Quadrupole mass spectrometry/mass spectrometry of ergot cyclol alkaloids

Plattner, Ronald D.; Yates, Scott R.; Porter, James K.

doi:10.1021/jf00118a026

Cited by 25 publications

(24 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…analysis of the ergot alkaloids isolated from infected grass and from cultures using MS include electron impact (EI) (Porter et al, 1979), chemical ionization ( CI) (Porter and Betowski, 1981;, and tandem mass (MS/MS) spectrometry (Plattner et al, 1983;Yates et al, 1985;Lyons et al, 1986;Porter et al, 1987). Under low resolution electron impact (70 eV), the ergopeptine alkaloids pyrolytically decompose into the lysergic acid amide, the cyclic peptide, and diketopiperazine fragments A, B, and C, respectively (Figure 1).…”

Section: Mass Spectrometry Identification and Quantitativementioning

confidence: 99%

“…Under isobutane CIMS, the lysergic acid amide ( A ) , cyclic peptide (B ) , and diketopiperazine ( C ) molecules ( Figure 1) abstract a proton from a t-butyl cation (which is generated in the mass spectrometer) and the resulting ion-molecule reaction produces spectra containing three major ions represented by AH, BH, and CH in Figure 1 and Table 1. These ions are 1 + amu greater than the parent fragments A, B, and C (Porter and Betowski, 1981;Plattner et al, 1983;Yates et al, 1985). The major fragments used to identify the known ergopeptine alkaloids by this method are outlined in Table 1.…”

Section: Mass Spectrometry Identification and Quantitativementioning

confidence: 99%

See 1 more Smart Citation

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

1995

Journal of Animal Science

162

110

View full text Add to dashboard Cite

Research on livestock toxicoses caused by Acremonium (endophyte)-infected grasses strongly implicate the ergopeptine alkaloids with A. coenophialum-infected fescue and paxilline and the lolitrem alkaloids with A. lolii-infected perennial ryegrass as the causative agents. Isolation, identification, and detection of these toxins involves extraction with appropriate solvents, clean-up procedures, and chromatographic methods with known standards. Thin-layer, high-performance liquid and gas chromatography along with ultraviolet and mass spectrometric (i.e., electron impact, chemical ionization, tandem mass) characterizations have been reported. These methods have varying degrees of success depending on the matrix from which the alkaloids have been extracted. Ergovaline is the primary ergopeptine alkaloid isolated from cultures of A. coenophialum and also from infected fescue grass and seeds toxic to livestock. Other compounds isolated from the endophyte-infected fescue include: lysergic acid amide (ergine), the clavine class of ergot alkaloids (chanoclavine I, agroclavine, elymoclavine, penniclavine), the pyrrolizidine alkaloids (N-formylloline, N-acetylloline, N-methyloline, N-acetylnorloline), and the unique pyrrolopyrazine alkaloid peramine. The loline alkaloids and peramine have been more associated with the insect-deterrent properties of the endophyte-infected fescue than with livestock toxicoses. Also, both peramine and the ergopeptine alkaloids (ergovaline, ergotamine) have been isolated from A. lolii-infected perennial ryegrass. More recently, paxilline and lolitrem B have been detected in laboratory cultures of A. coenophialum isolated from tall fescue. The ergot alkaloids in endophyte-infected perennial ryegrass may be more related to decreased animal productivity (weight gains, reproduction problems), whereas the lolitrems cause the staggers syndrome. The detection, isolation, identification, and analyses of these compounds from Acremonium-infected grasses is presented.

show abstract

Section: Mass Spectrometry Identification and Quantitativementioning

confidence: 99%

Section: Mass Spectrometry Identification and Quantitativementioning

confidence: 99%

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

1995

Journal of Animal Science

162

110

View full text Add to dashboard Cite

show abstract

“…3) or solely by the grass (such as perloline, Fig. 4 [Yates, 1983]), and others that appear only in infected plants but that have not been identified in fungal cultures, such as the lolines (Fig. 5).…”

Section: Animal Toxicitymentioning

confidence: 99%

“…gangrene of the extremities (fescue foot), hard masses of fat deposits that cause digestive and calving problems (fat necrosis), and a summer condition of heat intolerance, rough coat, poor weight gain, excessive salivation, lower milk production, and reduced pregnancy rate (summer slump syndrome). The observations that fescue toxicosis was linked to the presence of an endophyte [Bacon et al, 19771 and that alkaloid toxins were produced by the association of the endophyte and grass, and the detection of ergopeptine alkaloids by tandem mass spectrometry [Plattner et al, 1983;Yates et al, 19851 are milestones along the way of resolving the problems associated with grazing endophyte-infected tall fescue (EITF).…”

Section: Tall Fescuementioning

confidence: 99%

Alkaloid toxins in endophyte‐infected grasses

Powell

Petroski

1993

Natural Toxins

View full text Add to dashboard Cite

Grasses infected with clavicipitaceous fungi have been associated with a variety of diseases including classical ergotism in humans and animals, fescue foot and summer syndrome in cattle, and rye-grass staggers in sheep. During the last decade it has been recognized that many of these fungal infections are endophytic; a fungal endophyte is a fungus that grows entirely within the host plant. Inspection of field collections and herbarium specimens has revealed that such infections are widespread in grasses. The chemistry associated with these grass-fungal interactions has proved to be interesting and complex, as each grass-fungal pair results in a unique "fingerprint" of various alkaloids, of which some are highly toxic to herbivores. In many cases the presence of an endophyte appears to benefit the plant by increasing drought resistance, or by increasing resistance to attack by insects, thus improving the overall survivability of the grass. This review will focus on alkaloids that have been reported in endophyte-infected grasses.

show abstract

“…Daughter ions were collected for the ergocryptine parent ion m/Z 308. Typical daughter spectra were obtained with base peak m/Z 209 as described by Plattner, Yates & Porter (1983) and Rottinghaus et al (1993).…”

Section: Chemical Analysesmentioning

confidence: 99%

<i>Claviceps cyperi</i>, a new cause of severe ergotism in dairy cattle consuming maize silage and teff hay contaminated with ergotised <i>Cyperus esculentus</i> (nut sedge) on the Highveld of South Africa

Naudé¹,

Botha²,

Vorster³

et al. 2005

Onderstepoort J Vet Res

View full text Add to dashboard Cite

NAUDÉ, T.W., BOTHA, C.J., VORSTER, J.H., ROUX, C., VAN DER LINDE, E.J., VAN DER WALT, S.I., ROTTINGHAUS, G.E., VAN JAARSVELD, L. & LAWRENCE, A.N. 2005. Claviceps cyperi, a new cause of severe ergotism in dairy cattle consuming maize silage and teff hay contaminated with ergotised Cyperus esculentus (nut sedge) on the Highveld of South Africa. Onderstepoort Journal of Veterinary Research, During December/January 1996/97 typical summer syndrome (hyperthermia and a 30 % drop in milk yield) occurred in succession in two Holstein dairy herds (n = 240 and n = 150 milking cows, respectively) on the South African Highveld. These farms are situated in the midst of the prime maize and dairy farming areas of South Africa where this condition had never been diagnosed before.The individual components of the concentrate on both farms were negative for ergot alkaloids. Endophytic fungi and/or ergot infestation of teff and other grasses fed to the cows were then suspected of being involved, but neither endophytes nor ergot alkaloids could be implicated from these sources.By measuring the serum prolactin levels of groups of sheep (n = 5) fed the first farm's total mixed ration (TMR) or its three individual fibre components for a period of 11 days, the source of the ergot alkaloids was identified. A statistically significant decrease in the level of this hormone occurred only in the group on maize silage (which constituted 28 % on dry matter base of the TMR). The involvement of the maize silage was further chemically confirmed by the high levels of total ergot alkaloids, predominantly ergocryptine, found by LC-MS in the silage as well as in the TMR (115-975 ppb and 65-300 ppb, respectively). The ergot alkaloid content (mainly ergocryptine) of the maize silage on the second affected farm was 875 ppb. Withdrawal of contaminated silage resulted in gradual recovery of stock on both farms.Nut sedge (Cyperus esculentus and Cyperus rotundus of the family Cyperaceae) has a world-wide distribution and is a common weed in annual crops, and can be parasitized by Claviceps cyperi. Careful examination of the maize silage from both farms revealed that it was heavily contaminated 1 Division of Toxicology, ARC-Onderstepoort Veterinary Institute, Private Bag X05,

show abstract

Quadrupole mass spectrometry/mass spectrometry of ergot cyclol alkaloids

Cited by 25 publications

References 3 publications

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

Alkaloid toxins in endophyte‐infected grasses

<i>Claviceps cyperi</i>, a new cause of severe ergotism in dairy cattle consuming maize silage and teff hay contaminated with ergotised <i>Cyperus esculentus</i> (nut sedge) on the Highveld of South Africa

Contact Info

Product

Resources

About