KEGG   PATHWAY: ko00909
Entry
ko00909                     Pathway                                
Name
Sesquiterpenoid and triterpenoid biosynthesis
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
Pathway map
ko00909  Sesquiterpenoid and triterpenoid biosynthesis
ko00909

Other DBs
GO: 0016106 0016104
Orthology
K00801  farnesyl-diphosphate farnesyltransferase [EC:2.5.1.21]
K00511  squalene monooxygenase [EC:1.14.14.17]
K15793  acyclic sesquiterpene synthase [EC:4.2.3.49 4.2.3.47 3.1.7.6]
K15891  NAD+-dependent farnesol dehydrogenase [EC:1.1.1.354]
K14173  alpha-farnesene synthase [EC:4.2.3.46]
K14174  beta-farnesene/exo-alpha-bergamotene synthase [EC:4.2.3.47 4.2.3.81]
K22064  beta-farnesene synthase [EC:4.2.3.47]
K12645  epi-isozizaene 5-monooxygenase / beta-farnesene synthase [EC:1.14.15.39 4.2.3.47]
K14175  (3S,6E)-nerolidol synthase [EC:4.2.3.48]
K10156  epi-isozizaene synthase [EC:4.2.3.37]
K14176  epi-cedrol synthase [EC:4.2.3.39]
K21984  (+)-epi-alpha-bisabolol synthase [EC:4.2.3.138]
K14177  alpha-bisabolene synthase [EC:4.2.3.38]
K15794  (S)-beta-bisabolene synthase [EC:4.2.3.55]
K15795  (Z)-gamma-bisabolene synthase [EC:4.2.3.40]
K15796  (E)-gamma-bisabolene synthase [EC:4.2.3.59]
K15797  (S)-beta-macrocarpene synthase [EC:5.5.1.17]
K12249  trichodiene synthase [EC:4.2.3.6]
K14178  amorpha-4,11-diene synthase [EC:4.2.3.24]
K15798  santalene and bergamotene synthase [EC:4.2.3.50 4.2.3.53 4.2.3.54]
K15799  (+)-alpha-barbatene/beta-chamigrene/thujopsene synthase [EC:4.2.3.69 4.2.3.78 4.2.3.79]
K14179  germacrene-A synthase [EC:4.2.3.23]
K21927  alpha-muurolene/germacrene-A/gamma-muurolene/(+)-delta-cadinol synthase [EC:4.2.3.125 4.2.3.23 4.2.3.126 4.2.3.212]
K15800  germacrene A oxidase [EC:1.14.14.95]
K20561  costunolide synthase [EC:1.14.14.150]
K15801  (E,E)-germacrene B synthase [EC:4.2.3.71]
K15802  germacrene C synthase [EC:4.2.3.60]
K15803  (-)-germacrene D synthase [EC:4.2.3.75]
K10187  germacradienol/geosmin synthase [EC:4.2.3.22 4.2.3.75 4.1.99.16]
K14180  aristolochene synthase [EC:4.2.3.9]
K15804  5-epiaristolochene/(+)-2-epi-prezizaene/(-)-alpha-cedrene synthase [EC:4.2.3.61 4.2.3.226 4.2.3.227]
K15805  5-epiaristolochene 1,3-dihydroxylase [EC:1.14.14.149]
K14181  valencene/7-epi-alpha-selinene synthase [EC:4.2.3.73 4.2.3.86]
K14182  vetispiradiene synthase [EC:4.2.3.21]
K15472  premnaspirodiene oxygenase [EC:1.14.14.151]
K15806  (+)-delta-selinene synthase [EC:4.2.3.76]
K18109  5-epi-alpha-selinene synthase [EC:4.2.3.90]
K15807  patchoulol/alpha-guaiene/delta-guaiene synthase [EC:4.2.3.70 4.2.3.87 4.2.3.93]
K18110  avermitilol synthase [EC:4.2.3.96]
K15808  beta-caryophyllene synthase [EC:4.2.3.57]
K14184  alpha-humulene/beta-caryophyllene synthase [EC:4.2.3.104 4.2.3.57]
K18111  (+)-beta-caryophyllene/(+)-caryolan-1-ol synthase [EC:4.2.3.89 4.2.1.138]
K18112  (E)-2-epi-beta-caryophyllene synthase [EC:4.2.3.137]
K14185  longifolene/alpha-longipinene synthase [EC:4.2.3.58 4.2.3.80]
K14186  gamma-humulene synthase [EC:4.2.3.56]
K12250  pentalenene synthase [EC:4.2.3.7]
K15907  pentalenene oxygenase [EC:1.14.15.32]
K14183  (+)-delta-cadinene synthase [EC:4.2.3.13]
K22065  alpha-copaene/(+)-delta-cadinene synthase [EC:4.2.3.133 4.2.3.13]
K15809  cis-muuroladiene synthase [EC:4.2.3.67]
K26054  tetrahymanol synthase [EC:4.2.1.123]
K06045  squalene-hopene/tetraprenyl-beta-curcumene cyclase [EC:5.4.99.17 4.2.1.129]
K15810  dammaradiene synthase [EC:5.4.99.37]
K15811  protostadienol synthase [EC:5.4.99.32]
K15812  cucurbitadienol synthase [EC:5.4.99.33]
K19010  parkeol synthase [EC:5.4.99.47]
K15815  lupeol synthase 2 [EC:5.4.99.39 5.4.99.40 5.4.99.41]
K15813  beta-amyrin synthase [EC:5.4.99.39]
K20658  alpha/beta-amyrin synthase [EC:5.4.99.40 5.4.99.39]
K21928  delta/alpha/beta-amyrin synthase [EC:5.4.99.55 5.4.99.40 5.4.99.39]
K15814  beta-amyrin 24-hydroxylase [EC:1.14.14.134]
K15816  lupeol synthase 1 [EC:4.2.1.128 5.4.99.41]
K20659  lupeol synthase [EC:5.4.99.41]
K15817  dammarenediol II synthase [EC:4.2.1.125]
K15818  germanicol synthase [EC:5.4.99.34]
K15819  taraxerol synthase [EC:5.4.99.35]
K15820  isomultiflorenol synthase [EC:5.4.99.36]
K16204  seco-amyrin synthase [EC:5.4.99.52 5.4.99.54]
K16205  tirucalladienol synthase [EC:5.4.99.56]
K16206  baruol synthase [EC:5.4.99.57]
K15821  thalianol synthase [EC:5.4.99.31]
K15822  camelliol C synthase [EC:5.4.99.38]
K15823  arabidiol synthase [EC:4.2.1.124]
K19011  achilleol B synthase [EC:5.4.99.48]
K16207  marneral synthase [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
C16775  (S)-beta-Bisabolene
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
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
C20479  (+)-epi-alpha-Bisabolol
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
Related
pathway
ko00100  Steroid biosynthesis
ko00900  Terpenoid backbone biosynthesis
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