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

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Summary.

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.

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Authors and Affiliations

  1. Comparative and Ecological Phytochemistry Section, University of Vienna, A-1030, Vienna, Austria

    Johann Schinnerl, Elisabeth Kaltenegger, Thomas Pacher & Harald Greger

  2. Department of Botany, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand

    Srunya Vajrodaya

  3. Institute of Organic Chemistry, University of Vienna, A-1090, Vienna, Austria

    Otmar Hofer

Authors
  1. Johann Schinnerl
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  2. Elisabeth Kaltenegger
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  3. Thomas Pacher
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  4. Srunya Vajrodaya
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  5. Otmar Hofer
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  6. Harald Greger
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Corresponding authors

Correspondence to Otmar Hofer or Harald Greger.

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Schinnerl, J., Kaltenegger, E., Pacher, T. et al. New Pyrrolo[1,2-a]azepine Type Alkaloids from Stemona and Stichoneuron (Stemonaceae). Monatsh. Chem. 136, 1671–1680 (2005). https://doi.org/10.1007/s00706-005-0348-1

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  • DOI: https://doi.org/10.1007/s00706-005-0348-1

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