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Pathway Description
alpha-Linolenic Acid Metabolism
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2019-06-10
Last Updated: 2019-08-15
alpha-Linolenic acid is a poly-unsaturated fatty acid with an 18-carbon chain and three cis double bonds. Its primary role in Arabidopsis thaliana is in being a precursor of the phytohormone jasmonic acid. Being a precursor for jasmonic acid, it plays a role in gene responses to feeding from insects. It is also a precursor to other molecules involved in defense signalling such as cis-3-hexenyl acetate. alpha-Linolenic acid itself modulates gene transcription in response to hyperosmotic salinity, heat acclimation, and oxidative stress. alpha-Linolenic acid is released from the hydrolysis of a phosphatidylcholine membrane lipid. It then has a hydroperoxy group added by a dioxygenase in either the 2, 9, or 13 position to form 2(R)-HPOT, 9(S)-HPOT, or 13(S)-HPOT respectively. The oxidation of alpha-linolenic acid to 13(S)-HPOT is the first step in the jasmonic acid synthesis and leads to that separate pathway. 2(R)-HPOT is formed in an oil body and undergoes a spontaneous decarboxylation to form a heptadecatrienal. 9(S)-HPOT, or 13(S)-HPOT are both formed in a chloroplast and cleaved by probable inactive linolenate hydroperoxide lyase to form an aldehyde and an oxo-carboxylic acid. The hexenal from 13(S)-HPOT is reduced by alcohol dehydrogenase class-P to form a hexenol, which undergoes an esterification with acetyl-CoA to form 3-hexenyl acetate.
References
alpha-Linolenic Acid Metabolism References
Mata-Perez C, Sanchez-Calvo B, Begara-Morales JC, Luque F, Jimenez-Ruiz J, Padilla MN, Fierro-Risco J, Valderrama R, Fernandez-Ocana A, Corpas FJ, Barroso JB: Transcriptomic profiling of linolenic acid-responsive genes in ROS signaling from RNA-seq data in Arabidopsis. Front Plant Sci. 2015 Mar 17;6:122. doi: 10.3389/fpls.2015.00122. eCollection 2015.
Pubmed: 25852698
Vellosillo T, Martinez M, Lopez MA, Vicente J, Cascon T, Dolan L, Hamberg M, Castresana C: Oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade. Plant Cell. 2007 Mar;19(3):831-46. doi: 10.1105/tpc.106.046052. Epub 2007 Mar 16.
Pubmed: 17369372
D'Auria JC, Pichersky E, Schaub A, Hansel A, Gershenzon J: Characterization of a BAHD acyltransferase responsible for producing the green leaf volatile (Z)-3-hexen-1-yl acetate in Arabidopsis thaliana. Plant J. 2007 Jan;49(2):194-207. doi: 10.1111/j.1365-313X.2006.02946.x. Epub 2006 Dec 6.
Pubmed: 17163881
Cheng F, Hu T, An Y, Huang J, Xu Y: Purification and enzymatic characterization of alcohol dehydrogenase from Arabidopsis thaliana. Protein Expr Purif. 2013 Aug;90(2):74-7. doi: 10.1016/j.pep.2013.05.004. Epub 2013 May 24.
Pubmed: 23707506
Shimada TL, Takano Y, Shimada T, Fujiwara M, Fukao Y, Mori M, Okazaki Y, Saito K, Sasaki R, Aoki K, Hara-Nishimura I: Leaf oil body functions as a subcellular factory for the production of a phytoalexin in Arabidopsis. Plant Physiol. 2014 Jan;164(1):105-18. doi: 10.1104/pp.113.230185. Epub 2013 Nov 8.
Pubmed: 24214535
Ryu SB, Lee HY, Doelling JH, Palta JP: Characterization of a cDNA encoding Arabidopsis secretory phospholipase A2-alpha, an enzyme that generates bioactive lysophospholipids and free fatty acids. Biochim Biophys Acta. 2005 Sep 15;1736(2):144-51. doi: 10.1016/j.bbalip.2005.08.005.
Pubmed: 16140037
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
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
De Leon IP, Sanz A, Hamberg M, Castresana C: Involvement of the Arabidopsis alpha-DOX1 fatty acid dioxygenase in protection against oxidative stress and cell death. Plant J. 2002 Jan;29(1):61-2.
Pubmed: 12060227
Salanoubat M, Lemcke K, Rieger M, Ansorge W, Unseld M, Fartmann B, Valle G, Blocker H, Perez-Alonso M, Obermaier B, Delseny M, Boutry M, Grivell LA, Mache R, Puigdomenech P, De Simone V, Choisne N, Artiguenave F, Robert C, Brottier P, Wincker P, Cattolico L, Weissenbach J, Saurin W, Quetier F, Schafer M, Muller-Auer S, Gabel C, Fuchs M, Benes V, Wurmbach E, Drzonek H, Erfle H, Jordan N, Bangert S, Wiedelmann R, Kranz H, Voss H, Holland R, Brandt P, Nyakatura G, Vezzi A, D'Angelo M, Pallavicini A, Toppo S, Simionati B, Conrad A, Hornischer K, Kauer G, Lohnert TH, Nordsiek G, Reichelt J, Scharfe M, Schon O, Bargues M, Terol J, Climent J, Navarro P, Collado C, Perez-Perez A, Ottenwalder B, Duchemin D, Cooke R, Laudie M, Berger-Llauro C, Purnelle B, Masuy D, de Haan M, Maarse AC, Alcaraz JP, Cottet A, Casacuberta E, Monfort A, Argiriou A, flores M, Liguori R, Vitale D, Mannhaupt G, Haase D, Schoof H, Rudd S, Zaccaria P, Mewes HW, Mayer KF, Kaul S, Town CD, Koo HL, Tallon LJ, Jenkins J, Rooney T, Rizzo M, Walts A, Utterback T, Fujii CY, Shea TP, Creasy TH, Haas B, Maiti R, Wu D, Peterson J, Van Aken S, Pai G, Militscher J, Sellers P, Gill JE, Feldblyum TV, Preuss D, Lin X, Nierman WC, Salzberg SL, White O, Venter JC, Fraser CM, Kaneko T, Nakamura Y, Sato S, Kato T, Asamizu E, Sasamoto S, Kimura T, Idesawa K, Kawashima K, Kishida Y, Kiyokawa C, Kohara M, Matsumoto M, Matsuno A, Muraki A, Nakayama S, Nakazaki N, Shinpo S, Takeuchi C, Wada T, Watanabe A, Yamada M, Yasuda M, Tabata S: Sequence and analysis of chromosome 3 of the plant Arabidopsis thaliana. Nature. 2000 Dec 14;408(6814):820-2. doi: 10.1038/35048706.
Pubmed: 11130713
Duan H, Huang MY, Palacio K, Schuler MA: Variations in CYP74B2 (hydroperoxide lyase) gene expression differentially affect hexenal signaling in the Columbia and Landsberg erecta ecotypes of Arabidopsis. Plant Physiol. 2005 Nov;139(3):1529-44. doi: 10.1104/pp.105.067249. Epub 2005 Oct 28.
Pubmed: 16258015
Bevan M, Bancroft I, Bent E, Love K, Goodman H, Dean C, Bergkamp R, Dirkse W, Van Staveren M, Stiekema W, Drost L, Ridley P, Hudson SA, Patel K, Murphy G, Piffanelli P, Wedler H, Wedler E, Wambutt R, Weitzenegger T, Pohl TM, Terryn N, Gielen J, Villarroel R, De Clerck R, Van Montagu M, Lecharny A, Auborg S, Gy I, Kreis M, Lao N, Kavanagh T, Hempel S, Kotter P, Entian KD, Rieger M, Schaeffer M, Funk B, Mueller-Auer S, Silvey M, James R, Montfort A, Pons A, Puigdomenech P, Douka A, Voukelatou E, Milioni D, Hatzopoulos P, Piravandi E, Obermaier B, Hilbert H, Dusterhoft A, Moores T, Jones JD, Eneva T, Palme K, Benes V, Rechman S, Ansorge W, Cooke R, Berger C, Delseny M, Voet M, Volckaert G, Mewes HW, Klosterman S, Schueller C, Chalwatzis N: Analysis of 1.9 Mb of contiguous sequence from chromosome 4 of Arabidopsis thaliana. Nature. 1998 Jan 29;391(6666):485-8. doi: 10.1038/35140.
Pubmed: 9461215
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
Laudert D, Pfannschmidt U, Lottspeich F, Hollander-Czytko H, Weiler EW: Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP 74), the first enzyme of the octadecanoid pathway to jasmonates. Plant Mol Biol. 1996 May;31(2):323-35. doi: 10.1007/bf00021793.
Pubmed: 8756596
Kubigsteltig I, Laudert D, Weiler EW: Structure and regulation of the Arabidopsis thaliana allene oxide synthase gene. Planta. 1999 Jun;208(4):463-71. doi: 10.1007/s004250050583.
Pubmed: 10420644
Nakamura Y, Sato S, Kaneko T, Kotani H, Asamizu E, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. III. Sequence features of the regions of 1,191,918 bp covered by seventeen physically assigned P1 clones. DNA Res. 1997 Dec 31;4(6):401-14. doi: 10.1093/dnares/4.6.401.
Pubmed: 9501997
Hoeren FU, Dolferus R, Wu Y, Peacock WJ, Dennis ES: Evidence for a role for AtMYB2 in the induction of the Arabidopsis alcohol dehydrogenase gene (ADH1) by low oxygen. Genetics. 1998 Jun;149(2):479-90.
Pubmed: 9611167
Chang C, Meyerowitz EM: Molecular cloning and DNA sequence of the Arabidopsis thaliana alcohol dehydrogenase gene. Proc Natl Acad Sci U S A. 1986 Mar;83(5):1408-12. doi: 10.1073/pnas.83.5.1408.
Pubmed: 2937058
Hanfstingl U, Berry A, Kellogg EA, Costa JT 3rd, Rudiger W, Ausubel FM: Haplotypic divergence coupled with lack of diversity at the Arabidopsis thaliana alcohol dehydrogenase locus: roles for both balancing and directional selection? Genetics. 1994 Nov;138(3):811-28.
Pubmed: 7851777
D'Auria JC, Chen F, Pichersky E: Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. Plant Physiol. 2002 Sep;130(1):466-76. doi: 10.1104/pp.006460.
Pubmed: 12226525
Sato S, Nakamura Y, Kaneko T, Katoh T, Asamizu E, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 3. I. Sequence features of the regions of 4,504,864 bp covered by sixty P1 and TAC clones. DNA Res. 2000 Apr 28;7(2):131-5. doi: 10.1093/dnares/7.2.131.
Pubmed: 10819329
Seo YS, Kim EY, Kim JH, Kim WT: Enzymatic characterization of class I DAD1-like acylhydrolase members targeted to chloroplast in Arabidopsis. FEBS Lett. 2009 Jul 7;583(13):2301-7. doi: 10.1016/j.febslet.2009.06.021. Epub 2009 Jun 13.
Pubmed: 19527719
Ishiguro S, Kawai-Oda A, Ueda J, Nishida I, Okada K: The DEFECTIVE IN ANTHER DEHISCIENCE gene encodes a novel phospholipase A1 catalyzing the initial step of jasmonic acid biosynthesis, which synchronizes pollen maturation, anther dehiscence, and flower opening in Arabidopsis. Plant Cell. 2001 Oct;13(10):2191-209. doi: 10.1105/tpc.010192.
Pubmed: 11595796
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