KEGG   PATHWAY: ath00909Help
Entry
ath00909                    Pathway                                

Name
Sesquiterpenoid and triterpenoid biosynthesis - Arabidopsis thaliana (thale cress)
Description
Sesquiterpenoids (C15 terpenoids) are a group of terpenoids consisting of three isoprene units. They are derive from farnesyl diphosphate (FPP) and can be cyclized to produce various skeletal structures. Sesquiterpenoid biosynthesis begins with the loss of diphosphate from FPP under the action of sesquiterpene synthesis enzymes, generating an allylic cation that is highly susceptible to intramolecular attacks. Cyclization of the farnesyl cation may take place onto either of the remaining double bonds with the result that 6-, 10-, or 11-membered rings may be formed. Many sesquiterpenoids have been isolated from plants, fungi, marine organisms, and Streptomyces species. This map shows a few examples of acyclic and cyclic sesquiterpenoids.
Class
Metabolism; Metabolism of terpenoids and polyketides
BRITE hierarchy
Pathway map
ath00909  Sesquiterpenoid and triterpenoid biosynthesis
ath00909

Ortholog table
Other DBs
BSID: 170656
GO: 0016106 0016104
Organism
Arabidopsis thaliana (thale cress) [GN:ath]
Gene
AT4G34650  SQS2; squalene synthase 2 [KO:K00801] [EC:2.5.1.21]
AT4G34640  SQS1; squalene synthase 1 [KO:K00801] [EC:2.5.1.21]
AT1G58440  XF1; FAD/NAD(P)-binding oxidoreductase family protein [KO:K00511] [EC:1.14.14.17]
AT4G37760  SQE3; squalene epoxidase 3 [KO:K00511] [EC:1.14.14.17]
AT5G24140  SQP2; squalene monooxygenase 2 [KO:K00511] [EC:1.14.14.17]
AT5G24160  SQE6; squalene monooxygenase 6 [KO:K00511] [EC:1.14.14.17]
AT2G22830  SQE2; squalene epoxidase 2 [KO:K00511] [EC:1.14.14.17]
AT5G24150  SQP1; FAD/NAD(P)-binding oxidoreductase family protein [KO:K00511] [EC:1.14.14.17]
AT4G33360  FLDH; NAD(P)-binding Rossmann-fold superfamily protein [KO:K15891] [EC:1.1.1.354]
AT4G13280  TPS12; terpenoid synthase 12 [KO:K15795] [EC:4.2.3.40]
AT4G13300  TPS13; terpenoid synthase 13 [KO:K15795] [EC:4.2.3.40]
AT5G44630  Terpenoid cyclases/Protein prenyltransferases superfamily protein [KO:K15799] [EC:4.2.3.79 4.2.3.78 4.2.3.69]
AT5G23960  TPS21; terpene synthase 21 [KO:K14184] [EC:4.2.3.57 4.2.3.104]
AT1G78960  LUP2; lupeol synthase 2 [KO:K15815] [EC:5.4.99.41 5.4.99.40 5.4.99.39]
AT1G78950  BAS; Terpenoid cyclases family protein [KO:K15813] [EC:5.4.99.39]
AT1G78970  LUP1; lupeol synthase 1 [KO:K15816] [EC:5.4.99.41 4.2.1.128]
AT1G78500  Terpenoid cyclases family protein [KO:K16204] [EC:5.4.99.54 5.4.99.52]
AT5G36150  PEN3; putative pentacyclic triterpene synthase 3 [KO:K16205] [EC:5.4.99.56]
AT4G15370  BARS1; baruol synthase 1 [KO:K16206] [EC:5.4.99.57]
AT5G48010  THAS1; thalianol synthase 1 [KO:K15821] [EC:5.4.99.31]
AT1G78955  CAMS1; camelliol C synthase 1 [KO:K15822] [EC:5.4.99.38]
AT4G15340  PEN1; pentacyclic triterpene synthase 1 [KO:K15823] [EC:4.2.1.124]
AT5G42600  MRN1; marneral synthase [KO:K16207] [EC:5.4.99.53]
Compound
C00448  trans,trans-Farnesyl diphosphate
C00751  Squalene
C01054  (S)-2,3-Epoxysqualene
C01126  (2E,6E)-Farnesol
C01841  Pentalenene
C01860  Trichodiene
C02004  Aristolochene
C03220  (2Z,6E)-Farnesol
C03428  Presqualene diphosphate
C03461  2-trans,6-trans-Farnesal
C06079  PR-toxin
C06080  Nivalenol
C06083  Tetrahymanol
C06309  Diplopterol
C06310  Diploptene
C06394  delta-Cadinene
C07667  Gossypol
C08615  alpha-Amyrin
C08616  beta-Amyrin
C08628  Lupeol
C08637  Taraxerol
C09382  Costunolide
C09627  Capsidiol
C09629  beta-Caryophyllene
C09665  alpha-Farnesene
C09666  beta-Farnesene
C09672  Germacrene B
C09684  Humulene
C09699  Longifolene
C09704  Nerolidol
C09723  beta-Selinene
C09737  Solavetivone
C12142  Vetispiradiene
C16028  Amorpha-4,11-diene
C16141  (+)-Germacrene A
C16142  (-)-Germacrene D
C16143  (1E,4S,5E,7R)-Germacra-1(10),5-dien-11-ol
C16269  (+)-epi-Isozizaene
C16286  Geosmin
C16814  gamma-Bisabolene
C16829  gamma-Humulene
C17277  (+)-Valencene
C17953  (5S)-Albaflavenol
C17954  Albaflavenone
C17955  (5R)-Albaflavenol
C18245  8-epi-Cedrol
C19676  Germacra-1(10),4,11(13)-trien-12-ol
C19678  Germacrene A acid
C19708  5-Epiaristolochene
C19711  Solavetivol
C19732  24-Hydroxy-beta-amyrin
C19736  (+)-alpha-Santalene
C19740  (+)-alpha-Barbatene
C19742  (+)-delta-Selinene
C19746  (3R,6E)-Nerolidol
C19747  Germacrene C
C19748  (E)-gamma-Bisabolene
C19749  (E)-alpha-Bisabolene
C19751  (S)-beta-Bisabolene
C19752  (S)-beta-Macrocarpene
C19753  cis-Muurola-3,5-diene
C19755  Patchoulol
C19801  Isomultiflorenol
C19819  Cucurbitadienol
C19820  Protostadienol
C19828  Arabidiol
C19829  Dammarenediol II
C19832  Thalianol
C19833  Germanicol
C19834  Dammara-20,24-diene
C19835  Camelliol C
C19863  Lupan-3beta,20-diol
C19908  (+)-beta-Chamigrene
C19918  Parkeol
C19939  Pentalen-13-al
C19973  (+)-beta-Caryophyllene
C19974  (+)-Caryolan-1-ol
C20159  7-epi-alpha-Selinene
C20163  5-epi-alpha-Selinene
C20181  Avermitilol
C20187  Achilleol B
C20191  alpha-Seco-amyrin
C20192  Marneral
C20193  beta-Seco-amyrin
C20195  Tirucalla-7,24-dien-3beta-ol
C20200  Baruol
C20478  (E)-2-epi-beta-Caryophyllene
C20724  (+)-Thujopsene
Reference
PMID:9371761
  Authors
Crock J, Wildung M, Croteau R
  Title
Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-beta-farnesene.
  Journal
Proc Natl Acad Sci U S A 94:12833-8 (1997)
DOI:10.1073/pnas.94.24.12833
Reference
  Authors
Nagegowda DA, Gutensohn M, Wilkerson CG, Dudareva N
  Title
Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers.
  Journal
Plant J 55:224-39 (2008)
DOI:10.1111/j.1365-313X.2008.03496.x
Reference
  Authors
Bertea CM, Voster A, Verstappen FW, Maffei M, Beekwilder J, Bouwmeester HJ
  Title
Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library.
  Journal
Arch Biochem Biophys 448:3-12 (2006)
DOI:10.1016/j.abb.2006.02.026
Reference
  Authors
de Kraker JW, Franssen MC, Joerink M, de Groot A, Bouwmeester HJ
  Title
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.
  Journal
Plant Physiol 129:257-68 (2002)
DOI:10.1104/pp.010957
Reference
  Authors
Jaroszewski JW, Strom-Hansen T, Hansen SH, Thastrup O, Kofod H
  Title
On the botanical distribution of chiral forms of gossypol.
  Journal
Planta Med 58:454-8 (1992)
DOI:10.1055/s-2006-961512
Reference
PMID:9442047
  Authors
Steele CL, Crock J, Bohlmann J, Croteau R
  Title
Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase.
  Journal
J Biol Chem 273:2078-89 (1998)
DOI:10.1074/jbc.273.4.2078
Reference
  Authors
Fraga BM
  Title
Natural sesquiterpenoids.
  Journal
Nat Prod Rep 25:1180-209 (2008)
DOI:10.1039/b806216c
Reference
  Authors
Field B, Fiston-Lavier AS, Kemen A, Geisler K, Quesneville H, Osbourn AE
  Title
Formation of plant metabolic gene clusters within dynamic chromosomal regions.
  Journal
Proc Natl Acad Sci U S A 108:16116-21 (2011)
DOI:10.1073/pnas.1109273108
Reference
  Authors
Field B, Osbourn AE
  Title
Metabolic diversification--independent assembly of operon-like gene clusters in different plants.
  Journal
Science 320:543-7 (2008)
DOI:10.1126/science.1154990
Reference
  Authors
Qi X, Bakht S, Leggett M, Maxwell C, Melton R, Osbourn A
  Title
A gene cluster for secondary metabolism in oat: implications for the evolution of metabolic diversity in plants.
  Journal
Proc Natl Acad Sci U S A 101:8233-8 (2004)
DOI:10.1073/pnas.0401301101
KO pathway
ko00909   

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