Pyrrolidine alkaloids

The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine.^[1]

Occurrence

Alkaloids with partial pyrrolidine structure are usually sub-categorized based on their occurrence and biogenetic origin. Hygrin and cuscohygrin were isolated from the leaves of the coca shrub,^[2] while (-)-codonopsinine was isolated from the woodland vine tiger bell.^[3]

Coca shrub (Erythroxylum coca) with leaves and fruits.
Wood vine tiger bell (Codonopsis clematidea)

Representatives

Among the most important representatives of the pyrrolidine alkaloids are hygrin and cuscohygrin.^[2] Another representative is the (-)-codonopsinine.^[3] Furthermore, ruspolinone, norruspolinone and norruspoline also belong to this alkaloid group.^[4]

(+)-Hygrine
(-)-Codonopsinine
(-)-Ruspolinone
(R)-Norruspoline

Properties

Many plants containing cuscohygrin are used in the folk medicine of various peoples as sedatives or narcotics.^[5]

References

^ Entry on Pyrrolidin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ ^a ^b H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, p. 682, ISBN 978-3-662-47783-0
^ ^a ^b J. Reddy, B. Rao (2007), "A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid: (−)-Codonopsinine", The Journal of Organic Chemistry, vol. 72, no. 6, pp. 2224–2227, doi:10.1021/jo061940q, PMID 17316046
^ F. Roessler, D. Ganzinger, S. Johne, E.Schöpp, M. Hesse (1978), "Ruspolia hypercrateriformis M.R.:Isolierung und Strukturaufklärung von neuen Pyrrolidin-Alkaloiden. 169. Mitt. über organische Naturstoffe", Helvetica Chimica Acta, vol. 61, no. 3, pp. 1200–1206, doi:10.1002/hlca.19780610336{{citation}}: CS1 maint: multiple names: authors list (link)
^ Entry on Cuscohygrin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

[1] Entry on Pyrrolidin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

[Bio-2] H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, p. 682, ISBN 978-3-662-47783-0

[Lit-3] J. Reddy, B. Rao (2007), "A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid: (−)-Codonopsinine", The Journal of Organic Chemistry, vol. 72, no. 6, pp. 2224–2227, doi:10.1021/jo061940q, PMID 17316046

[4] F. Roessler, D. Ganzinger, S. Johne, E.Schöpp, M. Hesse (1978), "Ruspolia hypercrateriformis M.R.:Isolierung und Strukturaufklärung von neuen Pyrrolidin-Alkaloiden. 169. Mitt. über organische Naturstoffe", Helvetica Chimica Acta, vol. 61, no. 3, pp. 1200–1206, doi:10.1002/hlca.19780610336{{citation}}: CS1 maint: multiple names: authors list (link)

[5] Entry on Cuscohygrin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

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