In vitro chemopreventive potential of fucophlorethols from the brown alga Fucus vesiculosus L. by anti-oxidant activity and inhibition of selected cytochrome P450 enzymes

Sabine Parys; Stefan Kehraus; Anja Krick; Karl-Werner Glombitza; Shmuel Carmeli; Karin Klimo; Clarissa Gerhäuser; Gabriele M König

doi:10.1016/j.phytochem.2009.10.020

In vitro chemopreventive potential of fucophlorethols from the brown alga Fucus vesiculosus L. by anti-oxidant activity and inhibition of selected cytochrome P450 enzymes

Phytochemistry. 2010 Feb;71(2-3):221-9. doi: 10.1016/j.phytochem.2009.10.020. Epub 2009 Dec 1.

Authors

Sabine Parys¹, Stefan Kehraus, Anja Krick, Karl-Werner Glombitza, Shmuel Carmeli, Karin Klimo, Clarissa Gerhäuser, Gabriele M König

Affiliation

¹ Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, D-53115 Bonn, Germany.

PMID: 19954804
DOI: 10.1016/j.phytochem.2009.10.020

Abstract

Within a project focusing on the chemopreventive potential of algal phenols, two phloroglucinol derivatives, belonging to the class of fucophlorethols, and the known fucotriphlorethol A were obtained from the ethanolic extract of the brown alga Fucus vesiculosus L. The compounds trifucodiphlorethol A and trifucotriphlorethol A are composed of six and seven units of phloroglucinol, respectively. The compounds were examined for their cancer chemopreventive potential, in comparison with the monomer phloroglucinol. Trifucodiphlorethol A, trifucotriphlorethol A as well as fucotriphlorethol A were identified as strong radical scavengers, with IC(50) values for scavenging of 1,1-diphenyl-2 picrylhydrazyl radicals (DPPH) in the range of 10.0-14.4 microg/ml. All three compounds potently scavenged peroxyl radicals in the oxygen radical absorbance capacity (ORAC) assay. In addition, the compounds were shown to inhibit cytochrome P450 1A activity with IC(50) values in the range of 17.9-33 microg/ml, and aromatase (Cyp19) activity with IC(50) values in the range of 1.2-5.6 microg/ml.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology
Antineoplastic Agents, Phytogenic / therapeutic use
Antioxidants / isolation & purification
Antioxidants / pharmacology*
Antioxidants / therapeutic use
Aromatase Inhibitors / isolation & purification
Aromatase Inhibitors / pharmacology*
Aromatase Inhibitors / therapeutic use
Biphenyl Compounds / isolation & purification
Biphenyl Compounds / pharmacology*
Biphenyl Compounds / therapeutic use
Cell Line, Tumor
Cytochrome P-450 Enzyme Inhibitors*
Fucus / chemistry*
Humans
Inhibitory Concentration 50
Mice
Neoplasms / drug therapy
Phenyl Ethers / isolation & purification
Phenyl Ethers / pharmacology*
Phenyl Ethers / therapeutic use
Phloroglucinol / analogs & derivatives
Phloroglucinol / pharmacology*
Phloroglucinol / therapeutic use
Picrates
Plant Extracts / chemistry
Plant Extracts / pharmacology
Plant Extracts / therapeutic use
Terphenyl Compounds / isolation & purification
Terphenyl Compounds / pharmacology*
Terphenyl Compounds / therapeutic use

Substances

Antineoplastic Agents, Phytogenic
Antioxidants
Aromatase Inhibitors
Biphenyl Compounds
Cytochrome P-450 Enzyme Inhibitors
Phenyl Ethers
Picrates
Plant Extracts
Terphenyl Compounds
fucotriphlorethol A
trifucodiphlorethol A
trifucotriphlorethol A
1,1-diphenyl-2-picrylhydrazyl
Phloroglucinol