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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: detoxification of reactive carbonyls in chloroplasts

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.

Synonyms: detoxification of small reactive electrophile species in chloroplasts

Superclasses: Detoxification
Metabolic Clusters

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col

Expected Taxonomic Range: Embryophyta

Summary:
General Background

Oxidative stress in plants often occurs in response to biotic and abiotic stresses. The reactive oxygen species that form under oxidative stress can damage numerous biomolecules, including proteins and lipids. The chloroplast, an organelle often subject to oxidative stress, contains a high proportion of linolenic and linoleic acids in its membrane. When these prevalent fatty acids undergo lipid peroxidation, a variety of short-chain carbonyls may be formed. A subset of these, α,β-unsaturated carbonyls, such as acrolein are known to cause damage to cells and tissues. In chloroplasts, this damage can threaten to disrupt to vital process of photosynthesis [Yamauchi, Mano09, Almeras03]. Therefore, several mechnisms for detoxifying these reactive carbonyl compounds are present in chloroplasts [Yamauchi11]. Glutathione-S-transferase (GST)-based modification of toxic compounds is one robust system that is supported by high levels of glutathione in the chloroplast. But, there is evidence that compounds such as acrolein reduce the rate of photosynthesis when glutathione needed for detoxification in not available to allow the function of several Calvin cycle enzymes [Mano09]. The NADPH-dependent set of reactions depicted in this metabolic cluster provide another means for reducing the toxicity of reactive eletrophilic carbonyl compounds in the chloroplast [Yamauchi11, Simpson09].

Similar pathways for detoxification are likely to exist in the mitochondria and cytosol, but, they will be carried out by a set of related enzymes present in those compartments [Yamauchi11].

About This Pathway

Two different type of enzymatic activities that can be used to minimize the threat posed by reactive carbonyl compounds are shown in this metabolic cluster.

AOR acts to reduce the the unsaturated bond on α,β-unsaturated carbonyls, leading to the production of saturated ketones and aldehydes. Although the action of this enzyme is important, it cannot detoxify the whole assortment of reactive carbonyl compounds on its own. First, it does not show strong activity against α,β-unsaturated carbonyls that have more than 5 carbons. Second, the saturated aldehydes produced by AOR can also be dangerous to the plant. Therefore, additional enzymes with over-lapping substrate specificities, namely, a chloroplastic aldo-keto reductase and chloroplastic aldehyde reductase contribute to the protection of this organelle by reducing the carbonyl groups on toxic compounds to yield the corresponding alcohols [Yamauchi11, Simpson09].

Variants: (Z)-butanethiol-S-oxide biosynthesis , 4-hydroxy-2-nonenal detoxification , ascorbate glutathione cycle , baicalein degradation (hydrogen peroxide detoxification) , cyanate degradation , farnesylcysteine salvage pathway , fluoroacetate degradation , furfural degradation , glutathione-mediated detoxification I , glutathione-mediated detoxification II , mycothiol-mediated detoxification , oxidized GTP and dGTP detoxification , seleno-amino acid detoxification and volatilization III , superpathway of seleno-compound metabolism

Credits:
Created 05-Apr-2011 by Dreher KA , TAIR


References

Almeras03: Almeras E, Stolz S, Vollenweider S, Reymond P, Mene-Saffrane L, Farmer EE (2003). "Reactive electrophile species activate defense gene expression in Arabidopsis." Plant J 34(2);205-16. PMID: 12694595

Mano09: Mano J, Miyatake F, Hiraoka E, Tamoi M (2009). "Evaluation of the toxicity of stress-related aldehydes to photosynthesis in chloroplasts." Planta 230(4);639-48. PMID: 19578873

Simpson09: Simpson PJ, Tantitadapitak C, Reed AM, Mather OC, Bunce CM, White SA, Ride JP (2009). "Characterization of two novel aldo-keto reductases from Arabidopsis: expression patterns, broad substrate specificity, and an open active-site structure suggest a role in toxicant metabolism following stress." J Mol Biol 392(2);465-80. PMID: 19616008

Yamauchi: Yamauchi Y, Furutera A, Seki K, Toyoda Y, Tanaka K, Sugimoto Y "Malondialdehyde generated from peroxidized linolenic acid causes protein modification in heat-stressed plants." Plant Physiol Biochem 46(8-9);786-93. PMID: 18538576

Yamauchi11: Yamauchi Y, Hasegawa A, Taninaka A, Mizutani M, Sugimoto Y (2011). "NADPH-dependent Reductases Involved in the Detoxification of Reactive Carbonyls in Plants." J Biol Chem 286(9);6999-7009. PMID: 21169366

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

Asai96: Asai H, Imaoka S, Kuroki T, Monna T, Funae Y (1996). "Microsomal ethanol oxidizing system activity by human hepatic cytochrome P450s." J Pharmacol Exp Ther 277(2);1004-9. PMID: 8627510

Bondoc99: Bondoc FY, Bao Z, Hu WY, Gonzalez FJ, Wang Y, Yang CS, Hong JY (1999). "Acetone catabolism by cytochrome P450 2E1: studies with CYP2E1-null mice." Biochem Pharmacol 58(3);461-3. PMID: 10424765

Bruce08: Bruce TJ, Matthes MC, Chamberlain K, Woodcock CM, Mohib A, Webster B, Smart LE, Birkett MA, Pickett JA, Napier JA (2008). "cis-Jasmone induces Arabidopsis genes that affect the chemical ecology of multitrophic interactions with aphids and their parasitoids." Proc Natl Acad Sci U S A 105(12);4553-8. PMID: 18356298

Choi08: Choi HW, Lee BG, Kim NH, Park Y, Lim CW, Song HK, Hwang BK (2008). "A role for a menthone reductase in resistance against microbial pathogens in plants." Plant Physiol 148(1);383-401. PMID: 18599651

Grant03a: Grant AW, Steel G, Waugh H, Ellis EM (2003). "A novel aldo-keto reductase from Escherichia coli can increase resistance to methylglyoxal toxicity." FEMS Microbiol Lett 218(1);93-9. PMID: 12583903

Jeudy06: Jeudy S, Monchois V, Maza C, Claverie JM, Abergel C (2006). "Crystal structure of Escherichia coli DkgA, a broad-specificity aldo-keto reductase." Proteins 62(1);302-7. PMID: 16284956

Ko05: Ko J, Kim I, Yoo S, Min B, Kim K, Park C (2005). "Conversion of methylglyoxal to acetol by Escherichia coli aldo-keto reductases." J Bacteriol 187(16);5782-9. PMID: 16077126

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

Lee13a: Lee C, Kim I, Park C (2013). "Glyoxal detoxification in Escherichia coli K-12 by NADPH dependent aldo-keto reductases." J Microbiol 51(4);527-30. PMID: 23990306

Mano05: Mano J, Belles-Boix E, Babiychuk E, Inze D, Torii Y, Hiraoka E, Takimoto K, Slooten L, Asada K, Kushnir S (2005). "Protection against photooxidative injury of tobacco leaves by 2-alkenal reductase. Detoxication of lipid peroxide-derived reactive carbonyls." Plant Physiol 139(4);1773-83. PMID: 16299173

Miller09: Miller EN, Jarboe LR, Yomano LP, York SW, Shanmugam KT, Ingram LO (2009). "Silencing of NADPH-dependent oxidoreductase genes (yqhD and dkgA) in furfural-resistant ethanologenic Escherichia coli." Appl Environ Microbiol 75(13);4315-23. PMID: 19429550

Mumm08: Mumm R, Posthumus MA, Dicke M (2008). "Significance of terpenoids in induced indirect plant defence against herbivorous arthropods." Plant Cell Environ 31(4);575-85. PMID: 18208515

Rutschow08: Rutschow H, Ytterberg AJ, Friso G, Nilsson R, van Wijk KJ (2008). "Quantitative proteomics of a chloroplast SRP54 sorting mutant and its genetic interactions with CLPC1 in Arabidopsis." Plant Physiol 148(1);156-75. PMID: 18633119

Salas06: Salas JJ, Garcia-Gonzalez DL, Aparicio R (2006). "Volatile compound biosynthesis by green leaves from an Arabidopsis thaliana hydroperoxide lyase knockout mutant." J Agric Food Chem 54(21);8199-205. PMID: 17032029

Tooker02: Tooker JF, Koenig WA, Hanks LM (2002). "Altered host plant volatiles are proxies for sex pheromones in the gall wasp Antistrophus rufus." Proc Natl Acad Sci U S A 99(24);15486-91. PMID: 12438683

Van01: Van Poecke RM, Posthumus MA, Dicke M (2001). "Herbivore-induced volatile production by Arabidopsis thaliana leads to attraction of the parasitoid Cotesia rubecula: chemical, behavioral, and gene-expression analysis." J Chem Ecol 27(10);1911-28. PMID: 11710601

Vander92: Vander Jagt DL, Robinson B, Taylor KK, Hunsaker LA (1992). "Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications." J Biol Chem 267(7);4364-9. PMID: 1537826

Vukovic09: Vukovic N, Sukdolak S, Solujic S, Niciforovic N (2009). "Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia." J Med Food 12(2);435-41. PMID: 19459749


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, biocyc14.