» Articles » PMID: 30131775

Diastereoisomer-Specific Biotransformation of Hexabromocyclododecanes by a Mixed Culture Containing Strain 195

Overview
Journal Front Microbiol
Specialty Microbiology
Date 2018 Aug 23
PMID 30131775
Citations 4
Authors
Affiliations
Soon will be listed here.
Abstract

Hexabromocyclododecane (HBCD) stereoisomers may exhibit substantial differences in physicochemical, biological, and toxicological properties. However, there remains a lack of knowledge about stereoisomer-specific toxicity, metabolism, and environmental fate of HBCD. In this study, the biotransformation of (±)α-, (±)β-, and (±)γ-HBCD contained in technical HBCD by a mixed culture containing the organohalide-respiring bacterium strain 195 was investigated. Results showed that the mixed culture was able to efficiently biotransform the technical HBCD mixture, with 75% of the initial HBCD (∼12 μM) in the growth medium being removed within 42 days. Based on the metabolites analysis, HBCD might be sequentially debrominated via dibromo elimination reaction to form tetrabromocyclododecene, dibromocyclododecadiene, and 1,5,9-cyclododecatriene. The biotransformation of the technical HBCD was likely diastereoisomer-specific. The transformation rates of α-, β-, and γ-HBCD were in the following order: α-HBCD > β-HBCD > γ-HBCD. The enantiomer fractions of (±)α-, (±)β-, and (±)γ-HBCD were maintained at about 0.5 during the 28 days of incubation, indicating a lack of enantioselective biotransformation of these diastereoisomers. Additionally, the amendment of another halogenated substrate tetrachloroethene (PCE), which supports the growth of strain 195, had a negligible impact on the transformation patterns of HBCD diastereoisomers and enantiomers. This study provided new insights into the stereoisomer-specific transformation patterns of HBCD by anaerobic microbes and has important implications for microbial remediation of anoxic environments contaminated by HBCD using the mixed culture containing .

Citing Articles

Co-metabolic degradation and metabolite detection of hexabromocyclododecane by Shewanella oneidensis MR-1.

Shah S, Wang Y, Anwar N, Abbas S, Khan K, Wang S Appl Microbiol Biotechnol. 2023; 108(1):25.

PMID: 38157005 DOI: 10.1007/s00253-023-12905-6.


Transformation of HBCDs by Rhodococcus sp. stu-38.

Yu F, Luo W, Li Y, Meng S, Lin X, Li L Curr Microbiol. 2022; 79(7):200.

PMID: 35596087 DOI: 10.1007/s00284-022-02872-y.


Microbial debromination of hexabromocyclododecanes.

Yu F, Li Y, Wang H, Peng T, Wu Y, Hu Z Appl Microbiol Biotechnol. 2021; 105(11):4535-4550.

PMID: 34076715 DOI: 10.1007/s00253-021-11095-3.


Update of the risk assessment of hexabromocyclododecanes (HBCDDs) in food.

Schrenk D, Bignami M, Bodin L, Chipman J, Del Mazo J, Grasl-Kraupp B EFSA J. 2021; 19(3):e06421.

PMID: 33732387 PMC: 7938899. DOI: 10.2903/j.efsa.2021.6421.

References
1.
Loffler F, Yan J, Ritalahti K, Adrian L, Edwards E, Konstantinidis K . Dehalococcoides mccartyi gen. nov., sp. nov., obligately organohalide-respiring anaerobic bacteria relevant to halogen cycling and bioremediation, belong to a novel bacterial class, Dehalococcoidia classis nov., order Dehalococcoidales ord. nov. and.... Int J Syst Evol Microbiol. 2012; 63(Pt 2):625-635. DOI: 10.1099/ijs.0.034926-0. View

2.
Haukas M, Hylland K, Berge J, Nygard T, Mariussen E . Spatial diastereomer patterns of hexabromocyclododecane (HBCD) in a Norwegian fjord. Sci Total Environ. 2009; 407(22):5907-13. DOI: 10.1016/j.scitotenv.2009.08.024. View

3.
Gerecke A, Giger W, Hartmann P, Heeb N, Kohler H, Schmid P . Anaerobic degradation of brominated flame retardants in sewage sludge. Chemosphere. 2006; 64(2):311-7. DOI: 10.1016/j.chemosphere.2005.12.016. View

4.
Wang S, Chng K, Wilm A, Zhao S, Yang K, Nagarajan N . Genomic characterization of three unique Dehalococcoides that respire on persistent polychlorinated biphenyls. Proc Natl Acad Sci U S A. 2014; 111(33):12103-8. PMC: 4142991. DOI: 10.1073/pnas.1404845111. View

5.
Liu F, Fennell D . Dechlorination and detoxification of 1,2,3,4,7,8-hexachlorodibenzofuran by a mixed culture containing Dehalococcoides ethenogenes Strain 195. Environ Sci Technol. 2008; 42(2):602-7. DOI: 10.1021/es071380s. View