Preparative Separation of Phenylethanoid and Secoiridoid Glycosides from Ligustri Lucidi Fructus by High-Speed Counter-Current Chromatography Coupled with Ultrahigh Pressure Extraction.

Fengwei He,Li Chen,Jia Li,Xiao Wang,Jinqian Yu,Qian Liu

doi:10.3390/molecules23123353

Abstract

Three phenylethanoid glycosides, echinacoside (1), salidroside (3), and acteoside (6), and three secoiridoid glycosides, isonuezhenide (2), nuezhenoside G13 (4), and specnuezhenide (5), have been extracted and separated by a combined method of ultrahigh pressure extraction (UPE) and high-speed counter-current chromatography (HSCCC) from Ligustri Lucidi Fructus. For the UPE, the optimal extraction was developed with conditions including solvent of 90% ethanol, sample to solvent ratio of 1:20 g/mL, pressure of 200 MPa, and time of 2 min, which rendered the yields of compounds 4 and 5 were 15.0 and 78.0 mg/g, respectively. For the HSCCC separation, the strategy of changing flow rates between 1.0 and 2.0 mL/min allowed the acquisition for 2.7 mg of compound 1, 4.5 mg of compound 2, 6.8 mg of compound 3, 5.9 mg of compound 4, 11.2 mg of compound 5, and 2.2 mg of compound 6 in one separation run under the solvent system of ethyl acetate:n-butanol:water (2:1:3, v/v) from 200 mg of the UPE extract. The structures of these phenylethanoid and secoiridoid glycosides were elucidated by extensive spectroscopic methods.

Highlights

Ligustrum lucidum Ait., an evergreen shrub from the family of Oleaceae, is mainly distributed in the southern regions of China, such as Jiangsu, Guangxi, Yunnan and so on
The ultrahigh pressure extraction (UPE) extraction methodology was developed after measuring the individual effects of four extraction methodology developed The aftereffects measuring the individual effects of four major parameters using single-factorwas experiments
These experimental results indicated that UPE extraction needed shorter time and less solvent, produced higher yields when compared with conventional extraction methods

Summary

Introduction

Ligustrum lucidum Ait., an evergreen shrub from the family of Oleaceae, is mainly distributed in the southern regions of China, such as Jiangsu, Guangxi, Yunnan and so on. The dried mature fruits of L. lucidum, documented in the Chinese Pharmacopoeia as “Ligustri Lucidi Fructus”, have long been used in traditional Chinese medicine to invigorate muscles and bones, and tonify kidney and liver [1]. Ligustri Lucidi Fructus was recorded as a tonic and dietary supplement possessing the homology of medicine and food [2,3]. A literature survey indicated that phenylethanoid glycosides in Ligustri Lucidi Fructus were mainly composed of Molecules 2018, 23, 3353; doi:10.3390/molecules23123353 www.mdpi.com/journal/molecules. Molecules 2018, 23, x FOR PEER REVIEW salidroside, echinacoside, acteoside, and cimidahurinine, salidroside, echinacoside, acteoside, and cimidahurinine,asaswell wellasassecoiridoid secoiridoidglycosides glycosidesmainly mainly composed of of specnuezhenide, isonuezhenide, and nuezhenoside composed specnuezhenide, isonuezhenide, and nuezhenosideG13 G13[7]. LucidiFructus, Fructus,with withthe thelatter latterused used as the quality control marker in the Chinese. The extraction and as the quality control marker in the Chinese Pharmacopoeia 2015 [10]. The extraction separation of these compounds by some conventional techniques, such asasultrasonic and separation of polar these polar compounds by some conventional techniques, such ultrasonicand and heating extraction and column chromatography separation, often leads to high consumption of heating extraction and column chromatography separation, often leads to high consumption of solvent, solvent, highconsumption, time consumption, and irreversible adsorption of the polar compounds high time and irreversible adsorption of the polar compounds [11,12]. [11,12]

Methods

Results

Conclusion