Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum

Phytochemistry. 2014 Jul:103:188-195. doi: 10.1016/j.phytochem.2014.03.007. Epub 2014 Apr 23.

Abstract

An ongoing search for alkaloids in the Amaryllidaceae species using GC-MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum.

Keywords: Alkaloid; Amaryllidaceae; Circular dichroism; Crinine-type; Hippeastrum; X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Amaryllidaceae Alkaloids / chemistry*
  • Crystallography, X-Ray
  • Liliaceae / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Extracts / chemistry*

Substances

  • Alkaloids
  • Amaryllidaceae Alkaloids
  • Plant Extracts
  • crinine