Tumor cell proliferation and cyclooxygenase inhibitory constituents in horseradish (Armoracia rusticana) and Wasabi (Wasabia japonica)

J Agric Food Chem. 2005 Mar 9;53(5):1440-4. doi: 10.1021/jf048264i.

Abstract

Cyclooxygenase and human tumor cell growth inhibitory extracts of horseradish (Armoracia rusticana) and wasabi (Wasabia japonica) rhizomes upon purification yielded active compounds 1-3 from horseradish and 4 and 5 from wasabi rhizomes. Spectroscopic analyses confirmed the identities of these active compounds as plastoquinone-9 (1), 6-O-acyl-beta-d-glucosyl-beta-sitosterol (2), 1,2-dilinolenoyl-3-galactosylglycerol (3), linolenoyloleoyl-3-beta-galactosylglycerol (4), and 1,2-dipalmitoyl-3-beta-galactosylglycerol (5). 3-Acyl-sitosterols, sinigrin, gluconasturtiin, and phosphatidylcholines isolated from horseradish and alpha-tocopherol and ubiquinone-10 from wasabi rhizomes isolated were inactive in our assays. At a concentration of 60 microg/mL, compounds 1 and 2 selectively inhibited COX-1 enzyme by 28 and 32%, respectively. Compounds 3, 4, and 5 gave 75, 42, and 47% inhibition of COX-1 enzyme, respectively, at a concentration of 250 microg/mL. In a dose response study, compound 3 inhibited the proliferation of colon cancer cells (HCT-116) by 21.9, 42.9, 51.2, and 68.4% and lung cancer cells (NCI-H460) by 30, 39, 44, and 71% at concentrations of 7.5, 15, 30, and 60 microg/mL, respectively. At a concentration of 60 microg/mL, compound 4 inhibited the growth of colon, lung, and stomach cancer cells by 28, 17, and 44%, respectively. This is the first report of the COX-1 enzyme and cancer cell growth inhibitory monogalactosyl diacylglycerides from wasabi and horseradish rhizomes.

MeSH terms

  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Armoracia / chemistry*
  • Cell Division / drug effects
  • Cyclooxygenase 1
  • Cyclooxygenase Inhibitors / isolation & purification*
  • Cyclooxygenase Inhibitors / pharmacology
  • Galactolipids / isolation & purification
  • Galactolipids / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Membrane Proteins
  • Plastoquinone / isolation & purification
  • Plastoquinone / pharmacology
  • Prostaglandin-Endoperoxide Synthases
  • Rhizome / chemistry
  • Sitosterols / isolation & purification
  • Sitosterols / pharmacology
  • Tumor Cells, Cultured
  • Wasabia / chemistry*

Substances

  • Antineoplastic Agents
  • Cyclooxygenase Inhibitors
  • Galactolipids
  • Membrane Proteins
  • Sitosterols
  • Cyclooxygenase 1
  • PTGS1 protein, human
  • Prostaglandin-Endoperoxide Synthases
  • Plastoquinone