New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture

J Nat Prod. 2002 Jul;65(7):1006-10. doi: 10.1021/np0200919.

Abstract

Three new monoterpenoid indole alkaloids, 19(S),20(R)-dihydroperaksine (1), 19(S),20(R)-dihydroperaksine-17-al (2), and 10-hydroxy-19(S),20(R)-dihydroperaksine (3), along with 16 known alkaloids 4-19 were isolated from hairy root culture of Rauvolfia serpentina, and their structures were elucidated by 1D and 2D NMR analyses. Taking into account the stereochemistry of the new alkaloids and results of preliminary enzymatical studies, the putative biosynthetical relationships between the novel alkaloids are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Thin Layer
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Rauwolfia / chemistry*
  • Rhizobium / metabolism
  • Secologanin Tryptamine Alkaloids / chemistry*
  • Secologanin Tryptamine Alkaloids / isolation & purification*
  • Stereoisomerism

Substances

  • 10-hydroxy-19(S),20(R)-dihydroperaksine
  • 19(S),20(R)-dihydroperaksine
  • 19(S),20(R)-dihydroperaksine-17-al
  • Indole Alkaloids
  • Secologanin Tryptamine Alkaloids