Separation of betulin and its derivatives by high-performance liquid chromatography and their determination in extracts of some plants and chaga mushroom

References

• Tolstikova, T. G.; Sorokina, I. V.; Tolstikov, G. A.; Tolstikov, A. G.; Flekhter, O. B. Biological Activity and Pharmacological Prospects of Lupane Terpenoids: I. Natural Lupane Derivatives. Russ. J. Bioorg. Chem. 2006, 32, 37–49. DOI: 10.1134/S1068162006010031.
   Web of Science ®Google Scholar
• Tolstikov, G. A.; Flekhter, O. B.; Shultz, E. E.; Baltina, L. A.; Tolstikov, A. G. Betulin and Its Derivatives. Chemistry and Biological Activity. Chem. Sustainable Dev. 2005, 13, 1–29. https://sibran.ru/upload/iblock/4d9/betulin_and_its_derivatives_chemistry_and_biological_activity.pdf
   Web of Science ®Google Scholar
• Li, Y.-K.; Fan, P.; Xu, Y.-R.; Huang, Y.; Hu, Q.-F. Study on Determination of Triterpenoids in Chaenomeles by High Performance Liquid Chromatography and Sample Preparation with Matrix Solid Phase Dispersion. J. Chin. Chem. Soc. 2008, 55, 1332–1337. DOI: 10.1002/jccs.200800200.
   Web of Science ®Google Scholar
• Farzaneh, V.; Gominho, J.; Pereira, H.; Carvalho, I. S. Screening of the Antioxidant and Enzyme Inhibition Potentials of Portuguese Pimpinella Anisum L. Seeds by GC-MS. Food Anal. Methods 2018, 11, 2645–2656. DOI: 10.1007/s12161-018-1250-x.
   Web of Science ®Google Scholar
• Gobo, L. A.; Viana, C.; Lameira, O. A.; de Carvalho, L. M. A Liquid Chromatography-Atmospheric Pressure Photoionization Tandem Mass Spectrometric (LC-APPI-MS/MS) Method for the Determination of Triterpenoids in Medicinal Plant Extracts. J. Mass Spectrom. 2016, 51, 558–565. DOI: 10.1002/jms.3783.
   PubMed Web of Science ®Google Scholar
• Wu, H.; Li, G.; Liu, S.; Liu, D.; Chen, G.; Hu, N.; Suo, Y.; You, J. Simultaneous Determination of Six Triterpenic Acids in Some Chinese Medicinal Herbs Using Ultrasound-Assisted Dispersive Liquid–Liquid Microextraction and High-Performance Liquid Chromatography with Fluorescence Detection. J. Pharm. Biomed. Anal. 2015, 107, 98–107. DOI: 10.1016/j.jpba.2014.10.031.
   PubMed Web of Science ®Google Scholar
• Yin, Z.-P.; Xiong, Q.-Q.; Shang-Guan, X.-C.; Chen, J.-G. Chemical Fingerprint and Determination of Triterpenoids in Cultured Cyclocarya Paliurus Cells by High-Performance Liquid Chromatography. Anal. Lett. 2017, 50, 748–760. DOI: 10.1080/00032719.2016.1199026.
   Web of Science ®Google Scholar
• Gao, Q.-H.; Wu, C.-S.; Wang, M. The Jujube (Ziziphus jujuba Mill.) Fruit: A Review of Current Knowledge of Fruit Composition and Health Benefits. J. Agric. Food Chem. 2013, 61, 3351–3363. DOI: 10.1021/jf4007032.
   PubMed Web of Science ®Google Scholar
• Guo, S.; Duan, J.-A.; Tang, Y.; Su, S.; Shang, E.; Ni, S.; Qian, D. High-Performance Liquid Chromatography-Two Wavelength Detection of Triterpenoid Acids from the Fruits of Ziziphus jujuba Containing Various Cultivars in Different Regions and Classification Using Chemometric Analysis. J. Pharm. Biomed. Anal. 2009, 49, 1296–1302. DOI: 10.1016/j.jpba.2009.03.006.
   PubMed Web of Science ®Google Scholar
• Guo, S.; Duan, J.-A.; Tang, Y.-P.; Yang, N.-Y.; Qian, D.-W.; Su, S.-L.; Shang, E.-X. Characterization of Triterpenic Acids in Fruits of Ziziphus Species by HPLC-ELSD-MS. J. Agric. Food Chem. 2010, 58, 6285–6289. DOI: 10.1021/jf101022p.
   PubMed Web of Science ®Google Scholar
• Guo, S.; Duan, J.-A.; Qian, D.; Tang, Y.; Wu, D.; Su, S.; Wang, H.; Zhao, Y. Content Variations of Triterpenic Acid, Nucleoside, Nucleobase, and Sugar in Jujube (Ziziphus jujuba) Fruit During Ripening. Food Chem. 2015, 167, 468–474. DOI: 10.1016/j.foodchem.2014.07.013.
   PubMed Web of Science ®Google Scholar
• Guo, S.; Duan, J.-A.; Zhang, Y.; Qian, D.; Tang, Y.; Zhu, Z.; Wang, H. Contents Changes of Triterpenic Acids, Nucleosides, Nucleobases, and Saccharides in Jujube (Ziziphus Jujuba) Fruit During the Drying and Steaming Process. Molecules 2015, 20, 22329–22340. DOI: 10.3390/molecules201219852.
   PubMed Web of Science ®Google Scholar
• Kawabata, K.; Kitamura, K.; Irie, K.; Naruse, S.; Matsuura, T.; Uemae, T.; Taira, S.; Ohigashi, H.; Murakami, S.; Takahashi, M.; et al. Triterpenoids Isolated from Ziziphus jujuba Enhance Glucose Uptake Activity in Skeletal Muscle Cells. J. Nutr. Sci. Vitaminol. (Tokyo) 2017, 63, 193–199. DOI: 10.3177/jnsv.63.193.
   PubMed Web of Science ®Google Scholar
• Li, Y.; Guo, S.; Hua, T.; Wang, Y.; Wei, D.; Zhao, M.; Su, S.; Duan, J.-A. Comparative Pharmacokinetics of Triterpenic Acids in Normal and Immunosuppressed Rats after Oral Administration of Jujubae fructus Extract by UPLC-MS/MS. J. Chromatogr. B 2018, 1077-1078, 13–21. DOI: 10.1016/j.jchromb.2018.01.026.
   PubMed Web of Science ®Google Scholar
• Gao, Y.; Xu, H.; Lu, Z.; Xu, Z. Quantitative Determination of Steroids in the Fruiting Bodies and Submerged-Cultured Mycelia of Inonotus obliquus. Chin. J. Chromatogr. 2009, 27, 745–749.
   Google Scholar
• Géry, A.; Dubreule, C.; André, V.; Rioult, J.-P.; Bouchart, V.; Heutte, N.; de Pécoulas, P. E.; Krivomaz, T.; Garon, D. Chaga (Inonotus obliquus), a Future Potential Medicinal Fungus in Oncology? A Chemical Study and a Comparison of the Cytotoxicity against Human Lung Adenocarcinoma Cells (A549) and Human Bronchial Epithelial Cells (BEAS-2B). Integr. Cancer Ther. 2018, 17, 832–843. DOI: 10.1177/1534735418757912.
   PubMed Web of Science ®Google Scholar
• Zhao, G.; Yan, W.; Cao, D. Simultaneous Determination of Betulin and Betulinic Acid in White Birch Bark Using RP-HPLC. J. Pharm. Biomed. Anal. 2007, 43, 959–962. DOI: 10.1016/j.jpba.2006.09.026.
   PubMed Web of Science ®Google Scholar
• Felföldi-Gáva, A.; Simándi, B.; Plánder, Sz.; Szarka, Sz.; Szőke, É.; Kéry, Á. Betulaceae and Platanaceae Plants as Alternative Sources of Selected Lupane-Type Triterpenes. Their Composition Profile and Betulin Content. Acta Chromatogr. 2009, 21, 671–681. DOI: 10.1556/AChrom.21.2009.4.12.
   Web of Science ®Google Scholar
• Kosyakov, D. S.; Ul’yanovskii, N. V.; Falev, D. I. Determination of Triterpenoids from Birch Bark by Liquid Chromatography-Tandem Mass Spectrometry. J. Anal. Chem. 2014, 69, 1264–1269. DOI: 10.1134/S1061934814130061.
   Web of Science ®Google Scholar
• Popova, O. V.; Sursyakova, V. V.; Burmakina, G. V.; Levdansky, V. A.; Rubaylo, A. I. Determination of Stability Constants of Inclusion Complexes of Betulin Derivatives with β-Cyclodextrin by Capillary Electrophoresis. Dokl Chem. 2015, 461, 67–69. DOI: 10.1134/S0012500815030039.
   Web of Science ®Google Scholar
• Sursyakova, V. V.; Maksimov, N. G.; Levdansky, V. A.; Rubaylo, A. I. Combination of Phase-Solubility Method and Capillary Zone Electrophoresis to Determine Binding Constants of Cyclodextrins with Practically Water-Insoluble Compounds. J. Pharm. Biomed. Anal. 2018, 160, 12–18. DOI: 10.1016/j.jpba.2018.07.038.
   PubMed Web of Science ®Google Scholar
• Rhourri-Frih, B.; Chaimbault, P.; Dequeral, D.; André, P.; Lafosse, M. Investigation of Porous Graphitic Carbon for Triterpenoids and Natural Resinous Materials Analysis by High Performance Liquid Chromatography Hyphenated to Mass Spectrometry. J. Chromatogr. A 2012, 1240, 140–146. DOI: 10.1016/j.chroma.2012.03.094.
   PubMed Web of Science ®Google Scholar
• Sowa, I.; Wójciak-Kosior, M.; Rokicka, K.; Kocjan, R.; Szymczak, G. Application of Solid Phase Extraction with the Use of Silica Modified with Polyaniline Film for Pretreatment of Samples from Plant Material before HPLC Determination of Triterpenic Acids. Talanta 2014, 122, 51–57. DOI: 10.1016/j.talanta.2014.01.039.
   PubMed Web of Science ®Google Scholar
• Zhang, M.; Zhang, Y.; Xie, J. Simultaneous Determination of Jujuboside A, B and Betulinic Acid in Semen Ziziphi spinosae by High Performance Liquid Chromatography-Evaporative Light Scattering Detection. J. Pharm. Biomed. Anal. 2008, 48, 1467–1470. DOI: 10.1016/j.jpba.2008.09.022.
   PubMed Web of Science ®Google Scholar
• Lavoie, J.-M.; Stevanovic, T. Selective Ultrasound-Assisted Extractions of Lipophilic Constituents from Betula Alleghaniensis and B. papyrifera Wood at Low Temperatures. Phytochem. Anal. 2007, 18, 291–299. DOI: 10.1002/pca.981.
   PubMed Web of Science ®Google Scholar
• Hu, Z.; Guo, N.; Wang, Z.; Liu, Y.; Wang, Y.; Ding, W.; Zhang, D.; Wang, Y.; Yan, X. Development and Vlidation of an LC–ESI/MS/MS Method with Precolumn Derivatization for the Determination of Betulin in Rat Plasma. J. Chromatogr. B . 2013, 939, 38–44. DOI: 10.1016/j.jchromb.2013.09.005.
   PubMed Web of Science ®Google Scholar
• Gu, J.; Ding, G.; Chen, N.; Zhang, Z. Development and Validation of a Sensitive LC–MS-MS Assay for the Quantification of Betulonic Acid in Rat Plasma. J. Chromatogr. Sci. 2014, 52, 195–200. DOI: 10.1093/chromsci/bmt010.
   PubMed Web of Science ®Google Scholar
• Snyder, L. R.; Dolan, J. W. High-Performance Gradient Elution. The Practical Application of the Linear-Solvent-Strength Model; Wiley: New York, 2007.
   Google Scholar
• Snyder, L. R.; Dolan, J. W. Optimizing Selectivity During Reversed-Phase High Performance Liquid Chromatography Method Development: Prioritizing Experimental Conditions. J. Chromatogr. A 2013, 1302, 45–54. DOI: 10.1016/j.chroma.2013.05.082.
   PubMed Web of Science ®Google Scholar
• Levdanskii, V. A.; Levdanskii, A. V.; Kuznetsov, B. N. Method for Preparing Betulonic Acid from Betula pendula Birch Bark. Chem. Nat. Compd. 2016, 52, 766–768. DOI: 10.1007/s10600-016-1770-9.
   Web of Science ®Google Scholar