Bioactivity-guided isolation of cytotoxic sesquiterpenes of Rolandra fruticosa

Phytochemistry. 2010 Apr;71(5-6):635-40. doi: 10.1016/j.phytochem.2010.01.012. Epub 2010 Feb 25.

Abstract

Cytotoxicity-guided fractionation of a methanol extract of the leaves and twigs of Rolandra fruticosa using the HT-29 human colon cancer cell line led to the isolation of seven sesquiterpene lactones, including the hitherto unknown isorolandrolide, 13-methoxyisorolandrolide (1), and bourbonenolide, 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-isobutyroyloxybourbonen-12,6alpha-olide (2), as well as five known compounds, 13-acetoxyrolandrolide (3), 8-desacyl-13-acetoxyrolandrolide-8-O-tiglate (4), 2-epi-glaucolide E (5), 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-methacryloyloxybourbonen-12,6alpha-olide (6), and 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-tigloyloxybourbonen-12,6alpha-olide (7). The structures of the two sesquiterpenes were elucidated on the basis of spectroscopic methods. All isolates were evaluated for their cytotoxicity using the HT-29 cell line, and only 13-acetoxyrolandrolide (3) was found to possess a potent inhibitory effect against this cell line. Compounds 3, 5 and 6 were also tested in a NF-kappaB (p65) inhibition assay, and 3 was assessed in an in vivo hollow fiber assay.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antineoplastic Agents, Phytogenic / therapeutic use*
  • Asteraceae / chemistry*
  • Cell Line, Tumor
  • Colonic Neoplasms / drug therapy*
  • HT29 Cells
  • Humans
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Lactones / therapeutic use*
  • Mice
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • Phytotherapy*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Extracts / therapeutic use*
  • Plant Leaves
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology

Substances

  • 13-acetoxyrolandrolide
  • 13-methoxyisorolandrolide
  • Antineoplastic Agents, Phytogenic
  • Lactones
  • NF-kappa B
  • Plant Extracts
  • Sesquiterpenes
  • bourbonenolide