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Orellanine
Orellanine or orellanin is a toxin found in a group of mushrooms known as the Orellani within the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.
Orellanine first came to people's attention in 1952 when a mass poisoning of 102 people in Konin, Poland resulted in 11 deaths. Orellanine comes from a class of mushrooms that fall under the genus Cortinarius, and has been found in the species C. orellanus, rubellus, henrici, rainerensis and bruneofulvus. Poisonings related to these mushrooms have occurred predominately in Europe where mushroom foraging was common, though cases of orellanine poisoning have been reported in North America and Australia as well. There are several reported cases of people ingesting orellanine-containing mushrooms after mistaking them for edible or hallucinogenic mushrooms.
Orellanine was first isolated in 1962, when Stanisław Grzymala extracted and isolated orellanine from the mushroom C. orellanus. Grzymala was also able to demonstrate the nephrotoxicity of C. orellanus and determine various physical and chemical properties of orellanine. He found that the toxicity of the mushroom was due to both delayed and acute kidney injury.
The chemical structure of orellanine was first deduced by Antkowiak and Gessner in 1979, who identified it as 3,3',4,4'-tetrahydroxy- 2,2'-bipyridine-1,1'-dioxide.
The first successful synthesis of orellanine was reported in 1985. The total synthesis of orellanine starting with the bromination of 3-hydroxypyridine was reported a year later in 1986.
The first synthesis of orellanine was reported in 1985 by Dehmlow and Schulz, and required ten steps starting from 3-aminopyridine. The following year, Tiecco et al. reported the total synthesis of orellanine in nine steps starting from 3-hydroxypyridine.
Orellanine is a bipyridine N-oxide. Orellanine displays tautomerism, with the more stable tautomer being the pyridine N-oxide form.
The chemical structure of synthetically produced orellanine has been confirmed by X-ray crystallography. In this crystal structure, the two pyridine rings are nearly perpendicular to each other, making orellanine chiral. However, samples of orellanine extracted from mushrooms are optically inactive racemic mixtures, likely due to racemization during the extraction process.
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Orellanine
Orellanine or orellanin is a toxin found in a group of mushrooms known as the Orellani within the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.
Orellanine first came to people's attention in 1952 when a mass poisoning of 102 people in Konin, Poland resulted in 11 deaths. Orellanine comes from a class of mushrooms that fall under the genus Cortinarius, and has been found in the species C. orellanus, rubellus, henrici, rainerensis and bruneofulvus. Poisonings related to these mushrooms have occurred predominately in Europe where mushroom foraging was common, though cases of orellanine poisoning have been reported in North America and Australia as well. There are several reported cases of people ingesting orellanine-containing mushrooms after mistaking them for edible or hallucinogenic mushrooms.
Orellanine was first isolated in 1962, when Stanisław Grzymala extracted and isolated orellanine from the mushroom C. orellanus. Grzymala was also able to demonstrate the nephrotoxicity of C. orellanus and determine various physical and chemical properties of orellanine. He found that the toxicity of the mushroom was due to both delayed and acute kidney injury.
The chemical structure of orellanine was first deduced by Antkowiak and Gessner in 1979, who identified it as 3,3',4,4'-tetrahydroxy- 2,2'-bipyridine-1,1'-dioxide.
The first successful synthesis of orellanine was reported in 1985. The total synthesis of orellanine starting with the bromination of 3-hydroxypyridine was reported a year later in 1986.
The first synthesis of orellanine was reported in 1985 by Dehmlow and Schulz, and required ten steps starting from 3-aminopyridine. The following year, Tiecco et al. reported the total synthesis of orellanine in nine steps starting from 3-hydroxypyridine.
Orellanine is a bipyridine N-oxide. Orellanine displays tautomerism, with the more stable tautomer being the pyridine N-oxide form.
The chemical structure of synthetically produced orellanine has been confirmed by X-ray crystallography. In this crystal structure, the two pyridine rings are nearly perpendicular to each other, making orellanine chiral. However, samples of orellanine extracted from mushrooms are optically inactive racemic mixtures, likely due to racemization during the extraction process.