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The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom.
Hotti, Hannu; Rischer, Heiko.
Afiliação
  • Hotti H; VTT Technical Research Centre of Finland Ltd., P.O. Box 1000, 02044 Espoo, Finland. hannu.hotti@gmail.com.
  • Rischer H; VTT Technical Research Centre of Finland Ltd., P.O. Box 1000, 02044 Espoo, Finland. heiko.rischer@vtt.fi.
Molecules ; 22(11)2017 Nov 14.
Article em En | MEDLINE | ID: mdl-29135964
ABSTRACT
Coniine, a polyketide-derived alkaloid, is poisonous to humans and animals. It is a nicotinic acetylcholine receptor antagonist, which leads to inhibition of the nervous system, eventually causing death by suffocation in mammals. Coniine's most famous victim is Socrates who was sentenced to death by poison chalice containing poison hemlock in 399 BC. In chemistry, coniine holds two historical records It is the first alkaloid the chemical structure of which was established (in 1881), and that was chemically synthesized (in 1886). In plants, coniine and twelve closely related alkaloids are known from poison hemlock (Conium maculatum L.), and several Sarracenia and Aloe species. Recent work confirmed its biosynthetic polyketide origin. Biosynthesis commences by carbon backbone formation from butyryl-CoA and two malonyl-CoA building blocks catalyzed by polyketide synthase. A transamination reaction incorporates nitrogen from l-alanine and non-enzymatic cyclization leads to γ-coniceine, the first hemlock alkaloid in the pathway. Ultimately, reduction of γ-coniceine to coniine is facilitated by NADPH-dependent γ-coniceine reductase. Although coniine is notorious for its toxicity, there is no consensus on its ecological roles, especially in the carnivorous pitcher plants where it occurs. Lately there has been renewed interest in coniine's medical uses particularly for pain relief without an addictive side effect.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Piperidinas / Alcaloides Limite: Animals / Humans Idioma: En Ano de publicação: 2017 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Piperidinas / Alcaloides Limite: Animals / Humans Idioma: En Ano de publicação: 2017 Tipo de documento: Article