The phytohormone precursor OPDA is isomerized in the insect gut by a single, specific glutathione transferase

Proceedings of the National Academy of Sciences of the United States of America

Volumn 106, Issue 38, 2009, Pages 16304-16309

  Da̧browska, Paulina ^a   Freitak, Dalial ^a   Vogel, Heiko ^a   Heckel, David G ^a   Boland, Wilhelm ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

12 oxophytodienoic acid; Inactivation of OPDA

Indexed keywords

12 OXOPHYTODIENOIC ACID; GLUTATHIONE TRANSFERASE; HORMONE PRECURSOR; ISO 12 OXOPHYTODIENOIC ACID; PHYTOHORMONE; PROSTAGLANDIN A1; PROSTAGLANDIN B1; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CONJUGATION; CONTROLLED STUDY; INTESTINE; ISOMERIZATION; LARVA; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; WORM;

ANIMALS; DIGESTIVE SYSTEM; ELECTROPHORESIS, GEL, TWO-DIMENSIONAL; FATTY ACIDS, UNSATURATED; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLUTATHIONE TRANSFERASE; INSECT PROTEINS; INSECTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PLANT GROWTH REGULATORS; SPECIES SPECIFICITY; STEREOISOMERISM;

ALABAMA ARGILLACEA; GOSSYPIUM BARBADENSE; HELICOVERPA ARMIGERA; HEXAPODA; MAMMALIA; SPODOPTERA LITTORALIS;

EID: 70349504418     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0906942106     Document Type: Article

References (49)

1. Broadway RM, Duffey SS (1986) Plant proteinase-inhibitors-mechanism of action and effect on the growth and digestive physiology of larval Heliothis zea and Spodoptera exiqua. J Insect Physiol 32:827-833.
2. Turlings TCJ, et al. (1995) How caterpillar-damaged plants protect themselves by attracting parasitic wasps. Proc Natl Acad Sci USA 92:4169-4174.
3. Heil M (2004) Induction of two indirect defences benefits Lima bean (Phaseolus lunatus, Fabaceae) in nature. J Ecol 92:527-536.
4. Wasternack C (2007) Jasmonates: An update on biosynthesis, signal transduction and action in plant stress response, growth and development. Ann Bot 89:503-512.
5. Stelmach BA, et al. (1998) Quantitation of the octadecanoid 12-oxo-phytodienoic acid, a signaling compound in plant mechanotransduction. Phytochemistry 47:539-546.
6. Stintzi A, et al. (2001) Plant defense in the absence of jasmonic acid: The role of cyclopentenones. Proc Natl Acad Sci USA 98:12837-12842. (Pubitemid 33020031)
7. Strassner J, et al. (2002) Characterization and cDNA-microarray expression analysis of 12-oxophytodienoate reductases reveals differential roles for octadecanoid biosynthesis in the local versus the systemic wound response. Plant J 32:585-601. (Pubitemid 36814965)
8. Taki N, et al. (2005) 12-oxo-phytodienoic acid triggers expression of a distinct set of genes and plays a role in wound-induced gene expression in Arabidopsis. Plant Physiol 139:1268-1283. (Pubitemid 43786829)
9. Schulze B, Dabrowska P, Boland W (2007) Rapid enzymatic isomerization of 12- oxophytodienoic acid in the gut of lepidopteran larvae. Chembiochem 8:208-216. (Pubitemid 46232705)
10. Li XC, Schuler MA, Berenbaum MR (2002) Jasmonate and salicylate induce expression of herbivore cytochrome P450 genes. Nature 419:712-715.
11. Vollenweider S, et al. (2000) Fatty acid ketodienes and fatty acid ketotrienes: Michael addition acceptors that accumulate in wounded and diseased Arabidopsis leaves. Plant J 24:467-476. (Pubitemid 32003672)
12. Stanley DW, Miller JS (2006) Eicosanoid actions in insect cellular immune functions. Entomol Exp Appl 119:1-13.
13. Funke M, et al. (2008) Rapid hydrolysis of quorum-sensing molecules in the gut of lepidopteran larvae. ChemBioChem 9:1953-1959.
14. Jones RL (1970) A prostaglandin isomerase in cat plasma. Biochem J 119:P64.
15. Hayes JD, McLellan LI (1999) Glutathione and glutathione-dependent enzymes represent a co-ordinately regulated defence against oxidative stress. Free Radic Res 31:273-300.
16. Davoine C, et al. (2005) Conjugation of keto fatty acids to glutathione in plant tissues. Characterization and quantification by HPLC-tandem mass spectrometry. Anal Chem 77:7366-7372. (Pubitemid 41681405)
17. Davoine C, et al. (2006) Adducts of oxylipin electrophiles to glutathione reflect a 13 specificity of the downstream lipoxygenase pathway in the tobacco hypersensitive response. Plant Physiol 140:1484-1493. (Pubitemid 43956231)
18. Mueller S, et al. (2008) General detoxification and stress responses are mediated by oxidized lipids through transcription factors in Arabidopsis. Plant Cell 20:768-785. (Pubitemid 352844006)
19. Thoma I, et al. (2003) Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants. Plant J 34:363-375. (Pubitemid 36579860)
20. Iqbal M, et al. (2005) Total synthesis and biological activity of 13,14-dehydro-12-oxophytodienoic acids [deoxy-J(1)-phytoprostanes]. Chembiochem 6:276-280. (Pubitemid 40879737)
21. Cagen LM, Fales HM, Pisano JJ (1976) Formation of glutathione conjugates of prostaglandin- A1 in human red blood-cells. J Biol Chem 251:6550-6554.
22. Cox B, et al. (2002) Human colorectal cancer cells efficiently conjugate the cyclopentenone prostaglandin, prostaglandin J(2), to glutathione. Biochim Biophys Acta Mol Cell Biol Lipids 1584:37-45. (Pubitemid 35223228)
23. Benson AM, et al. (1977) Relationship between soluble glutathione-dependent delta- 5-3-ketosteroid isomerase and glutathione S-transferases of liver. Proc Natl Acad Sci USA 74:158-162.
24. Schulze B, et al. (2006) Profiling of structurally labile oxylipins in plants by in situ derivatization with pentafluorobenzyl hydroxylamine. Anal Biochem 348:269-283. (Pubitemid 41832531)
25. Wee CW, et al. (2008) Identification of candidate genes for fenvalerate resistance in Helicoverpa armigera using cDNA-AFLP. Insect Mol Biol 17:351-360.
26. Hayes JD, Flanagan JU, Jowsey IR (2005) Glutathione transferases. Annu Rev Pharmacol Toxicol 45:51-88.
27. Ranson H, Hemingway J (2005) Glutathione Transferases. In Comprehensive Molecular Insect Science, Vol 5, Pharmacology, eds Gilbert LI, Iatrou K, Gill SS (Elsevier, Amsterdam), pp 383-402.
28. Jones RL, Cammock S, Horton EW (1972) Partial-purification and properties of cat plasma prostaglandin-A isomerase. Biochim Biophys Acta 280:588-601.
29. Blackburn M, et al. (1997) Characterization of the enzymatic and nonenzymatic reaction of 13-oxooctadecanoic acid with glutathione. Chem Res Toxicol 10:1364-1371. (Pubitemid 28018925)
30. Habig WH, Pabst MJ, Jakoby WB (1974) Glutathione S-transferases-First enzymatic step in mercapturic acid formation. J Biol Chem 249:7130-7139.
31. Jakoby WB (1978) The glutathione S-transferases: A group of multi-functional detoxification proteins. Adv Enzymol 46:383-414.
32. Ranson H, et al. (2002) Evolution of supergene families associated with insecticide resistance. Science 298:179-181.
33. Ding YC, et al. (2003) The Anopheles gambiae glutathione transferase supergene family: annotation, phylogeny and expression profiles. BMC Genomics 4.
34. Board PG, et al. (2000) Identification, characterization, and crystal structure of the omega class glutathione transferases. J Biol Chem 275:24798-24806.
35. Yu SJ (1996) Insect glutathione S-transferases. Zool Stud 35:9-19.
36. Francis F, Vanhaelen N, Haubruge E (2005) Glutathione S-transferases in the adaptation to plant secondary metabolites in the Myzus persicae aphid. Arch Insect Biochem Physiol 58:166-174. (Pubitemid 40451903)
37. Mukanganyama S, et al. (2003) Effects of DIMBOA on detoxification enzymes of the aphid Rhopalosiphum padi (Homoptera:Aphididae). J Insect Physiol 49:223-229. (Pubitemid 36409026)
38. Arora GK, Rup PJ, Sohal SK (2008) Influence of coumarin on the enzymatic activity in nymphs of Lipaphis erysimi (Kalt.). Allelopathy J 22:221-229.
39. Yu SJ (1984) Interactions of allelochemicals with detoxication enzymes of insecticidesusceptible and resistant Fall Armyworms. Pestic Biochem Physiol 22:60-68.
40. Dixon DP, Edwards R (2009) Selective binding of glutathione conjugates of fatty acid derivatives by plant glutathione transferases. J Biol Chem 284:21249-21256.
41. Altiok N, et al. (2008) A plant oxylipin, 12-oxophytodienoic acid, inhibits proliferation of human breast cancer cells by targeting cyclin D1. Breast Cancer Res Treat 109:315-323. (Pubitemid 351644856)
42. Straus DS, Glass CK (2001) Cyclopentenone prostaglandins: New insights on biological activities and cellular targets. Med Res Rev 21:185-210.
43. Murphy RC, Zarini S (2002) Glutathione adducts of oxyeicosanoids. Prostaglandins Other Lipid Mediat 68-9:471-482.
44. Jones RL (1974) Inhibitors of rabbit plasma prostaglandin A isomerase. Biochem J 139:381-389.
45. Lannoo N, et al. (2007) The jasmonate-induced expression of the Nicotiana tabacum leaf lectin. Plant Cell Physiol 48:1207-1218. (Pubitemid 47283660)
46. Paschold A, et al. (2008) Jasmonate perception regulates jasmonate biosynthesis and JA-Ile metabolism: The case of COI1 in Nicotiana attenuata. Plant Cell Physiol 49:1165-1175.
47. Bergomaz R, Boppre M (1986) A simple instant diet for rearing Arctiidae and other Moths. J Lepidopterists' Soc 40:131-137.
48. Perkins WDR, et al. (1973) Artificial diet for mass rearing the corn earworm (Heliothis zea). USDA Prod Res Rep 154.
49. Shelton AM, et al. (1991) Comparative-analysis of 2 rearing procedures for Diamondback Moth (Lepidoptera, Plutellidae). J Entomol Sci 26:17-26.