New class of steroidal alkaloids from Fritillaria imperialis

Phytochemistry. 2003 May;63(1):115-22. doi: 10.1016/s0031-9422(02)00569-1.

Abstract

Two members of a new class of C-nor-D-homo steroidal alkaloids, impranine (1). and dihydroimpranine (2). along with a new pyridyl-pregnane-type steroidal alkaloid, fetisinine (3). and a known base, korsevine (4). were isolated from the bulbs of Fritillaria imperialis. The structures of the compounds were established on the basis of spectroscopic techniques and some chemical transformations. Compounds 1 and 2 form a new class of steroidal alkaloids, named as "impranane."

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / biosynthesis
  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Ferric Compounds
  • Fritillaria / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Metalloporphyrins
  • Nuclear Magnetic Resonance, Biomolecular
  • Steroids / biosynthesis
  • Steroids / chemistry*
  • Steroids / isolation & purification

Substances

  • 5,10,15,20-tetrakis(2,4,6-trimethyl-3,3-disulfonatophenyl)porphyrinato iron(III)
  • Alkaloids
  • Ferric Compounds
  • Metalloporphyrins
  • Steroids