Simultaneous analysis of hyoscyamine, scopolamine, 6β-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography

Kursinszki, L.; Hank, H.; Imre, László; Szöke, Éva

doi:10.1016/j.chroma.2005.07.016

Cited by 66 publications

(40 citation statements)

References 39 publications

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“…The analysis of scopolamine and atropine was performed according to the procedure of [33,46], with modifications. Scharlau HPLC grade methanol and 10 mM sodium phosphate buffer, pH 3.0 were used.…”

Section: Hplc Analysis Of Alkaloids In the Nectarmentioning

confidence: 99%

Protein and alkaloid patterns of the floral nectar in some solanaceous species

Kerchner¹,

Darók²,

Bacskay³

et al. 2015

Acta Biologica Hungarica

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The family Solanaceae includes several melliferous plants, which tend to produce copious amounts of nectar. Floral nectar is a chemically complex aqueous solution, dominated by sugars, but minor components such as amino acids, proteins, flavonoids and alkaloids are present as well. This study aimed at analysing the protein and alkaloid profile of the nectar in seven solanaceous species. Proteins were examined with SDS-PAGE and alkaloids were analyzed with HPLC. The investigation of protein profile revealed significant differences in nectar-protein patterns not only between different plant genera, but also between the three Nicotiana species investigated. SDS-PAGE suggested the presence of several Nectarin proteins with antimicrobial activity in Nicotiana species. The nectar of all tobacco species contained the alkaloid nicotine, N. tabacum having the highest nicotine content. The nectar of Brugmansia suaveolens, Datura stramonium, Hyoscyamus niger and Lycium barbarum contained scopolamine, the highest content of which was measured in B. suaveolens. The alkaloid concentrations in the nectars of most solanaceous species investigated can cause deterrence in honeybees, and the nectar of N. rustica and N. tabacum can be considered toxic for honeybees.

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Section: Hplc Analysis Of Alkaloids In the Nectarmentioning

confidence: 99%

Protein and alkaloid patterns of the floral nectar in some solanaceous species

Kerchner¹,

Darók²,

Bacskay³

et al. 2015

Acta Biologica Hungarica

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“…Ultraviolet (UV) based methods are of limited value, since the TAs considered in this opinion show rather low absorption values at rather unspecific wavelengths (Bogusz and Erkens, 1994;Dräger, 2002;Kursinszki et al, 2005).…”

Section: Spectroscopic Methodsmentioning

confidence: 99%

Scientific Opinion on Tropane alkaloids in food and feed

2013

EFS2

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The European Food Safety Authority (EFSA) was asked to deliver a scientific opinion on the risks to human and animal health related to the presence of tropane alkaloids (TAs) in food and feed. TAs are secondary metabolites which occur in several plant families. Although more than 200 different TAs have been identified in various plants, respective data on toxicity and occurrence in food and feed are limited. Therefore, the EFSA Panel on Contaminants in the Food Chain (CONTAM Panel) could only perform a risk assessment on (-)-hyoscyamine and (-)-scopolamine, the two TAs for which occurrence and toxicity data were available. Since the pharmacological effects of (-)-hyoscyamine and (-)-scopolamine occur within a short time after administration, the CONTAM Panel concluded that it was appropriate to establish an Acute Reference Dose (ARfD) for these substances. Based on the results for decreased heart rate in a human volunteer study, the CONTAM Panel established a group ARfD of 0.016 µg/kg body weight (b.w.) expressed as the sum of (-)-hyoscyamine and (-)-scopolamine, assuming equivalent potency. Results on TAs in 124 food and 611 feed samples were collected in two Member States. Most of the food and feed samples were left-censored (below limit of detection/limit of quantification). A reliable exposure estimate was only possible for one food and one age class (toddlers). Based on the limited information, the CONTAM Panel concluded that the dietary exposure of toddlers could be up to seven times the group ARfD and could exceed the group ARfD on approximately 11 to 18 % of consumption days. TA toxicosis in livestock and companion animals is relatively rare. © European SUMMARYFollowing a request from the European Commission, the EFSA Panel on Contaminants in the Food Chain (CONTAM Panel) was asked to deliver a scientific opinion on the risks to human and animal health related to the presence of tropane alkaloids (TA) in food and feed.TAs are secondary metabolites which naturally occur in plants of several families including Brassicaceae, Solanaceae (e.g. mandrake, henbane, deadly nightshade, Jimson weed) and Erythroxylaceae (including coca). The TAs are found in all parts of the plants and are responsible for the toxic effects of some of these plants. TAs contain an azabicyclo[3.2.1]octane ring structure. The common structural element is the tropane skeleton, (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octane. The group of TAs comprises more than 200 compounds and the wide range of compounds occurring especially in the Solanaceae family arises from the esterification of tropine with a variety of acids, such as acetic acid, propanoic acid, isobutyric acid, isovaleric acid, 2-methylbutyric acid, tiglic acid, (+)-α-hydroxy-β-phenylpropionic acid, tropic acid, and atropic acid.Although more than 200 different TAs were so far identified in various plants, respective data on their occurrence in food and feed and on toxicity are limited. The most studied TAs are (-)-hyoscyamine and (-)-scopolamine, which in contrast to the (+...

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“…This method has the advantage of high precision and efficiency in the analysis, but the samples are exposed to rather high temperatures, which may cause decomposition of some alkaloids. At present, high performance liquid chromatography (HPLC) with reversed phase columns are considered as method of choice (Friedman and Levin, 1989;Papadoyannis, 1995) and various individual methods have been described in detail (Paphassarang, 1985;He et al, 1989;, Papadoyannis et al 1993Kursinszki et al 2005, andMroczek et al 2006). HPLC methods have also been developed specifically for the analysis of tropane alkaloid in animal feeds , and for tropane alkaloids in biological samples such as serum and urine (Namera et al, 2002).…”

Section: Methods Of Analysismentioning

confidence: 99%

Tropane alkaloids (from Datura sp.) as undesirable substances in animal feed - Scientific Opinion of the Panel on Contaminants in the Food Chain

2008

EFSA Journal

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SUMMARYThe term tropane alkaloids refers to a group of more than 200 compounds best known for their occurrence in the family Solanaceae comprising over 100 genera and 3000 plant species. They have in common a two-ringed structure characterized by a pyrrolidine and a piperidine ring sharing a single nitrogen atom and two carbons atoms. The nitrogen atom at the end of the molecule, which characterizes the compounds as alkaloids, is in this group characteristically methylated. The most important natural tropane alkaloids are (-)-hyoscyamine and (-)-scopolamine (also known as hyoscine). High concentrations of these alkaloids have been found particularly in Datura stramonium and Datura ferox, as well as in Datura innoxia. The pattern of tropane alkaloids differs significantly and in Datura stramonium (also known as thorn apple or Jimson weed) hyoscyamine prevails in most parts of the plant, whereas in Datura ferox scopolamine is the major alkaloid Tropane alkaloids as undesirable substances in animal feedThe EFSA Journal (2008) 691, 2-55 produced. Datura plants are toxic for animals if ingested in larger amounts. Their seeds, which contain significant amounts of hyoscyamine and scopolamine, can be found as botanical impurities in feed materials, particularly in soybean and linseed products.Very little information on the actual contamination of feed materials is available, and previous reports on adverse health effects in animals refer in most cases to accidental intoxications following the consumption of Datura plants rather than to the contamination of linseed and sobean contaning feed materials. Hence no conclusive exposure assessment could be presented for farm animals.Overall, pigs have been shown to be among the most sensitive species to Datura poisoning. A worst case exposure estimate indicated that adverse pharmacological effects in pigs following exposure to Datura ferox seeds, mainly containing scopolamine, can not be entirely excluded at the current statutory limits of 3000 mg/kg feed. However, the limited data also suggested that it is not likely that the presence of Datura stramonium impurities in animals feed up to the current statutory level of 1000 mg/kg would present a risk to animal health.The mechanism of action of tropane alkaloids relates to their competitive antagonism at muscarinic acetylcholine receptors, preventing the binding of acetylcholine. According to the specificity and selectivity of muscarinergic acetylcholine receptors in different organs, the functions of smooth muscles and exocrine gland cells, as well as the heart rate, respiration and functions in the central nervous system are modulated. Certain tropanes such as atropine (the racemic mixture of (-)-and (+)hyoscyamine) as well as scopolamine (mainly as butylscopolamine bromide) are used in human and veterinary therapy for a variety of related indications. Reports of poisoning of livestock and experimental feeding studies describe as most common symptoms associated with tropane alkaloids exposure dryness of the mucosa in the uppe...

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Simultaneous analysis of hyoscyamine, scopolamine, 6β-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography

Cited by 66 publications

References 39 publications

Protein and alkaloid patterns of the floral nectar in some solanaceous species

Protein and alkaloid patterns of the floral nectar in some solanaceous species

Scientific Opinion on Tropane alkaloids in food and feed

Tropane alkaloids (from Datura sp.) as undesirable substances in animal feed - Scientific Opinion of the Panel on Contaminants in the Food Chain

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