Pyrrolidine alkaloids
From Wikipedia the free encyclopedia
The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine.[1]
Occurrence[edit]
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]
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Coca shrub (Erythroxylum coca) with leaves and fruits. -
Wood vine tiger bell (Codonopsis clematidea)
Representatives[edit]
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]
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(+)-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[edit]
Many plants containing cuscohygrin are used in the folk medicine of various peoples as sedatives or narcotics.[5]
References[edit]
- ^ 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}}}.