ENTRY       mtr00909                    Pathway
NAME        Sesquiterpenoid and triterpenoid biosynthesis - Medicago truncatula (barrel medic)
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 mtr00909  Sesquiterpenoid and triterpenoid biosynthesis
DBLINKS     GO: 0016106 0016104
ORGANISM    Medicago truncatula (barrel medic) [GN:mtr]
GENE        11441556  squalene synthase 2 [KO:K00801] [EC:2.5.1.21]
            11415396  squalene monooxygenase SE1 isoform X1 [KO:K00511] [EC:1.14.14.17]
            25496080  squalene monooxygenase SE1 isoform X1 [KO:K00511] [EC:1.14.14.17]
            25496089  squalene monooxygenase SE1 [KO:K00511] [EC:1.14.14.17]
            25490000  squalene monooxygenase SE1 [KO:K00511] [EC:1.14.14.17]
            25482032  squalene monooxygenase SE1 [KO:K00511] [EC:1.14.14.17]
            11431375  putative dihydroflavonol 4-reductase [KO:K15891] [EC:1.1.1.354]
            11422412  alpha-farnesene synthase [KO:K14173] [EC:4.2.3.46]
            25493246  (3S,6E)-nerolidol synthase 1 [KO:K14175] [EC:4.2.3.48]
            25493247  (3S,6E)-nerolidol synthase 1 [KO:K14175] [EC:4.2.3.48]
            120575864  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120575865  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120575943  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120575944  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576871  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576874  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576876  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576878  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576881  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            120576884  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            25498399  LOW QUALITY PROTEIN: probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            11407907  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            11426332  probable sesquiterpene synthase [KO:K15803] [EC:4.2.3.75]
            25491517  (-)-germacrene D synthase-like [KO:K15803] [EC:4.2.3.75]
            25496253  probable terpene synthase 2 isoform X1 [KO:K15803] [EC:4.2.3.75]
            120580864  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            25492939  (-)-germacrene D synthase [KO:K15803] [EC:4.2.3.75]
            11432484  (-)-germacrene D synthase [KO:K15803] [EC:4.2.3.75]
            11411115  probable terpene synthase 2 [KO:K15803] [EC:4.2.3.75]
            11416693  (-)-germacrene D synthase [KO:K15803] [EC:4.2.3.75]
            25498009  beta-amyrin synthase [KO:K15813] [EC:5.4.99.39]
            25479596  beta-amyrin synthase [KO:K15813] [EC:5.4.99.39]
            25490441  beta-amyrin synthase [KO:K15813] [EC:5.4.99.39]
            11434381  beta-amyrin synthase [KO:K15813] [EC:5.4.99.39]
            25491157  beta-amyrin synthase [KO:K15813] [EC:5.4.99.39]
            25498254  beta-amyrin 24-hydroxylase [KO:K15814] [EC:1.14.14.134]
            25497034  lupeol synthase isoform X1 [KO:K20659] [EC:5.4.99.41]
            25496085  lupeol synthase [KO:K20659] [EC:5.4.99.41]
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   PMID:18363779
  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   PMID:16579958
  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   PMID:12011356
  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   PMID:17226502
  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   PMID:19030608
  AUTHORS   Fraga BM
  TITLE     Natural sesquiterpenoids.
  JOURNAL   Nat Prod Rep 25:1180-209 (2008)
            DOI:10.1039/b806216c
REFERENCE   PMID:21876149
  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   PMID:18356490
  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   PMID:15148404
  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
REL_PATHWAY mtr00100  Steroid biosynthesis
            mtr00900  Terpenoid backbone biosynthesis
KO_PATHWAY  ko00909
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