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

Jadhav, Pramodkumar D.; Okinyo-Owiti, Denis P.; Ahiahonu, Pearson W. K.; Reaney, Martin J.T.

doi:10.1016/j.foodchem.2012.10.126

Cited by 32 publications

(50 citation statements)

References 29 publications

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“…12 The absence of known flax orbitides 4 and 9 suggested that the flaxseed oil had not yet undergone extensive oxidation. 8,12,23,24 The remaining known flax orbitides 18 and 19 that were recently identified were not detected in this extract probably due to either their occurrence at low concentration and/or the extraction procedure. 11 In addition to the 16 known peptides detected, signals for novel cyclolinopeptides 21, 22, 23, 24, and 25 were also observed ( Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 87%

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Glycine-Containing Flaxseed Orbitides

et al. 2015

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Five new orbitides, cyclolinopeptides 21-25, were identified in flaxseed oil (Linum usitatissimum) extracts. Their HPLC-ESIMS quasimolecular ion peaks at m/z 1097.7 (21), 1115.6 (22), 1131.6 (23), 1018.6 (24), and 1034.6 (25) [M + H](+) corresponded to the molecular formulae C59H89N10O10, C58H87N10O10S, C58H87N10O11S, C53H80N9O9S, and C53H80N9O10S, respectively. Their structures were elucidated by extensive HPLC-ESIMS/MS analyses, and their presence was confirmed by precursor proteins identified in flax genomic DNA sequence data. The amino acid sequences of these orbitides were confirmed as [1-10-NαC]-GILVPPFFLI, [1-10-NαC]-GMLIPPFFVI, [1-10-NαC]-GOLIPPFFVI, [1-9-NαC]-GMLVFPLFI, and [1-9-NαC]-GOLVFPLFI for cyclolinopeptides 21-25, respectively. Previously reported orbitides, [1-9-NαC]-ILVPPFFLI (1), [1-9-NαC]-MLIPPFFVI (2), [1-9-NαC]-OLIPPFFVI (3), [1-8-NαC]-MLVFPLFI (7), and [1-8-NαC]-OLVFPLFI (8), were also present in flaxseed oil. The precursors of orbitides 21, 22, and 24 also produced orbitides 1, 2, and 7 by alternative cyclization. Cyclolinopeptides 3, 8, 23, and 25 contain MetO (O) and are not directly encoded, but are products of post-translational modification of the Met present in 2, 7, 22, and 24, respectively. Sufficient cyclolinopeptide 23 was isolated for characterization via 1D ((1)H and (13)C) and 2D (NOESY and HMBC) NMR spectroscopy. These compounds have been named as cyclolinopeptides U, V, W, X, and Y for 21, 22, 23, 24, and 25, respectively.

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Section: ■ Results and Discussionmentioning

confidence: 87%

“…Once understood, the innate capability of flax to produce an extended array of cyclic peptides might be exploited for the large-scale agronomic production of custom cyclopeptides. It is proposed that the five new cyclolinopeptides 21,22,23,24, and 25 should be named U, V, W, X, and Y, respectively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Glycine-Containing Flaxseed Orbitides

et al. 2015

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“…The peptides may also be used as scaffolds for synthesis of methionine modified peptides [28]. Although orbitides display remarkable biological activities [11], their potential applicability in pharmaceuticals is hindered by their occurrence at relatively low concentrations [15]. However, by using SMB chromatography CLs can be obtained in sufficient quantities for chemical synthesis, crystallization and larger scale assays of biological activity.…”

Section: Resultsmentioning

confidence: 99%

“…Solid phase synthesis of plant orbitides would face this difficulty. Isolation of orbitides from flaxseed (Linum usitatissimum) [14] is difficult as these compounds occur as complex mixtures and in low concentrations of just 0.2% in flaxseed oil [15]. Reaney et al [16] developed methods for concentrating flax orbitides.…”

Section: Introductionmentioning

confidence: 99%

Simulated moving bed purification of flaxseed oil orbitides: Unprecedented separation of cyclolinopeptides C and E

Okinyo-Owiti

Burnett

Reaney

2014

Journal of Chromatography B

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“…The first one was CLA, a nonapeptide discovered in linseed oil in 1959 [1]. CLs B-E [2,3] and F-I [4] were found in Linum usitatissimum, J and K in flaxseed oil [5], and X in Linum album [6]. CLs A-C and K are nonapeptides, while the other CLs are octapeptides.…”

Section: Introductionmentioning

confidence: 99%

The structure of cyclolinopeptide A in chloroform refined by RDC measurements

Huben

Jewgiński

Pabis³

et al. 2014

Journal of Peptide Science

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Three-dimensional structures of molecules traditionally assigned from nuclear Overhauser effects and vicinal coupling constants are recently complemented by measurements of residual dipolar couplings. Residual dipolar couplings measured in a stretched poly(dimethylsiloxane) gel were used to determine the structure of cyclolinopeptide A in chloroform solution at -50 °C. After structure refinement, conformational details of main cluster were discussed in relation to crystal and nuclear Overhauser effect derived structures.

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

Cited by 32 publications

References 29 publications

Glycine-Containing Flaxseed Orbitides

Glycine-Containing Flaxseed Orbitides

Simulated moving bed purification of flaxseed oil orbitides: Unprecedented separation of cyclolinopeptides C and E

The structure of cyclolinopeptide A in chloroform refined by RDC measurements

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