Occurrence of the Fungal Toxin Orellanine as a Diglucoside and Investigation of Its Biosynthesis

✍ Scribed by Peter Spiteller; Michael Spiteller; Wolfgang Steglich

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 114 KB
• Volume: 42
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200351066

✦ Synopsis

Dedicated to Professor Meinhart H. Zenk on the occasion of his 70th birthday

The deadly poisonous toadstool Cortinarius orellanus (Fr.) Fr. [1] causes an irreversible loss of kidney function within one to two weeks after ingestion. [2] The toxicity of this fungus was recognized nearly 50 years ago after a tragic mass poisoning in Poland, which caused several deaths. [3] The responsible toxin, orellanine, [4] was assigned the structure 2,2'-bipyridine-3,3',4,4'-tetrol-1,1'-dioxide (1), [5] which has been confirmed by several syntheses [6] and a crystal structure analysis. [7] In this communication we report initial investigations on the biosynthesis of orellanine and the discovery that the toxin occurs mainly as the water-soluble 4,4'-diglucopyranoside 5.