This includes product samples (Martinez-Giron et al. 2010), water samples (Wang
et al. 2013a, b; Lee et al. 2016), aquatic organisms (Franke et al. 1999; Gatermann
et al. 2002a, b) and others. A first review on the environmental implications of
polycyclic musks was already published in 1999 (Kallenborn et al. 1999a, b, c) and
comprehensively described in a dedicated book (Rimkus 2004). In addition to
potential toxicological aspects, the chirality of polycyclic musks and their transformation products is currently also discussed in the context of pheromone-like effects
and potential behavioural consequences for higher organisms (Kallenborn et al.
1999a, b, c; Rimkus 2004; van der Burg et al. 2008). Detailed information and
relevant examples on this interesting compound group will be provided when uptake
and distribution profile in higher organisms, as well as human exposure is discussed.
In recent years, scientific information on enantiomer-selective microbial transformation has been extended into several emerging contaminant groups containing
chiral member substances. This includes currently used pesticides (Monkiedje et al.
2003; Monkiedje and Spiteller 2005; Tan et al. 2008; Garrison et al. 2011a, b; Liu
et al. 2015a, b, 2016a, b; Frkova et al. 2016), polychlorinated biphenyl atropisomers
(Pakdeesusuk et al. 2003; Ross et al. 2011a, b), cyclodiene pesticides (Huang et al.
2017; Sanchez-Osorio et al. 2017) and pharmaceuticals (Ribeiro et al. 2014;
Sanganyado et al. 2017).
8.2 Transformation/Accumulation of Chiral Xenobiotics
in Higher Organisms
8.2.1 Marine and Freshwater Organisms
8.2.1.1 α-Hexachlorocyclohexane
In 1991, Kallenborn et al. were the first to report on the successful application of
enantioselective cGC in vertebrate tissue samples. The here-reported study aimed at
investigating the enantiomer-selective transformation of α-HCH in seabird tissue
samples (Kallenborn et al. 1991). The authors collected carcasses from common
Eiders (Somateria mollissima (L.)) drown in local fishing nets from the Oehe/
Schleimünde wildlife refuge on the German Baltic coast. Organ samples were
taken, thus, only from healthy animals. The common Eider duck was chosen,
because it largely favours molluscs, but in that region particularly blue mussels
(Mytilus edulis L.) in its diet (Kallenborn et al. 1994a, b). Blue mussels, in turn, are
capable of strongly enriching pollutants and thus serve as “indicator organisms” in
many national monitoring programs in order to provide insight into the state of an
aquatic environment (Beyer et al. 2017). Thus, due to the highly specialist food
habits of common eiders in this region, a simple and almost complete “food chain”
can be assumed (water ! mussel ! common Eider duck) for this study. The tissue
samples (mussel, liver, kidney and pectoral muscle) were homogenised with a threeto five-fold amount of anhydrous sodium sulphate (Na 2 SO 4 ), followed by the
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8 Enantiomer-Specific Fate and Behaviour of Chiral Contaminants
et al. 2013a, b; Lee et al. 2016), aquatic organisms (Franke et al. 1999; Gatermann
et al. 2002a, b) and others. A first review on the environmental implications of
polycyclic musks was already published in 1999 (Kallenborn et al. 1999a, b, c) and
comprehensively described in a dedicated book (Rimkus 2004). In addition to
potential toxicological aspects, the chirality of polycyclic musks and their transformation products is currently also discussed in the context of pheromone-like effects
and potential behavioural consequences for higher organisms (Kallenborn et al.
1999a, b, c; Rimkus 2004; van der Burg et al. 2008). Detailed information and
relevant examples on this interesting compound group will be provided when uptake
and distribution profile in higher organisms, as well as human exposure is discussed.
In recent years, scientific information on enantiomer-selective microbial transformation has been extended into several emerging contaminant groups containing
chiral member substances. This includes currently used pesticides (Monkiedje et al.
2003; Monkiedje and Spiteller 2005; Tan et al. 2008; Garrison et al. 2011a, b; Liu
et al. 2015a, b, 2016a, b; Frkova et al. 2016), polychlorinated biphenyl atropisomers
(Pakdeesusuk et al. 2003; Ross et al. 2011a, b), cyclodiene pesticides (Huang et al.
2017; Sanchez-Osorio et al. 2017) and pharmaceuticals (Ribeiro et al. 2014;
Sanganyado et al. 2017).
8.2 Transformation/Accumulation of Chiral Xenobiotics
in Higher Organisms
8.2.1 Marine and Freshwater Organisms
8.2.1.1 α-Hexachlorocyclohexane
In 1991, Kallenborn et al. were the first to report on the successful application of
enantioselective cGC in vertebrate tissue samples. The here-reported study aimed at
investigating the enantiomer-selective transformation of α-HCH in seabird tissue
samples (Kallenborn et al. 1991). The authors collected carcasses from common
Eiders (Somateria mollissima (L.)) drown in local fishing nets from the Oehe/
Schleimünde wildlife refuge on the German Baltic coast. Organ samples were
taken, thus, only from healthy animals. The common Eider duck was chosen,
because it largely favours molluscs, but in that region particularly blue mussels
(Mytilus edulis L.) in its diet (Kallenborn et al. 1994a, b). Blue mussels, in turn, are
capable of strongly enriching pollutants and thus serve as “indicator organisms” in
many national monitoring programs in order to provide insight into the state of an
aquatic environment (Beyer et al. 2017). Thus, due to the highly specialist food
habits of common eiders in this region, a simple and almost complete “food chain”
can be assumed (water ! mussel ! common Eider duck) for this study. The tissue
samples (mussel, liver, kidney and pectoral muscle) were homogenised with a threeto five-fold amount of anhydrous sodium sulphate (Na 2 SO 4 ), followed by the
130
8 Enantiomer-Specific Fate and Behaviour of Chiral Contaminants