Extraction and purification of cis/trans asarone from Acorus tatarinowii Schott: Accelerated solvent extraction and silver ion coordination high-speed counter-current chromatography. 2021

Heng Zhu, and Iftikhar Ali, and Hidayat Hussain, and Manzoor Hussain, and Xing-Bao Wang, and Xiangyun Song, and Ge Luo, and Zhenfang Zhang, and Zhigang Wang, and Daijie Wang
School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China.

Acorus tatarinowii Schott is a traditional Chinese medicine used to treat memory and cognitive dysfunction. Because of their efficacy and lower toxic effects, research on α- and β-asarone, the phytoconstituents, has attracted attention owing to their remarkable pharmacological activities. Silver ion coordination complexation high-speed counter-current chromatography was used to separate these isomers from A. tatarinowii extract, coupled with accelerated solvent extraction. Accelerated solvent extraction parameters were investigated with single-factor and orthogonal testing. A two-phase solvent system composed of n-hexane-ethyl acetate-ethanol-water (2:1:2:1, v/v) with 0.50 mol/L silver ions was selected for separation. From 2.0 g crude extract, 1.4 g of β-asarone and 0.09 g of α-asarone were obtained with purities over 98% by sequential sample loading in 20 h. The isolated compounds were identified by electrospray ionization mass spectrometry, 1H and 13C NMR. Silver ions significantly increased the separation factor and retention of the stationary phase. The chromatographic behavior indicated that cis-configuration was more strongly complexed with the silver ion. This was further demonstrated with the help of computational analysis. In conclusion, the established method could be employed to separate other cis-trans or E/Z isomers that form coordination complexes.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D010936 Plant Extracts Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard. Herbal Medicines,Plant Extract,Extract, Plant,Extracts, Plant,Medicines, Herbal
D003377 Countercurrent Distribution A method of separation of two or more substances by repeated distribution between two immiscible liquid phases that move past each other in opposite directions. It is a form of liquid-liquid chromatography. (Stedman, 25th ed) Chromatography, Countercurrent,Countercurrent Chromatography,Distribution, Countercurrent
D000077318 Density Functional Theory A theory that is used to describe the electronic ground state properties of matter. It forms the basis of methods in obtaining a solution to the Schrodinger equation for a many-body system, and to investigate the structural, magnetic, and electronic properties of molecules and materials. Density Functional Calculations,Density Functional Computations,Density Functional Theory Calculations,Density Functional Theory Computations,Td-DFT,Td-DFT Calculations,Td-DFT Computations,Time-Dependent Density Functional Theory,Time-Dependent Density Functional Theory Calculations,Time-Dependent Density Functional Theory Computations,DFT Calculations,KS-DFT,Kohn-Sham Density Functional Theory,Calculation, Density Functional,Calculation, Td-DFT,Computation, Density Functional,Computation, Td-DFT,DFT Calculation,Density Functional Calculation,Density Functional Computation,Density Functional Theories,Functional Calculation, Density,Functional Calculations, Density,Functional Computation, Density,Kohn Sham Density Functional Theory,Td DFT Calculations,Td DFT Computations,Td-DFT Calculation,Td-DFT Computation,Time Dependent Density Functional Theory,Time Dependent Density Functional Theory Calculations,Time Dependent Density Functional Theory Computations
D000081248 Allylbenzene Derivatives Compounds that include a single 1-phenyl-2-propene moiety in their structure. 1-Methyl-1-phenylethylene Derivatives,1-Phenyl-2-propene Derivatives,2-Propenylbenzene Derivatives,3-Ethenylmethylbenzene Derivatives,Allylbenzenes,Vinyl Toluene Derivatives
D000840 Anisoles A group of compounds that are derivatives of methoxybenzene and contain the general formula R-C7H7O. Methylphenyl Ethers,Ethers, Methylphenyl
D012834 Silver An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.
D059625 Liquid-Liquid Extraction The removal of a soluble component from a liquid mixture by contact with a second liquid, immiscible with the carrier liquid, in which the component is preferentially soluble. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Liquid Phase Extraction,Extraction, Liquid Phase,Extraction, Liquid-Liquid,Extractions, Liquid Phase,Extractions, Liquid-Liquid,Liquid Liquid Extraction,Liquid Phase Extractions,Liquid-Liquid Extractions,Phase Extraction, Liquid,Phase Extractions, Liquid
D021241 Spectrometry, Mass, Electrospray Ionization A mass spectrometry technique used for analysis of nonvolatile compounds such as proteins and macromolecules. The technique involves preparing electrically charged droplets from analyte molecules dissolved in solvent. The electrically charged droplets enter a vacuum chamber where the solvent is evaporated. Evaporation of solvent reduces the droplet size, thereby increasing the coulombic repulsion within the droplet. As the charged droplets get smaller, the excess charge within them causes them to disintegrate and release analyte molecules. The volatilized analyte molecules are then analyzed by mass spectrometry. ESI Mass Spectrometry,Electrospray Ionization Mass Spectrometry,Mass Spectrometry, ESI,Spectrometry, ESI Mass

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