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Pathway Description
Farnesene Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2017-02-23
Last Updated: 2026-01-07
Farnesene biosynthesis is a pathway that begins in the chloroplast and ends in the cytosol by which isopentenyl diphosphate becomes a farnesene, a set of six closely related chemical compounds which all are sesquiterpenes. alpha-Farnesene and beta-farnesene are isomers, differing by the location of one double bond. Two of the alpha-farnesene stereoisomers are reported to occur in nature. beta-Farnesene has only one naturally occurring isomer . First, isopentenyl diphosphate isomerase catalyzes the reversible synthesis of dimethylallyl diphosphate from isopentenyl diphosphate. This enzyme requires FAD, NAD(P)H, and a divalent cation (e.g. magnesium) as cofactors. Second, geranylpyrophosphate uses magnesium ion as a cofactor to convert dimethylallyl diphosphate into geranyl diphosphate. Third, (2E,6E)-farnesyl diphosphate synthase catalyzes the conversion of geranyl diphosphate into farnesyl diphosphate. Farnesyl diphosphate then must be transported out of the chloroplast and into the cytosol via a predicted farnesyl diphosphate transporter. Three different enzymes then convert farnesyl diphosphate into different farnesenes. (E,E)-alpha-farnesene synthase converts farnesyl diphosphate into (E,E)-alpha-farnesene. Sesquiterpene synthase converts farnesyl diphosphate into (E)-beta-farnesene. Both of these enzymes requires a magnesium or manganese ion as cofactors. A predicted enzyme, (Z,E)-alpha-farnesene synthase is theorized to catalyze the conversion of farnesyl diphosphate into (Z,E)-alpha-farnesene.
References
Farnesene Biosynthesis References
Cunillera N, Arro M, Delourme D, Karst F, Boronat A, Ferrer A: Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes. J Biol Chem. 1996 Mar 29;271(13):7774-80.
Pubmed: 8631820
Huang M, Abel C, Sohrabi R, Petri J, Haupt I, Cosimano J, Gershenzon J, Tholl D: Variation of herbivore-induced volatile terpenes among Arabidopsis ecotypes depends on allelic differences and subcellular targeting of two terpene synthases, TPS02 and TPS03. Plant Physiol. 2010 Jul;153(3):1293-310. doi: 10.1104/pp.110.154864. Epub 2010 May 12.
Pubmed: 20463089
Campbell M, Hahn FM, Poulter CD, Leustek T: Analysis of the isopentenyl diphosphate isomerase gene family from Arabidopsis thaliana. Plant Mol Biol. 1998 Jan;36(2):323-8. doi: 10.1023/a:1005935516274.
Pubmed: 9484444
Sato S, Kotani H, Nakamura Y, Kaneko T, Asamizu E, Fukami M, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. I. Sequence features of the 1.6 Mb regions covered by twenty physically assigned P1 clones. DNA Res. 1997 Jun 30;4(3):215-30. doi: 10.1093/dnares/4.3.215.
Pubmed: 9330910
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
Bouvier F, Suire C, d'Harlingue A, Backhaus RA, Camara B: Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells. Plant J. 2000 Oct;24(2):241-52.
Pubmed: 11069698
Jun L, Saiki R, Tatsumi K, Nakagawa T, Kawamukai M: Identification and subcellular localization of two solanesyl diphosphate synthases from Arabidopsis thaliana. Plant Cell Physiol. 2004 Dec;45(12):1882-8. doi: 10.1093/pcp/pch211.
Pubmed: 15653808
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
Cunillera N, Boronat A, Ferrer A: The Arabidopsis thaliana FPS1 gene generates a novel mRNA that encodes a mitochondrial farnesyl-diphosphate synthase isoform. J Biol Chem. 1997 Jun 13;272(24):15381-8. doi: 10.1074/jbc.272.24.15381.
Pubmed: 9182568
Asamizu E, Sato S, Kaneko T, Nakamura Y, Kotani H, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. VIII. Sequence features of the regions of 1,081,958 bp covered by seventeen physically assigned P1 and TAC clones. DNA Res. 1998 Dec 31;5(6):379-91. doi: 10.1093/dnares/5.6.379.
Pubmed: 10048488
Faldt J, Arimura G, Gershenzon J, Takabayashi J, Bohlmann J: Functional identification of AtTPS03 as (E)-beta-ocimene synthase: a monoterpene synthase catalyzing jasmonate- and wound-induced volatile formation in Arabidopsis thaliana. Planta. 2003 Mar;216(5):745-51. doi: 10.1007/s00425-002-0924-0. Epub 2002 Oct 25.
Pubmed: 12624761
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
Wu S, Schoenbeck MA, Greenhagen BT, Takahashi S, Lee S, Coates RM, Chappell J: Surrogate splicing for functional analysis of sesquiterpene synthase genes. Plant Physiol. 2005 Jul;138(3):1322-33. doi: 10.1104/pp.105.059386. Epub 2005 Jun 17.
Pubmed: 15965019
Tholl D, Chen F, Petri J, Gershenzon J, Pichersky E: Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers. Plant J. 2005 Jun;42(5):757-71. doi: 10.1111/j.1365-313X.2005.02417.x.
Pubmed: 15918888
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