Further bioactive piperidine alkaloids from the flowers and green fruits of Cassia spectabilis

J Nat Prod. 2004 May;67(5):908-10. doi: 10.1021/np0303963.

Abstract

The flowers of Cassia spectabilis yielded three new piperidine alkaloids, (-)-3-O-acetylspectaline (1), (-)-7-hydroxyspectaline (2), and iso-6-spectaline (3), together with the known (-)-spectaline (4). The green fruits of this plant were also investigated, resulting in the isolation of 1 and 4. Their structures were elucidated using a combination of multidimensional NMR and MS techniques, and relative stereochemistries were established by NOESY correlations and analysis of coupling constants. The DNA-damaging activity of these compounds was evaluated using a mutant yeast, Saccharomyces cerevisiae, assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Brazil
  • Cassia / chemistry*
  • DNA Damage
  • Flowers / chemistry
  • Fruit / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Piperidines / chemistry
  • Piperidines / isolation & purification*
  • Piperidines / pharmacology
  • Plants, Medicinal / chemistry*
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / genetics
  • Stereoisomerism

Substances

  • 3-O-acetylspectaline
  • 7-hydroxyspectaline
  • Alkaloids
  • Piperidines
  • iso-6-spectaline
  • spectaline