Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite.

To determine whether they could serve as non-toxic or less damaging alternative antifouling (AF) agents, 17 flavone and isoflavone derivatives were isolated from terrestrial plant extracts, purified and examined for their ability to inhibit the settlement of barnacle (Balanus amphitrite) cyprids. In larval bioassays, eight compounds showed strong anti-larval settlement activities, with EC(50) values <10 microg ml(-1). Through an analysis of the structure-activity relationship of these compounds, it was found that (1) the structural difference between flavones and isoflavones did not affect their AF activities; (2) the 5-hydroxyl group on the skeletons played a key role in AF activities; and (3) the presence of hydroxyl group or bulky group on C3 significantly reduced AF activities. A hydrolysis experiment using genistein, a typical active compound in this study, indicated that it was decomposed in the marine environment by hydrolysis reaction and that the degradation speed was significantly affected by pH. In a field AF test, genistein inhibited the attachment of B. amphitrite on panels coated with genistein-paint mixtures.