Glycine-containing flaxseed orbitides

Journal of Natural Products
Peta-Gaye G BurnettMartin J T Reaney

Abstract

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. Suff...Continue Reading

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Mar 19, 2015·Journal of Natural Products·Youn Young ShimMartin J T Reaney

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Citations

Mar 19, 2015·Journal of Natural Products·Youn Young ShimMartin J T Reaney
Jun 4, 2016·Journal of Agricultural and Food Chemistry·Peta-Gaye Gillian BurnettMartin John Tarsisius Reaney
Oct 6, 2015·Chemistry : a European Journal·Pramodkumar D JadhavMartin J T Reaney
Nov 13, 2018·Plant Direct·Mark F FisherJoshua S Mylne
May 23, 2018·BMC Plant Biology·Peta-Gaye Gillian BurnettMartin John Tarsisius Reaney
Oct 21, 2016·Bioconjugate Chemistry·Pramodkumar D JadhavMartin J T Reaney

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