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

Published online by Cambridge University Press:  18 December 2002

TOSHIYUKI SHIBATA ,
KUNIKO YAMAGUCHI ,
KOHKI NAGAYAMA ,
SHIGEO KAWAGUCHI  and
TAKASHI NAKAMURA
TOSHIYUKI SHIBATA
Affiliation:
Laboratory of Marine Resource Chemistry, Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
KUNIKO YAMAGUCHI
Affiliation:
Laboratory of Marine Resource Chemistry, Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
KOHKI NAGAYAMA
Affiliation:
Laboratory of Marine Resource Chemistry, Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
SHIGEO KAWAGUCHI
Affiliation:
Laboratory of Marine Biology, Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
TAKASHI NAKAMURA
Affiliation:
Laboratory of Marine Resource Chemistry, Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
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Abstract

The crude phlorotannins from 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 α-fucosidase, β-galactosidase and β-mannosidase partially purified from T. cornutus, while phloroglucinol, eckol and the unidentified tetramer were weakly active. Dieckol was a competitive inhibitor of α-fucosidase with an inhibition constant (Ki) 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 living algae. These findings indicate that the phlorotannins deter the feeding of marine herbivorous gastropods by inhibiting the glycosidases.

Keywords

α-fucosidasebrown algaEisenia bicyclisfeeding deterrentglycosidase inhibitionphlorotanninturban shellTurbo cornutus
Type
Research Article
Information
European Journal of Phycology , Volume 37 , Issue 4 , November 2002 , pp. 493 - 500
Copyright
© 2002 British Phycological Society

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