MetaCyc Pathway: parathion degradation
Inferred from experiment

Enzyme View:

Pathway diagram: parathion degradation

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds Degradation

Some taxa known to possess this pathway include : Brevundimonas diminuta, Sphingobium fuliginis

Expected Taxonomic Range: Bacteria

General Background

Organophosphate pesticides such as parathion and methyl parathion have been used extensively as insecticides, fungicides, and herbicides. Parathion, which is a cholinesterase inhibitor (see EC and for cholinesterases), is extremely toxic to most animals including humans (in which LD50 is 5 to 10 mg/kg), and may cause death by inducing respiratory failure. The use of Parathion is banned in many countries due to its toxicity and pollutant properties.

About This Pathway

Some bacterial strains are able to degrade parathion and related compounds. A mixed culture of at least 9 isolates was able to grow on parathion as a sole carbon and energy source [Munnecke76, Munnecke76a], although so far no single organism was shown to use parathion as the sole carbon source [Liu05b, Sethunathan73].

Two organisms that have been studied in detail are Sphingobium fuliginis [Sethunathan73] and Brevundimonas diminuta [Dumas89]. In both cases parathion degradation starts with the hydrolysis of parathion to 4-nitrophenol and diethylthiophosphate, followed by a second hydrolysis of diethylthiophosphate to diethylphosphate [Munnecke76]. In these organisms, 4-nitrophenol (PNP) was not degraded further, and was released into the environment. The rate of this enzymatic hydrolysis was more than 2000 fold faster than the chemical reaction, as catalyzed by 0.1N sodium hydroxide [Munnecke76a]. This initial hydrolysis of parathion reduces the toxicity by nearly 120-fold [Munnecke79].

The key enzyme in parathion degradation is parathion hydrolase, which has been described in a variety of bacteria. In the bacteria Sphingobium fuliginis and Brevundimonas diminuta the enzyme is encoded by related opd plasmid-borne genes [Mulbry86, McDaniel88, Harper88, Siddavattam03]. Similar enzymes have been purified from additional organisms, and are apparently encoded by genes non-related to the opd genes [Mulbry89]. Parathion hydrolases often have broad substrate range, broad temperature and pH optima, and high stability [Cohen79, Keil89].

Both products of this pathway, 4-nitrophenol and diethylthiophosphate, can be degraded by microorganisms. Two pathways of 4-nitrophenol degradation have been described (see 4-nitrophenol degradation I and 4-nitrophenol degradation II), and the degradation of diethylthiophosphate has been described in several mixed cultures [Shelton88, Ha07a]. However, the exact nature of this degradation pathway is not known yet.

It should be mentioned that in the case of the related compound methyl parathion, complete mineralization by a single organism has been reported several times. For more details, see methyl parathion degradation.

This pathway was curated based on a pathway curated in the UM-BBD database [Cornett97].

Relationship Links: Eawag-BBD-Pathways:RELATED-TO:pthn

Revised 23-Feb-2007 by Caspi R, SRI International


Cohen79: Cohen S (1979). "Teaching a patient how to use crutches." Am J Nurs 79(6);1111-26. PMID: 255328

Cornett97: Cornett, C. (1997). "The UM-BBD Parathion Pathway."

Dumas89: Dumas DP, Caldwell SR, Wild JR, Raushel FM (1989). "Purification and properties of the phosphotriesterase from Pseudomonas diminuta." J Biol Chem 264(33);19659-65. PMID: 2555328

Ha07a: Ha J, Engler CR, Wild JR (2007). "Biodegradation of chlorferon and diethylthiophosphate by consortia enriched from waste cattle dip solution." Bioresour Technol 98(10);1916-23. PMID: 16987656

Harper88: Harper LL, McDaniel CS, Miller CE, Wild JR (1988). "Dissimilar plasmids isolated from Pseudomonas diminuta MG and a Flavobacterium sp. (ATCC 27551) contain identical opd genes." Appl Environ Microbiol 54(10);2586-9. PMID: 3202637

Keil89: Keil TU (1989). "[AIDS fungus infections. Fluconazole--a new preparation in development]." Fortschr Med 107(10);69-70. PMID: 2541058

Liu05b: Liu H, Zhang JJ, Wang SJ, Zhang XE, Zhou NY (2005). "Plasmid-borne catabolism of methyl parathion and p-nitrophenol in Pseudomonas sp. strain WBC-3." Biochem Biophys Res Commun 334(4);1107-14. PMID: 16039612

McDaniel88: McDaniel CS, Harper LL, Wild JR (1988). "Cloning and sequencing of a plasmid-borne gene (opd) encoding a phosphotriesterase." J Bacteriol 170(5);2306-11. PMID: 2834339

Mulbry86: Mulbry WW, Karns JS, Kearney PC, Nelson JO, McDaniel CS, Wild JR (1986). "Identification of a plasmid-borne parathion hydrolase gene from Flavobacterium sp. by southern hybridization with opd from Pseudomonas diminuta." Appl Environ Microbiol 51(5);926-30. PMID: 3015022

Mulbry89: Mulbry WW, Karns JS (1989). "Purification and characterization of three parathion hydrolases from gram-negative bacterial strains." Appl Environ Microbiol 55(2);289-93. PMID: 2541658

Munnecke76: Munnecke DM, Hsieh DP (1976). "Pathways of microbial metabolism of parathion." Appl Environ Microbiol 1976;31(1);63-9. PMID: 8005

Munnecke76a: Munnecke DM (1976). "Enzymatic hydrolysis of organophosphate insecticides, a possible pesticide disposal method." Appl Environ Microbiol 32(1);7-13. PMID: 9901

Munnecke79: Munnecke DM (1979). "Hydrolysis of organophosphate insecticides by an immobilized-enzyme system." Biotechnol Bioeng 21(12);2247-61. PMID: 42449

Sethunathan73: Sethunathan N, Yoshida T (1973). "A Flavobacterium sp. that degrades diazinon and parathion." Can J Microbiol 19(7);873-5. PMID: 4727806

Shelton88: Shelton DR (1988). "Mineralization of Diethylthiophosphoric Acid by an Enriched Consortium from Cattle Dip." Appl Environ Microbiol 54(10);2572-2573. PMID: 16347763

Siddavattam03: Siddavattam D, Khajamohiddin S, Manavathi B, Pakala SB, Merrick M (2003). "Transposon-like organization of the plasmid-borne organophosphate degradation (opd) gene cluster found in Flavobacterium sp." Appl Environ Microbiol 69(5);2533-9. PMID: 12732518

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Benning94: Benning MM, Kuo JM, Raushel FM, Holden HM (1994). "Three-dimensional structure of phosphotriesterase: an enzyme capable of detoxifying organophosphate nerve agents." Biochemistry 33(50);15001-7. PMID: 7999757

Bondarenko04: Bondarenko S, Gan J, Haver DL, Kabashima JN (2004). "Persistence of selected organophosphate and carbamate insecticides in waters from a coastal watershed." Environ Toxicol Chem 23(11);2649-54. PMID: 15559280

Khajamohiddin06: Khajamohiddin S, Babu PS, Chakka D, Merrick M, Bhaduri A, Sowdhamini R, Siddavattam D (2006). "A novel meta-cleavage product hydrolase from Flavobacterium sp. ATCC27551." Biochem Biophys Res Commun 351(3);675-81. PMID: 17078928

Kitagawa04: Kitagawa W, Kimura N, Kamagata Y (2004). "A novel p-nitrophenol degradation gene cluster from a gram-positive bacterium, Rhodococcus opacus SAO101." J Bacteriol 186(15);4894-902. PMID: 15262926

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Omburo92: Omburo GA, Kuo JM, Mullins LS, Raushel FM (1992). "Characterization of the zinc binding site of bacterial phosphotriesterase." J Biol Chem 267(19);13278-83. PMID: 1320014

Perry07: Perry LL, Zylstra GJ (2007). "Cloning of a gene cluster involved in the catabolism of p-nitrophenol by Arthrobacter sp. strain JS443 and characterization of the p-nitrophenol monooxygenase." J Bacteriol 189(21);7563-72. PMID: 17720792

Serdar89: Serdar, C.M., Murdock, D.C., Rohde, M.F. (1989). "Parathion Hydrolase Gene from Pseudomonas diminuta MG: Subcloning, Complete Nucleotide Sequence, and Expression of the Mature Portion of the Enzyme in Escherichia coli." Bio/Technology 7: 1151-1155.

Spain91: Spain JC, Gibson DT (1991). "Pathway for Biodegradation of p-Nitrophenol in a Moraxella sp." Appl Environ Microbiol 57(3);812-819. PMID: 16348446

Williams79: Williams BT (1979). "Omental abscess: an unusual complication of cesarean section." South Med J 72(8);1025-6. PMID: 472806

Zhang09a: Zhang JJ, Liu H, Xiao Y, Zhang XE, Zhou NY (2009). "Identification and characterization of catabolic para-nitrophenol 4-monooxygenase and para-benzoquinone reductase from Pseudomonas sp. strain WBC-3." J Bacteriol 191(8);2703-10. PMID: 19218392

Zhang12: Zhang S, Sun W, Xu L, Zheng X, Chu X, Tian J, Wu N, Fan Y (2012). "Identification of the para-nitrophenol catabolic pathway, and characterization of three enzymes involved in the hydroquinone pathway, in pseudomonas sp. 1-7." BMC Microbiol 12;27. PMID: 22380602

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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