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

被引：46

作者：

Appendino, Giovanni ^{[1
,2
]}

Pollastro, Federica ^{[1
,2
]}

Verotta, Luisella ^{[3
]}

Ballero, Mauro ^{[2
]}

Romano, Adriana ^{[4
]}

Wyrembek, Paulina ^{[5
]}

Szczuraszek, Katarzyna ^{[5
]}

Mozrzymas, Jerzy W. ^{[5
]}

Taglialatela-Scafati, Orazio ^{[4
]}

机构：

[1] Univ Piemonte Orientale, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy

[2] COSMESE, I-09123 Cagliari, Italy

[3] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[4] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

[5] Wroclaw Med Univ, Dept Biophys, Neurosci Lab, PL-50368 Wroclaw, Poland

来源：

JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 05期

基金：

英国惠康基金;

关键词：

D O I：

10.1021/np8007717

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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).

引用

页码：962 / 965

页数：4

共 21 条

[1] Immunoglobulins from motoneurone disease patients enhance glutamate release from rat hippocampal neurones in culture [J].