Abstract

Xenobiotic chlorinated phenols have been found in fresh and marine waters and are toxic to many aquatic organisms. Metabolism of 2,4-dichlorophenol (2,4-DCP) in the marine microalga Tetraselmis marina was studied. The microalga removed more than 1mM of 2,4-DCP in a 2l photobioreactor over a 6 day period. Two metabolites, more polar than 2,4-DCP, were detected in the growth medium by reverse phase HPLC and their concentrations increased at the expense of 2,4-DCP. The metabolites were isolated by a C8 HPLC column and identified as 2,4-dichlorophenyl-beta-d-glucopyranoside (DCPG) and 2,4-dichlorophenyl-beta-d-(6-O-malonyl)-glucopyranoside (DCPGM) by electrospray ionization-mass spectrometric analysis in a negative ion mode. The molecular structures of 2,4-DCPG and 2,4-CPGM were further confirmed by enzymatic and alkaline hydrolyses. Thus, it was concluded that the major pathway of 2,4-DCP metabolism in T. marina involves an initial conjugation of 2,4-DCP to glucose to form 2,4-dichlorophenyl-beta-d-glucopyranoside, followed by acylation of the glucoconjugate to form 2,4-dichlorophenyl-beta-d-(6-O-malonyl)-glucopyranoside. The microalga ability to detoxify dichlorophenol congeners other than 2,4-DCP was also investigated. This work provides the first evidence that microalgae can use a combined glucosyl and malonyl transfer to detoxify xenobiotics such as dichlorophenols.