Gyromitrin, das gift der fruehjahrslorchel, gyromitra (helvella) esculenta fr.

Natural Products Containing a Nitrogen–Nitrogen Bond

“…Gyromitrin (107) and small concentrations of various derivatives (108−113) were isolated from Gyromitra esculenta in 1967. 104 It is believed that several high molecular weight adducts and glycosylated derivatives of gyromitrin (107) also exist in the flesh of the mushroom. 105 The mushroom G. esculenta and its relatives, commonly known as false morel, had been long suspected of poisonings known as "Gyromitra syndrome", the effects of which range from gastrointestinal symptoms to coma and fatality.…”

Natural Toxicants in Foods

“…False morels are used as food after cooking or drying (Schmidlin-Meszaros, 1975). The structure of gyromitrin was reported in 1967 (list and Luft, 1967) (Fig. 36).…”

Mushroom Toxins: Chemistry and Toxicology

“…A toxin, acetaldehyde N-methyl-N-formylhydrazone, was isolated from G. esculenta in 1967 and was named gyromitrin (Ia, 43). 117 Homologues of gyromitrin, 44−51, were discovered in 1975 and 1976 (Figure 6). 116,118 Gyromitrin (LD 50 20−50 mg/kg) is a slightly volatile and heat-sensitive liquid, easily decomposing to the more toxic Nmethyl-N-formlhydrazin (MFH), followed by N-methylhydrazine (monomethylhydrazine, MH, LD 50 4.8−8 mg/kg) (Scheme 8) at high temperature or under specific physiological conditions.…”

“…Interestingly, this mushroom must be boiled or dried before eating, as fresh or incompletely processed false morel is highly poisonous, causing many fatal cases, which are worse if the associated juices or broth are not discarded. , These facts suggest that the toxic substances are heat-sensitive, volatile, and water-soluble. A toxin, acetaldehyde N -methyl- N -formylhydrazone, was isolated from G. esculenta in 1967 and was named gyromitrin (Ia, 43 ) . Homologues of gyromitrin, 44 – 51 , were discovered in 1975 and 1976 (Figure ).…”