Strychnus alkaloids

Common refractory nut ( Strychnos nux-vomica ) fruiting

Seeds of Strychnos nux-vomica

Strychnos alkaloids are natural substances that are found mainly in the seeds of the common peanut nut ( Strychnos nux-vomica ) and in the Catharanth ( Catharanthus ).

Occurrence

The seeds of the common peanut nut contain up to 2.5% strychnine and brucine.

Representative

The main representative of this group of alkaloids is strychnine . Another alkaloid is brucine . Other representatives are vomicin and akuammicin .

Strychnine
Brucine
Vomicin
Akuammicin

Stereochemistry

The naturally occurring Strychnos alkaloids are all chiral and sterically uniform. If in this article or in the scientific literature one of these alkaloids is named without any additional name, it actually means:

Akuammicin for (-) - Akuammicin,
Brucine for (-) - brucine,
Strychnine for (-) - strychnine and
Vomicin for (+) - Vomicin.

The expressions in brackets stand for the sense of rotation of the optical activity of these substances.

Use and pharmacological effect

Strychnine is very toxic. In low doses it has a stimulating or euphoric effect. A higher dose leads to convulsive states. 100 to 130 mg is considered fatal to an adult human.

Brucine is similar to strychnine in its structure and physiological effect. It is considered to be less toxic. Both alkaloids are used as rat poison and as optically active bases in the separation of enantiomers of racemic acids.

history

Strychnine was extracted from the Ignatius bean ( Strychnos ignatii ) as early as 1818 by Pierre Joseph Pelletier and Joseph Bienaimé Caventou . Hermann Leuchs , Robert Robinson and Heinrich Wieland were mainly concerned with the structure elucidation of strychnine . The structure was finally secured by total synthesis ( Robert B. Woodward , 1954).

Individual evidence

↑ ^a ^b ^c P. Nuhn: Naturstoffchemie . 4th edition. S. Hirzel Verlag, Stuttgart 2006, ISBN 978-3-7776-1363-5 , p. 613 .
↑ O. Kayser, N. Averesch: Technical Biochemistry . Springer Fachmedien, Wiesbaden 2015, ISBN 978-3-658-05548-6 , pp. 613 f .
↑ ^a ^b G. Habermehl, P. Hammann, H. Krebs: Naturstoffchemie . 2nd Edition. Springer-Verlag, Berlin / Heidelberg 2002, ISBN 978-3-540-43952-3 , p. 191 .
↑ ^a ^b E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 50 .
↑ A. Wollrab: Organic Chemistry . 4th edition. Springer-Verlag, Berlin 2014, ISBN 978-3-642-45144-7 , pp. 1048 .
↑ Winfried R. Pötsch, Annelore Fischer and Wolfgang Müller with the collaboration of Heinz Cassebaum: Lexicon of important chemists , VEB Bibliographisches Institut Leipzig, 1988, ISBN 3-323-00185-0 , pp. 81–82.

[Naturstoff-1] P. Nuhn: Naturstoffchemie . 4th edition. S. Hirzel Verlag, Stuttgart 2006, ISBN 978-3-7776-1363-5 , p. 613 .

[Biochem-2] O. Kayser, N. Averesch: Technical Biochemistry . Springer Fachmedien, Wiesbaden 2015, ISBN 978-3-658-05548-6 , pp. 613 f .

[Natur-3] G. Habermehl, P. Hammann, H. Krebs: Naturstoffchemie . 2nd Edition. Springer-Verlag, Berlin / Heidelberg 2002, ISBN 978-3-540-43952-3 , p. 191 .

[Alkaloide-4] E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 50 .

[Woll-5] A. Wollrab: Organic Chemistry . 4th edition. Springer-Verlag, Berlin 2014, ISBN 978-3-642-45144-7 , pp. 1048 .

[Pötsch-6] Winfried R. Pötsch, Annelore Fischer and Wolfgang Müller with the collaboration of Heinz Cassebaum: Lexicon of important chemists , VEB Bibliographisches Institut Leipzig, 1988, ISBN 3-323-00185-0 , pp. 81–82.