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Pathway Description
Camalexin Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2019-05-09
Last Updated: 2019-08-28
Camalexin is a compound produced by Arabadopsis thaliana, used in plant defense. Its accumulation is induced by contact with parasites, and it inhibits the growth of those parasites.
Synthesis of camalexin starts with L-tryptophan, which reacts using tryptophan N-monooxygenases 1 and 2 to form N-hydroxy-L-tryptophan. This then reacts using the same enzyme to form N,N-dihydroxy-L-tryptophan, which spontaneously forms (E)-indol-3-ylacetaldoxime.
(E)-indol-3-ylacetaldoxime reversibly reacts with a indoleacetaldoxime dehydratase enzyme to form (Z)-indol-3-ylacetaldoxime, its isomer. The isomer then loses a water molecule via indoleacetaldoxime dehydratase again, forming 3-indoleacetonitrile. Another reaction with indoleacetaldoxime dehydratase forms 2-hydroxy-2-(1H-indol-3-yl0acetonitrile, which then reacts one final time with the indoleacetaldoxime dehydratase enzyme to lose a water molecule and form dehydro(indole-3-yl)acetonitrile.
At this point, a glutatione molecule is added using glutatione S-transferase F6 to form (glutation-S-yl)(1H-indol-3-yl)acetonitrile. A water molecule is added by gamma-glutamyl peptidases 1 and 3, as well as glutathione hydrolase 3, forming L-glutamic acid as a side product, as well as (L-cysteinylglycin-S-yl)(1H-indol-3-yl)acetonitrile. An unknown enzyme then catalyzes a reaction that adds a water molecule and removes a glycine, forming 2-(cystein-S-yl)-2-(1H-indol-3-yl)-acetonitrile. Then, in a reaction using bifunctional dihydrocamalexate synthase/camalexin synthase, an oxygen molecule is added, a hydrogen ion, hydrogen cyanide molecule and water molecule are removed, and (R)-dihydrocamalexate is formed. Finally, the same enzyme catalyzes the formation of camalexin, the final product of this pathway.
References
Camalexin Biosynthesis References
Bottcher C, Westphal L, Schmotz C, Prade E, Scheel D, Glawischnig E: The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana. Plant Cell. 2009 Jun;21(6):1830-45. doi: 10.1105/tpc.109.066670. Epub 2009 Jun 30.
Pubmed: 19567706
Geu-Flores F, Moldrup ME, Bottcher C, Olsen CE, Scheel D, Halkier BA: Cytosolic gamma-glutamyl peptidases process glutathione conjugates in the biosynthesis of glucosinolates and camalexin in Arabidopsis. Plant Cell. 2011 Jun;23(6):2456-69. doi: 10.1105/tpc.111.083998. Epub 2011 Jun 28.
Pubmed: 21712415
Glawischnig E, Hansen BG, Olsen CE, Halkier BA: Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis. Proc Natl Acad Sci U S A. 2004 May 25;101(21):8245-50. doi: 10.1073/pnas.0305876101. Epub 2004 May 17.
Pubmed: 15148388
Glawischnig E: The role of cytochrome P450 enzymes in the biosynthesis of camalexin. Biochem Soc Trans. 2006 Dec;34(Pt 6):1206-8. doi: 10.1042/BST0341206.
Pubmed: 17073786
Muller TM, Bottcher C, Morbitzer R, Gotz CC, Lehmann J, Lahaye T, Glawischnig E: TRANSCRIPTION ACTIVATOR-LIKE EFFECTOR NUCLEASE-Mediated Generation and Metabolic Analysis of Camalexin-Deficient cyp71a12 cyp71a13 Double Knockout Lines. Plant Physiol. 2015 Jul;168(3):849-58. doi: 10.1104/pp.15.00481. Epub 2015 May 7.
Pubmed: 25953104
Nafisi M, Goregaoker S, Botanga CJ, Glawischnig E, Olsen CE, Halkier BA, Glazebrook J: Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Plant Cell. 2007 Jun;19(6):2039-52. doi: 10.1105/tpc.107.051383. Epub 2007 Jun 15.
Pubmed: 17573535
Schuhegger R, Nafisi M, Mansourova M, Petersen BL, Olsen CE, Svatos A, Halkier BA, Glawischnig E: CYP71B15 (PAD3) catalyzes the final step in camalexin biosynthesis. Plant Physiol. 2006 Aug;141(4):1248-54. doi: 10.1104/pp.106.082024. Epub 2006 Jun 9.
Pubmed: 16766671
Su T, Xu J, Li Y, Lei L, Zhao L, Yang H, Feng J, Liu G, Ren D: Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana. Plant Cell. 2011 Jan;23(1):364-80. doi: 10.1105/tpc.110.079145. Epub 2011 Jan 14.
Pubmed: 21239642
Zook M, Hammerschmidt R: Origin of the thiazole ring of camalexin, a phytoalexin from Arabidopsis thaliana. Plant Physiol. 1997 Feb;113(2):463-8.
Pubmed: 9046593
Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA: Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. J Biol Chem. 2000 Oct 27;275(43):33712-7. doi: 10.1074/jbc.M001667200.
Pubmed: 10922360
Mayer K, Schuller C, Wambutt R, Murphy G, Volckaert G, Pohl T, Dusterhoft A, Stiekema W, Entian KD, Terryn N, Harris B, Ansorge W, Brandt P, Grivell L, Rieger M, Weichselgartner M, de Simone V, Obermaier B, Mache R, Muller M, Kreis M, Delseny M, Puigdomenech P, Watson M, Schmidtheini T, Reichert B, Portatelle D, Perez-Alonso M, Boutry M, Bancroft I, Vos P, Hoheisel J, Zimmermann W, Wedler H, Ridley P, Langham SA, McCullagh B, Bilham L, Robben J, Van der Schueren J, Grymonprez B, Chuang YJ, Vandenbussche F, Braeken M, Weltjens I, Voet M, Bastiaens I, Aert R, Defoor E, Weitzenegger T, Bothe G, Ramsperger U, Hilbert H, Braun M, Holzer E, Brandt A, Peters S, van Staveren M, Dirske W, Mooijman P, Klein Lankhorst R, Rose M, Hauf J, Kotter P, Berneiser S, Hempel S, Feldpausch M, Lamberth S, Van den Daele H, De Keyser A, Buysshaert C, Gielen J, Villarroel R, De Clercq R, Van Montagu M, Rogers J, Cronin A, Quail M, Bray-Allen S, Clark L, Doggett J, Hall S, Kay M, Lennard N, McLay K, Mayes R, Pettett A, Rajandream MA, Lyne M, Benes V, Rechmann S, Borkova D, Blocker H, Scharfe M, Grimm M, Lohnert TH, Dose S, de Haan M, Maarse A, Schafer M, Muller-Auer S, Gabel C, Fuchs M, Fartmann B, Granderath K, Dauner D, Herzl A, Neumann S, Argiriou A, Vitale D, Liguori R, Piravandi E, Massenet O, Quigley F, Clabauld G, Mundlein A, Felber R, Schnabl S, Hiller R, Schmidt W, Lecharny A, Aubourg S, Chefdor F, Cooke R, Berger C, Montfort A, Casacuberta E, Gibbons T, Weber N, Vandenbol M, Bargues M, Terol J, Torres A, Perez-Perez A, Purnelle B, Bent E, Johnson S, Tacon D, Jesse T, Heijnen L, Schwarz S, Scholler P, Heber S, Francs P, Bielke C, Frishman D, Haase D, Lemcke K, Mewes HW, Stocker S, Zaccaria P, Bevan M, Wilson RK, de la Bastide M, Habermann K, Parnell L, Dedhia N, Gnoj L, Schutz K, Huang E, Spiegel L, Sehkon M, Murray J, Sheet P, Cordes M, Abu-Threideh J, Stoneking T, Kalicki J, Graves T, Harmon G, Edwards J, Latreille P, Courtney L, Cloud J, Abbott A, Scott K, Johnson D, Minx P, Bentley D, Fulton B, Miller N, Greco T, Kemp K, Kramer J, Fulton L, Mardis E, Dante M, Pepin K, Hillier L, Nelson J, Spieth J, Ryan E, Andrews S, Geisel C, Layman D, Du H, Ali J, Berghoff A, Jones K, Drone K, Cotton M, Joshu C, Antonoiu B, Zidanic M, Strong C, Sun H, Lamar B, Yordan C, Ma P, Zhong J, Preston R, Vil D, Shekher M, Matero A, Shah R, Swaby IK, O'Shaughnessy A, Rodriguez M, Hoffmann J, Till S, Granat S, Shohdy N, Hasegawa A, Hameed A, Lodhi M, Johnson A, Chen E, Marra M, Martienssen R, McCombie WR: Sequence and analysis of chromosome 4 of the plant Arabidopsis thaliana. Nature. 1999 Dec 16;402(6763):769-77. doi: 10.1038/47134.
Pubmed: 10617198
Cheng CY, Krishnakumar V, Chan AP, Thibaud-Nissen F, Schobel S, Town CD: Araport11: a complete reannotation of the Arabidopsis thaliana reference genome. Plant J. 2017 Feb;89(4):789-804. doi: 10.1111/tpj.13415. Epub 2017 Feb 10.
Pubmed: 27862469
Lin X, Kaul S, Rounsley S, Shea TP, Benito MI, Town CD, Fujii CY, Mason T, Bowman CL, Barnstead M, Feldblyum TV, Buell CR, Ketchum KA, Lee J, Ronning CM, Koo HL, Moffat KS, Cronin LA, Shen M, Pai G, Van Aken S, Umayam L, Tallon LJ, Gill JE, Adams MD, Carrera AJ, Creasy TH, Goodman HM, Somerville CR, Copenhaver GP, Preuss D, Nierman WC, White O, Eisen JA, Salzberg SL, Fraser CM, Venter JC: Sequence and analysis of chromosome 2 of the plant Arabidopsis thaliana. Nature. 1999 Dec 16;402(6763):761-8. doi: 10.1038/45471.
Pubmed: 10617197
Hull AK, Vij R, Celenza JL: Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc Natl Acad Sci U S A. 2000 Feb 29;97(5):2379-84. doi: 10.1073/pnas.040569997.
Pubmed: 10681464
Castelli V, Aury JM, Jaillon O, Wincker P, Clepet C, Menard M, Cruaud C, Quetier F, Scarpelli C, Schachter V, Temple G, Caboche M, Weissenbach J, Salanoubat M: Whole genome sequence comparisons and "full-length" cDNA sequences: a combined approach to evaluate and improve Arabidopsis genome annotation. Genome Res. 2004 Mar;14(3):406-13. doi: 10.1101/gr.1515604.
Pubmed: 14993207
Kiyosue T, Yamaguchi-Shinozaki K, Shinozaki K: Characterization of two cDNAs (ERD11 and ERD13) for dehydration-inducible genes that encode putative glutathione S-transferases in Arabidopsis thaliana L. FEBS Lett. 1993 Dec 6;335(2):189-92. doi: 10.1016/0014-5793(93)80727-c.
Pubmed: 8253194
Theologis A, Ecker JR, Palm CJ, Federspiel NA, Kaul S, White O, Alonso J, Altafi H, Araujo R, Bowman CL, Brooks SY, Buehler E, Chan A, Chao Q, Chen H, Cheuk RF, Chin CW, Chung MK, Conn L, Conway AB, Conway AR, Creasy TH, Dewar K, Dunn P, Etgu P, Feldblyum TV, Feng J, Fong B, Fujii CY, Gill JE, Goldsmith AD, Haas B, Hansen NF, Hughes B, Huizar L, Hunter JL, Jenkins J, Johnson-Hopson C, Khan S, Khaykin E, Kim CJ, Koo HL, Kremenetskaia I, Kurtz DB, Kwan A, Lam B, Langin-Hooper S, Lee A, Lee JM, Lenz CA, Li JH, Li Y, Lin X, Liu SX, Liu ZA, Luros JS, Maiti R, Marziali A, Militscher J, Miranda M, Nguyen M, Nierman WC, Osborne BI, Pai G, Peterson J, Pham PK, Rizzo M, Rooney T, Rowley D, Sakano H, Salzberg SL, Schwartz JR, Shinn P, Southwick AM, Sun H, Tallon LJ, Tambunga G, Toriumi MJ, Town CD, Utterback T, Van Aken S, Vaysberg M, Vysotskaia VS, Walker M, Wu D, Yu G, Fraser CM, Venter JC, Davis RW: Sequence and analysis of chromosome 1 of the plant Arabidopsis thaliana. Nature. 2000 Dec 14;408(6814):816-20. doi: 10.1038/35048500.
Pubmed: 11130712
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