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).

Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus / G., Appendino; F., Pollastro; L., Verotta; M., Ballero; A., Romano; P., Wyrembek; K., Szczuraszek; J. W., Mozrzymas; TAGLIALATELA SCAFATI, Orazio. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 72:(2009), pp. 962-965. [10.1021/np8007717]

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

TAGLIALATELA SCAFATI, ORAZIO
2009

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).
2009
Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus / G., Appendino; F., Pollastro; L., Verotta; M., Ballero; A., Romano; P., Wyrembek; K., Szczuraszek; J. W., Mozrzymas; TAGLIALATELA SCAFATI, Orazio. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 72:(2009), pp. 962-965. [10.1021/np8007717]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/351741
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