Iridoid Derivatives with Cytotoxic Activity from Pedicularis uliginosa Bunge

Chem Biodivers. 2019 Feb;16(2):e1800524. doi: 10.1002/cbdv.201800524. Epub 2019 Jan 23.

Abstract

Three new iridoids, rel-(4aR,7S,7aS)-7-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carbaldehyde (1), 1-methoxy-7-methyl-1,3,5,6-tetrahydrocyclopenta[c]pyran-4-carbaldehyde (2), and rel-(1R,4S,4aS,7R,7aR)-7-methylhexahydro-1,4-(epoxymethano)cyclopenta[c]pyran-3(1H)-one (3), together with seven known analogues, were isolated from the 95 % EtOH extract of the whole plants of Pedicularis uliginosa Bunge. Their structures were elucidated via extensive NMR spectroscopy and mass spectral data. In terms of inhibitory effects on human tumor cells, compounds 1, 2, 6, 7, and 8 exhibited better inhibitory activities against ACHN cells than the positive control (vinblastine).

Keywords: NMR spectroscopy; Pedicularis uliginosa Bunge; cytotoxicity; iridoids; structure elucidation.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Humans
  • Iridoids / chemistry
  • Iridoids / isolation & purification*
  • Molecular Structure
  • Pedicularis / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Iridoids
  • Plant Extracts