Alkaloids in the human food chain – Natural occurrence and possible adverse effects

Koleva, Irina; Beek, T.A. van; Soffers, A.E.M.F.; Dusemund, Birgit; Rietjens, Ivonne M. C. M.

doi:10.1002/mnfr.201100165

Cited by 162 publications

(89 citation statements)

References 121 publications

(160 reference statements)

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“…Steroids in mammals are products of terpenoid metabolism (9). More than 12,000 alkaloids have been discovered (10). Flavonols and flavones are produced widely in plants and are mainly concentrated in the outer tissues.…”

Section: Resultsmentioning

confidence: 99%

Drug Discovery Inspired by Mother Nature: Seeking Natural Biochemotypes and the Natural Assembly Rules of the Biochemome

Yan

2013

J Pharm Pharm Sci

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Purpose. The Human Genome Project is producing a new biological ‘periodic table’, which defines all genes for making macromolecules (proteins, DNA, RNA, etc) and the relations between genes and their biological functions. We now need to consider whether to initiate a biochemome project aimed at discovering biochemistry’s ‘periodic table’, which would define all molecular parts for making small molecules (natural products) and the relations between the parts and their functions to regulate genes. By understanding the Biochemome, we might be able to design biofunctional molecules based upon a set of molecular parts for drug innovation. Methods. A number of algorithms for processing chemical structures are used to systematically derive chemoyls (natural building blocks) from a database of compounds identified in Traditional Chinese Medicine (TCM). The rules to combine chemoyls for biological activities are then deduced by mining an annotated TCM structure-activity database (ATCMD). Based upon the rules and the basic chemoyls, a chemical library can be biochemically profiled, virtual synthetic routes can be planned, and lead compounds can be identified for a specific drug target. Conclusions. The Biochemome is the complete set of molecular components (chemoyls) in an organism and Biochemomics studies the rules governing their assembly and their evolution, together with the relations between the Biochemome and drug targets. This approach provides a new paradigm for drug discovery that is based on a comprehensive knowledge of the synthetic origins of biochemical diversity, and helps to direct biomimetic syntheses aimed at assembling quasi-natural product libraries for drug screening. This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

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Section: Resultsmentioning

confidence: 99%

Drug Discovery Inspired by Mother Nature: Seeking Natural Biochemotypes and the Natural Assembly Rules of the Biochemome

Yan

2013

J Pharm Pharm Sci

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“…PAs' acute and chronic liver toxicity in humans and other animals is well known, and some symptoms of acute PA poisoning are abdominal pain, nausea, vomiting, diarrhea, and edema (Koleva et al 2012). Highly toxic carcinogenic and genotoxic effects are reported as the main mechanism of action of PAs (Shimshoni et al 2015).…”

Section: Toxicity To Humans and Other Vertebratesmentioning

confidence: 99%

“…TAs are alkaloids derived from ornithine, and in many parts of the world, TA-containing plants have been used for folkloric and medicinal purposes due to their powerful anticholinergic (e.g., scopolamine) and hallucinogenic effects (e.g., hyoscyamine and atropine), causing constipation, photophobia, pupil dilatation, vision disturbance, and dryness of upper digestive and respiratory tract mucosa. Contaminations with TAs often occur via ingestion of food containing Datura, which accumulates high concentrations of scopolamine and hyoscyamine (Koleva et al 2012).…”

Section: Toxicity To Humans and Other Vertebratesmentioning

confidence: 99%

Plant Alkaloids: Main Features, Toxicity, and Mechanisms of Action

Matsuura

Fett-Neto

2015

Plant Toxins

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Alkaloids are one of the largest groups of plant secondary metabolites, being present in several economically relevant plant families. Alkaloids encompass neuroactive molecules, such as caffeine and nicotine, as well as life-saving medicines including emetine used to fight oral intoxication and the antitumorals vincristine and vinblastine. Alkaloids can act as defense compounds in plants, being efficient against pathogens and predators due to their toxicity. Fast perception of aggressors and unfavorable environmental conditions, followed by efficient and specific signal transduction for triggering alkaloid accumulation, are key steps in successful plant protection. Toxic effects, in general, depend on specific dosage, exposure time, and individual characteristics, such as sensitivity, site of action, and developmental stage. At times, toxicity effects can be both harmful and beneficial depending on the ecological or pharmacological context. Different strategies are used to study alkaloid metabolism and accumulation. An efficient approach is to monitor gene expression, enzyme activities, and concentration of precursors and of the alkaloid itself during controlled attacks of pathogens and herbivores or upon the simulation of their presence through physical or chemical stimulation. Detailed understanding of alkaloid biosynthesis and mechanisms of action is essential to improve production of alkaloids of interest, to discover new bioactive molecules, and to sustainably exploit them against targets of interest, such as herbivores, pathogens, cancer cells, or unwanted physiological conditions.

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“…Hall et al, 1977;Tiongson and Salen, 1998). Poisonings of humans by TA containing plants have been reviewed by Adamse and Egmond (2010) and Koleva et al (2012) and are mostly due to intake of parts of Brugmansia spp./Datura spp. or of Atropa belladonna.…”

Section: Intoxications Associated With Plants Containing Tropane Alkamentioning

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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Alkaloids in the human food chain – Natural occurrence and possible adverse effects

Cited by 162 publications

References 121 publications

Drug Discovery Inspired by Mother Nature: Seeking Natural Biochemotypes and the Natural Assembly Rules of the Biochemome

Drug Discovery Inspired by Mother Nature: Seeking Natural Biochemotypes and the Natural Assembly Rules of the Biochemome

Plant Alkaloids: Main Features, Toxicity, and Mechanisms of Action

Scientific Opinion on Tropane alkaloids in food and feed

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