Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax

Food Chemistry

Volumn 138, Issue 2-3, 2013, Pages 1757-1763

  Jadhav, Pramodkumar D ^a   Okinyo Owiti, Denis P ^a   Ahiahonu, Pearson W K ^a   Reaney, Martin J T ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Ageing; Characterisation; Cyclolinopeptides; Flax; Isolation

Indexed keywords

2-D NMR; AGEING; CHARACTERISATION; CYCLOLINOPEPTIDES; EXPOSED TO; FLAX OIL; HPLC-MS/MS; ISOLATION; J AND K; METHIONINE SULFOXIDE; OXIDATIVE STABILITY;

AMINO ACIDS; FLAX; FOOD PRODUCTS; LINEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OILS AND FATS; PEPTIDES; YARN;

OILSEEDS;

CYCLOLINOPEPTIDE J; CYCLOLINOPEPTIDE K; CYCLOPEPTIDE; LINSEED OIL; METHIONINE SULFONE; UNCLASSIFIED DRUG;

AGING PLANT; ARTICLE; CRYSTAL STRUCTURE; FLAX; FOOD; FOOD INDUSTRY; ISOLATION PROCEDURE; LINSEED; OXIDATION; PEPTIDE SYNTHESIS; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN STABILITY; THERMOSTABILITY;

FLAX; FOOD STORAGE; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; TANDEM MASS SPECTROMETRY; TIME FACTORS;

LINUM USITATISSIMUM;

EID: 84873718235     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.10.126     Document Type: Article

References (35)

1. J.L. Adolphe, S.J. Whiting, B.H.J. Juurlink, L.U. Thorpe, and J. Alcorn Health effects with consumption of the flax lignan secoisolariciresinol diglucoside British Journal of Nutrition 103 7 2010 929 938
2. R. Afonso, A. Mendes, and L. Gales Peptide-based solids: Porosity and zeolitic behavior Journal of Materials Chemistry 22 5 2012 1709 1723
3. G. Barceló-Coblijn, E.J. Murphy, R. Othman, M.H. Moghadasian, T. Kashour, and J.K. Friel Flaxseed oil and fish-oil capsule consumption alters human red blood cell n-3 fatty acid composition: A multiple-dosing trial comparing 2 sources of n-3 fatty acid American Journal of Clinical Nutrition 88 3 2008 801 809
4. L. Brühl, B. Matthäus, E. Fehling, B. Wiege, B. Lehmann, and H. Luftmann Identification of bitter off-taste compounds in the stored cold pressed linseed oil Journal of Agricultural and Food Chemistry 55 19 2007 7864 7868
5. D. Chatterji, M.B. Sankaram, and D. Balasubramanian Conformational and ion-binding properties of cyclolinopeptide A isolated from linseed Journal of Biosciences 11 1987 473 484
6. T. Cordes, D. Weinrich, S. Kempa, K. Riesselmann, S. Herre, and C. Hoppmann Hemithioindigo-based photoswitches as ultrafast light trigger in chromopeptides Chemical Physics Letters 428 1-3 2006 167 173
7. Covello, P. S.; Datla, R. S.; Stone, S. L.; Balsevich, J. L.; Reaney, M. J.; Harnison, P. G.; et al. (2010). DNA sequences encoding caryophyllaceae and caryophyllacea-like cyclopeptide precursors and methods of use. Patent No. WO/2010/130030.
8. S. Fukumitsu, K. Aida, H. Shimizu, and K. Toyoda Flaxseed lignan lowers blood cholesterol and decreases liver disease risk factors in moderately hypercholesterolemic men Nutrition Research 30 7 2010 441 446
9. S. Fukumitsu, K. Aida, N. Ueno, S. Ozawa, Y. Takahashi, and M. Kobori Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice British Journal of Nutrition 100 3 2008 669 676
10. S.K. Gebauer, T.L. Psota, W.S. Harris, and P.M. Kris-Etherton N-3 Fatty acid dietary recommendations and food sources to achieve essentiality and cardiovascular benefits American Journal of Clinical Nutrition 83 6 2006 1526S 1535S
11. A. Gorski, M. Kasprzycka, M. Nowaczyk, Z. Wieczoreck, I.Z. Siemion, and W. Szelejewski Cyclolinopeptide: A novel immunosuppressive agent with potential anti-lipemic activity Transplantation Proceedings 33 1-2 2001 553
12. Gui, B. (2011). Cyclolinopeptides in flaxseed and flaxseed products. M.Sc. Thesis, University of Saskatchewan, Saskatoon, SK, Canada.
13. P. Jadhav, G. Schatte, S. Labiuk, P.G. Burnett, B. Li, and D. Okinyo-Owiti Cyclolinopeptide K butanol disolvate monohydrate Acta Crystallographica, Section E: Structure Reports Online 67 9 2011 o2360 o2361
14. A.J. Jhala, and L.M. Hall Flax (Linum usitatissimum L.): Current uses and future applications Australian Journal of Basic and Applied Sciences 4 9 2010 4304 4312
15. H.P. Kaufmann, and A. Tobschirbel Uber ein oligopeptid aus leinsamen Chemische Berichte-Recueil 92 11 1959 2805 2809
16. N. Kaul, R. Kreml, J.A. Austria, M.N. Richard, A.L. Edel, and E. Dibrov A comparison of fish oil, flaxseed oil and hempseed oil supplementation on selected parameters of cardiovascular health in healthy volunteers Journal of the American College of Nutrition 27 1 2008 51 58
17. H. Kemmer, D. Tripier, K. Jouvenal, D. Scriba, G. Zanotti, and A.M. Maione Binding proteins for cyclic and linear oligopeptides in plasma membranes and the cytosol of rat hepatocytes Biochemical Pharmacology 54 1997 481 490
18. T. Matsumoto, A. Shishido, H. Morita, H. Itokawa, and K. Takeya Cyclolinopeptides F-I, cyclic peptides from linseed Phytochemistry 57 2 2001 251 260
19. T. Matsumoto, A. Shishido, and K. Takeya New cyclic peptides from higher plants Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 43 2001 407 412
20. H. Morita, A. Shishido, T. Matsumoto, H. Itokawa, and K. Takeya Cyclolinopeptides B-E, new cyclic peptides from Linum usitatissimum Tetrahedron 55 4 1999 967 976
21. H. Morita, A. Shishido, T. Matsumoto, K. Takeya, H. Itokawa, and T. Hirano A new immunosuppressive cyclic nonapeptide, cycloinopeptide B from Linum usitatissimum Bioorganic & Medicinal Chemistry Letters 7 10 1997 1269 1272
22. H. Morita, and K. Takeya Bioactive cyclic peptides from higher plants Heterocycles 80 2 2010 739 764
23. A.B. Pomilio, M.E. Battista, and A.A. Vitale Naturally-occurring cyclopeptides: Structures and bioactivity Current Organic Chemistry 10 16 2006 2075 2121
24. K. Prasad Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed Circulation 99 10 1999 1355 1362
25. K. Prasad Antihypertensive activity of secoisolariciresinol diglucoside (SDG) isolated from flaxseed: Role of guanylate cyclase International Journal of Angiology 13 1 2004 7 14
26. K. Prasad Flaxseed and cardiovascular health Journal of Cardiovascular Pharmacology 54 5 2009 369 377
27. J.W. Quail, J. Shen, M.J.T. Reaney, and R. Sammynaiken Cyclolinopeptide A methanol solvate Acta Crystallographica, Section E: Structure Reports Online E65 2009 o1913 o1914
28. Reaney, M. J.; Jia, Y.; Shen, J.; Schock, C.; Tyler, N.; Elder, J.; et al. (2009). Recovery of hydrophobic peptides from oils. Patent No. WO 2009079792.
29. B. Rempel, B. Gui, J. Maley, M. Reaney, and R. Sammynaiken Biomolecular interaction study of Cyclolinopeptide A with human serum albumin Journal of Biomedicine and Biotechnology 2010 1 8
30. J. Ryu, and C.B. Park High stability of self-assembled peptide nanowires against thermal, chemical, and proteolytic attacks Biotechnology and Bioengineering 105 2 2010 221 230
31. J.K. Saggar, J. Chen, P. Corey, and L.U. Thompson The effect of secoisolariciresinol diglucoside and flaxseed oil, alone and in combination, on MCF-7 tumor growth and signaling pathways Nutrition and Cancer 62 4 2010 533 542
32. G. Schatte, S. Labiuk, B. Li, P.-G. Burnett, M. Reaney, and P. Grochulski Cyclolinopeptide B methanol trisolvate Acta Crystallographica, Section E: Structure Reports Online E68 2012 o50 o51
33. P. Stefanowicz Detection and sequencing of new cyclic peptides from linseed by electrospray ionization mass spectrometry Acta Biochimica Polonica 48 4 2001 1125 1129
34. N.H. Tan, and J. Zhou Plant cyclopeptides Chemical Reviews 106 3 2006 840 895
35. Z. Wieczorek, B. Bengtsson, J. Trojnar, and I.Z. Siemion Immunosuppressive activity of cyclolinopeptide A Peptide Research 4 5 1991 275 283