Pyrrolidine alkaloids

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

pyrrolidine, the fundamental chemical structure of pyrrolidine alkaloids.

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.
    Coca shrub (Erythroxylum coca) with leaves and fruits.
  • Wood vine tiger bell (Codonopsis clematidea)
    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
    (+)-Hygrine
  • (-)-Codonopsinine
    (-)-Codonopsinine
  • (-)-Ruspolinone
    (-)-Ruspolinone
  • (R)-Norruspoline
    (R)-Norruspoline

Properties

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

References
  1. Entry on Pyrrolidin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
  2. H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, p. 682, ISBN 978-3-662-47783-0
  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}}}.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.