Toxicity and metabolism of p-chlorophenol in the marine microalga Tetraselmis marina

Petroutsos, D; Wang, J; Katapodis, P; Kekos, D; Sommerfeld, M; Hu, Q

dc.contributor.author	Petroutsos, D	en
dc.contributor.author	Wang, J	en
dc.contributor.author	Katapodis, P	en
dc.contributor.author	Kekos, D	en
dc.contributor.author	Sommerfeld, M	en
dc.contributor.author	Hu, Q	en
dc.date.accessioned	2014-03-01T01:27:29Z
dc.date.available	2014-03-01T01:27:29Z
dc.date.issued	2007	en
dc.identifier.issn	0166-445X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/18475
dc.subject	Biotransformation	en
dc.subject	Chlorophenol metabolism	en
dc.subject	Marine microalgae	en
dc.subject	Tetraselmis marina	en
dc.subject	Toxicity	en
dc.subject.classification	Marine & Freshwater Biology	en
dc.subject.classification	Toxicology	en
dc.subject.other	4 chlorophenol	en
dc.subject.other	chlorophenol	en
dc.subject.other	ester	en
dc.subject.other	glucopyranoside	en
dc.subject.other	glucose	en
dc.subject.other	malonic acid	en
dc.subject.other	xenobiotic agent	en
dc.subject.other	biotransformation	en
dc.subject.other	chlorophenol	en
dc.subject.other	detoxification	en
dc.subject.other	glucose	en
dc.subject.other	hydrolysis	en
dc.subject.other	inhibition	en
dc.subject.other	metabolism	en
dc.subject.other	metabolite	en
dc.subject.other	microalga	en
dc.subject.other	toxicity	en
dc.subject.other	acylation	en
dc.subject.other	algal growth	en
dc.subject.other	article	en
dc.subject.other	biotransformation	en
dc.subject.other	cell density	en
dc.subject.other	chemical structure	en
dc.subject.other	detoxification	en
dc.subject.other	ecotoxicity	en
dc.subject.other	electrospray mass spectrometry	en
dc.subject.other	hydrolysis	en
dc.subject.other	marine environment	en
dc.subject.other	microalga	en
dc.subject.other	microscopy	en
dc.subject.other	nonhuman	en
dc.subject.other	photosynthesis	en
dc.subject.other	priority journal	en
dc.subject.other	reversed phase high performance liquid chromatography	en
dc.subject.other	Tetraselmis marina	en
dc.subject.other	Acylation	en
dc.subject.other	Algae, Green	en
dc.subject.other	beta-Glucosidase	en
dc.subject.other	Chlorophenols	en
dc.subject.other	Chromatography, High Pressure Liquid	en
dc.subject.other	Glycosides	en
dc.subject.other	Hydrolysis	en
dc.subject.other	Microscopy, Polarization	en
dc.subject.other	Seawater	en
dc.subject.other	Spectrometry, Mass, Electrospray Ionization	en
dc.subject.other	Time Factors	en
dc.subject.other	Toxicity Tests	en
dc.subject.other	Water Pollutants, Chemical	en
dc.subject.other	Xenobiotics	en
dc.subject.other	Tetraselmis marina	en
dc.title	Toxicity and metabolism of p-chlorophenol in the marine microalga Tetraselmis marina	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.aquatox.2007.09.007	en
heal.identifier.secondary	http://dx.doi.org/10.1016/j.aquatox.2007.09.007	en
heal.language	English	en
heal.publicationDate	2007	en
heal.abstract	Toxicity and metabolism of para-chlorophenol (p-CP) in the marine microalga Tetraselmis marina have been studied. The inhibition constant EC50 for p-CP was 272 +/- 17 mu M (34.8 +/- 2.2 mg L-1) under the experimental conditions. Two metabolites were detected in the growth medium in the presence of p-CP by reverse phase HPLC and their concentrations increased at the expense of p-CP. The two metabolites, which were found to be more polar than p-CP, were isolated by a C 18 column. They were identified as p-chlorophenyl-beta-D-glucopyranoside (p-CPG) and p-chlorophenyl-beta-D-(6-O-malonyl)-glucopyranoside (p-CPGM) by electrospray ionization-mass spectrometric analysis in a negative ion mode. The molecular structures of p-CPG and p-CPGM were further confirmed by enzymatic and alkaline hydrolyses. Treatment with beta-glucosidase released free p-CP and glucose from p-CPG, whereas p-CPGM was completely resistant. Alkaline hydrolysis completely cleaved the esteric bond of the malonylated glucoconjugate and yielded p-CPG and malonic acid. It was concluded that the pathway of p-CP metabolism in T. marina involves an initial conjugation of p-CP to glucose to form p-chlorophenyl-beta-D-glucopyranoside, followed by acylation of the glucoconjugate to form p-chlorophenyl-beta-D-(6-O-malonyl)-glucopyranoside. The metabolism of p-CP in T. marina was mainly driven by photosynthesis, and to a lesser extent by anabolic metabolism in the dark. Accordingly, the detoxification rate under light was about seven times higher than in the darkness. This work provides the first evidence that microalgae can adopt a combined glucosyl transfer and malonyl transfer process as a survival strategy for detoxification of such xenobiotics as p-CP. (c) 2007 Elsevier B.V. All rights reserved.	en
heal.publisher	ELSEVIER SCIENCE BV	en
heal.journalName	Aquatic Toxicology	en
dc.identifier.doi	10.1016/j.aquatox.2007.09.007	en
dc.identifier.isi	ISI:000251639100004	en
dc.identifier.volume	85	en
dc.identifier.issue	3	en
dc.identifier.spage	192	en
dc.identifier.epage	201	en