Liquid chromatography coupled to different atmospheric pressure ionization sources-quadrupole-time-of-flight mass spectrometry and post-column addition of metal salt solutions as a powerful tool for the metabolic profiling of Fusarium oxysporum

Cirigliano, Adriana M.; Rodríguez, María Alejandra; Gagliano, M. Laura; Bertinetti, Brenda V.; Godeas, Alicia Margarita; Cabrera, Gabriela M.

doi:10.1016/j.chroma.2015.11.073

Cited by 11 publications

(6 citation statements)

References 34 publications

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“…The fraction C (eluting with MC:MeOH = 50:1) was subjected to semi-preparative reversed phase (RP) HPLC to give six peak-collected samples (C1-C6, Figure S1). Among them, only three isolates [C1 (Rt 19 min), C4 (Rt 25 min), and C5 (Rt 33 min)] were found to be relatively stable and their structures were determined to be fusarubin (1), solaniol (4), and javanicin (5) by comparing measured spectroscopic data with the reported records [13][14][15][16].…”

Section: Isolation Of Secondary Metabolites From the Fermentation Bromentioning

confidence: 99%

Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus Fusarium sp. QF001 from the Roots of Scutellaria baicalensis

Maharjan

Lee²,

Kim

et al. 2020

Molecules

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The filamentous fungal pathogen Fusarium sp. causes several crop diseases. Some Fusarium sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, Fusarium sp. QF001, isolated from the inner rotten part of old roots of Scutellariae baicalensis resulted in the isolation of two new photosensitive geometrical isomers of lucilactaene (compounds 2 and 3) along with lucilactaene (6) and six other known compounds (fusarubin (1), (+)-solaniol (4), javanicin (5), 9-desmethylherbarine (7), NG391 (8) and NG393 (9)). Newly isolated isomers and lucilactaene were unstable under light at room temperature and tended to be a mixture in equilibrium state when exposed to a polar protic solvent during reversed phase chromatography. Normal phase chromatography under dim light conditions with an aprotic mobile phase led to the successful isolation of the relatively unstable isomers 2 and 3. Their structures were elucidated as 8(Z)-lucilactaene (2) and 4(Z)-lucilactaene (3) based on spectroscopic data. The absolute configuration of 4 was speculated to be R by computer-assisted specific rotation analysis. The isolated compounds could inhibit NO production and suppress pro-inflammatory cytokines expression in LPS-stimulated macrophage cells. These properties of the isolated compounds indicate their potential use as anti-inflammatory drugs.

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Section: Isolation Of Secondary Metabolites From the Fermentation Bromentioning

confidence: 99%

Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus Fusarium sp. QF001 from the Roots of Scutellaria baicalensis

Maharjan

Lee²,

Kim

et al. 2020

Molecules

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“…The known indole derivatives N-acetyltryptamine (4) and 1H-indole-3-carbaldehyde (9) and the diketopiperazines (5), (6), and (7) were isolated previously from Fusarium genus, but it is the first time isolated from F. proliferatum species [42,43]. Compound 2,4-dihydroxypyrimidine (8) (uracil) is commonly identified in endophytic fungus Fusarium sp.…”

Section: Resultsmentioning

confidence: 99%

Mycotoxins from Fusarium proliferatum: new inhibitors of papain-like cysteine proteases

et al. 2020

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Papain-like cysteine proteases (PLCPs) in plants are essential to prevent phytopathogen invasion. In order to search for cysteine protease inhibitors and to investigate compounds that could be associated to pineapple Fusarium disease, a chemistry investigation was performed on Fusarium proliferatum isolated from Ananas comosus (pineapple) and cultivated in Czapek medium. From F. proliferatum extracts, nine secondary metabolites were isolated and characterized by nuclear magnetic resonance spectroscopy and mass spectrometry experiments: beauvericin (1), fusaric acid (2), N-ethyl-3-phenylacetamide (3), Nacetyltryptamine (4), cyclo(L-Val-L-Pro) cyclodipeptide (5), cyclo(L-Leu-L-Pro) cyclodipeptide (6), cyclo(L-Leu-L-Pro) diketopiperazine (7), 2,4-dihydroxypyrimidine (8), and 1H-indole-3-carbaldehyde (9). Compounds 1, 3, and 6 showed significant inhibition of papain, with IC 50 values of 25.3 ± 1.9, 39.4 ± 2.5, and 7.4 ± 0.5 μM, respectively. Compound 1 also showed significant inhibition against human cathepsins V and B with IC 50 of 46.0 ± 3.0 and 6.8 ± 0.7 μM, respectively. The inhibition of papain by mycotoxins (fusaric acid and beauvericin) may indicate a mechanism of Fusarium in the roles of infection process.

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“…Electrospray ionization (ESI), a soft ionization technique able to transfer ions from solution to the gas phase, has been previously employed for the evaluation of the metal binding nature of secondary metabolites. Metal ions of alkali, alkaline earth and transition metals have been widely used in ESI, in order to record spectra of mixtures of metal salt solutions and samples, or by post-HPLC column addition of metal salt solutions [ 11 , 12 ]. In particular, the latter technique has been applied as a screening method for the detection of compounds with metal binding properties [ 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

Donalle

Martorell

Siless

et al. 2022

Nat. Prod. Bioprospect.

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The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The absolute configuration of the amino acids was determined by Marfey’s method, with HPLC analysis of FDVA (Nα-(2,4-dinitro-5-fluorphenyl)-l-valinamide) derivatives making use of a PFP column. Remarkably, cadophorin 2 possesses both the uncommon d-Ile and d-allo-Ile in its structure. The peptides have metal binding properties as shown by LCMS with post column addition of metal salt solutions. These results were supported by DFT calculations. Graphical Abstract

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Liquid chromatography coupled to different atmospheric pressure ionization sources-quadrupole-time-of-flight mass spectrometry and post-column addition of metal salt solutions as a powerful tool for the metabolic profiling of Fusarium oxysporum

Cited by 11 publications

References 34 publications

Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus Fusarium sp. QF001 from the Roots of Scutellaria baicalensis

Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus Fusarium sp. QF001 from the Roots of Scutellaria baicalensis

Mycotoxins from Fusarium proliferatum: new inhibitors of papain-like cysteine proteases

Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

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