Literature Survey

Chromatography of Cholesterol, Plant Sterols and Sterol Oxides

The subject of sterol analysis is a huge one with a specialized literature. The following references deal mainly with chromatographic methods for cholesterol, plant sterols and sterol oxides (but not steroidal hormones), and they were collected as part of our regular literature reviews for our own research purposes from main-stream lipid or analytical journals. We are sure that we have not covered the subject exhaustively, but we have done our best. We hope that this will be a good starting point at least. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. The survey covers the years 1990 onwards, and will be updated at approximately six-monthly intervals.

  • Abidi,S.L. Chromatographic analysis of plant sterols in foods and vegetable oils. J. Chromatogr. A, 935, 173-201 (2001).
  • Abidi,S.L. Capillary electrochromatography of sterols and related steryl esters derived from vegetable oils. J. Chromatogr. A, 1059, 199-208 (2004).
  • Abidi,S.L., Thiam,S., and Warner,I.M. Elution behavior of unsaponifiable lipids with various capillary electrochromatographic stationary phases. J. Chromatogr. A, 949, 195-207 (2002).
  • Adachi,J., Asano,M., Naito,T., Ueno,Y. and Tatsuno,Y. Chemiluminescent determination of cholesterol hydroperoxides in human erythrocyte membrane. Lipids, 33, 1235-1240 (1998).
  • Adachi,J., Hojo,K., Naito,T. and Tatsuno,Y. Oxysterols found in opacified cornea of fish. Lipids, 31, 1039-1043 (1996).
  • Aitzetmuller,K., Bruhl,L. and Fiebig,H.J. Analysis of sterol content and composition in fats and oils by capillary-gas liquid chromatography using an internal standard. Comments on the German sterol method. Fett-Lipid, 100, 429-435 (1998).
  • Ala-Korpela, M., Korhonen,A., Keisala,J., Horkko,S., Korpi,P., Ingman,L.P., Jokisaari,J., Savolainen,M.J. and Kesaniemi,Y.A. 1H NMR-based absolute quantification of human lipoproteins and their lipid contents directly from plasma. J. Lipid Res., 35, 2292-2304 (1994).
  • Al-Hasani, S.M., Hlavac,J. and Carpenter,M.W. Rapid determination of cholesterol in single and multicomponent prepared foods. J. Ass. Off. Anal. Chem. Int., 76, 902-906 (1993).
  • Alonso, L., Lozada,L., Fontecha,J. and Juarez,M. Determination of cholesterol in milk fat by gas chromatography with direct injection and sample saponification. Chromatographia, 41, 23-28 (1995).
  • Amelio, M., Rizzo,R. and Varazini,F. Determination of sterols, erythrodiol, uvaol and alkanols in olive oils using combined solid-phase extraction, HPLC and high-resolution GC techniques. J. Chromatogr. A, 606, 179-185 (1992).
  • Andrade, I., Santos, L. and Ramos, F. Advances in analytical methods to study cholesterol metabolism: the determination of serum noncholesterol sterols. Biomed. Chromatogr., 27, 1234-1242 (2013).
  • Angulo, A.J., Romera,J.M., Ramirez,M. and Gil,A. Determination of cholesterol oxides in dairy products. Effect of storage conditions. J. Agric. Food Chem., 45, 4318-4323 (1997).
  • Annan, M., Lequesne,P.W. and Vouros,P. Trimethylsilyl group migration in the mass spectra of trimethylsilyl ethers of cholesterol oxidation products. Product ion characterization by linked-scan tandem MS. J. Am. Soc. Mass Spectrom., 4, 327-335 (1993).
  • Ansari, G.A.S. and Smith,L.L. Assay of cholesterol autoxidation. Methods Enzymol., 233, 332-338 (1994).
  • Aparicio, R. and Aparicio-Ruiz,R. Authentication of vegetable oils by chromatographic techniques J. Chromatogr. A, 881, 93-104 (2000).
  • Arborati, M., Benchorba,D., Lesieur,I., Bizot-Espiard,J.G., Guardiola-Lemaitre,B., Chapman,M.J. and Ninio,E. Oxidative degradation of cholesteryl esters in low-density lipoproteins: Analysis by liquid chromatography-light scattering and protection by a new synthetic antioxidant, S20478. Fund. Clin. Pathol., 11, 68-77 (1997).
  • Armanino,C., De Acutis,R. and Festa,M.R. Wheat lipids to discriminate species, varieties, geographical origins and crop years. Anal. Chim. Acta, 454, 315-326 (2002).
  • Artiss,J.D., Feldbruegge,D.H., Kroll,M.H., McQueen,M.J., Pry,T., Zak,B. and Ziegenhorn,J. Measurement of cholesterol concentration. In: 'Lipid and Lipoprotein Risk Factors', pp. 33-49 (edited by N. Rifai and G.R. Warnick, AACC Press) (1991).
  • Asperger,A., Engewald,W. and Fabian,G. Thermally assisted hydrolysis and methylation - a simple and rapid online derivatization method for the gas chromatographic analysis of natural waxes. J. Anal. Appl. Pyrol., 61, 91-109 (2001).
  • Auerbach,B.J., Parks,J.S. and Applebaum-Bowden,D. A rapid and sensitive micro-assay for the enzymatic determination of plasma and lipoprotein cholesterol. J. Lipid Res., 31, 738-742 (1990).
  • Ayciriex, S., Regazzetti, A., Gaudin, M., Prost, E., Dargere, D., Massicot, F., Auzeil, N. and Laprevote, O. Development of a novel method for quantification of sterols and oxysterols by UPLC-ESI-HRMS: application to a neuroinflammation rat model. Anal. Bioanal. Chem.,404, 3049-3059 (2012).
  • Azadmard-Damirchi,S. and Dutta,P.C. A single step solid-phase extraction method for complete separation of sterol oxidation products in food lipids. J. Chromatogr. A, 1216, 36-42 (2009).
  • Azadmard-Damirchi,S. and Dutta,P.C. Novel solid-phase extraction method to separate 4-desmethyl-, 4-monomethyl-, and 4,4'-dimethylsterols in vegetable oils. J. Chromatogr. A, 1108, 183-187 (2006).
  • Azadmard-Damirchi,S. and Dutta.P.C. Rapid separation of methylsterols from vegetable oils by solid-phase extraction. Lipid Technology, 18, 231-234 (2006).
  • Badeau,M., Vihma,V., Mikkola,T.S., Tiitinen,A. and Tikkanen,M.J. Estradiol fatty acid esters in adipose tissue and serum of pregnant and pre- and postmenopausal women. J. Clin. Endocrinol. Metab., 92, 4327-4331 (2007).
  • Baguet,E., Magot,T., Ouguerram,K., Robins,R.J. and Weesie,R.J. Simultaneous quantification of free and esterified cholesterol extracted from plasma by C-13 NMR spectroscopy. Analusis, 27, 876-881 (1999).
  • Ballesteros,E., Gallego,M. and Valcarcel,M. Gas chromatographic determination of cholesterol and tocopherols in edible oils and fats with automatic removal of interfering triglycerides. J. Chromatogr. A, 719, 221-227 (1996).
  • Ballesteros,E., Gallego,M. and Valcarcel,M. Simultaneous determination of sterols in edible oils by use of a continuous separation module coupled to a gas chromatograph. Anal. Chim. Acta, 308, 253-260 (1995).
  • Barnsteiner,A., Esche, R., di Gianvito, A., Chiavaro, E., Schmid, W. and Engel, K.H. Capillary gas chromatographic analysis of complex phytosteryl/-stanyl ester mixtures in enriched skimmed milk-drinking yoghurts. Food Control, 27, 275-283 (2012).
  • Barnsteiner,A., Lubinus,T., Di Gianvito,A., Schmid,W. and Engel,K.H. GC-based analysis of plant stanyl fatty acid esters in enriched foods. J. Agric. Food Chem., 59, 5204-5214 (2011).
  • Beaumier-Gallon,G., Lanfranchi,J,. Vergnes,M.F., Lairon,D., Pastor,J., Pauli,A.M. and Portugal,H. Method for simultaneous measurements of traces of heptadeuterated cholesterol and cholesterol by gas chromatography-mass spectrometry: application in humans. J. Chromatogr. B, 718, 23-32 (1998).
  • Berdeaux,O., Dutta,P., Dobarganes,M. and Sebedio,J.L. Analytical methods for quantification of modified fatty acids and sterols formed as a result of processing. Food Anal. Methods, 2, 30-40 (2009).
  • Bernert,J.T., Akins,J.R., Cooper,G.R., Poulose,A.K., Myers,G.L. and Sampson,E.J. Factors influencing the accuracy of the national reference system total cholesterol reference method. Clin. Chem., 37, 2053-2061 (1991).
  • Biedermann,M., Grob,K. and Mariani,C. Transesterification and on-line LC-GC for determining the sum of free and esterified sterols in edible oils and fats. Fat Sci. Technol., 95, 127-133 (1993).
  • Biedermann,M., Grob,K., Mariani,C. and Schmidt,J.P. Detection of desterolized sunflower oil in olive oil through isomerized delta-7-sterols. Z. Lebensm.-Unters. Forsch., 202, 199-204 (1996).
  • Bittner,A., Marbach,R. and Heise,H.M. Multivariate calibration for protein, cholesterol and triglycerides in human plasma using short-wave near-infrared spectrometry. J. Mol. Struct., 349, 341-344 (1995).
  • Blache,D., Durand,P., Girodon,F., Gesquiere,L. and Loreau,N. Determination of sterols, oxysterols, and fatty acids of phospholipids in cells and lipoproteins: A one-sample method. J. Am. Oil Chem. Soc., 75, 107-113 (1998).
  • Bocos,C., Castro,M., Orozco,E., Contreras,J.A,. and Herrera,E. A rapid and sensitive method for hplc cholesterol determination in bile. Revista Espan. Fisiol., 48, 211-214 (1992).
  • Bodin,K. and Diczfalusy,U. Analysis of cholesterol oxidation products in plasma, tissues and food. Eur. J. Lipid Sci. Technol., 104, 435-439 (2002).
  • Bortolomeazzi,R., Frega,N. and Lercker,G. Rapid determination of free and esterified sterols using prepacked silica columns. Ital. J. Food Sci., 2, 265-268 (1990).
  • Bortolomeazzi,R., Pizzale,L., Vichi,S. and Lercker,G. Analysis of isomers of cholesteryl acetate hydroperoxides by HPLC and GC-ITDMS. Chromatographia, 39, 577-580 (1994).
  • Boselli,E., Caboni,M.F. and Lercker,G. Determination of free cholesterol from dried egg yolk by on-line coupling of supercritical fluid extraction with solid phase extraction. Z. Lebensm.-Unters. Forsch., 205, 356-359 (1997).
  • Boselli,E., Velazco,V., Caboni,M.F. and Lercker,G. Pressurized liquid extraction of lipids for the determination of oxysterols in egg-containing food. J. Chromatogr. A, 917, 239-244 (2001).
  • Bowden,J.A., Albert,C.J., Barnaby,O.S. and Ford,D.A. Analysis of cholesteryl esters and diacylglycerols using lithiated adducts and electrospray ionization-tandem mass spectrometry. Anal. Biochem., 417, 202-210 (2011).
  • Bowden,J.A., Shao,F., Albert,C.J., Lally,J.W., Brown,R.J., Procknow,J.D., Stephenson,A.H. and Ford,D.A. Electrospray ionization tandem mass spectrometry of sodiated adducts of cholesteryl esters. Lipids, 46, 1169-1179 (2011)
  • Breinholder, P., Mosca,L. and Lindner,W. Concept of sequential analysis of free and conjugated phytosterols in different plant matrices. J. Chromatogr. B, 777, 67-82 (2002).
  • Breuer, O., Dzeletovic,S., Lund,E. and Diczfalusy,U. The oxysterols cholest-5-ene-3-beta,4-alpha-diol, cholest-5-ene-3-beta,4 beta-diol and cholestane-3-beta,5-alpha,6-alpha-triol are formed during in vitro oxidation of low-density-lipoprotein, and are present in human atherosclerotic plaques. Biochim. Biophys. Acta, 1302, 145-152 (1996).
  • Brown, R.J., Shao, F., Baldan, A., Albert, C.J. and Ford, D.A. Cholesterol efflux analyses using stable isotopes and mass spectrometry. Anal. Biochem., 433, 56-64 (2013).
  • Brufau ,G., Codony,R., Canela,M.A. and Rafecas,M. Rapid and quantitative determination of total sterols of plant and animal origin in liver samples by gas chromatography. Chromatographia, 64, 559-563 (2006).
  • Caballero, G.M., Gros,E.G., Centurion,O.T. and Galagovsky,L.R. Fast-atom bombardment mass spectrometry of brassinosteroid analogs. J. Am. Soc. Mass Spectrom., 8, 270-274 (1997).
  • Caboni,M.F., Costa,A,. Rodriguez-Estrada,M.T. and Lercker,G. High performance liquid chromatographic separation of cholesterol oxidation products. Chromatographia, 46, 151-155 (1997).
  • Caboni,M.F., Iafelice,G., Pelillo,M. and Marconi,E. Analysis of fatty acid steryl esters in tetraplold and hexaploid wheats: Identification and comparison between chromatographic methods. J. Agric. Food Chem., 53, 7465-7472 (2005).
  • Calvo,M.V., Ramos,L. and Fontecha,J. Determination of cholesterol oxides content in milk products by solid phase extraction and gas chromatography-mass spectrometry. J. Sep. Sci., 26, 927-931 (2003).
  • Cardenas,M.S., Ballesteros,E., Gallego,M. and Valcarcel,M. Automatic gas chromatographic determination of the high-density-lipoprotein cholesterol and total cholesterol in serum. J. Chromatogr. B, 672, 7-16 (1995).
  • Cardenia,V., Rodriguez-Estrada, M.T., Baldacci, E., Savioli, S. and Lercker, G. Analysis of cholesterol oxidation products by Fast gas chromatography/mass spectrometry. J. Sep. Sci., 35, 424-430 (2012).
  • Careri,M., Elviri,L. and Mangia,E.A. Liquid chromatography-UV determination and liquid chromatography-atmospheric pressure chemical ionization mass spectrometric characterization of sitosterol and stigmasterol in soybean oil. J. Chromatogr. A, 935, 249-257 (2001).
  • Careri,M., Ferretti,D., Manini,P. and Musci,M. Evaluation of particle beam high-performance liquid chromatography mass spectrometry for analysis of cholesterol oxides. J. Chromatogr. A, 794, 253-262 (1998).
  • Careri,M., Mangia,A., Musci,M. and Parolari,G. Development of gas chromatographic method for determination of cholesterol oxides in meat products. Chromatographia, 47, 42-48 (1998).
  • Carlson,T., Skorupinska-Tudek,K., Hertel,J., Chojnacki,T., Olsson,J.M. and Swiezewska,E. Single polyprenol and dolichol isolation by semi-preparative high-performance liquid chromatography technique. J. Lipid Res., 41, 1177-1180 (2000).
  • Carr,T.P., Andresen,C.J. and Rudel,L.L. Enzymatic determination of triglyceride, free cholesterol, and total cholesterol in tissue lipid extracts. Clin. Biochem., 26, 39-42 (1993).
  • Carretero,A.S., Carrasco-Pancorbo,A., Cortacero,S., Gori,A., Cerretani,L. and Fernández-Gutiérrez,A. A simplified method for HPLC-MS analysis of sterols in vegetable oil. Eur. J. Lipid Sci. Technol., 110, 1142-1149 (2008).
  • Castro-Perez,J., Previs,S.F., McLaren,D.G., Shah,V., Herath,K., Bhat,G., Johns,D.G., Wang,S.P., Mitnaul,L., Jensen,K., Vreeken,R., Hankemeier,T., Roddy,T.P. and Hubbard,B.K. In vivo D2O labeling to quantify static and dynamic changes in cholesterol and cholesterol esters by high resolution LC/MS. J. Lipid Res., 52, 159-169 (2011).
  • Cercaci,L., Rodriguez-Estrada,M.T. and Lercker,G. Solid-phase extraction-thin-layer chromatography-gas chromatography method for the detection of hazelnut oil in olive oils by determination of esterified sterols. J. Chromatogr. A, 985, 211-220 (2003).
  • Cert,A. and Moreda,W. New method of stationary phase preparation for silver ion column chromatography: application to the isolation of steroidal hydrocarbons in vegetable oils. J. Chromatogr. A, 823, 291-297 (1998).
  • Cert,A., Moreda,W. and Perez-Camino,M.C. Chromatographic analysis of minor constituents in vegetable oils. J. Chromatogr. A, 881, 131-148 (2000).
  • Chamoin,M.-C., Charbonnier,M., Lafont,H. and Ternaux,J.-P. Highly sensitive chemiluminescent assay for cholesterol. Biochim. Biophys. Acta, 1210, 151-156 (1994).
  • Chen,B.H. and Chen,Y.C. Evaluation of the analysis of cholesterol oxides by liquid chromatography. J. Chromatogr. A, 661, 127-136 (1994).
  • Chmilenko,F.A., Minaeva,N.P. and Sidorova,L.P. Complex chromatographic determination of the adulteration of dairy products: A new approach. J. Anal. Chem., 66, 572-581 (2011).
  • Clariana,M., Diaz,I., Sarraga,C. and Garcia-Regueiro,J.A. Comparison of the determination of eight cholesterol oxides in dry-cured shoulder by GC-FID, GC-MS, and GC tandem mass spectrometry. Food Anal. Methods, 4, 465-474 (2011)
  • Cocito,C. and Delfini,C. Simultaneous determination by GC of free and combined fatty acids and sterols in grape musts and yeasts as silanized compounds. Food Chem., 50, 297-305 (1994).
  • Contois,J.H., Warnick,G.R. and Sniderman,A.D. Reliability of low-density lipoprotein cholesterol, non-high-density lipoprotein cholesterol, and apolipoprotein B measurement. J. Clin. Lipidol., 5, 264-272 (2011).
  • Contreras,J.A., Castro,M., Brocos,C., Herrera,E. and Lasuncion,M.A. Combination of an enzymatic method and HPLC for the quantitation of cholesterol in cultured cells. J. Lipid Res., 33, 931-936 (1992).
  • Corso,G., D'Apolito,O., Garofalo,D., Paglia,G. and Dello Russo,A. Profiling of acylcarnitines and sterols from dried blood or plasma spot by atmospheric pressure thermal desorption chemical ionization (APTDCI) tandem mass spectrometry. Biochim. Biophys. Acta, 1811, 669-679 (2011)
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  • Dinan,L., Harmatha,J. and Lafont,R. Chromatographic procedures for the isolation of plant steroids. J. Chromatogr. A, 935, 105-123 (2001).
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  • Esche, R., Barnsteiner, A., Scholz, B. and Engel, K.H. Simultaneous analysis of free phytosterols/phytostanols and intact phytosteryl/phytostanyl fatty acid and phenolic acid esters in cereals. J. Agric. Food Chem., 60, 5330-5339 (2012).
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  • Esche, R., Scholz, B. and Engel, K.H. Analysis of free phytosterols/stanols and their intact fatty acid and phenolic acid esters in various corn cultivars. J. Cereal Sci., 58, 333-340 (2013).
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  • Gomez-Coca, R.B., Perez-Camino, M.D. and Moreda, W. On the glucoside analysis: Simultaneous determination of free and esterified steryl glucosides in olive oil. Detailed analysis of standards as compulsory first step. Food Chem., 141, 1273-1280 (2013).
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  • Griffiths, W.J. and Wang,Y.Q. Analysis of neurosterols by GC-MS and LC-MS/MS. J. Chromatogr. B, 877, 2778-2805 (2009).
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