Polyacetylenes from sardinian Oenanthe fistulosa: a molecular clue to risus sardonicus.
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).
Appendino
Giovanni
G
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Viale Ferrucci 33, 28100 Novara, Italy. appendino@pharm.unipmn.it
Pollastro
Federica
F
Verotta
Luisella
L
Ballero
Mauro
M
Romano
Adriana
A
Wyrembek
Paulina
P
Szczuraszek
Katarzyna
K
Mozrzymas
Jerzy W
JW
Taglialatela-Scafati
Orazio
O
D019661:Apiaceae / Q000737:chemistry*; D053280:Diynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000506:poisoning; D053281:Enediynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000506:poisoning; D005233:Fatty Alcohols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000506:poisoning; D018756:GABA Antagonists / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D058787:GABA-A Receptor Antagonists; D007558:Italy; D015394:Molecular Structure; D009498:Neurotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000506:poisoning; D031050:Oenanthe / Q000506:poisoning; D010939:Plant Poisoning / Q000209:etiology*; D018517:Plant Roots / Q000737:chemistry; D053279:Polyynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000506:poisoning; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D053280:Diynes; D053281:Enediynes; D005233:Fatty Alcohols; D018756:GABA Antagonists; D058787:GABA-A Receptor Antagonists; D009498:Neurotoxins; D053279:Polyynes; C010719:enanthotoxin; C010697:cicutoxin