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

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.