Metabolites of 2,2'-dichlorobiphenyl and 2,6-dichlorobiphenyl in hairy root culture of black nightshade Solanum nigrum SNC-90

0383626 - ÚOCHB 2013 RIV GB eng J - Journal Article
Rezek, Jan - Macek, Tomáš - Doubský, Jan - Macková, M.
Metabolites of 2,2'-dichlorobiphenyl and 2,6-dichlorobiphenyl in hairy root culture of black nightshade Solanum nigrum SNC-90.
Chemosphere. Roč. 89, č. 4 (2012), s. 383-388. ISSN 0045-6535. E-ISSN 1879-1298
Grant - others:GA MŠMT(CZ) ME09024; GA ČR(CZ) GA525/09/1058
Program: GA
Institutional research plan: CEZ:AV0Z40550506
Keywords : PCB * plant * GCxGC/TOFMS * phytoremediation * hydroxy-PCB * methoxy-PCB * hydroxy-methoxy-PCB
Subject RIV: CC - Organic Chemistry
Impact factor: 3.137, year: 2012

The hairy root culture of black nightshade (Solanum nigrum) SNC-90 was exposed to 2,2'-dichlorobiphenyl (PCB 4) and 2,6-dichlorobiphenyl (PCB 10) to follow the metabolites produced. The analytical standards of 4-hydroxy-2,2'-dichlorobiphenyl, 5'-hydroxy-2,2'-dichlorobiphenyl, 4-hydroxy-2,6-dichlorobiphenyl, 2-hydroxy-2',6'-dichlorobiphenyl, 3-hydroxy-2',6'-dichlorobiphenyl and 4-hydroxy-2',6'-dichlorobiphenyl have been synthesized. Hydroxy-metabolites of both PCB 4 and PCB 10 were present in the biomass. These appeared mainly as conjugates rather than as free hydroxy-PCBs, both maintained in plant cells. The concentrations of non-conjugated hydroxy-PCBs ranged between 0.9 and 35.2 mu g kg(-1) of biomass fresh weight and the concentration of the conjugated ones ranged between 2.0 and 113.0 mu g kg(-1) depending on the position of hydroxyl. The para- position of biphenyl (4 or 4') seems to be preferred for hydroxylation. Methoxy-PCBs and hydroxy-methoxy-PCBs have also been identified in plant cells. Hydroxyl in the meta-position (3, 3' . 5 or 5') appears to be preferred for methylation in hydroxy-PCBs. Hydroxy-methoxy-PCBs have occurred in the conjugated form as well.
Permanent Link: http://hdl.handle.net/11104/0213507