| Entry |
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| Name |
Sesquiterpenoid and triterpenoid biosynthesis
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| 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.
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| Class |
Metabolism; Metabolism of terpenoids and polyketides
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| Pathway map |
| Sesquiterpenoid and triterpenoid biosynthesis |

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| Other DBs |
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| Enzyme |
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| Compound |
| trans,trans-Farnesyl diphosphate | | Squalene | | (S)-2,3-Epoxysqualene | | (2E,6E)-Farnesol | | Pentalenene | | Trichodiene | | Aristolochene | | (2Z,6E)-Farnesol | | Presqualene diphosphate | | 2-trans,6-trans-Farnesal | | PR-toxin | | Nivalenol | | Tetrahymanol | | Diplopterol | | Diploptene | | delta-Cadinene | | Gossypol | | alpha-Amyrin | | beta-Amyrin | | Lupeol | | Taraxerol | | Costunolide | | Capsidiol | | beta-Caryophyllene | | alpha-Farnesene | | beta-Farnesene | | Germacrene B | | Humulene | | Longifolene | | Nerolidol | | beta-Selinene | | Solavetivone | | Vetispiradiene | | Amorpha-4,11-diene | | (+)-Germacrene A | | (-)-Germacrene D | | (1E,4S,5E,7R)-Germacra-1(10),5-dien-11-ol | | (+)-epi-Isozizaene | | Geosmin | | gamma-Bisabolene | | gamma-Humulene | | (+)-Valencene | | (5S)-Albaflavenol | | Albaflavenone | | (5R)-Albaflavenol | | 8-epi-Cedrol | | Germacra-1(10),4,11(13)-trien-12-ol | | Germacrene A acid | | 5-Epiaristolochene | | Solavetivol | | 24-Hydroxy-beta-amyrin | | (+)-alpha-Santalene | | (+)-alpha-Barbatene | | (+)-delta-Selinene | | (3R,6E)-Nerolidol | | Germacrene C | | (E)-gamma-Bisabolene | | (E)-alpha-Bisabolene | | (S)-beta-Bisabolene | | (S)-beta-Macrocarpene | | cis-Muurola-3,5-diene | | Patchoulol | | Isomultiflorenol | | Cucurbitadienol | | Protostadienol | | Arabidiol | | Dammarenediol II | | Thalianol | | Germanicol | | Dammara-20,24-diene | | Camelliol C | | Lupan-3beta,20-diol | | Pentalen-13-al | | alpha-seco-Amyrin | | Marneral | | beta-seco-Amyrin | | Tirucalla-7,24-dien-3beta-ol | | Baruol |
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| Reference |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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) |