Antineoplastic unsaturated fatty acids from Fijian macroalgae

Abstract

Phytochemical analysis of Fijian populations of the green alga Tydemania expeditionis led to the isolation of two unsaturated fatty acids, 3(ζ)-hydroxy-octadeca-4( E),6( Z),15( Z)-trienoic acid ( 1) and 3(ζ)-hydroxy-hexadeca-4( E),6( Z)-dienoic acid ( 2), along with the known 3(ζ)-hydroxy-octadeca-4( E),6( Z)-dienoic acid ( 4). Investigations of the red alga Hydrolithon reinboldii led to identification of a glycolipid, lithonoside ( 3), and five known compounds, 15-tricosenoic acid, hexacosa-5,9-dienoic methyl ester, β-sitosterol, 10( S)-hydroxypheophytin A, and 10( R)-hydroxypheophytin A. The structures of 1– 3 were elucidated by spectroscopic methods (1D and 2D NMR spectroscopy and ESI-MS). Compounds 1, 2, and 4, containing conjugated double bonds, demonstrated moderate inhibitory activity against a panel of tumor cell lines (including breast, colon, lung, prostate and ovarian cells) with IC 50 values ranging from 1.3 to 14.4 μM. The similar cell selectivity patterns of these three compounds suggest that they might act by a common, but unknown, mechanism of action.