Cytotoxic germacranolide sesquiterpene from Inula cappa

Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1258-60. doi: 10.1248/cpb.55.1258.

Abstract

A new germacranolide, inulacappolide (1), was isolated from the EtOH extract of the whole plant of Inula cappa along with 16 known compounds. The structure of inulacappolide was a rare 1(10)-saturated type of germacran-6,12-olide, identified as 2alpha-acetoxy-3beta-hydroxy-9beta-angeloyloxygermacra-4-en-6alpha,12-olide by spectral analysis (IR, HR-ESI/MS, (1)H-NMR, (13)C-NMR, HMQC, HMBC, NOESY). In vitro, it showed antiproliferative effects against human cervical cancer HeLa, human leukemia K562 and human nasopharyngeal carcinoma KB cell lines with IC(50) values of 1.2 microM, 3.8 microM and 5.3 microM, respectively.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Ethanol
  • HeLa Cells
  • Humans
  • Inula / chemistry*
  • K562 Cells
  • KB Cells
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Sesquiterpenes, Germacrane / chemistry*
  • Sesquiterpenes, Germacrane / isolation & purification
  • Sesquiterpenes, Germacrane / pharmacology*
  • Solvents
  • Spectrometry, Mass, Electrospray Ionization
  • Tetrazolium Salts
  • Thiazoles

Substances

  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes
  • Sesquiterpenes, Germacrane
  • Solvents
  • Tetrazolium Salts
  • Thiazoles
  • germacranolide
  • Ethanol
  • thiazolyl blue