Chemistry: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
-Hygrine_Structural_Formula_V2.svg)
-Codonopsinine_Structural_Formula_V2.svg)
-Ruspolinone_Structural_Formula_V1.svg)
-Norruspoline_Structural_Formula_V1.svg)
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}}}.
- ↑ 2.0 2.1 H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, pp. 682, ISBN 978-3-662-47783-0
- ↑ 3.0 3.1 J. Reddy, B. Rao (2007), "A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid: (−)-Codonopsinine", The Journal of Organic Chemistry 72 (6): 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 61 (3): 1200–1206, doi:10.1002/hlca.19780610336
- ↑ Entry on Cuscohygrin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
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