Sterols isolated from Nuruk (Rhizopus oryzae KSD-815) inhibit the migration of cancer cells

J Microbiol Biotechnol. 2009 Nov;19(11):1328-32. doi: 10.4014/jmb.0902.072.

Abstract

An activity-guided fractionation method was used to isolate anticancer components from Nuruk (Rhizopus oryzae KSD-815:KSD-815). Dried powder of KSD-815 was extracted with 80% methanol and partitioned successively using nhexane, ethyl acetate, n-butanol, and water. The n-hexane and n-butanol fractions showed a strong antimigratory effect on human cancer cells. Both of these fractions were subjected to separation and purification procedures using silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies to afford four purified compounds. These were identified as ergosterol peroxide (1), stigmast- 5-en-3beta,7beta-diol (2), ergosta-7,22-dien-3beta,5alpha,6beta,9alpha-tetraol (3), and daucosterol (4), respectively, by spectroscopic methods such as nuclear magnetic resonance spectrometry, mass spectrometry, and infrared spectroscopy, and comparison with those in the literature. Compounds 1-4 were isolated from KSD-815 for the first time. Compounds 1 and 4 inhibited the migration of MDA-MB-231 cells at concentrations lower than 20 micronM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / pathology
  • Breast Neoplasms / physiopathology
  • Cell Line, Tumor
  • Cell Movement / drug effects*
  • Edible Grain / microbiology*
  • Ergosterol / analogs & derivatives
  • Ergosterol / chemistry
  • Ergosterol / isolation & purification
  • Ergosterol / pharmacology
  • Female
  • Food Microbiology*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Rhizopus / chemistry*
  • Rhizopus / isolation & purification
  • Sitosterols / chemistry
  • Sitosterols / isolation & purification
  • Sitosterols / pharmacology
  • Spectrophotometry, Infrared
  • Sterols / chemistry
  • Sterols / isolation & purification*
  • Sterols / pharmacology*
  • Stigmasterol / analogs & derivatives
  • Stigmasterol / chemistry
  • Stigmasterol / isolation & purification
  • Stigmasterol / pharmacology

Substances

  • Sitosterols
  • Sterols
  • ergosta-7,22-dien-3beta,5alpha,6beta,9alpha-tetraol
  • stigmast-5-en-3beta,7beta-diol
  • Stigmasterol
  • lyoniside
  • ergosterol-5,8-peroxide
  • Ergosterol