Vetter W, Scholz E, Luckas B, Maruya K A
Institut fur Ernahrungswissenschaften, Friedrich-Schiller-Universitat Jena, Dornburger Strasse 25, D-07743 Jena, Germany.
J Agric Food Chem. 2001 Feb;49(2):759-65. doi: 10.1021/jf000212f.
A Cl(7) component of technical toxaphene (CTT), previously detected in marine mammals and fish and referred to as "7-1", was isolated from contaminated estuarine sediment using preparative solid-liquid chromatography followed by reversed-phase HPLC. The structure of this compound, elucidated by GC/MS and (1)H NMR, was 2-endo,3-exo,5-endo,6-exo,8,8,10-heptachlorobornane (hereafter referred to as B7-1000). This newly identified CTT eluted in the nonpolar fraction from silica and shares the alternating endo-exo chlorine substitution pattern with other relatively nonpolar, persistent congeners (e.g., B8-1413 and B9-1679). Based on ECNI-MS response, levels of B7-1000 in tissue samples of various higher organisms including humans were as high as 16% of B8-1413. Enantioselective determination of B7-1000 using a modified cyclodextrin chiral stationary phase (beta-BSCD) resulted in enantiomer ratios that were depleted in adipose tissue of a marine bird (skua) and Weddell seal blubber (0.3 and 0.5, respectively), but not in elephant seal blubber (1.1). Elucidation of the structure of B7-1000 thus validates previous predictions of persistence based on structure-activity relationships, chromatographic properties, and molecular modeling.
