Pyrrolidine alkaloids
File:Pyrrolidine Structural Formula V1.svg, the fundamental chemical structure of pyrrolidine alkaloids.]]
The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine.{{RömppOnline|ID=RD-16-05263|Name=Pyrrolidin|Abruf=2020-05-21}}
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, while (-)-codonopsinine was isolated from the woodland vine tiger bell.
Erythroxylum coca.jpg|Coca shrub (Erythroxylum coca) with leaves and fruits.
Codonopsis clematidea Dzwonkowiec powojnikowaty 2015 03.jpg|Wood vine tiger bell (Codonopsis clematidea)
Representatives
Among the most important representatives of the pyrrolidine alkaloids are hygrin and cuscohygrin.{{citation|author=H. Latscha, U. Kazmaier|date=2016|edition=4|isbn=978-3-662-47783-0|location=Berlin Heidelberg|pages=682|publisher=Springer Spektrum|title=Chemie für Biologen}} Another representative is the (-)-codonopsinine.{{citation|author=J. Reddy, B. Rao|date=2007|doi=10.1021/jo061940q|issue=6|pages=2224–2227|periodical=The Journal of Organic Chemistry|title=A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid: (−)-Codonopsinine|volume=72|pmid=17316046 }} Furthermore, ruspolinone, norruspolinone and norruspoline also belong to this alkaloid group.{{citation|author=F. Roessler, D. Ganzinger, S. Johne, E.Schöpp, M. Hesse|date=1978|doi=10.1002/hlca.19780610336|issue=3|pages=1200–1206|periodical=Helvetica Chimica Acta|title=Ruspolia hypercrateriformis M.R.:Isolierung und Strukturaufklärung von neuen Pyrrolidin-Alkaloiden. 169. Mitt. über organische Naturstoffe|volume=61}}
(+)-Hygrine Structural Formula V2.svg|(+)-Hygrine
(-)-Codonopsinine Structural Formula V2.svg|(-)-Codonopsinine
(-)-Ruspolinone Structural Formula V1.svg|(-)-Ruspolinone
(R)-Norruspoline Structural Formula V1.svg|(R)-Norruspoline
Properties
Many plants containing cuscohygrin are used in the folk medicine of various peoples as sedatives or narcotics.{{RömppOnline|ID=RD-03-02974|Name=Cuscohygrin|Abruf=2020-05-21}}