Symbioimine exhibiting inhibitory effect of osteoclast differentiation, from the symbiotic marine dinoflagellate Symbiodinium sp

J Am Chem Soc. 2004 Apr 21;126(15):4794-5. doi: 10.1021/ja049277f.

Abstract

An amphoteric iminium metabolite, symbioimine (1), was isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Its structure was deduced by spectroscopic analysis and X-ray crystallographic analysis. Symbioimine (1) has a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts, whereas its cell viability was not affected. Thus, symbioimine (1) is an antiresorptive drug candidate for the prevention and treatment of osteoporosis in postmenopausal women.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Differentiation / drug effects
  • Cell Line
  • Dinoflagellida / chemistry*
  • Imines / chemistry
  • Imines / isolation & purification*
  • Imines / pharmacology*
  • Mice
  • Models, Molecular
  • Molecular Weight
  • Nuclear Magnetic Resonance, Biomolecular
  • Optical Rotation
  • Osteoclasts / cytology
  • Osteoclasts / drug effects*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Imines