Ricinoleic Acid as a Marker for Ergot Impurities in Rye and Rye Products

Franzmann, Carolin; Wachter, J.K.; Dittmer, Natascha; Humpf, Hans‐Ulrich

doi:10.1021/jf1006903

Cited by 35 publications

(53 citation statements)

References 18 publications

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“…4. In the rye itself, no ergot alkaloids were detectable regarding to a limit of quantification of 1.1-6.7 µg/kg for each single ergot alkaloid (Franzmann et al 2010).…”

Section: Resultsmentioning

confidence: 99%

“…Analysis of ricinoleic acid Ricinoleic acid was analyzed with GC-FID and quantified by use of the internal standard 15-hydroxypentadecanoic acid after hydrolysis of the fat and extraction of the fatty acids (Franzmann et al 2010). Analysis of ergot alkaloids Ergot alkaloids were analyzed by use of HPLC-FLD and quantified by means of the internal standard methysergide after an alkaline organic extraction according to Mϋller et al (2009).…”

Section: Methodsmentioning

confidence: 99%

“…An average amount of 0.2% (0.01-0.5%) is given by Lorenz (1979). However, our own measurements of the ergot alkaloid contents of 63 ergot sclerotia samples resulted in an average amount of 0.08% (757 mg/kg) (Franzmann et al 2010).…”

Section: Introductionmentioning

confidence: 98%

“…Our recent investigations have shown that the ricinoleic acid concentration (average amount in the ergot sclerotia: 103 g/ kg, n=55) correlates with the total ergot content (Franzmann et al 2010).…”

Section: Introductionmentioning

confidence: 99%

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Distribution of ergot alkaloids and ricinoleic acid in different milling fractions

et al. 2010

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The sclerotia of the fungus Claviceps sp. are still a challenge for the milling industry. Ergot sclerotia are a constant contamination of the rye crop and have to be removed by modern milling technologies. Changing sizes and coloration of the sclerotia make it difficult to separate them from the grain. Ergot sclerotia are a problem when cleaning is insufficient and non-separated specimens or sclerotia fragments get into the milling stream and thus ergot alkaloids are distributed into the different cereal fractions. In model milling experiments, the residues of ergot in rye flour and the distribution of ergot into different milling fractions were investigated. Rye grains were mixed with whole ergot sclerotia and in another experiment with ergot powder and cleaned afterwards before milling. The ergot alkaloids ergometrine, ergosine, ergotamine, ergocornine, ergocryptine, ergocristineand their related isomeric forms (-inine-forms), and additionally ricinoleic acid as a characteristic component of ergot, were quantified in the different milling fractions. From the first experiment, it can be shown that after harvesting even simple contact of sclerotia with bulk grains during ordinary handling or movement of bulk grain in the granary is sufficient to contaminate all the healthy or sound rye grains with ergot alkaloids. Thereby, the amount of ergot residue correlates with the amount of peripheral layers of rye grains in the flour. In an additional experiment without sclerotia specimens, bulk rye grains were loaded with powder of sclerotia. After subsequent cleaning, aconcentration of ergot alkaloids was detected, which was tenfold higher than the ergot alkaloidconcentration of the experiment with intact ergot sclerotia.

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“…4. In the rye itself, no ergot alkaloids were detectable regarding to a limit of quantification of 1.1-6.7 µg/kg for each single ergot alkaloid (Franzmann et al 2010).…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Distribution of ergot alkaloids and ricinoleic acid in different milling fractions

et al. 2010

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“…Ergotamine/-inine and ergocristine/-inine were used as model compounds, since they differ only slightly in their toxicity, but are nearly structurally identical. It is also reported, that the main alkaloid composition of sclerotia is up to 58% ergotamine and ergocristine, along with their corresponding 8-(S) isomers [37,38].…”

Section: Barrier Integritymentioning

confidence: 88%

Permeability of ergot alkaloids across the blood‐brain barrier in vitro and influence on the barrier integrity

Mulac

Hüwel

Galla

et al. 2011

Molecular Nutrition Food Res

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ScopeErgot alkaloids are secondary metabolites of Claviceps spp. and they have been in the focus of research for many years. Experiments focusing on ergotamine as a former migraine drug referring to the ability to reach the brain revealed controversial results. The question to which extent ergot alkaloids are able to cross the blood-brain barrier is still not answered.Methods and resultsIn order to answer this question we have studied the ability of ergot alkaloids to penetrate the blood-brain barrier in a well established in vitro model system using primary porcine brain endothelial cells. It could clearly be demonstrated that ergot alkaloids are able to cross the blood-brain barrier in high quantities in only a few hours. We could further identify an active transport for ergometrine as a substrate for the BCRP/ABCG2 transporter. Investigations concerning barrier integrity properties have identified ergocristinine as a potent substance to accumulate in these cells ultimately leading to a weakened barrier function.ConclusionFor the first time we could show that the so far as biologically inactive described 8-(S) isomers of ergot alkaloids seem to have an influence on barrier integrity underlining the necessity for a risk assessment of ergot alkaloids in food and feed.

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Alkaloids, Pharmaceutical Analysis of

Gilpin

2000

Encyclopedia of Analytical Chemistry

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As a major class of compounds, alkaloids are naturally occurring bases with a wide range of structures, chemical, and physical properties, and pharmacological activities. The use of alkaloids as medical agents in the form of crude plant powders and extracts predates the modern pharmaceutical industry by almost four millennia and in some instances prior to modern science. Mass poisonings have resulted from their inadvertent usage and was prevalent in Europe during the Middle Ages as the result of the general populace eating bread contaminated with Claviceps purpurea . The C. purpurea fungus produces an ergot alkaloid that first affects the central nervous system causing hallucinogenic effects and later death if enough is ingested. Ergot poisoning in the Middles Ages is perhaps best known for its effect on the painters “of‐the‐day” and their impressionistic styles and use of vivid colors.

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Ricinoleic Acid as a Marker for Ergot Impurities in Rye and Rye Products

Cited by 35 publications

References 18 publications

Distribution of ergot alkaloids and ricinoleic acid in different milling fractions

Distribution of ergot alkaloids and ricinoleic acid in different milling fractions

Permeability of ergot alkaloids across the blood‐brain barrier in vitro and influence on the barrier integrity

Alkaloids, Pharmaceutical Analysis of

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