Sedum alkaloids

Stonecrop ( Sedum sarmentosum )

Spicy stonecrop ( Sedum acre )

Sedum alkaloids are natural substances of the piperidine alkaloid type. Sedum alkaloids are 2- or 2,6-substituted piperidine derivatives that have similarities in structure and biosynthesis to the Punica and Lobelia alkaloids .

Occurrence

The Sedum alkaloids can be derived from Sedum species ( Crassulaceae), u. a. Sedum sarmentosum and Sedum acre are isolated. Both (-) - Sedamin and (+) - Sedamin can be isolated from the Sedum acre plant .

Representative

The best-known representative is the Sedamin . Further representatives are sedridine , allosedridine , N -methylisopelletierin and N -methylallosedridine .

(+) - Sedamin

(+) - sedridine

(-) - Allosedridine

properties

Sedamin is responsible for the pungent taste of the stonecrop . Sedum alkaloids are not considered to be toxic. Pharmacological effects are not clearly proven.

synthesis

N -methyl-α-phenacylpiperidine (“sedamine ketone”) is used as the starting material . The racemic sedamine is preferably formed by reducing the keto group with lithium alanate. In the case of catalytic hydrogenation, for example of the hydrochloride , with Raney nickel , a mixture of equal parts of racemic sedamine and racemic allosedamine is formed .

Individual evidence

↑ ^a ^b Entry on Sedum alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on April 21, 2020.
^ Sedum alkaloids. Retrieved April 22, 2020 .
↑ ^a ^b G. Habermehl, P. Hammann, H. Krebs: Naturstoffchemie . 2nd Edition. Springer-Verlag, Berlin Heidelberg 2002, ISBN 3-540-43952-8 , pp. 140 f .
^ B. Franck: Alkaloids in Sedum acre and related Sedum species . In: Chem. Ber. 1958, p. 2803 , doi : 10.1002 / cber.19580911236 .
↑ Clemens Schöpf , Günter Dummer, Willi Wüst, Richard Rausch: Synthesis and absolute configuration of (-) - Sedamin and of (-) - 8 ‐ Phenyl ‐ lobelol ‐ i [(-) - Allosedamin] . In: Justus Liebig's Annals of Chemistry . tape 626 , no. 1 , 1959, p. 134−149 , doi : 10.1002 / jlac.19596260116 .

[Römpp-1] Entry on Sedum alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on April 21, 2020.

[Pepper-2] Sedum alkaloids. Retrieved April 22, 2020 .

[Natur-3] G. Habermehl, P. Hammann, H. Krebs: Naturstoffchemie . 2nd Edition. Springer-Verlag, Berlin Heidelberg 2002, ISBN 3-540-43952-8 , pp. 140 f .

[4] B. Franck: Alkaloids in Sedum acre and related Sedum species . In: Chem. Ber. 1958, p. 2803 , doi : 10.1002 / cber.19580911236 .

[5] Clemens Schöpf , Günter Dummer, Willi Wüst, Richard Rausch: Synthesis and absolute configuration of (-) - Sedamin and of (-) - 8 ‐ Phenyl ‐ lobelol ‐ i [(-) - Allosedamin] . In: Justus Liebig's Annals of Chemistry . tape 626 , no. 1 , 1959, p. 134−149 , doi : 10.1002 / jlac.19596260116 .