Compound degraded:Lindane

General Description (About POP compound)

Lindane, an organochlorine pesticide, has been extensively used across the world to control a range of plant harming insects and pest. Lindane causes detrimental impacts on the environment and human health owing to its high toxicity, low degradation, and bioaccumulation. Its toxic nature can be overcome by biological and eco-friendly approaches involving its degradation and detoxification. 

Biodegradation pathway

Publications

Abstract Title Authors Article Link
Lindane, an organochlorine pesticide, causes detrimental impacts on the environment and human health owing to its high toxicity, low degradation, and bioaccumulation. Its toxic nature can be overcome by biological and eco-friendly approaches involving its degradation and detoxification. The biodegradation of lindane was assessed using actinobacterial species Thermobifida cellulosilytica TB100 (T. cellulosilytica), Thermobifida halotolerans DSM 44931 (T. halotolerans) and Streptomyces coelicolor A3 (S. coelicolor). The degradation conditions of Lindane such as pH, temperature, inoculum volume, glucose concentration and number of days were optimized under broth conditions. Lindane degradation at different concentrations was studied in soil using reverse phase-high performance liquid chromatography over a 30 day period. A bioassay test was performed on seeds of Lactuca sativa (Lettuce) to assess the success of bioremediated soil. Maximum lindane degradation in soil was observed using T. cellulosilytica sp. The degradation trend for different concentrations of lindane using T. halotolerans in sterilized soil was 55 mg kg?1 (82%) ? 155 mg kg?1 (75%) ? 255 mg kg?1 (70%) after an incubation period of 30 days. Lindane degradation in soil followed the first order reaction kinetics. Phytotoxicity test on seeds of Lactuca sativa showed considerably good vigor index values for the bioremediated sterilized and non-sterilized soil by T. cellulosilytica, T. halotolerans and S. coelicolor in comparison to the contaminated soil without bacteria. This confirms that these actinobacterial species can be implemented in bioaugmentation of contaminated sites to efficiently remediate high lindane concentrations. Bioremediation of lindane contaminated soil: Exploring the potential of actinobacterial strains Usmani et al., 2021 Link
A fungal strain able to use lindane as a carbon and energy source under aerobic conditions was isolated from Agave tequilana leaves by enrichment techniques. With molecular techniques, it was identified as Fusarium verticillioides. The effect of a number of nutritional and environmental factors on the pesticide biodegradation was investigated using a Plackett–Burman design. Lindane biodegradation was higher in the presence of limited amounts of nitrogen and phosphorus. The addition of agave leaves to the culture medium and the use of higher concentrations of lindane, copper, and yeast extract improved the efficiency of the biodegradation process. The analysis of the metabolites using GC–MS identified ?-pentachlorocyclohexene and benzoic acid derivatives. This finding suggests that there is an aerobic carboxylation step, reported for the first time, in the lindane biodegradation pathway of F. verticillioides. Adding organic matter such as Agave tequilana leaves to the culture medium improved the fungal viability, eliminated the lag growth phase for fungal growth, and increased the pH value of the culture medium. The increased pH helped to overcome the toxicity of the benzoic acid derivatives that were released during lindane degradation. Lindane biodegradation by the Fusarium verticillioides AT-100 strain, isolated from Agave tequilana leaves: Kinetic study and identification of metabolites Guillén-Jiménez et al., 2012 Link
The pesticide ?-hexachlorocyclohexane (?-HCH) is a persistent organic pollutant (POP) that raises public health and environmental pollution concerns worldwide. Although several isolates of ?-HCH-degrading bacteria are available, inoculating them directly into ?-HCH-contaminated soil is ineffective because of the bacterial survival rate. Cucurbita species incorporate significant amounts of POPs from soils compared with other plant species. Here, we describe a novel bioremediation strategy that combines the bacterial degradation of ?-HCH and the efficient uptake of ?-HCH by Cucurbita species. We produced transgenic hairy root cultures of Cucurbita moschata that expressed recombinant bacterial linA, isolated from the bacterium Sphingobium japonicum UT26. The LinA protein was accumulated stably in the hairy root cultures by fusing an endoplasmic reticulum (ER)-targeting signal peptide to LinA. Then, we demonstrated that the cultures degraded more than 90 % of ?-HCH (1 ppm) overnight and produced the ?-HCH metabolite 1,2,4-trichlorobenzene, indicating that LinA degraded ?-HCH. These results indicate that the gene linA has high potential for phytoremediation of environmental ?-HCH. Biodegradation of ?-hexachlorocyclohexane by transgenic hairy root cultures of Cucurbita moschata that accumulate recombinant bacterial LinA Nanasato et al., 2016 Link
Palladium nanoparticles stabilized in microcellular high-density polyethylene prepared through supercritical foaming, supercritical impregnation, and H2 reduction are used for the hydrodechlorination of lindane and hexachlorobenzene in supercritical carbon dioxide below 100 °C. Both lindane and hexachlorobenzene can be almost 100% transformed to cyclohexane in 1 h. Reaction intermediates, such as lower chlorinated products or benzene, are not observed or exist in trace amount indicating that most of them may undergo reactions without leaving the metal surface. Degradation of lindane and hexachlorobenzene in supercritical carbon dioxide using palladium nanoparticles stabilized in microcellular high-density polyethylene Wu et al., 2016 Link
The ? isomer of hexachlorocyclohexane (HCH), also known as lindane, is a carcinogenic persistent organic pollutant. Lindane was used worldwide as an agricultural insecticide. Legacy soil and groundwater contamination with lindane and other HCH isomers is still a big concern. The biotic reductive dechlorination of HCH to nondesirable and toxic lower chlorinated compounds such as monochlorobenzene (MCB) and benzene, among others, has been broadly documented. Here, we demonstrate that complete biodegradation of lindane to nontoxic end products is attainable using a sequential treatment approach with three mixed anaerobic microbial cultures referred to as culture I, II, and III. Biaugmentation with culture I achieved dechlorination of lindane to MCB and benzene. Culture II was able to dechlorinate MCB to benzene, and finally, culture III carried out methanogenic benzene degradation. Distinct Dehalobacter populations, corresponding to different 16S rRNA amplicon sequence variants in culture I and culture II, were responsible for lindane and MCB dechlorination, respectively. This study continues to highlight key roles of Dehalobacter as chlorobenzene- and HCH -respiring bacteria and demonstrates that sequential treatment with specialized anaerobic cultures may be explored at field sites in order to address legacy soil and groundwater contamination with HCH. Biodegradation of Lindane (?-Hexachlorocyclohexane) To Nontoxic End Products by Sequential Treatment with Three Mixed Anaerobic Microbial Cultures Jácome et al., 2021 Link
Technical hexachlorocyclohexane (HCH) and lindane are obsolete pesticides whose former production and use led to widespread contaminations posing serious and lasting health and environmental risks. Out of nine possible stereoisomers, ?-, ?-, ?-, and ?-HCH are usually present at contaminated sites, and research for a better understanding of their biodegradation has become essential for the development of appropriate remediation technologies. Because haloalkane dehalogenase LinB was recently found responsible for the hydroxylation of ?-HCH, ?-HCH, and ?-pentachlorocyclohexene (?-PCCH), we decided to examine whether ?- and ?-PCCH, which can be formed by LinA from ?- and ?-HCH, respectively, were also converted by LinB. Incubation of such substrates with Escherichia coli BL21 expressing functional LinB originating from Sphingobium indicum B90A showed that both ?-PCCH and ?-PCCH were direct substrates of LinB. Furthermore, we identified the main metabolites as 3,4,5,6-tetrachloro-2-cyclohexene-1-ols and 2,5,6-trichloro-2-cyclohexene-1,4-diols by nuclear magnetic resonance spectroscopy and gas chromatography?mass spectrometry. In contrast to ?-HCH, ?-HCH was not a substrate for LinB. On the basis of our data, we propose a modified ?-HCH degradation pathway in which ?-PCCH is converted to 2,5-cyclohexadiene-1,4-diol via 3,4,5,6-tetrachloro-2-cyclohexene-1-ol and 2,5,6-trichloro-2-cyclohexene-1,4-diol. New Metabolites in the Degradation of ?- and ?-Hexachlorocyclohexane (HCH): Pentachlorocyclohexenes Are Hydroxylated to Cyclohexenols and Cyclohexenediols by the Haloalkane Dehalogenase LinB from Sphingobium indicum B90A Raina et al., 2008 Link
Growth characteristics of the aerobic bacterial strain Arthrobacter citreus BI-100 in mineral salts medium with ?-hexachlorocyclohexane (?-HCH) as the sole source of carbon and degradation of ?-HCH by the strain are reported. The highest yield of the bacteria is observed at a ?-HCH concentration of 100 mg/L. At this concentration, the bacteria entered the exponential phase of growth without any lag. At 8 h of growth, no residual HCH, but its metabolites, was detectable in the medium. The bacterium attained its stationary phase at 48 h and at 72 h; no metabolite of ?-HCH could be detected by gas chromatography. Six metabolic intermediates of ?-HCH produced by A. citreus BI-100 at different periods of growth were characterized by using gas chromatography-mass spectrometry and high-performance liquid chromatography, which furnished evidence for the presence of ?-1,3,4,5,6-pentachlorocyclohexene, tetrachlorocyclohexene, trichlorocyclohexa-diene, 2-chlorophenol, phenol, and catechol, among others. Metabolism of ?-hexachlorocyclohexane by Arthrobacter citreus strain BI-100: Identification of metabolites Datta et al., 2000 Link
?-Hexachlorocyclohexane (?-HCH, also called ?-BHC and lindane) is a halogenated organic insecticide that causes serious environmental problems. The aerobic degradation pathway of ?-HCH was extensively revealed in bacterial strain Sphingobium japonicum (formerly Sphingomonas paucimobilis) UT26. ?-HCH is transformed to 2,5-dichlorohydroquinone through sequential reactions catalyzed by LinA, LinB, and LinC, and then 2,5-dichlorohydroquinone is further metabolized by LinD, LinE, LinF, LinGH, and LinJ to succinyl-CoA and acetyl-CoA, which are metabolized in the citrate/tricarboxylic acid cycle. In addition to these catalytic enzymes, a putative ABC-type transporter system encoded by linKLMN is also essential for the ?-HCH utilization in UT26. Preliminary examination of the complete genome sequence of UT26 clearly demonstrated that lin genes for the ?-HCH utilization are dispersed on three large circular replicons with sizes of 3.5 Mb, 682 kb, and 191 kb. Nearly identical lin genes were also found in other HCH-degrading bacterial strains, and it has been suggested that the distribution of lin genes is mainly mediated by insertion sequence IS6100 and plasmids. Recently, it was revealed that two dehalogenases, LinA and LinB, have variants with small number of amino acid differences, and they showed dramatic functional differences for the degradation of HCH isomers, indicating these enzymes are still evolving at high speed. Aerobic degradation of lindane (?-hexachlorocyclohexane) in bacteria and its biochemical and molecular basis Nagata et al., 2007 Link
Actinobacteria are well-known degraders of toxic materials that have the ability to tolerate and remove organochloride pesticides; thus, they are used for bioremediation. The biodegradation of organochlorines by actinobacteria has been demonstrated in pure and mixed cultures with the concomitant production of metabolic intermediates including ?-pentachlorocyclohexene (?-PCCH); 1,3,4,6-tetrachloro-1,4-cyclohexadiene (1,4-TCDN); 1,2-dichlorobenzene (1,2-DCB), 1,3-dichlorobenzene (1,3-DCB), or 1,4-dichlorobenzene (1,4-DCB); 1,2,3-trichlorobenzene (1,2,3-TCB), 1,2,4-trichlorobenzene (1,2,4-TCB), or 1,3,5-trichlorobenzene (1,3,5-TCB); 1,3-DCB; and 1,2-DCB. Chromatography coupled to mass spectrometric detection, especially GC–MS, is typically used to determine HCH-isomer metabolites. The important enzymes involved in HCH isomer degradation metabolic pathways include hexachlorocyclohexane dehydrochlorinase (LinA), haloalkane dehalogenase (LinB), and alcohol dehydrogenase (LinC). The metabolic versatility of these enzymes is known. Advances have been made in the identification of actinobacterial haloalkane dehydrogenase, which is encoded by linB. This knowledge will permit future improvements in biodegradation processes using Actinobacteria. The enzymatic and genetic characterizations of the molecular mechanisms involved in these processes have not been fully elucidated, necessitating further studies. New advances in this area suggest promising results. The scope of this paper encompasses the following: (i) the aerobic degradation pathways of hexachlorocyclohexane (HCH) isomers; (ii) the important genes and enzymes involved in the metabolic pathways of HCH isomer degradation; and (iii) the identification and quantification of intermediate metabolites through gas chromatography coupled to mass spectrometry (GC–MS). Streptomyces sp. is a powerful biotechnological tool for the biodegradation of HCH isomers: biochemical and molecular basis Cuozzo et al., 2017 Link
Lindane (?-HCH) is a pesticide that has mainly been used in agriculture. Lindane and the other HCH isomers are highly chlorinated hydrocarbons. The presence of a large number of electron withdrawing chlorine groups makes some of the HCH isomers rather recalcitrant in oxic environments. Especially ?-HCH is poorly degraded by aerobic bacteria. The chlorine groups make HCH isomers more accessible for an initial reductive attack, a common mechanism in anoxic environments. Among the HCH isomers, ?-HCH is degraded most easily while ?-HCH is most persistent. Little is known about the diversity of the microorganisms involved in anaerobic HCH degradation. Thus far, species within the genera Clostridium and Bacillus, two Desulfovibrio species, and one species each of Desulfococcus, Desulfobacter, Citrobacter and Dehalobacter have been found to metabolize lindane and other HCH isomers. Benzene and monochlorobenzene are the end products of anaerobic degradation, while in some studies pentachlorocyclohexane, tetrachlorocyclohexene, chlorobenzenes and chlorophenols have been detected as intermediates. Enzymes and coding genes involved in the reductive dechlorination of HCH isomers are largely unknown. Recently, a metagenomic analysis has indicated the presence of numerous putative reductive dehalogenase genes in the genome of ?-HCH degrading Dehalobacter sp. High-throughput omics techniques can help to explore the key players and enzymes involved in the reductive dehalogenation of lindane and other HCH isomers. Anaerobic Degradation of Lindane and Other HCH Isomers. Mehboob et al., 2013 Link
Gamma-hexachlorocyclohexane (?-HCH or lindane), one of the most commonly used insecticides, has been mainly used in agriculture. Organochloride compounds are known to be highly toxic and persistent, causing serious water and soil pollution. The objective of the present study is the evaluation of the anaerobic degradation of ?-, ?-, ?-, ?-HCH in liquid and slurry cultures. The slurry system with anaerobic sludge appears as an effective alternative in the detoxification of polluted soils with HCH, as total degradation of the four isomers was attained. While ?- and ?-HCH disappeared after 20–40 d, the most recalcitrant isomers: ?- and ?-HCH were only degraded after 102 d. Intermediate metabolites of HCH degradation as pentachlorocyclohexane (PCCH), tetrachlorocyclohexene (TCCH), tri-, di- and mono-chlorobenzenes were observed during degradation time. Anaerobic degradation of hexachlorocyclohexane isomers in liquid and soil slurry systems Quintero et al., 2005 Link
Lindane (?-hexachlorocyclohexane) is an organochlorine pesticide that has been widely used in agriculture over the last seven decades. The increasing residues of lindane in soil and water environments are toxic to humans and other organisms. Large-scale applications and residual toxicity in the environment require urgent lindane removal. Microbes, particularly Gram-negative bacteria, can transform lindane into non-toxic and environmentally safe metabolites. Aerobic and anaerobic microorganisms follow different metabolic pathways to degrade lindane. A variety of enzymes participate in lindane degradation pathways, including dehydrochlorinase (LinA), dehalogenase (LinB), dehydrogenase (LinC), and reductive dechlorinase (LinD). However, a limited number of reviews have been published regarding the biodegradation and bioremediation of lindane. This review summarizes the current knowledge regarding lindane-degrading microbes along with biodegradation mechanisms, metabolic pathways, and the microbial remediation of lindane-contaminated environments. The prospects of novel bioremediation technologies to provide insight between laboratory cultures and large-scale applications are also discussed. This review provides a theoretical foundation and practical basis to use lindane-degrading microorganisms for bioremediation. Insights Into the Biodegradation of Lindane (?-Hexachlorocyclohexane) Using a Microbial System Zhang et al., 2020 Link
Lindane, the ?-isomer of hexachlorocyclohexane (HCH), is a potent insecticide. Purified lindane or unpurified mixtures of this and ?-, ?-, and ?-isomers of HCH were widely used as commercial insecticides in the last half of the 20th century. Large dumps of unused HCH isomers now constitute a major hazard because of their long residence times in soil and high nontarget toxicities. The major pathway for the aerobic degradation of HCH isomers in soil is the Lin pathway, and variants of this pathway will degrade all four of the HCH isomers although only slowly. Sequence differences in the primary LinA and LinB enzymes in the pathway play a key role in determining their ability to degrade the different isomers. LinA is a dehydrochlorinase, but little is known of its biochemistry. LinB is a hydrolytic dechlorinase that has been heterologously expressed and crystallized, and there is some understanding of the sequence-structure-function relationships underlying its substrate specificity and kinetics, although there are also some significant anomalies. The kinetics of some LinB variants are reported to be slow even for their preferred isomers. It is important to develop a better understanding of the biochemistries of the LinA and LinB variants and to use that knowledge to build better variants, because field trials of some bioremediation strategies based on the Lin pathway have yielded promising results but would not yet achieve economic levels of remediation. Biochemistry of Microbial Degradation of Hexachlorocyclohexane and Prospects for Bioremediation Lal et al., 2010 Link