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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
BRITE hierarchy
Pathway map
Sesquiterpenoid and triterpenoid biosynthesis
ko00909

All organismsOrtholog table
Drug
D00883  
Naftifine hydrochloride (USP)
D08245  
Naftifine (INN)
Other DBs
Orthology
K00801  
farnesyl-diphosphate farnesyltransferase [EC:2.5.1.21]
K00511  
squalene monooxygenase [EC:1.14.13.132]
K15793  
acyclic sesquiterpene synthase [EC:3.1.7.6 4.2.3.47 4.2.3.49]
K15891  
farnesol dehydrogenase [EC:1.1.1.216]
K14173  
alpha-farnesene synthase [EC:4.2.3.46]
K14174  
beta-farnesene synthase [EC:4.2.3.47]
K14175  
(3S,6E)-nerolidol synthase [EC:4.2.3.48]
K10156  
epi-isozizaene synthase [EC:4.2.3.37]
K12645  
epi-isozizaene 5-monooxygenase [EC:1.14.13.106]
K14176  
epi-cedrol synthase [EC:4.2.3.39]
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:4.2.3.54 4.2.3.53 4.2.3.50]
K15799  
(+)-alpha-barbatene/beta-chamigrene/thujopsene synthase [EC:4.2.3.79 4.2.3.78 4.2.3.69]
K14179  
germacrene-A synthase [EC:4.2.3.23]
K15800  
germacrene A oxidase [EC:1.14.13.123 1.1.1.314]
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 4.2.3.22]
K10187  
germacradienol/geosmin synthase [EC:4.1.99.16 4.2.3.75 4.2.3.22]
K14180  
aristolochene synthase [EC:4.2.3.9]
K15804  
5-epiaristolochene synthase [EC:4.2.3.61]
K15805  
5-epiaristolochene 1,3-dihydroxylase [EC:1.14.13.119]
K14181  
valencene/7-epi-alpha-selinene synthase [EC:4.2.3.86 4.2.3.73]
K14182  
vetispiradiene synthase [EC:4.2.3.21]
K15472  
premnaspirodiene oxygenase [EC:1.14.13.121]
K15806  
(+)-delta-selinene synthase [EC:4.2.3.76]
K18109  
5-epi-alpha-selinene synthase [EC:4.2.3.90]
K15807  
patchoulol synthase [EC:4.2.3.70]
K18110  
avermitilol synthase [EC:4.2.3.96]
K15808  
beta-caryophyllene synthase [EC:4.2.3.57]
K14184  
alpha-humulene/beta-caryophyllene synthase [EC:4.2.3.57 4.2.3.-]
K18111  
(+)-beta-caryophyllene/(+)-caryolan-1-ol synthase [EC:4.2.1.138 4.2.3.89]
K18112  
(E)-2-epi-beta-caryophyllene synthase [EC:4.2.3.137]
K14185  
longifolene synthase [EC:4.2.3.58]
K14186  
gamma-humulene synthase [EC:4.2.3.56]
K12250  
pentalenene synthase [EC:4.2.3.7]
K15907  
pentalenene oxygenase [EC:1.14.13.133]
K14183  
(+)-delta-cadinene synthase [EC:4.2.3.13]
K15809  
cis-muuroladiene synthase [EC:4.2.3.67]
K06045  
squalene-hopene/tetraprenyl-beta-curcumene cyclase [EC:4.2.1.129 5.4.99.17]
K15810  
dammaradiene synthase [EC:5.4.99.37]
K15811  
protostadienol synthase [EC:5.4.99.32]
K15812  
cucurbitadienol synthase [EC:5.4.99.33]
K15813  
beta-amyrin synthase [EC:5.4.99.39]
K15814  
beta-amyrin 24-hydroxylase [EC:1.14.99.43]
K15815  
lupeol synthase 2 [EC:5.4.99.41 5.4.99.40 5.4.99.39]
K15816  
lupeol synthase 1 [EC:5.4.99.41 4.2.1.128]
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:5.4.99.54 5.4.99.52]
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]
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
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
C19939  
Pentalen-13-al
C19973  
(+)-beta-Caryophyllene
C19974  
(+)-Caryolan-1-ol
C20159  
7-epi-alpha-Selinene
C20163  
5-epi-alpha-Selinene
C20181  
Avermitilol
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)
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)
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)
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)
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)
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)
Reference
  Authors
Fraga BM
  Title
Natural sesquiterpenoids.
  Journal
Nat Prod Rep 25:1180-209 (2008)
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)
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)
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)

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