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dc.contributor.authorKoulman, Albert
dc.contributor.authorLee, T. Verne
dc.contributor.authorFraser, Karl
dc.contributor.authorJohnson, Linda J.
dc.contributor.authorArcus, Vickery L.
dc.contributor.authorLott, J. Shaun
dc.contributor.authorRasmussen, Carl Edward
dc.contributor.authorLane, Geoffrey A.
dc.coverage.spatialUnited Statesen_NZ
dc.date.accessioned2013-03-11T21:02:35Z
dc.date.available2013-03-11T21:02:35Z
dc.date.copyright2012-03
dc.date.issued2012
dc.identifier.citationKoulman, A., Lee, T. V., Fraser, K., Johnson, L.J., Arcus, V., Lott, J. S., & Lane, G. (2012). Identification of extracellular siderophores and a related peptide from the endophytic fungus Epichloë/festucae in culture and endophyte-infected Lolium perenne. Phytochemistry, 75, 128-139.en_NZ
dc.identifier.issn0031-9422
dc.identifier.urihttps://hdl.handle.net/10289/7341
dc.description.abstractA number of genes encoding non-ribosomal peptide synthetases (NRPSs) have been identified in fungi of Epichloë/Neotyphodium species, endophytes of Pooid grasses, including sidN, putatively encoding a ferrichrome siderophore-synthesizing NRPS. Targeted gene replacement and complementation of sidN in Epichloë festucae has established that extracellular siderophore epichloënin A is the major product of the SidN enzyme complex (Johnson et al., 2007a). We report here high resolution mass spectrometric fragmentation experiments and NMR analysis of an isolated fraction establishing that epichloënin A is a siderophore of the ferrichrome family, comprising a cyclic sequence of four glycines, a glutamine and three Nδ-trans-anhydromevalonyl–Nδ-hydroxyornithine (AMHO) moieties. Epichloënin A is unusual among ferrichrome siderophores in comprising an octapeptide rather than hexapeptide sequence, and in incorporating a glutamine residue. During this investigation we have established that desferrichrome siderophores with pendant trans-AMHO groups can be distinguished from those with pendant cis-AMHO groups by the characteristic neutral loss of an hydroxyornithine moiety in the MS/MS spectrum. A minor component, epichloënin B, has been characterized as the triglycine variant by mass spectrometry. A peptide characterized by mass spectrometry as the putative deoxygenation product, epichloëamide has been detected together with ferriepichloënin A in guttation fluid from ryegrass (Lolium perenne) plants infected with wild-type E. festucae, but not in plants infected with the ΔsidN mutant strain, and also detected at trace levels in wild-type E. festucae fungal culture.en_NZ
dc.language.isoen
dc.publisherElsevieren_NZ
dc.relation.ispartofPhytochemistry
dc.subjectEpichloë festucaeen_NZ
dc.subjectClavicipitaceaeen_NZ
dc.subjectLolium perenneen_NZ
dc.subjectPoaceaeen_NZ
dc.subjectSiderophoreen_NZ
dc.subjectCyclic peptideen_NZ
dc.subjectLC-MSnen_NZ
dc.subjectHigh resolution MSn (HRMSnen_NZ
dc.subjectNMRen_NZ
dc.titleIdentification of extracellular siderophores and a related peptide from the endophytic fungus Epichloë festucae in culture and endophyte-infected Lolium perenneen_NZ
dc.typeJournal Articleen_NZ
dc.identifier.doi10.1016/j.phytochem.2011.11.020en_NZ
dc.relation.isPartOfPhytochemistryen_NZ
pubs.begin-page1en_NZ
pubs.elements-id36998
pubs.end-page12en_NZ
pubs.volumeonlineen_NZ
uow.identifier.article-noCen_NZ


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