Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge

Bioorg Med Chem. 2015 Mar 1;23(5):966-75. doi: 10.1016/j.bmc.2015.01.021. Epub 2015 Jan 19.

Abstract

Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells.

Keywords: (+)-Dictyoceratin-A (smenospondiol); (+)-Dictyoceratin-C; Absolute stereochemistry; Hypoxia-selective growth inhibitor; Total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Hypoxia
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Drug Screening Assays, Antitumor
  • Growth Inhibitors / chemical synthesis*
  • Growth Inhibitors / chemistry
  • Growth Inhibitors / pharmacology*
  • Humans
  • Hydroxybenzoates / chemical synthesis*
  • Hydroxybenzoates / chemistry
  • Hydroxybenzoates / pharmacology*
  • Male
  • Marine Biology
  • Porifera / chemistry*
  • Prostatic Neoplasms / pathology
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology*
  • Stereoisomerism

Substances

  • Growth Inhibitors
  • Hydroxybenzoates
  • Sesquiterpenes
  • dictyoceratin-C
  • smenospondiol