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Characterization and complete separation of major cyclolinopeptides in flaxseed oil by reversed-phase chromatography.
J Sep Sci. 2014 Jul; 37(14):1788-96.JS

Abstract

Organoleptic properties of flaxseed oil deteriorate during storage due to methionine oxidation in its major cyclolinopeptides. Cyclolinopeptide E was previously identified as being responsible for the manifestation of bitter taste with flaxseed oil ageing. We developed a chromatographic procedure to monitor the oxidation of major cyclic peptides in flaxseed oil. We also used liquid chromatography with mass spectrometry and high-efficiency core-shell reversed-phase sorbents to study the separation of cyclolinopeptides in detail. The Kinetex(TM) family of stationary phases (C8, C18, phenyl-hexyl) was tested, along with the standard porous Luna(TM) C18(2) media. We found that only the phenyl-hexyl stationary phase allows for complete resolution of major cyclolinopeptides, thus permitting direct UV monitoring of degree of conversion for cyclolinopeptide B into C and L into E. We also report, for the first time, a significant effect of peak splitting for some methionine S-oxide (Mso) containing cyclolinopeptides, which most likely appear due to diastereomerization. This results in poor separation efficiency for cyclolinopeptides F, G, and E, and gives baseline resolution of diastereomeric pairs for cyclolinopeptides I and P. Thus, a single oxidation of cyclolinopeptide N yields three distinct chromatographic peaks corresponding to cyclolinopeptide T (cyclo-MsoLMPFFWV, reported for the first time) and pair of cyclolinopeptide I (cyclo-MLMsoPFFWV) diastereomers.

Authors+Show Affiliations

Department of Chemistry, University of Manitoba, Winnipeg, Canada.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24788784

Citation

Lao, Ying W., et al. "Characterization and Complete Separation of Major Cyclolinopeptides in Flaxseed Oil By Reversed-phase Chromatography." Journal of Separation Science, vol. 37, no. 14, 2014, pp. 1788-96.
Lao YW, Mackenzie K, Vincent W, et al. Characterization and complete separation of major cyclolinopeptides in flaxseed oil by reversed-phase chromatography. J Sep Sci. 2014;37(14):1788-96.
Lao, Y. W., Mackenzie, K., Vincent, W., & Krokhin, O. V. (2014). Characterization and complete separation of major cyclolinopeptides in flaxseed oil by reversed-phase chromatography. Journal of Separation Science, 37(14), 1788-96. https://doi.org/10.1002/jssc.201400193
Lao YW, et al. Characterization and Complete Separation of Major Cyclolinopeptides in Flaxseed Oil By Reversed-phase Chromatography. J Sep Sci. 2014;37(14):1788-96. PubMed PMID: 24788784.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization and complete separation of major cyclolinopeptides in flaxseed oil by reversed-phase chromatography. AU - Lao,Ying W, AU - Mackenzie,Kim, AU - Vincent,William, AU - Krokhin,Oleg V, PY - 2014/02/20/received PY - 2014/04/16/revised PY - 2014/04/23/accepted PY - 2014/5/3/entrez PY - 2014/5/3/pubmed PY - 2015/5/12/medline KW - Cyclolinopeptides KW - Flaxseed oil KW - Mass spectrometry KW - Methionine oxidation KW - Reversed-phase chromatography SP - 1788 EP - 96 JF - Journal of separation science JO - J Sep Sci VL - 37 IS - 14 N2 - Organoleptic properties of flaxseed oil deteriorate during storage due to methionine oxidation in its major cyclolinopeptides. Cyclolinopeptide E was previously identified as being responsible for the manifestation of bitter taste with flaxseed oil ageing. We developed a chromatographic procedure to monitor the oxidation of major cyclic peptides in flaxseed oil. We also used liquid chromatography with mass spectrometry and high-efficiency core-shell reversed-phase sorbents to study the separation of cyclolinopeptides in detail. The Kinetex(TM) family of stationary phases (C8, C18, phenyl-hexyl) was tested, along with the standard porous Luna(TM) C18(2) media. We found that only the phenyl-hexyl stationary phase allows for complete resolution of major cyclolinopeptides, thus permitting direct UV monitoring of degree of conversion for cyclolinopeptide B into C and L into E. We also report, for the first time, a significant effect of peak splitting for some methionine S-oxide (Mso) containing cyclolinopeptides, which most likely appear due to diastereomerization. This results in poor separation efficiency for cyclolinopeptides F, G, and E, and gives baseline resolution of diastereomeric pairs for cyclolinopeptides I and P. Thus, a single oxidation of cyclolinopeptide N yields three distinct chromatographic peaks corresponding to cyclolinopeptide T (cyclo-MsoLMPFFWV, reported for the first time) and pair of cyclolinopeptide I (cyclo-MLMsoPFFWV) diastereomers. SN - 1615-9314 UR - https://www.unboundmedicine.com/medline/citation/24788784/Characterization_and_complete_separation_of_major_cyclolinopeptides_in_flaxseed_oil_by_reversed_phase_chromatography_ L2 - https://doi.org/10.1002/jssc.201400193 DB - PRIME DP - Unbound Medicine ER -