Inhibitory activity of brown algal phlorotannins against glycosidases from the viscera of the turban shell Turbo cornutus

The crude phlorotannins front the brown alga Eisenia bicyclis showed inhibitory activity against 10 of 13 kinds of glycosidases present in the viscera of the turban shell Turbo cornutus. Phloroglucinol and its oligomers - eckol (a trimer), phlorofucofuroeckol A (a pentamer). dieckol and 8.8'-bieckol (hexamers), and an unidentified tetramer - were isolated from the crude phlorotannins by column and thin-layer chromatography. Phlorofucofuroeckol A. dieckol and 8,8'-bieckol inhibited alpha-fucosidase, beta-galactosidase and beta-mannosidase partially purified from T. cornutus, while phloroglucinol. eckol and the unidentified tetramer were weakly active, Dieckol was a competitive inhibitor of alpha-fucosidase with an inhibition constant (K-i) of 0.12 mM. The amounts of phlorotannins released after the immersion of freshly collected E. bicyclis in seawater or deionized water were estimated by high-performance liquid chromatography. Nearly all the phlorotannins were exuded into the medium following the death of the algae, whereas no phlorotannins were detected in the medium of licking algae. These findings indicate that the phlorotannins deter the Feeding of marine herbivorous gastropods by inhibiting the glycosidases.