Preparative separation of structural isomeric pentacyclic triterpene oleanolic acid and ursolic acid from natural products by pH-zone-refining countercurrent chromatography

Abstract

pH-zone-refining countercurrent chromatography was investigated in preparative separation of oleanolic acid and ursolic acid from three different natural products, Aralia chinensis, apple peels and Eriobotrya japonica Thunb.

Ursolic Acid and Oleanolic Acid Dissolved in Methanol/Acetone + Water Blends: Thermodynamic Solubility, Intermolecular Interactions, and Solvation Behavior

“…Oleanolic acid (OA, C 30 H 48 O 3 , Figure a) and ursolic acid (UA, C 30 H 48 O 3 , Figure b) are two pentacyclic triterpenic acids that have attracted considerable attention owing to their similar therapeutic potential and biological activities, including anti-inflammatory activities, antidiabetic properties, and anticancer effects . However, there are still discrepancies between the two isomers regarding their bioavailability, biological characteristics, and toxicity. , Due to frequent coexistence in the same sources, − their separation is of tremendous application value for decreasing the adverse effects on the human body and increasing the efficacy. OA and UA are typically extracted using different solvents and should be purified from extracts .…”

Solubilities of Oleanolic Acid and Ursolic Acid in Different Organic Solvents and 2-Propanol + Water Binary Solvent Mixtures at Different Temperatures: Experimental Measurement and Modeling

“…Oleanolic acid (OA, C 30 H 48 O 3 , molar mass 456.70) and ursolic acid (UA, C 30 H 48 O 3 , molar mass 456.70), two pentacyclic triterpenic acids, display many similar biological activities and therapeutic potential, such as antidiabetic properties, anti-inflammatory activities, anticancer effects, and the fighting metabolic syndrome, because they are isomers and have very similar chemical structure as shown in Figure . However, some differences in the biological properties, bioavailability, and toxicity still exist between the two isomers. , In order to increase the efficacy and reduce the side effects on the human body, their separation is of great application value because they often coexist in the same natural sources. − Crystallization separation is a powerful tool for separating the isomers based on the solubility difference between each component in different solvents or at different temperatures. Therefore, the knowledge of the solubilities of OA and UA in different solvents is the key issue.…”