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Entry
map00909                    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
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Sesquiterpenoid and triterpenoid biosynthesis
map00909

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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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