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Glycine-containing flaxseed orbitides.

Peta-Gaye G Burnett1, Pramodkumar D Jadhav1, Denis P Okinyo-Owiti1

  • 1†Department of Plant Sciences, College of Agriculture and Bioresources, University of Saskatchewan, Saskatoon, SK S7N 5A8, Canada.

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This summary is machine-generated.

Five new cyclolinopeptides (21-25) were discovered in flaxseed oil, with structures elucidated by mass spectrometry and confirmed via genomic data. Some compounds result from post-translational modifications and alternative cyclization pathways.

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Area of Science:

  • Natural Product Chemistry
  • Proteomics
  • Plant Biochemistry

Background:

  • Flaxseed oil (Linum usitatissimum) is a source of bioactive compounds.
  • Orbitides are cyclic peptides with diverse biological activities.
  • Previous research has identified various cyclolinopeptides in flaxseed.

Purpose of the Study:

  • To identify and characterize novel cyclolinopeptides in flaxseed oil.
  • To elucidate the structures and amino acid sequences of new cyclolinopeptides.
  • To investigate the relationship between identified cyclolinopeptides and their precursor proteins.

Main Methods:

  • High-Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry (HPLC-ESIMS) for identification and molecular formula determination.
  • HPLC-ESIMS/MS for structural elucidation of orbitides.
  • Analysis of flax genomic DNA sequence data to identify precursor proteins.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (1D and 2D) for detailed structural characterization of cyclolinopeptide 23.

Main Results:

  • Five new cyclolinopeptides (cyclolinopeptides 21-25, named U-Y) were identified in flaxseed oil extracts.
  • The molecular formulae and amino acid sequences of these new orbitides were determined.
  • Presence of previously reported cyclolinopeptides (1, 2, 3, 7, 8) was confirmed.
  • Evidence for alternative cyclization pathways producing known orbitides from precursors of new ones.
  • Identification of post-translational modifications (MetO) in cyclolinopeptides 3, 8, 23, and 25.

Conclusions:

  • Flaxseed oil contains a complex mixture of cyclolinopeptides, including novel compounds.
  • The study provides insights into the biosynthesis and structural diversity of cyclolinopeptides in flax.
  • The findings contribute to the understanding of flaxseed's chemical composition and potential bioactivity.