Rapid enrichment and separation of two novel minor phenols from Malus hupehensis utilizing liquid–liquid extraction with three‐phase solvent system and high‐speed counter‐current chromatography based on the polarity parameter

Abstract

For a rapid enrichment and separation of minor components from Malus hupehensis, the selection of suitable solvent system is the great challenge for liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography. According to the concept of "like dissolves like," the similarity of the average polarity between solvent system and target compounds was the significant characteristic of liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography separation. The polarity parameter model provides a way to calculate the polarity of unknown compounds. Under the guidance of the polarity, an efficient enrichment and separation approach was established through liquid-liquid extraction and high-speed counter-current chromatography with solvent systems composed of n-hexane-ethyl acetate-acetonitrile-water (5:3:5:7, v/v), n-hexane-ethyl acetate-methanol-water (1:2:1:2, v/v), respectively. Thus, the total content of minor compounds was increased from 2.6% to 17.2%, and two novel compounds (6ťť-O-coumaroyl-2ť-O-glucopyranosylphloretin and 3ťťť-methoxy-6ťť-O-feruloy-2ť-glucopyranosylphloretin) were obtained. The discovery of the new dihydrochalcones expanded the structural diversity of compounds produced by the genus Malus. The experimental results demonstrated that compound polarity can be described by the polarity parameter model and is an important reference for investigating optimum solvent systems for liquid-liquid extraction with a three-phase solvent system and high-speed counter-current chromatography.

A simple and practical solvent system selection strategy for high-speed countercurrent chromatography based on the HPLC polarity parameter model

“…Six benzaldehyde derivatives and two minor avonoids were obtained from Hypsizygus marmoreus and Malus hupehensis, respectively, using HSCCC in combination with the polarity parameter model. 20,21 The present method required only 1 to 2 HPLC analyses, shortened the solvent selection time to no more than 30% of the total time for the multiple HPLC experiments, and was wellsuited for the rapid analysis of multiple samples. However, the ow rates, columns and methanol concentrations of HPLC experiments can inuence the calculation of the compound polarity.…”

Comprehensive separation of a wide variety of compounds from olive leaves by counter‐current chromatography with three‐phase solvent system

“…In view of its advantages, CCC was considered to be an efficacious separation technique for active compounds in natural products and has aroused tremendous interest [6,7]. Traditional CCC solvent system is composed of two immiscible solvents in most cases [8,9], which can be easily prepared [10,11]. Nevertheless, the separation of strongly polar samples is difficult due to the fact that highly polar compounds would reduce the retention rate of the stationary phase [12,13].…”

Large‐scale preparation of two minor polar polyphenols from Phyllanthus emblica Linn. by macroporous resin column chromatography and high‐temperature preparative high‐speed counter‐current chromatography

“…Based on this, HSCCC is most suitable for the preparation of minor compounds. There have been reports on the separation of minor compounds by HSCCC [13][14][15]. However, the preparation scale remained at a level of "mg", which couldn't provide pure compounds in quantities sufficient for further study of their pharmacological, biological, and clinical effects both in vitro and in vivo.…”