Novel marine sponge amino acids, 10. Xestoaminols from Xestospongia sp

J Nat Prod. 1990 Jul-Aug;53(4):978-82. doi: 10.1021/np50070a033.

Abstract

The study of the anthelminthic components from a Fiji sponge Xestospongia sp. has yielded new amino alcohols, xestoaminols A-C. Xestoaminol B, (2S*)-aminotetradeca-11, 13-dien-(3R*)-ol [2], is isomeric to known Xestospongia products, (2S)-aminotetradeca-5,7-dien-(3R)-ol [6] and (2S)-aminotetradeca-5,7-dien-(3S)-ol [7], recently reported by Gulavita and Scheuer. Xestoaminols A [1] and C [3] are, respectively, the dihydro and tetrahydro derivatives of xestoaminol B. A combined nmr and molecular mechanics study on the oxazolidinone of xestoaminol A provided the basis for the relative stereochemistry assigned at C-2 and C-3 in xestoaminol A. This compound was extremely active in assays testing for action against parasites, microbes, and reverse transcriptase.

Publication types

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

MeSH terms

  • Amino Alcohols / isolation & purification*
  • Amino Alcohols / pharmacology
  • Animals
  • Anthelmintics / isolation & purification*
  • Anti-Infective Agents / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera / analysis*
  • Reverse Transcriptase Inhibitors*

Substances

  • Amino Alcohols
  • Anthelmintics
  • Anti-Infective Agents
  • Reverse Transcriptase Inhibitors