scholarly journals 2.2-Diphenic Acid: A Reliable Biomarker Of Phenanthrene Biodegradation

Author(s):  
Emmanuel Fenibo

Phenanthrene is among the 16 priority pollutant and its mitigation in the environment has been a global concern. It serves as a model compound when it comes to biodgradation study of polyaromatic hydrocarbons (PAHs) because it has both the Bay- and K-region found in most PAH pollutants. Like other PAH pollutants, different means are available for its remediation in the environment, including microbial biodegradation. Diverse species of bacteria and fungi metabolize phenanthrenes as their sole source of carbon and energy. However, bacteria are more diverse in comparison to fungi. This has been shown in published pathways of phenanthrene biodegradation implicating various intermediary metabolites, including 2,2-diphenic acid, which is a downline metabolite of 9,10-dihydroxyphenanthrene. Though the 2,2-diphenic acid has been widely demonstrated to produce carbon (iv) oxide and linked to phthalate, only few has traced salicylic acid as its downstream molecule. 2,2-diphenic acid mounts equivalent position to 1-hydroxy-2-naphthoic acid, metabolite that ends the phenanthrene metabolic pathway. This is because they both produce phthalic acid and salicylic acid. As a product of bacteria and fungi during phenanthrene degradation, 2,2-diphenic acid can serve as a dependable biomarker of phenanthrene metabolism in a polluted habitat, where microbial community exist freely.

2011 ◽  
Vol 77 (18) ◽  
pp. 6606-6613 ◽  
Author(s):  
Dhan Prakash ◽  
Ravi Kumar ◽  
R. K. Jain ◽  
B. N. Tiwary

ABSTRACTThe organismAcinetobactersp. RKJ12 is capable of utilizing 2-chloro-4-nitrobenzoic acid (2C4NBA) as a sole source of carbon, nitrogen, and energy. In the degradation of 2C4NBA by strain RKJ12, various metabolites were isolated and identified by a combination of chromatographic, spectroscopic, and enzymatic activities, revealing a novel assimilation pathway involving both oxidative and reductive catabolic mechanisms. The metabolism of 2C4NBA was initiated by oxidativeorthodehalogenation, leading to the formation of 2-hydroxy-4-nitrobenzoic acid (2H4NBA), which subsequently was metabolized into 2,4-dihydroxybenzoic acid (2,4-DHBA) by a mono-oxygenase with the concomitant release of chloride and nitrite ions. Stoichiometric analysis indicated the consumption of 1 mol O2per conversion of 2C4NBA to 2,4-DHBA, ruling out the possibility of two oxidative reactions. Experiments with labeled H218O and18O2indicated the involvement of mono-oxygenase-catalyzed initial hydrolytic dechlorination and oxidative denitration mechanisms. The further degradation of 2,4-DHBA then proceeds via reductive dehydroxylation involving the formation of salicylic acid. In the lower pathway, the organism transformed salicylic acid into catechol, which was mineralized by theorthoring cleavage catechol-1,2-dioxygenase tocis, cis-muconic acid, ultimately forming tricarboxylic acid cycle intermediates. Furthermore, the studies carried out on a 2C4NBA−derivative and a 2C4NBA+transconjugant demonstrated that the catabolic genes for the 2C4NBA degradation pathway possibly reside on the ∼55-kb transmissible plasmid present in RKJ12.


2013 ◽  
Vol 1 (3) ◽  
pp. 97-105 ◽  
Author(s):  
Nirmal Kumar J.I. ◽  
Megha Barot ◽  
Shamiyan R Khan

The PAHs compounds are known to be carcinogenic, teratogenic, mutagenic and toxic to all living organism. Handful of literature is available on biodegradation of these compounds by bacteria and fungi, however, scanty work is done by using microalgae on biodegradation of these two PAHs. In this investigation, the efficiency of Aulosira fertilissima Ghose to remove fluoranthene (0.001gm.ml-1), phenanthrene (0.001gm.ml-1) and a mixture of both (each at concentration of 0.0005gm.ml-1) were evaluated for intermediate bio-transformants during biodegradation by using GCMS. The result showed that the efficiency of Aulosira fertilissima for removal and biodegradation of phenanthrene was higher than fluoranthene, indicate fluoranthene was more stable and recalcitrant. PAHs uptake after 7-days of treatment was 80% and 66% of these phenanthrene and fluoranthene, respectively by the cyanobacteria. The synergetic effect of fluoranthene on phenanthrene was observed, presence of fluoranthene stimulate the degradation of phenanthrene due to which phenanthrene produce more bio-transformants. Some intermediates were observed like Methyl linoleate, 4-(2,2- dimethyl-6-methylenecyclohexylidene)-3-methyl-,(Z)- etc. for phenanthrene biodegradation process while 2,3-dihydrofluoranthene, (1R,5R)-2-isopropyl-5-methylcyclohexanol, for fluoranthene degradation. Moreover, 3-isopropylidene-2,2-dimethyl-6-phenyl-1,4-oxathiane, 7- phenyltridecane, diphenylacetylene, for mixture of two PAHs applied.DOI: http://dx.doi.org/10.3126/ijasbt.v1i3.8232 Int J Appl Sci Biotechnol, Vol. 1(3) 2013 : 97-105


Author(s):  
James Ronald Lawrence ◽  
Gwendoline Joan Baxter ◽  
John Robert Paterson

Analyses in non-aspirin takers finding salicylic acid (SA) and hydroxylated metabolites in serum also SA and salicyluric acid (SU) in urine led to a re-evaluation of dietary sources of salicylates. Fruit and vegetable sources explained higher levels found in drug-free vegetarians, which overlapped with those from patients on low dose aspirin. That drug’s chemo-protective action in cancer is, at least partially, attributable to its principal metabolite, SA—which we believe contributes to the benefits of a vegetarian diet. However, diet is unlikely to be the sole source of the circulating salicylate found in aspirin-free animals and man. We adduced evidence for its persistence in prolonged fasting and biosynthesis in vivo from labelled benzoic acid. We review the roles, defined and potential, of SA in the biosphere. Emphasis on the antiplatelet effect of aspirin in man has detracted from the likely pivotal role of SA in many potential areas of bioregulation—probably as important in animals as in plants. In this expanding field, some aspirin effects, mediated by apparently conserved receptors responding to SA, are discussed. The perspectives revealed may lead to re-evaluation of the place of salicylates in therapeutics and potentially improve formulations and drug delivery systems.


Author(s):  
Sunil Kumar Narwal ◽  
Reena Gupta

The continuous accumulation of recalcitrant xenobiotic compounds into the ecosystem released from various sources caused a serious global concern. Xenobiotics compounds are carcinogenic, mutagenic, causing teratogenic effect and persist over a long period of time in the environment. Therefore there is an urgent need for the detoxification of these compounds. Biodegradation is a technique that employs natural biological processes to completely degrade toxic contaminants from the environment. The microorganisms possess a wide range of catabolic biodegradation pathways and, thus, use these toxic xenobiotics as the sole source of carbon and energy. Bacteria and fungi are source of xenobiotic degradation. For the development of successful and improved bioremediation processes, understanding of the biochemical and molecular aspects of xenobiotics biodegradation is required. The chapter aims to provide an overview of xenobiotic compounds, factors affecting biodegradation, the metabolic pathways and genetic adaptation in microorganisms for degradation of recalcitrant xenobiotic compounds.


2007 ◽  
Vol 73 (9) ◽  
pp. 2832-2838 ◽  
Author(s):  
Zhonghui Gai ◽  
Bo Yu ◽  
Li Li ◽  
Ying Wang ◽  
Cuiqing Ma ◽  
...  

ABSTRACT A carbazole-utilizing bacterium was isolated by enrichment from petroleum-contaminated soil. The isolate, designated Sphingomonas sp. strain XLDN2-5, could utilize carbazole (CA) as the sole source of carbon, nitrogen, and energy. Washed cells of strain XLDN2-5 were shown to be capable of degrading dibenzofuran (DBF) and dibenzothiophene (DBT). Examination of metabolites suggested that XLDN2-5 degraded DBF to 2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-2,4-hexadienic acid and subsequently to salicylic acid through the angular dioxygenation pathway. In contrast to DBF, strain XLDN2-5 could transform DBT through the ring cleavage and sulfoxidation pathways. Sphingomonas sp. strain XLDN2-5 could cometabolically degrade DBF and DBT in the growing system using CA as a substrate. After 40 h of incubation, 90% of DBT was transformed, and CA and DBF were completely removed. These results suggested that strain XLDN2-5 might be useful in the bioremediation of environments contaminated by these compounds.


2008 ◽  
Vol 32 (6) ◽  
pp. 927-955 ◽  
Author(s):  
Ri-He Peng ◽  
Ai-Sheng Xiong ◽  
Yong Xue ◽  
Xiao-Yan Fu ◽  
Feng Gao ◽  
...  

Microbiology ◽  
2014 ◽  
Vol 160 (5) ◽  
pp. 892-902 ◽  
Author(s):  
Piyali Pal Chowdhury ◽  
Jayita Sarkar ◽  
Soumik Basu ◽  
Tapan K. Dutta

Burkholderia sp. strain BC1, a soil bacterium, isolated from a naphthalene balls manufacturing waste disposal site, is capable of utilizing 2-hydroxy-1-naphthoic acid (2H1NA) and naphthalene individually as the sole source of carbon and energy. To deduce the pathway for degradation of 2H1NA, metabolites isolated from resting cell culture were identified by a combination of chromatographic and spectrometric analyses. Characterization of metabolic intermediates, oxygen uptake studies and enzyme activities revealed that strain BC1 degrades 2H1NA via 2-naphthol, 1,2,6-trihydroxy-1,2-dihydronaphthalene and gentisic acid. In addition, naphthalene was found to be degraded via 1,2-dihydroxy-1,2-dihydronaphthalene, salicylic acid and gentisic acid, with the putative involvement of the classical nag pathway. Unlike most other Gram-negative bacteria, metabolism of salicylic acid in strain BC1 involves a dual pathway, via gentisic acid and catechol, with the latter being metabolized by catechol 1,2-dioxygenase. Involvement of a non-oxidative decarboxylase in the enzymic transformation of 2H1NA to 2-naphthol indicates an alternative catabolic pathway for the bacterial degradation of hydroxynaphthoic acid. Furthermore, the biochemical observations on the metabolism of structurally similar compounds, naphthalene and 2-naphthol, by similar but different sets of enzymes in strain BC1 were validated by real-time PCR analyses.


2004 ◽  
Vol 70 (6) ◽  
pp. 3552-3557 ◽  
Author(s):  
S. C. Corgi� ◽  
T. Beguiristain ◽  
C. Leyval

ABSTRACT Rhizodegradation of organic pollutants, such as polycyclic aromatic hydrocarbons, is based on the effect of root-produced compounds, known as exudates. These exudates constitute an important and constant carbon source that selects microbial populations in the plant rhizosphere, modifying global as well as specific microbial activities. We conducted an experiment in two-compartment devices to show the selection of bacterial communities by root exudates and phenanthrene as a function of distance to roots. Using direct DNA extraction, PCR amplification, and thermal gradient gel electrophoresis screening, bacterial population profiles were analyzed in parallel to bacterial counts and quantification of phenanthrene biodegradation in three layers (0 to 3, 3 to 6, and 6 to 9 mm from root mat) of unplanted-polluted (phenanthrene), planted-polluted, and planted-unpolluted treatments. Bacterial community differed as a function of the distance to roots, in both the presence and the absence of phenanthrene. In the planted and polluted treatment, biodegradation rates showed a strong gradient with higher values near the roots. In the nonplanted treatment, bacterial communities were comparable in the three layers and phenanthrene biodegradation was high. Surprisingly, no biodegradation was detected in the section of planted polluted treatment farthest from the roots, where the bacterial community structure was similar to those of the nonplanted treatment. We conclude that root exudates and phenanthrene induce modifications of bacterial communities in polluted environments and spatially modify the activity of degrading bacteria.


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