Contribution to the TLC separation of ursolic and oleanolic acid mixture
The aim of the study was to develop a rapid, simple, effective and reproducible TLC method for separation of a naturally occurring mixture of ursolic and oleanolic acids. Because of the similarity of chemical structures, in situ derivatisation by iodine was necessary to separate these triterpenic acids. Separation was achieved on silica gel plates. After derivatisation, a chromatographic plate was developed with the mobile phase consisting of light petrol, ethyl acetate and acetone (8.2:1.8:0.1, v/v/v) following visualisation by spraying with sulphuric acid in diethylether (25%, v/v) and heating to 120°C for 5 min. The method used enabled chromatographical differentiation of ursolic and oleanolic acid mixtures in all tested mutual ratios.
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JANICSÁK, G. - VERES, K. - KAKASY, Z. - MÁTHÉ, I.: Study of the oleanolic and urso lic acid contents of some species of the Lamiaceae. Biochem. Syst. Ecol. 34, 2006, p. 392-396.
AMELIO, M. - RIZZO, R. - VARAZINI, F.: Determination of sterols erythroidol uvaol and alkanols in olive oils using combined solid-phase extraction high-performance liquid chromatographic and high-resolution gas chromatographic techniques. J Chromatogr 606, 1992, p. 179-185.
SHIBATA, S.: Chemistry and cancer preventing activities of ginseng saponins and some related triterpenoid compounds. J Korean Med Sci 16, 2001, (Suppl) p. 28-37.
HUGUERT, A. I. - del CARMEN RECIO, M. - MÁNEZ, S. - GINER, R. M. - RÍOS J. L.: Effect of triterpenoids on the inflammation induced by protein kinase C activators, neuronally acting irritants and other agents. Eur. J. Pharmacol. 410, 2000, p. 69-81.
SOMOVA, L. I. - SHODE, F. O. - MIPANDO, M.: Cardiotonic and antidysrhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvaol. Phytomedicine 11, 2004, p.121-129.
TAKADA, K. - NAKANE, T. - MASUDA, K. - ISHII, H.: Ursolic acid and oleanolic acid, members of pentacyclic triterpenoid acids, suppress TNF-α-induced E-selectin expression by cultured umbilical vein endothelial cells. Phytomedicine 17, 2010, p. 1114-1119.
OVESNÁ, Z. - VACHÁLKOVÁ, A. - HORVÁTOVÁ, K. - TÓTHOVÁ, D.: Pentacyclic triterpenoic acids: new chemoprotective compounds. Neoplasma 51, 2004, p. 327-333.
ZACCHIGNA, M. -CATENI, F. - FAUDALE, M. - SOSA, S. - DELLA LOGGIA, R.: Rapid HPLC Analysis for Quantitative Determination of the Two Isomeric Triterpenic Acids, Oleanolic acid and Ursolic acid, in Plantago Major. Sci Pharm. 77, 2009, p. 79-86.
MARTELANC, M. -VOVK, I. - SIMONOVSKA, B.: Separation and identification of some common isomeric plant triterpenoids by thin-layer chromatography and high-performance liquid chromatography. J. Chromatography A. 1216, 2009, p. 6662-6670.
WOJCIAK-KOSIOR, M.: Application of high performance thin-layer chromatography to separation of oleanolic, ursolic and betulinic acids. J Pre-Clin Clin Res 1, 2008, p. 176-178.
YANG, P. - LI, Y. - LIU, X. - JIANG, S.: Determination of free isomeric oleanolic acid and ursolic acid in Pterocephalus hookeri by capillary zone electrophoresis. J. Pharm. Biomed. Anal. 43, 2007, p. 1331-1334.
ISLAMČEVIĆ RAZBORŠEK, M. - BRODNJAK VONČINA, D. - DOLEČEK, V. VONČINA, E.: Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives. Chromatographia 67, 2008, p. 433-440.
WOJCIAK-KOSIOR, M.: Separation and determination of closely related triterpenic acids by high performance thin-layer chromatography after iodine derivatization. J. Pharm. Biomed. Anal. 45, 2007, p. 337-340.