Improved Method of Analysis for Ergovaline in Tall Fescue by High-Performance Liquid Chromatography

Shelby, Richard A.; Flieger, Miroslav

doi:10.1021/jf9605759

Cited by 23 publications

(20 citation statements)

References 24 publications

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“…The presence of peramine, lolitrem B, and ergovaline was evaluated as described by Shelby & Flieger (1997), Gallagher et al (1985), and Tapper et al (1989), respectively, using an HPLC (Jasco Gulliver Series; Jasco, Tokyo, Japan).…”

Section: Alkaloid Analysesmentioning

confidence: 99%

Fungal loline alkaloids in grass–endophyte associations confer resistance to the rice leaf bug, Trigonotylus caelestialium

Shiba¹,

Sugawara

2008

Entomologia Exp Applicata

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Plant symbiotic fungi (endophytes) of the genus Neotyphodium [anamorphs, asexual derivatives of Epichloë (Ascomycota: Clavicipitaceae)] often associate with grass species of the subfamily Pooideae, which includes important forage and turf species. These endophytes are known to produce a range of alkaloids that enhance their host's resistance to insects or are toxic to grazing animals. Among the alkaloids, loline alkaloids (saturated 1-aminopyrrolizidines) are generally observed in the highest concentrations in many Neotyphodium -grass symbiotic associations, and are known to be toxic to insects but not to mammals. Some Neotyphodium -infected grasses have enhanced resistance to rice leaf bug, Trigonotylus caelestialium (Kirkaldy) (Heteroptera: Miridae), one of the major pests for rice production in Japan. Our laboratory experiments quantified the effects of purified loline ( N-formylloline) and in planta synthesis of loline alkaloids by meadow fescue [ Lolium pratense (Huds.) S.J. Darbyshire (syn. Festuca pratensis Huds.)]-Neotyphodium uncinatum (Gams, Petrini & Schmidt) Glenn, Bacon & Hanlin and Italian ryegrass ( Lolium multiflorum Lam.)-Neotyphodium occultans Moon, Scott & Christensen associations on the development and survival of T. caelestialium . No-choice feeding assays with laboratory populations of the insect revealed that their growth was significantly decreased by the infected grasses, and the effect was greater for N. uncinatum than for N. occultans , in keeping with differences in N-formylloline concentrations in the plants. Artificial feeding of N-formylloline through feeding sachets indicated that the chemical has an adverse effect on survival of larvae, even at the lowest concentration tested (50 μ g/g), which was considerably lower than the typical concentrations in many Neotyphodium -grass association s . The results confirmed the ability of Neotyphodium -infected forage grasses to control T. caelestialium propagation in meadows, which may cause damages to nearby rice paddies.

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Section: Alkaloid Analysesmentioning

confidence: 99%

Fungal loline alkaloids in grass–endophyte associations confer resistance to the rice leaf bug, Trigonotylus caelestialium

Shiba¹,

Sugawara

2008

Entomologia Exp Applicata

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“…The reaction mixture was dialyzed three times in 36 h against phosphate-buffered saline (PBS, Sigma P-4477). The degree of conjugation was measured by sampling PBS dialysate for free ergovalinine using quantitative HPLC (Shelby & Flieger, 1997). Additionally, conjugates were tested by spotting onto thin-layer silica gel chromatography plates (Whatman MK6F, 25 X 75 mm) and developing in CHCl 3 :MeOH, 95:5.…”

Section: Ergovaline Conjugatesmentioning

confidence: 99%

“…When infected by this fungus, the forage often produces a toxic syndrome in grazing livestock, known as 'fescue toxicosis' (Garner et al, 1993). Because the ergot peptides are highly bioactive compounds, producing such effects as vasoconstriction, endocrine and behavioral changes, a number of quantitative assays have been developed to measure this alkaloid in tall fescue (Craig et al, 1994;Hill et al, 1993;Shelby & Flieger, 1997;Rottinghaus et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

Determination of ergovaline in tall fescue by a specific monoclonal antibody

Shelby¹,

Bridgman²,

Smith³

et al. 1998

Food and Agricultural Immunology

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A monoclonal antibody (EV5B3) was developed using a conjugate of ergovaline and bovine serum albumin linked at the indole N(1) of the ergovaline molecule. This resulted in an antibody specific for the distal cyclol peptide moiety of ergovaline. As a result the antibody was specific for ergot peptide alkaloids having an isopropyl group at the C(5') position of the peptide. In a competitive indirect ELISA (CI-ELISA) the antibody could be used to detect ergovaline in plant material down to 16 ng g-1 , and the assay was highly correlated with the standard HPLC method of detection for this compound.

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“…The first one is an extraction of water soluble salts (tartarates, phosphates, acetates or others) [1][2][3][4][5] with water, water/alcohol, and water/acetonitrile mixtures. The obtained crude extracts are generally alkalized with NH 4 OH (pH 9) to remove the co-extracted compounds and free alkaloid bases are re-extracted into organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Liquid chromatography–tandem mass spectrometry characterization of ergocristam degradation products

Olšovská

Šulc

Novák

et al. 2008

Journal of Chromatography B

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Improved Method of Analysis for Ergovaline in Tall Fescue by High-Performance Liquid Chromatography

Cited by 23 publications

References 24 publications

Fungal loline alkaloids in grass–endophyte associations confer resistance to the rice leaf bug, Trigonotylus caelestialium

Fungal loline alkaloids in grass–endophyte associations confer resistance to the rice leaf bug, Trigonotylus caelestialium

Determination of ergovaline in tall fescue by a specific monoclonal antibody

Liquid chromatography–tandem mass spectrometry characterization of ergocristam degradation products

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