Identification of new pyrrole alkaloids from the fruits of Lycium chinense

Arch Pharm Res. 2016 Mar;39(3):321-7. doi: 10.1007/s12272-015-0695-3. Epub 2015 Dec 17.

Abstract

Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.

Keywords: Absolute configuration; ECD; Lycium chinense; Pyrrole alkaloid; Solanaceae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Circular Dichroism
  • Fruit / chemistry
  • Lycium / chemistry*
  • Molecular Structure
  • Plant Extracts / chemistry
  • Pyrroles / chemistry*
  • Pyrroles / isolation & purification

Substances

  • Alkaloids
  • Plant Extracts
  • Pyrroles