62. Oenanthotoxin and cicutoxin. Isolation and structures

Abstract

0.2 IIg. suspended in lecithin-saline administered intraperitoneally to a mouse of ca. 20 g. Carbon.Skeletons and Oxygept Functions.-Oenanihotoxiii and cicutoxin are diols, oenanthetol and cicutol alcohols, and oenanthetone is an unconjugated ketone. The oxygen functions were disclosed by the usual reagents but the products were very difficult

Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform

“…This notwithstanding, the isolation of Cicutoxin (2) was reported as early as 1915 3 and its structural determination along with the first (low-yielding) racemic total synthesis waited until 1953. 4,5 The stereochemical assignment of Cicutoxin (2) and Virol A (1) along with their relative toxicity was first reported much later in 1999, 6 followed by the first asymmetric total synthesis of Virol A…”

Water Hemlock (Cicuta Douglasii) Toxicoses in Sheep: Pathologic Description and Prevention of Lesions and Death

“…Cicutoxin (C 17 H 22 O 2 ) is a potent neurotoxin, whereas the alcohol cicutol (C 17 H 22 O) is relatively nontoxic, as demonstrated in a mouse bioassay. 1 Similarly, the isomeric form of cicutoxin, oenanthotoxin (C 17 H 22 O 2 ) from Oenanthe crocata (hemlock water dropwort) found in England, was equally toxic, whereas oenanthetol (C 17 H 22 O) was nontoxic. 1 A similar compound found in carrots (Daucus carota L.), trans-1, 10-heptadecadiene-5, 7-diyne-3-ol (C 17 H 24 O), was toxic in mice (LD 50 = 100 mg/kg).…”

“…1 Similarly, the isomeric form of cicutoxin, oenanthotoxin (C 17 H 22 O 2 ) from Oenanthe crocata (hemlock water dropwort) found in England, was equally toxic, whereas oenanthetol (C 17 H 22 O) was nontoxic. 1 A similar compound found in carrots (Daucus carota L.), trans-1, 10-heptadecadiene-5, 7-diyne-3-ol (C 17 H 24 O), was toxic in mice (LD 50 = 100 mg/kg). 6 Because of the small amount of this compound found in carrots, it is not considered a human health concern.…”

“…This oily substance contains The long-term effects may include electroencephaloconcentrated quantities of the toxin and has been used graphic abnormalities (up to 3 months after poisoning) in extraction and identification experiments. 1,2 The and occasional anxiety neurosis. 11 Full recovery was toxicant, cicutoxin (C 17 H 22 O 2 ), is a long-chain highly noted 6 months after the poisoning episode.…”

Toxic Alcohols: Aliphatic Unsaturated Alcohols

“…Oenanthotoxin is an isomer of cicutoxin isolated from a water hemlock (Cicuta virosa L.), with the only difference in the position of a single double bond, located next to the secondary oxymethine in cicutoxin and adjacent to the primary hydroxyl in oenanthotoxin (Anet et al, 1952(Anet et al, , 1953. Recently it has been revealed that oenanthotoxin and other polyacetylene compounds downregulate GABAergic currents (Appendino et al, 2009), induce open channel block and allosterically modulate GABA A receptors (Wyrembek et al, 2010).…”