scholarly journals Identification and Structure Elucidation of Epoxyjanthitrems from Lolium perenne Infected with the Endophytic Fungus Epichloë festucae var. lolii and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I

Toxins ◽  
2020 ◽  
Vol 12 (8) ◽  
pp. 526 ◽  
Author(s):  
Sarah C. Finch ◽  
Michèle R. Prinsep ◽  
Alison J. Popay ◽  
Alistair L. Wilkins ◽  
Nicola G. Webb ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Lolium Perenne ◽  
Endophytic Fungus ◽  
Structure Elucidation ◽  
Insect Pests ◽  
Resonance Assignments ◽  
Epichloë Festucae ◽  
Insect Activity ◽  
Dose Dependent

Epoxyjanthitrems I–IV (1–4) and epoxyjanthitriol (5) were isolated from seed of perennial ryegrass (Lolium perenne) infected with the endophytic fungus Epichloë festucae var. lolii. Although structures for epoxyjanthitrems I–IV have previously been proposed in the literature, this is the first report of a full structural elucidation yielding NMR (Nuclear magnetic resonance) assignments for all five epoxyjanthitrem compounds, and additionally, it is the first isolation of epoxyjanthitriol (5). Epoxyjanthitrem I induced tremors in mice and gave a dose dependent reduction in weight gain and feeding for porina (Wiseana cervinata), a common pasture pest in New Zealand. These data suggest that epoxyjanthitrems are involved in the observed effects of the AR37 endophyte on livestock and insect pests.

Computational methods for NMR and MS for structure elucidation II: database resources and advanced methods

2019 ◽  
Vol 4 (11) ◽  
Author(s):  
Marilia Valli ◽  
Helena Mannochio Russo ◽  
Alan Cesar Pilon ◽  
Meri Emili Ferreira Pinto ◽  
Nathalia B. Dias ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Computational Methods ◽  
Structure Elucidation ◽  
Computational Tools ◽  
Technological Advances ◽  
Similarity Networks ◽  
Product Chemistry

Abstract Technological advances have contributed to the evolution of the natural product chemistry and drug discovery programs. Recently, computational methods for nuclear magnetic resonance (NMR) and mass spectrometry (MS) have speeded up and facilitated the process of structural elucidation even in high complex biological samples. In this chapter, the current computational tools related to NMR and MS databases and spectral similarity networks, as well as their applications on dereplication and determination of biological biomarkers, are addressed.

The Pyoverdins of Pseudomonas syringae and Pseudomonas cichorii

2004 ◽  
Vol 59 (9-10) ◽  
pp. 613-618 ◽  
Author(s):  
Alain Bultreys ◽  
Isabelle Gheysen ◽  
Mathias Schäfer ◽  
Herbert Budzikiewicz ◽  
Bernard Wathelet
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Pseudomonas Syringae ◽  
Structure Elucidation ◽  
Side Chain ◽  
Closely Related Species ◽  
Pseudomonas Cichorii

Abstract The structure elucidation of the cyclic (lactonic) forms of the pyoverdins with a succinamide side chain originally produced by the closely related species Pseudomonas syringae and P. cichorii is reported. Mass spectrometry and nuclear magnetic resonance analyses as well as the determination of the configuration of the amino acids after degradation indicate that these two pyoverdins differ only by the replacement of the first in-chain serine by glycine. The pyoverdins of P. syringae and P. cichorii and the dihydropyoverdin of P. syringae can be used by both species as siderophores.

scholarly journals Identification of extracellular siderophores and a related peptide from the endophytic fungus Epichloë festucae in culture and endophyte-infected Lolium perenne

2012 ◽  
Vol 75 ◽  
pp. 128-139 ◽  
Author(s):  
Albert Koulman ◽  
T. Verne Lee ◽  
Karl Fraser ◽  
Linda Johnson ◽  
Vickery Arcus ◽  
...  
Keyword(s):  
Lolium Perenne ◽  
Endophytic Fungus ◽  
Epichloë Festucae ◽  
Related Peptide

Identification and Structure Elucidation of Janthitrems A and D fromPenicillium janthinellumand Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B

2018 ◽  
Vol 66 (50) ◽  
pp. 13116-13125 ◽  
Author(s):  
Jacob V. Babu ◽  
Alison J. Popay ◽  
Christopher O. Miles ◽  
Alistair L. Wilkins ◽  
Margaret E. di Menna ◽  
...  
Keyword(s):  
Structure Elucidation ◽  
Insect Activity

scholarly journals Comparison of Plant Metabolites in Root Exudates of Lolium perenne Infected with Different Strains of the Fungal Endophyte Epichloë festucae var. lolii

2021 ◽  
Vol 7 (2) ◽  
pp. 148
Author(s):  
Aurora Patchett ◽  
Jonathan A. Newman
Keyword(s):  
Lolium Perenne ◽  
Root Exudates ◽  
Root Exudate ◽  
Plant Biomass ◽  
Insect Pests ◽  
Plant Root ◽  
Fungal Endophyte ◽  
Plant Metabolites ◽  
Primary And Secondary Metabolites ◽  
Epichloë Festucae

Lolium perenne infected with the fungal endophyte Epichloë festucae var. lolii have specific, endophyte strain-dependent, chemical phenotypes in their above-ground tissues. Differences in these chemical phenotypes have been largely associated with classes of fungal-derived alkaloids which protect the plant against many insect pests. However, the use of new methodologies, such as various omic techniques, has demonstrated that many other chemical changes occur in both primary and secondary metabolites. Few studies have investigated changes in plant metabolites exiting the plant in the form of root exudates. As root exudates play an essential role in the acquisition of nutrients, microbial associations, and defense in the below-ground environment, it is of interest to understand how plant root exudate chemistry is influenced by the presence of strains of a fungal endophyte. In this study, we tested the influence of four strains of E. festucae var. lolii (E+ (also known as Lp19), AR1, AR37, NEA2), and uninfected controls (E−), on L. perenne growth and the composition of root exudate metabolites. Root exudates present in the hydroponic water were assessed by untargeted metabolomics using Accurate-Mass Quadrupole Time-of-Flight (Q–TOF) liquid chromatography–mass spectrometry (LC–MS). The NEA2 endophyte strain resulted in the greatest plant biomass and the lowest endophyte concentration. We found 84 metabolites that were differentially expressed in at least one of the endophyte treatments compared to E− plants. Two compounds were strongly associated with one endophyte treatment, one in AR37 (m/z 135.0546 RT 1.17), and one in E+ (m/z 517.1987 RT 9.26). These results provide evidence for important changes in L. perenne physiology in the presence of different fungal endophyte strains. Further research should aim to connect changes in root exudate chemical composition with soil ecosystem processes.

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