Monatshefte für Chemie / Chemical Monthly

, Volume 136, Issue 9, pp 1671–1680 | Cite as

New Pyrrolo[1,2-a]azepine Type Alkaloids from Stemona and Stichoneuron (Stemonaceae)

  • Johann Schinnerl
  • Elisabeth Kaltenegger
  • Thomas Pacher
  • Srunya Vajrodaya
  • Otmar HoferEmail author
  • Harald GregerEmail author


Three new pyrroloazepine type alkaloids, stichoneurines A and B and 6-hydroxycroomine were isolated from the lipophilic root extracts of Stichoneuron caudatum and Stemona tuberosa collected in Thailand together with the already known croomine, tuberostemonine, and tuberostemonine A. The structures were elucidated by spectroscopic methods including H/H-COSY, HMQC, and HMBC. Information on the relative stereochemistries and conformational behaviour was obtained by analysis of the NOESY spectra. The formation of pyrroloazepine alkaloids in the genus Stichoneuron is reported for the first time and supports its affiliation to the family Stemonaceae. The occurrence of two different types of alkaloids, of the tuberostemonine and croomine series, in different geographical provenances of Stemona tuberosa is of special chemosystematic interest and may contribute to a more natural species delimitation within that complex group.

Keywords. Stichoneurines A-B; Tuberostemonine A; 6-Hydroxycroomine; Pyrroloazepine alkaloids; Stichoneuron caudatum; Stemona tuberosa


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Copyright information

© Springer-Verlag/Wien 2005

Authors and Affiliations

  • Johann Schinnerl
    • 1
  • Elisabeth Kaltenegger
    • 1
  • Thomas Pacher
    • 1
  • Srunya Vajrodaya
    • 2
  • Otmar Hofer
    • 3
    Email author
  • Harald Greger
    • 1
    Email author
  1. 1.Comparative and Ecological Phytochemistry SectionUniversity of ViennaViennaAustria
  2. 2.Department of Botany, Faculty of ScienceKasetsart UniversityBangkokThailand
  3. 3.Institute of Organic Chemistry, University of ViennaViennaAustria

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