Mezerein
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| General | ||||||||||||||||
| Surname | Mezerein | |||||||||||||||
| other names |
12 β - [( E , E ) -5-phenyl-2,4-pentadienoyloxy] daphnetoxin |
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| Molecular formula | C 38 H 38 O 10 | |||||||||||||||
| Brief description |
colorless solid |
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| properties | ||||||||||||||||
| Molar mass | 654.71 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Mezerein is an ester of 12 β -hydroxy daphnetoxins with the xanthophyll Juarezinsäure (C 11 H 10 O 2 ). The substance showed an anti-tumor effect in animal experiments .
Occurrence and history
Mezerein is mainly in the seeds of Seidelbast such as Daphne mezereum ( Daphne Mezereum ) before. Only the seeds contain up to 0.1% of the toxin, as well as daphnetoxin . The fruits and the rest of the plant are much less toxic. In the past, the seeds of Daphne mezereum were popularly used as emetics, for constipation and to treat cancer . Externally it was used for gout, rheumatism and skin diseases. In agriculture, the seeds were also used as fish poison.
Effect and hazard information
In the standard protocol of the National Cancer Institute ( NCI ), an ethanol / water extract of the seeds has an oral antileukemic effect against both P-388 and in a dose of 50 μg / kg against P-1210 mouse leukemia. When administered dermally in doses between 12 and 13 μg / application, Mezerein had a strong tumor-promoting effect .
For humans, the mezerein and thus the seeds are highly toxic and lead to severe symptoms of illness with burning in the mouth and throat, swelling of the face and lips, feeling thirsty , vomiting and bloody diarrhea after just a few hours of oral intake . Chronic consumption of mezerein damages the kidneys. About 10–12 seeds lead to death. Externally, the toxin has a strong skin irritation with the formation of swellings, blisters and severe itching. The dermal threshold is around 1 μg.
literature
- Ronlán, A. and Wickberg, B .: The structure of mezerein, a major toxic principle of Daphne mezereum L Tetrahedron Lett. 1970 Oct; 49: 4261-4, PMID 5495053 .
Individual evidence
- ↑ a b c data sheet Mezerein, from Daphne mezereum, ≥ 97% (HPLC) from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).
- ↑ a b c H. HJ Hager, F. v. Bruchhausen: Hager's handbook of pharmaceutical practice . Vol. 2, Drugs AK, pp. 503-505, Birkhäuser-Verlag, ISBN 3-540-61618-7 .
- ^ R. Hegnauer, M. Hegnauer: Chemotaxonomie Der Pflanzen: An overview of the distribution and the systematic importance of plant substances, Birkhäuser-Verlag, 1973, ISBN 3-7643-0667-X .
- ↑ E. Beubler: Compendium of Pharmacology: Usual Medicines in Practice. P. 248, Springer-Verlag , 2007, ISBN 3-211-72054-5 .