Identification of the toxic trigger in mushroom poisoning

Masanori Matsuura; Yoko Saikawa; Kosei Inui; Koichi Nakae; Masayuki Igarashi; Kimiko Hashimoto; Masaya Nakata

doi:10.1038/nchembio.179

Identification of the toxic trigger in mushroom poisoning

Nat Chem Biol. 2009 Jul;5(7):465-7. doi: 10.1038/nchembio.179.

Authors

Masanori Matsuura¹, Yoko Saikawa, Kosei Inui, Koichi Nakae, Masayuki Igarashi, Kimiko Hashimoto, Masaya Nakata

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama, Japan.

PMID: 19465932
DOI: 10.1038/nchembio.179

Abstract

We have isolated the small, highly strained carboxylic acid cycloprop-2-ene carboxylic acid from the Asian toxic mushroom Russula subnigricans. This compound is responsible for fatal rhabdomyolysis, a new type of mushroom poisoning that is indicated by an increase in serum creatine phosphokinase activity in mice. We found that polymerization of the compound at high concentrations via ene reaction abolishes its toxicity.

MeSH terms

Agaricales / chemistry*
Animals
Carboxylic Acids / chemical synthesis
Carboxylic Acids / isolation & purification*
Carboxylic Acids / toxicity
Cell Line, Tumor
Cyclopropanes / chemical synthesis
Cyclopropanes / isolation & purification*
Cyclopropanes / toxicity
Lethal Dose 50
Magnetic Resonance Spectroscopy
Mice
Mice, Inbred ICR
Molecular Structure
Mushroom Poisoning / etiology*
Mycotoxins / chemical synthesis
Mycotoxins / isolation & purification*
Mycotoxins / toxicity
Rhabdomyolysis / etiology*

Substances

Carboxylic Acids
Cyclopropanes
Mycotoxins
cycloprop-2-ene carboxylic acid