Polyacetylenes from sardinian Oenanthe fistulosa: a molecular clue to risus sardonicus.

Abstract

An investigation of Oenanthe fistulosa from Sardinia afforded oenanthotoxin (1a) and dihydrooenanthotoxin (1b) from the roots and the diacetylenic epoxydiol 2 from the seeds. The absolute configuration of 1a and 1b was established as R by the modified Mosher's method, and the structure of 2 by chemical correlation with (+)-(3R,8S)-falcarindiol. Oenanthotoxin (1a) and dihydrooenanthotoxin (1b) were found to potently block GABAergic responses, providing a molecular rationale for the symptoms of poisoning from water-dropwort (Oenanthe crocata) and related plants. These observations bear relevance for a series of historical and ethnopharmacological observations on the identification of the Sardonic herb and the molecular details of the facial muscular contraction caused by its ingestion (risus sardonicus).

• Authors: Giovanni Appendino, Federica Pollastro, Luisella Verotta, Mauro Ballero, Adriana Romano, Paulina Wyrembek, Katarzyna Szczuraszek, Jerzy W Mozrzymas, Orazio Taglialatela-Scafati
• Journal: Journal of natural products (J Nat Prod) Vol. 72 Issue 5 Pg. 962-5 (May 22 2009) ISSN: 1520-6025 [Electronic] United States
• PMID: 19245244 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Diynes
• Enediynes
• Fatty Alcohols
• GABA Antagonists
• GABA-A Receptor Antagonists
• Neurotoxins
• Polyynes
• enanthotoxin
• cicutoxin

Topics

• Apiaceae (chemistry)
• Diynes (chemistry, isolation & purification, pharmacology, poisoning)
• Enediynes (chemistry, isolation & purification, pharmacology, poisoning)
• Fatty Alcohols (chemistry, isolation & purification, pharmacology, poisoning)
• GABA Antagonists (chemistry, isolation & purification, pharmacology)
• GABA-A Receptor Antagonists
• Italy
• Molecular Structure
• Neurotoxins (chemistry, isolation & purification, pharmacology, poisoning)
• Oenanthe (poisoning)
• Plant Poisoning (etiology)
• Plant Roots (chemistry)
• Polyynes (chemistry, isolation & purification, pharmacology, poisoning)
• Seeds (chemistry)
• Stereoisomerism
• Structure-Activity Relationship