Login Register Cart 0
Generic placeholder image

Current Chromatography

Editor-in-Chief

ISSN (Print): 2213-2406
ISSN (Online): 2213-2414

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

A Quantitative Estimation of the Behaviour of Unsaturated Lipid Molecular Species During Their Argentation Liquid Chromatographic Separation

Author(s): Vasiliy P. Pchelkin*

Volume 9, Issue 1, 2022

Published on: 10 June, 2022

Article ID: e200122200392 Pages: 10

DOI: 10.2174/2213240609666220120113938

Price: $65

Abstract

Background: Analysis of experimental retention data upon several variants of argentation liquid chromatographic separations of different mixtures of the same lipid class into their molecular species was made to estimate new parameters of their π-complexes for every unsaturated fatty acid residue as its silver ion cluster.

Methods: Planar reversed-phase liquid chromatography, both in the presence and absence of silver ions as well as adsorption argentation liquid chromatography was applied for the separation of complex rac-1,2-diacylglycerol samples from three plant sources (cocoa butter, poppy seed, and linseed oils).

Results: Every value of the argentation liquid chromatographic separation selectivity for any lipid molecular species upon both planar and column variants of reversed-phase fractionation of different complex samples from native sources into their molecular components is described by additive relative polarity levels of their fatty acid residues. These levels are always connected with equivalent lipophilicity values for every lipid molecule and its potential chemical variations during all variants of reversed-phase liquid chromatography in the presence of silver ion clusters.

Conclusion: New parameters for several fatty acid residues of major native polyunsaturated lipid samples may be reflected by different coordination numbers of single silver atoms of its triangular pyramidal nanoclusters. Both hydrophobicity and total polarity levels of the coordination complexes of different lipid molecular species upon their adsorption argentation liquid chromatography may also be quantitatively estimated by their fixed methylene unit variations of these molecular species for two centigrade lipid scales.

Keywords: Argentation LC, silver clusters, liquid chromatography, lipids, nanoclusters, unsaturated lipophilic compounds.

[1]
Menta S, Ciogli A, Villani C, Gasparrini F, Pierini M. Recognition mechanism of aromatic derivatives resolved by argentation chromatography: The driving role played by substituent groups. Anal Chim Acta 2018; 1019: 135-41.
[http://dx.doi.org/10.1016/j.aca.2018.02.038] [PMID: 29625679]
[2]
Wang L, Longo WM, Dillon JT, et al. An efficient approach to eliminate steryl ethers and miscellaneous esters/ketones for gas chromatographic analysis of alkenones and alkenoates. J Chromatogr A 2019; 1596: 175-82.
[http://dx.doi.org/10.1016/j.chroma.2019.02.064] [PMID: 30898380]
[3]
Zhang C-W, Wang C-Z, Tao R, Ye J-Z. Separation of polyprenols from Ginkgo biloba leaves by a nano silica-based adsorbent containing silver ions. J Chromatogr A 2019; 1590: 58-64.
[http://dx.doi.org/10.1016/j.chroma.2019.01.047] [PMID: 30712816]
[4]
Lu H, Zhu H, Dong H, Guo L, Ma T, Wang X. Purification of pyrethrins from flowers of Chrysanthemum cineraraeflium by high-speed counter-current chromatography based on coordination reaction with silver nitrate. J Chromatogr A 2020; 1613: 460660.
[http://dx.doi.org/10.1016/j.chroma.2019.460660] [PMID: 31685247]
[5]
Li M, Pham PJ, Pittman CU, Li TY. SBA-15-supported ionic liquid compounds containing silver salts: novel mesoporous π- complexing sorbents for separating polyunsaturated fatty acid methyl esters. Microporous Mesoporous Mater 2009; (1): 436-44.
[http://dx.doi.org/10.1016/j.micromeso.2008.07.017]
[6]
Ganji N, Khan IA, Bothun GD. Surface activity of poly(ethylene glycol)-coated silver nanoparticles in the presence of a lipid monolayer. Langmuir 2018; 34(5): 2039-45.
[http://dx.doi.org/10.1021/acs.langmuir.7b03743] [PMID: 29309159]
[7]
Hua X, Li HW, Long YT. Investigation of silver nanoparticle induced lipids changes on a single cell surface by time-of-flight secondary ion mass spectrometry. Anal Chem 2018; 90(2): 1072-6.
[http://dx.doi.org/10.1021/acs.analchem.7b04591] [PMID: 29260555]
[8]
Fardin-Kia AR. Preparation, isolation and identification of non- conjugated C18:2 fatty acid isomers. Chem Phys Lipids 2016; 201: 50-8.
[http://dx.doi.org/10.1016/j.chemphyslip.2016.10.003] [PMID: 27769894]
[9]
Souza ID, Nan H, Queiroz MEC, Anderson JL. Tunable silver-containing stationary phases for multidimensional gas chromatography. Anal Chem 2019; 91(8): 4969-74.
[http://dx.doi.org/10.1021/acs.analchem.9b00472] [PMID: 30901521]
[10]
Byrdwell WC. Comprehensive dual liquid chromatography with quadruple mass spectrometry (lc1ms2 × lc1ms2 = lc2ms4) for analysis of parinari curatellifolia and other seed oil triacylglycerols. Anal Chem 2017; 89(19): 10537-46.
[http://dx.doi.org/10.1021/acs.analchem.7b02753] [PMID: 28850221]
[11]
Delmonte P, Milani A, Bhangley S. Structural determination and occurrence in ahiflower oil of stearidonic acid trans fatty acids. Lipids 2018; 53(2): 255-66.
[http://dx.doi.org/10.1002/lipd.12009] [PMID: 29537611]
[12]
Zheng Z, Dai Z, Cao Y. Isolation, purification of DPAn-3 from the seal oil ethyl ester. Eur J Lipid Sci Technol 2018; 120(11): 225-31.
[http://dx.doi.org/10.1002/ejlt.201800225]
[13]
Nikolova-Damyanova B, Christie WW, Herslöf BG. High-performance liquid chromatography of fatty acid derivatives in the combined silver ion and reversed-phase mode. J Chromatogr A 1993; 653: 15-23.
[http://dx.doi.org/10.1016/0021-9673(93)80387-N]
[14]
Pchelkin VP, Vereshchagin AG. Separation of polar lipid classes into their molecular species components by planar and column liquid chromatography. Adv Chromatogr 1992; 32: 87-129.
[PMID: 1727331]
[15]
Vahmani P, Rolland DC, Gzyl KE, Dugan MER. Non-conjugated cis/trans 18:2 in beef fat are mainly δ-9 desaturation products of trans-18:1 isomers. Lipids 2016; 51(12): 1427-33.
[http://dx.doi.org/10.1007/s11745-016-4207-0] [PMID: 27853932]
[16]
Dabrowska M, Sokalska K, Gumulka P, Binert-Kusztal Z, Starek M. Quantification of ω-3 fatty acids in dietary supplements and cooking products available on the polish market by thin-layer chromatography-densitometry. JPC-. J Planar Chromatogr Mod TLC 2019; 32(1): 13-24.
[http://dx.doi.org/10.1556/1006.2019.32.1.2]
[17]
Pchelkin VP, Vereshchagin AG. Identification of individual diacylglycerols by adsorption thin-layer chromatography of their coordination complexes. J Chromatogr A 1991; 538(2): 373-83.
[http://dx.doi.org/10.1016/S0021-9673(01)88858-0]
[18]
Pchelkin VP, Vereshchagin AG. Reversed-phase thin-layer chromatography of diacylglycerols in the presence of silver ions. J Chromatogr A 1992; 603: 213-22.
[http://dx.doi.org/10.1016/0021-9673(92)85363-X]
[19]
Golushko J, Mekšs P, Golushko S, Kamenchuk A, Šhiškina I. Computer-aided method for characterization and comparison of reversed-phase HPLC column I. I Theory Latv Ķim Ž 2007; (1): 43-8.
[20]
Golushko J, Mekšs P, Golushko S, Kamenchuk A, Šhiškina I. Computer-aided method for characterization and comparison of reversed-phase HPLC columns II. Column characterization Latv Ķim Ž 2007; (2): 147-54.
[21]
Kim JY, Morisada S, Kawakita H, Ohto K. Comparison of interfacial behavior and silver extraction kinetics with various types calix[4]arene derivatives at heterogeneous liquid-liquid interfaces. J Chromatogr A 2018; 1558: 107-14.
[http://dx.doi.org/10.1016/j.chroma.2018.04.013] [PMID: 29754946]
[22]
Pchelkin VP. Hydrophobicity of coordination complexes of unsaturated lipids in the presence of silver ions. Rus J Phys Chem 2003; 77(9): 1467-72.
[23]
Rafferty JL, Zhang L, Siepmann JI, Schure MR. Retention mechanism in reversed-phase liquid chromatography: a molecular perspective. Anal Chem 2007; 79(17): 6551-8.
[http://dx.doi.org/10.1021/ac0705115] [PMID: 17668929]
[24]
Zhao J, Carr PW. Synthesis and evaluation of an aromatic polymer-coated zirconia for reversed-phase liquid chromatography. Anal Chem 1999; 71(22): 5217-24.
[http://dx.doi.org/10.1021/ac9900477] [PMID: 10575967]
[25]
Yan B, Zhao J, Brown JS, Blackwell J, Carr PW. High-temperature ultrafast liquid chromatography. Anal Chem 2000; 72(6): 1253-62.
[http://dx.doi.org/10.1021/ac991008y] [PMID: 10740867]
[26]
Leasor C, Chen K-H, Closson T, Li Z. Revealing the structural complex of adsorption and assembly of benzoic acids at electrode-electrolyte interfaces using electrochemical scanning tunneling microscopy. J Phys Chem C 2019; 123(22): 13600-9.
[http://dx.doi.org/10.1021/acs.jpcc.9b01705]
[27]
Pchelkin VP. Calculations of the hydrophobicity of lipid molecules by the elution strength of the chromatographic solvent. J Anal Chem 2020; 75(5): 615-21.
[http://dx.doi.org/10.1134/S1061934820050159]
[28]
Wang X, Peng Q, Li Y. Interface-mediated growth of monodispersed nanostructures. Acc Chem Res 2007; 40(8): 635-43.
[http://dx.doi.org/10.1021/ar600007y] [PMID: 17500508]
[29]
Du Z, Ding P, Tai X, Pan Z, Yang H. Facile preparation of Ag-Coated superhydrophobic/superoleophilic mesh for efficient oil/water separation with excellent corrosion resistance. Langmuir 2018; 34(23): 6922-9.
[http://dx.doi.org/10.1021/acs.langmuir.8b00640] [PMID: 29723467]
[30]
Zins EL. Microhydration of a Carbonyl Group. How does the molecular electrostatic potential (MESP) impact the formation of (H2O)n:(R2CO) complexes? J Phys Chem A 2020; 124(9): 1720-34.
[http://dx.doi.org/10.1021/acs.jpca.9b09992] [PMID: 32049521]
[31]
Krzykawska A, Szwed M, Ossowski J, Cyganik P. Odd-even effect in molecular packing of self-assembled monolayers of biphenyl-substituted fatty acid on Ag(111). J Phys Chem C 2018; 122(1): 919-28.
[http://dx.doi.org/10.1021/acs.jpcc.7b10806]
[32]
Arroyave JM, Ambrusi RE, Pronsato ME, Juan A, Pistonesi MF, Centurión ME. Experimental and DFT studies of hybrid silver/cdots nanoparticles. J Phys Chem B 2020; 124(12): 2425-35.
[http://dx.doi.org/10.1021/acs.jpcb.9b10430] [PMID: 32134662]
[33]
Taheri S, Ruiz J-C, Michelmore A, et al. Binding of nanoparticles to aminated plasma polymer surfaces is controlled by primary amine density and solution pH. J Phys Chem C 2018; 122(26): 14986-95.
[http://dx.doi.org/10.1021/acs.jpcc.8b03382]

Rights & Permissions Print Cite
Article Metrics
18
3
© 2024 Bentham Science Publishers | Privacy Policy