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Pathway Description
Monoterpenoid Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2017-05-19
Last Updated: 2025-02-08
Monoterpenoids are kind of volatile oils, which are derived from geranyl diphosphate (Geranyl-PP/GPP) that are also consisted of two isoprene units. In Arabidopsis thaliana, most reactions in monoterpenoid biosynthesis take place in the chloroplast and require either magnesium or manganese ions as cofactors. S-(+)-linalool synthase catalyzes the conversion of geranyl diphosphate into (+)-linalool. Two different enzymes can function as myrcene synthases and catalyze the conversion of geranyl diphosphate into myrcene: tricyclene synthase and beta-myrcene/(E)-beta-ocimene synthase 2. 1,8-cineole synthase catalyzes two successive reactions in monoterpenoid biosynthesis: the conversion of geranyl diphosphate into alpha-terpineol and the conversion of alpha-terpineol into eucalyptol (1,8-cineole). It also catalyzes four other conversions, all of geranyl diphosphate, into (-)-beta-pinene, (-)-alpha-pinene, sabinene and terpinolene, all with varying frequency. Additionally, (E,E)-alpha-farnesene synthase, an enzyme used in the conversion of farnesyl diphosphate to isomers of farnesene, can additionally catalyze the conversion of geranyl diphosphate into trans-ocimen. Finally, the beta-myrcene/(E)-beta-omicine synthase 2 enzyme can also work to catalyze the conversion of geranyl diphosphate into (-)-limonene. Distinct from the other enzymes listed, (+)-Neomenthol dehydrogenase is an enzyme found in the cytosol that catalyzes the conversion of (-)-menthone into (+)-neomenthol.
References
Monoterpenoid Biosynthesis References
Chen F, Tholl D, D'Auria JC, Farooq A, Pichersky E, Gershenzon J: Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell. 2003 Feb;15(2):481-94.
Pubmed: 12566586
Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D: Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Plant Physiol. 2004 Aug;135(4):1956-66. doi: 10.1104/pp.104.044388. Epub 2004 Aug 6.
Pubmed: 15299125
Chen F, Tholl D, D'Auria JC, Farooq A, Pichersky E, Gershenzon J: Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell. 2003 Feb;15(2):481-94. doi: 10.1105/tpc.007989.
Pubmed: 12566586
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
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
Bohlmann J, Martin D, Oldham NJ, Gershenzon J: Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase. Arch Biochem Biophys. 2000 Mar 15;375(2):261-9. doi: 10.1006/abbi.1999.1669.
Pubmed: 10700382
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
Kaneko T, Katoh T, Sato S, Nakamura A, Asamizu E, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 3. II. Sequence features of the 4,251,695 bp regions covered by 90 P1, TAC and BAC clones. DNA Res. 2000 Jun 30;7(3):217-21. doi: 10.1093/dnares/7.3.217.
Pubmed: 10907853
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
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
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
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