google Scholar
• Colin, F. P.; Salwa, K. P. Extraction of Organic Compounds with Room Temperature Ionic Liquids. J. Chromatogr. A. 2010, 1217, 2268–2286. DOI: 10.1016/j.chroma.2009.09.011.
   PubMed Web of Science ®Google Scholar
• Lou, Z.; Wang, H.; Zhu, S.; Chen, S.; Zhang, M.; Wang, Z. Ionic Liquids Based Simultaneous Ultrasonic and Microwave Assisted Extraction of Phenolic Compounds from Burdock Leaves. Anal. Chim. Acta. 2012, 716, 28–33. DOI: 10.1016/j.aca.2011.03.012.
   PubMed Web of Science ®Google Scholar
• David, A.; Saïd, S.; Gérard, B. Beyond Conventional Supercapacitors: Hierarchically Conducting Polymer-Coated 3D Nanostructures for Integrated on-Chip Micro-Supercapacitors Employing Ionic Liquid Electrolytes. Synth. Met. 2019, 247, 131–143. DOI: 10.1016/j.synthmet.2018.11.022.
   Web of Science ®Google Scholar
• Dinh, T. V.; Saravana, P. S.; Woo, H. C.; Chun, B. S. Ionic Liquid-Assisted Subcritical Water Enhances the Extraction of Phenolics from Brown Seaweed and Its Antioxidant Activity. Sep. Purif. Technol. 2018, 196, 287–299. DOI: 10.1016/j.seppur.2017.06.009.
   Web of Science ®Google Scholar
• Zhang, Y.; Liu, Z.; Li, Y.; Chi, R. Optimization of Ionic Liquid-Based Microwave-Assisted Extraction of Isoflavones from Radix puerariae by Response Surface Methodology. Sep. Purif. Technol. 2014, 129, 71–79. DOI: 10.1016/j.seppur.2014.03.022.
   Web of Science ®Google Scholar
• Ma, C.; Liu, T.; Yang, L.; Zu, Y.; Wang, S.; Zhang, R. Study on Ionic Liquid-Based Ultrasonic-Assisted Extraction of Biphenyl Cyclooctene Lignans from the Fruit of Schisandra chinensis Baill. Anal. Chim. Acta. 2011, 689, 110–116. DOI: 10.1016/j.aca.2011.01.012.
   PubMed Web of Science ®Google Scholar
• Wu, H.; Chen, M.; Fan, Y.; Elsebaei, F.; Zhu, Y. Determination of Rutin and Quercetin in Chinese Herbal Medicine by Ionic Liquid-Based Pressurized Liquid Extraction-Liquid Chromatography-Chemiluminescence Detection. Talanta. 2012, 88, 222–229. DOI: 10.1016/j.talanta.2011.10.036.
   PubMed Web of Science ®Google Scholar
• Federica, P.; Francesco, P. P.; Davide, B.; Stefania, B. An Efficient Chemical Analysis of Phenolic Acids and Flavonoids in Raw Propolis by Microwave-Assisted Extraction Combined with High-Performance Liquid Chromatography Using the Fused-Core Technology. J. Pharm. Biomed. Anal. 2013, 81–82, 126–132. DOI: 10.1016/j.jpba.2013.04.003.
   PubMed Web of Science ®Google Scholar
• Gu, H.; Chen, F.; Zhang, Q.; Zang, J. Application of Ionic Liquids in Vacuum Microwave-Assisted Extraction Followed by Macroporous Resin Isolation of Three Flavonoids Rutin, Hyperoside and Hesperidin from Sorbus Tianschanica Leaves. J. Chromatogr. B. 2016, 1014, 45–55. DOI: 10.1016/j.jchromb.2016.01.045.
   PubMed Web of Science ®Google Scholar
• Wei, W.; Fu, Y.; Zu, Y.; Wang, W.; Luo, M.; Zhao, C.; Li, C.; Zhang, L.; Wei, Z. Ionic Liquid-Based Microwave-Assisted Extraction for the Determination of Flavonoid Glycosides in Pigeon Pea Leaves by High-Performance Liquid Chromatography-Diode Array Detector with Pentafluorophenyl Column. J. Sep. Sci. 2012, 35, 2875–2883. DOI: 10.1002/jssc.201200473.
   PubMed Web of Science ®Google Scholar
• Zhang, Q.; Zhao, S.; Chen, J.; Zhang, L. Application of Ionic Liquid-Based Microwave-Assisted Extraction of Flavonoids from Scutellaria baicalensis Georgi. J. Chromatogr. B. 2015, 1002, 411–417. DOI: 10.1016/j.jchromb.2015.08.021.
   PubMed Web of Science ®Google Scholar
• Xu, W.; Chu, K.; Li, H.; Zhang, Y.; Zheng, H.; Chen, R.; Chen, L. Ionic Liquid-Based Microwave-Assisted Extraction of Flavonoids from Bauhinia championii (Benth.) Benth. Molecules. 2012, 17, 14323–14335. DOI: 10.3390/molecules171214323.
   PubMed Web of Science ®Google Scholar
• Gao, S.; You, J.; Wang, Y.; Zhang, R.; Zhang, R.; Zhang, H. On-Line Continuous Sampling Dynamic Microwave-Assisted Extraction Coupled with High Performance Liquid Chromatographic Separation for the Determination of Lignans in Wuweizi and Naphthoquinones in Zicao. J. Chromatogr. B. 2012, 887, 35–42. DOI: 10.1016/j.jchromb.2012.01.005.
   PubMed Web of Science ®Google Scholar
• Lair, A.; Ferronato, C.; Chovelon, J. M.; Herrmann, J. M. Naphthalene Degradation in Water by Heterogeneous Photocatalysis: An Investigation of the Influence of Inorganic Anions. J. Photochem. Photobiol. A 2008, 193, 193–203. DOI: 10.1016/j.jphotochem.2007.06.025.
   Web of Science ®Google Scholar
• Lu, C.; Wang, H.; Lv, W.; Ma, C.; Xu, P.; Zhu, J.; Xie, J.; Liu, B.; Zhou, Q. Ionic Liquid-Based Ultrasonic/Microwave-Assisted Extraction Combined with UPLC for the Determination of Anthraquinones in Rhubarb. Chromatographia. 2011, 74, 139–144. DOI: 10.1007/s10337-011-2023-5.
   Web of Science ®Google Scholar
• Michael, E.; Robert, L.; John, S. Thermochemistry of Ionic Liquid Heat-Transfer Fluids. Thermochim. Acta. 2005, 425, 181–188. DOI: 10.1016/j.tca.2004.11.013.
   Web of Science ®Google Scholar
• Choi, J.; Kim, J. K.; Kim, J. H.; Kweon, D. K.; Lee, J. W. Degradation of Hyaluronic Acid Powder by Electron Beam Irradiation, Gamma Ray Irradiation, Microwave Irradiation and Thermal Treatment: A Comparative Study. Carbohydr. Polym. 2010, 79, 1080–1085. DOI: 10.1016/j.carbpol.2009.10.041.
   Web of Science ®Google Scholar
• Li, M.; Chen, X.; Hu, S.; Wang, R.; Peng, X.; Bai, X. Determination of Blood Concentrations of Main Active Compounds in Zi-Cao-Cheng-Qi Decoction and Their Total Plasma Protein Binding Rates Based on Hollow Fiber Liquid Phase Microextraction Coupled with High Performance Liquid Chromatography. J. Chromatogr. B 2018, 1027, 355–361. DOI: 10.1016/j.jchromb.2017.11.046.
   Web of Science ®Google Scholar
• Woo, Y.-A.; Kim, H.-J.; Cho, J.; Chung, H. Discrimination of Herbal Medicines according to Geographical Origin with near Infrared Reflectance Spectroscopy and Pattern Recognition Techniques. J. Pharm. Biomed. Anal. 1999, 21, 407–413. DOI: 10.1016/S0731-7085(99)00145-4.
   PubMed Web of Science ®Google Scholar