Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa

Phytochemistry. 2006 Jan;67(1):52-7. doi: 10.1016/j.phytochem.2005.10.004. Epub 2005 Nov 21.

Abstract

An alkaloid named 6alpha-hydroxycroomine (1) as well as the known croomine (2), both belonging to the tuberostemospironine-alkaloid type, were isolated from Stemona tuberosa as the major components. The structure of 1 was elucidated through extensive spectroscopic analyses. Comparison of the HPLC profiles of the total alkaloids and the crude methanol extract showed that both compounds are naturally occurring. The first isolation of 1 and 2 from S. tuberosa has chemotaxonomic significance, confirming the close relationship between Stemona and Croomia. The trnL sequences of plants from the four genera of Stemonaceae cluster together as a clade, further lending support to retaining them in a single family.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification*
  • Chromatography, High Pressure Liquid
  • DNA / genetics
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Molecular Sequence Data
  • Phylogeny
  • Pyrrolidines / chemistry*
  • Pyrrolidines / isolation & purification*
  • Reference Standards
  • Species Specificity
  • Spiro Compounds / chemistry*
  • Spiro Compounds / isolation & purification*
  • Stemonaceae / chemistry*
  • Stemonaceae / genetics

Substances

  • 6-hydroxycroomine
  • Alkaloids
  • Pyrrolidines
  • Spiro Compounds
  • croomine
  • DNA

Associated data

  • GENBANK/AF303701
  • GENBANK/AF364600
  • GENBANK/AF508514
  • GENBANK/AJ441164
  • GENBANK/AJ441168
  • GENBANK/AY337693
  • GENBANK/AY337702
  • GENBANK/AY337709
  • GENBANK/AY430569