Orellanine
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| Names | |
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IUPAC name
3,3′,4,4′-Tetrahydroxy-2,2′-bipyridine-N,N′-dioxide
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| Other names
Orellanin,
2,2-Bipyridine-3,3-4,4-tetrol-1,1-dioxide |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.232.424 |
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| Properties | |
| C10H8N2O6 | |
| Molar mass | 252.18 g·mol−1 |
| Hazards | |
| Main hazards | Highly toxic |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Orellanine or orellanin is a mycotoxin found in a group of mushrooms known as the Orellani of the Cortinariaceae family. Structurally, it is a pyridine N-oxide.
Orellanine first came to people's attention in 1957 when there was a mass poisoning of 135 people in Bydgoszcz, Poland, which resulted in 19 deaths. Orellanine comes from a class of mushrooms that fall under the genus Cortinarius. Although not all the species in this genus are poisonous/contain orellanine, it was found that Cortinarius orellanus, rubellus, henrici, rainerensis and bruneofulvus contain orellaine. Poisonings pertaining to these mushrooms were predominately in Europe where foraging was a major source of nourishment, although there are cases of orellanine poisoing in North America as well. Orellanine has been found to cause acute renal failure and there are many cases where people have taken this mushroom mistaking it for causing hallucinogenic effects.
It wasn't until 1962 until the first isolation of orellanine was done. The first methanolic extraction and isolation of orellanine was done by Stanisław Grzymala and isolated from the mushroom Cortinarius orellanus. Along with the isolation of orellanine, Grzymala was also able to demonstrate the nephrotoxicity of Cortinarius orellanus and determine various physical and chemical properties of orellanine. He found that the toxicity of the mushrooms was linked to delayed and acute renal failure, as well as when the isolated white crystalline substance was heated above 150 ̊C it began to slowly decompose. After this first isolation of orellanine, the structure of orellanine was first discovered by Antkowiak and Gessner in 1979. Orellanine’s structure was found to be 3,3',4,4'-tetrahydroxy- 2,2'-bipyridine-l,l'-dioxide. Antkowiak and Gessner were also able to determine that orellanine was the mono-N-oxide of orelline, which was the decomposition product of orellanine. It was also found that orelline was non-toxic. The first successful synthesis of orellanine was done in 1985. Tiecco, M. et. Al. completed a total synthesis of orellanine using commercially available 3-hydroxypyridine. After the first successful synthesis, the structure was confirmed in 1987 by Cohen-Addad et al. in 1987 by X-ray crystallography.
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