Highly polar spiroisoxazolines from the sponge Aplysina fulva

J Nat Prod. 2007 Jul;70(7):1191-4. doi: 10.1021/np070109l. Epub 2007 Jun 19.

Abstract

Two new highly polar brominated spiroisoxazolines, araplysillin N9-sulfamate (1) and an N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxy]-4-aminobutanoic acid (2), were isolated from a sample of Aplysina fulva collected in the Florida Keys. The absolute stereostructures of the new compounds were determined from analysis of MS, 1H and 13C NMR, and CD spectroscopy. Compound 2 provides a structural clue that may unify the biosynthesis of brominated spiroisoxazolines.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Florida
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / isolation & purification*
  • Isoxazoles / chemistry
  • Isoxazoles / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*

Substances

  • Hydrocarbons, Brominated
  • Isoxazoles
  • N-((5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro(4.5)deca-2,6,8-triene-3-carboxy)-4-aminobutanoic acid
  • Spiro Compounds
  • araplysillin N9-sulfamate