Absolute stereochemistry of neohalicholactone from the brown alga Laminaria sinclairii

J Nat Prod. 1994 Dec;57(12):1717-9. doi: 10.1021/np50114a016.

Abstract

Phytochemical analysis of an extract from the brown alga Laminaria sinclairii led to the isolation of neohalicholactone, a cyclopropyl-containing oxylipin previously isolated from a marine sponge, Halichondria okadai. Unequivocal stereochemical analysis of the C-15 hydroxyl group showed this isolate to be of opposite overall absolute stereochemistry compared to that proposed for halicholactone, a related compound from the sponge, and by our inference, sponge-derived neohalicholactone. Comparison of chiroptical data for all three compounds indicates the absolute stereochemistry of the sponge compounds is most probably opposite to that previously proposed.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cyclopropanes / chemistry*
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Phaeophyceae / chemistry*

Substances

  • Cyclopropanes
  • Lactones
  • neohalicholactone