The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom
Abstract
:1. Introduction
2. Hemlock Alkaloids and Their Chemistry
3. Plant Containing Hemlock Alkaloids
3.1. Conium sp.
3.2. Aloe sp.
3.3. Sarracenia sp.
3.4. Other Plants Possibly Containing Hemlock Alkaloids
4. Biosynthesis of Hemlock Alkaloids
5. Biological Activity of Hemlock Alkaloids
5.1. Mode of Action of Hemlock Alkaloids in Organisms
5.2. Pharmacology of Poison Hemlock and Hemlock Alkaloids
5.3. Toxicity to Animals
5.4. Teratogenicity to Animals
5.5. Toxicity to Humans
5.6. Socrates
6. Ecological Role of Hemlock Alkaloids
7. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Language | Name |
---|---|
Argentina | cicuta, denta |
Belgium | dolle kervel, gevlekte scheerling |
Brazil | cicuta, cicuta da europa, cigue, cuquta maior, funcho selvagem |
Chile | cicuta, sarrac |
Denmark | skarntyde |
Finland | myrkkykatko |
France | grande cique |
Germany | Gefleckter Schierling |
Italy | cicuta maggiore |
Japan | doku-ninjin |
Portugal | ansarina-malhada |
Spain | perejillon cicuta |
Sweden | odört |
Turkey | tri baldiran |
Aloe Species | Alkaloids |
---|---|
A. ballyii Reynolds | γ-coniceine, conhydrinone |
A. deltoideodonta Baker | γ-coniceine, a trace of pseudoconhydrine |
A. descoingsii Reynolds | coniine, conhydrine |
A. gariepensis Pillans | γ-coniceine, conhydrine, a trace of coniine and N-methylconiine |
A. globuligemma Pole Evans | γ-coniceine, coniine, conhydrine, N-methylconiine |
A. gracilicaulis Reynolds and P.R.O. Bally | γ-coniceine |
A. ibitiensis Perrier | γ-coniceine |
A. krapholiana Marloth. | coniine, conhydrine |
A. ortholopha Christian and Milne-Redh. | coniine, conhydrine |
A. ruspoliana Baker | γ-coniceine |
A. sabaea Schweinf. (syn. A. gillilandii Reynolds) | γ-coniceine, coniine, N,N-dimethylconiine |
A. viguieri Perrier | coniine, γ-coniceine, N-methylconiine |
EC50 of the Cell Line Expressing nAChR | ||
---|---|---|
Alkaloid | TE-671 | SH-SY5Y |
(−)-coniine | 115 μM | 9.6 μM |
(±)-coniine | 208 μM | 51.4 μM |
(+)-coniine | 900 μM | 10.2 μM |
γ-coniceine | 1.3 μM | - |
(−)-N-methylconiine | 105 μM | - |
(±)-N-methylconiine | 405 μM | - |
(+)-N-methylconiine | 3000 μM | - |
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Hotti, H.; Rischer, H. The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom. Molecules 2017, 22, 1962. https://doi.org/10.3390/molecules22111962
Hotti H, Rischer H. The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom. Molecules. 2017; 22(11):1962. https://doi.org/10.3390/molecules22111962
Chicago/Turabian StyleHotti, Hannu, and Heiko Rischer. 2017. "The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom" Molecules 22, no. 11: 1962. https://doi.org/10.3390/molecules22111962