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Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax.
Food Chem. 2013 Jun 01; 138(2-3):1757-63.FC

Abstract

Methionine sulfone containing peptides CLs J (11) and K (12) may be produced from their reduced forms by oxidation but it is not known if these compounds occur in foods that contain flax. These compounds have been reported to possess greater immunosuppressive activity than their reduced methionine sulfoxide peptide forms 4 and 6, respectively. Since 11 and 12 have not been detected in commercial flax oil and milled flax seed, we tested for their presence in flax food products. Here we report that 11 and 12 accumulate in ground flaxseed that is exposed to air and heat (100°C) for more than 4h. Standards of 11 and 12 were prepared, isolated and extensively characterised using HPLC-MS/MS, 1D and 2D NMR methods. We also report the excellent thermal and oxidative stability of these peptides. Due to the harsh conditions required to produce 11 and 12, it is expected that their levels in flax based foods would be low and therefore their presence could serve as an indicative measure of severe oxidation of a food product.

Authors+Show Affiliations

Department of Food and Bioproduct Sciences, University of Saskatchewan, Saskatoon, SK, Canada S7N5A8.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23411308

Citation

Jadhav, Pramodkumar D., et al. "Detection, Isolation and Characterisation of Cyclolinopeptides J and K in Ageing Flax." Food Chemistry, vol. 138, no. 2-3, 2013, pp. 1757-63.
Jadhav PD, Okinyo-Owiti DP, Ahiahonu PW, et al. Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax. Food Chem. 2013;138(2-3):1757-63.
Jadhav, P. D., Okinyo-Owiti, D. P., Ahiahonu, P. W., & Reaney, M. J. (2013). Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax. Food Chemistry, 138(2-3), 1757-63. https://doi.org/10.1016/j.foodchem.2012.10.126
Jadhav PD, et al. Detection, Isolation and Characterisation of Cyclolinopeptides J and K in Ageing Flax. Food Chem. 2013 Jun 1;138(2-3):1757-63. PubMed PMID: 23411308.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax. AU - Jadhav,Pramodkumar D, AU - Okinyo-Owiti,Denis P, AU - Ahiahonu,Pearson W K, AU - Reaney,Martin J T, Y1 - 2012/11/16/ PY - 2012/06/22/received PY - 2012/10/01/revised PY - 2012/10/24/accepted PY - 2013/2/16/entrez PY - 2013/2/16/pubmed PY - 2013/8/21/medline SP - 1757 EP - 63 JF - Food chemistry JO - Food Chem VL - 138 IS - 2-3 N2 - Methionine sulfone containing peptides CLs J (11) and K (12) may be produced from their reduced forms by oxidation but it is not known if these compounds occur in foods that contain flax. These compounds have been reported to possess greater immunosuppressive activity than their reduced methionine sulfoxide peptide forms 4 and 6, respectively. Since 11 and 12 have not been detected in commercial flax oil and milled flax seed, we tested for their presence in flax food products. Here we report that 11 and 12 accumulate in ground flaxseed that is exposed to air and heat (100°C) for more than 4h. Standards of 11 and 12 were prepared, isolated and extensively characterised using HPLC-MS/MS, 1D and 2D NMR methods. We also report the excellent thermal and oxidative stability of these peptides. Due to the harsh conditions required to produce 11 and 12, it is expected that their levels in flax based foods would be low and therefore their presence could serve as an indicative measure of severe oxidation of a food product. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/23411308/Detection_isolation_and_characterisation_of_cyclolinopeptides_J_and_K_in_ageing_flax_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0308-8146(12)01700-1 DB - PRIME DP - Unbound Medicine ER -