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).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Apiaceae / chemistry*
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Diynes / chemistry
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Diynes / isolation & purification*
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Diynes / pharmacology
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Diynes / poisoning
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Enediynes / chemistry
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Enediynes / isolation & purification*
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Enediynes / pharmacology*
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Enediynes / poisoning
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Fatty Alcohols / chemistry
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Fatty Alcohols / isolation & purification*
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Fatty Alcohols / pharmacology*
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Fatty Alcohols / poisoning
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GABA Antagonists / chemistry
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GABA Antagonists / isolation & purification*
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GABA Antagonists / pharmacology*
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GABA-A Receptor Antagonists*
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Italy
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Molecular Structure
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Neurotoxins / chemistry
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Neurotoxins / isolation & purification*
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Neurotoxins / pharmacology*
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Neurotoxins / poisoning
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Oenanthe / poisoning
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Plant Poisoning / etiology*
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Plant Roots / chemistry
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Polyynes / chemistry
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Polyynes / isolation & purification*
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Polyynes / pharmacology*
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Polyynes / poisoning
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Seeds / chemistry
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Diynes
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Enediynes
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Fatty Alcohols
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GABA Antagonists
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GABA-A Receptor Antagonists
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Neurotoxins
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Polyynes
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enanthotoxin
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cicutoxin