title: Metabolites of 2,2'-dichlorobiphenyl and 2,6-dichlorobiphenyl in hairy root culture of black nightshade Solanum nigrum SNC-9O.
abstract: The hairy root culture of black nightshade (Solanum nigrum) SNC-9O 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 μg kg(-1) of biomass fresh weight and the concentration of the conjugated ones ranged between 2.0 and 113.0 μg 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.
authors: Joint Laboratory of the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Institute of Chemical Technology Prague, Flemingovo namesti 2, 166 10 Prague 6, Czech Republic.
authors: Jan
authors: J
authors: Rezek
authors: Tomas
authors: T
authors: Macek
authors: Jan
authors: J
authors: Doubsky
authors: Martina
authors: M
authors: Mackova
mesh_terms: D002849:Chromatography, Gas; D004785:Environmental Pollutants / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D013058:Mass Spectrometry; D018517:Plant Roots / Q000378:metabolism; D011078:Polychlorinated Biphenyls / Q000737:chemistry / Q000378:metabolism*; D032324:Solanum nigrum / Q000378:metabolism*
chemical_list: D004785:Environmental Pollutants; C029908:2,6-dichlorobiphenyl; C012280:2,2'-dichlorobiphenyl; D011078:Polychlorinated Biphenyls