Structure and absolute stereochemistry of syphonoside, a unique macrocyclic glycoterpenoid from marine organisms

J Org Chem. 2007 Jul 20;72(15):5625-30. doi: 10.1021/jo0704917. Epub 2007 Jun 20.

Abstract

The glycoterpenoid syphonoside (1) is the main secondary metabolite of both the marine mollusk Syphonota geographica and the sea-grass Halophila stipulacea, two Indo-Pacific species migrated to the Mediterranean Sea through the Suez Canal. The structure and the absolute stereochemistry of 1, which displays unique structural features, has been accomplished by using a combination of spectroscopic techniques, degradation reactions, and conformational analysis methods. Compound 1 was able to inhibit high density induced apoptosis in a number of human and murine carcinoma cell lines.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / isolation & purification
  • Macrocyclic Compounds / pharmacology
  • Magnetic Resonance Spectroscopy
  • Marine Biology*
  • Mice
  • Molecular Structure
  • Poaceae / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • Terpenes / chemistry*
  • Terpenes / isolation & purification
  • Terpenes / pharmacology

Substances

  • Macrocyclic Compounds
  • Terpenes
  • syphonoside