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Polyacetylenes from Sardinian Oenanthe fistulosa : A Molecular Clue to risus sardonicus

2009; American Chemical Society; Volume: 72; Issue: 5 Linguagem: Inglês

10.1021/np8007717

1520-6025

Giovanni Appendino, Federica Pollastro, Luisellá Verotta, Mauro Ballero, Adriana Romano, Paulina Wyrembek, Katarzyna Szczuraszek, Jerzy W. Mozrzymas, Orazio Taglialatela‐Scafati,

Alkaloids: synthesis and pharmacology

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).