Oleoresin sesquiterpene volatiles biosynthesis (Oryza sativa)

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1-4plastid stromacytosolPPilongifolenePPigamma-humulene(E)-alpha-bisabolenedelta-selineneTerpene synthase(E)-beta-caryophyllenePPiFarnesyl diphosphatealpha-longipinene


Description

Pathway summary from MetaCyc

General background

Oleoresin (also simply termed "resin" or "pitch") is a viscous secretion common in coniferous trees, which is involved in the chemical and physical defense of conifers against predators (such as beetles and fungal pathogens). The accumulated resin is released upon tissue injury and/or produced at the site of infestation (for review, see [Trapp01]). The predator is killed, encased in resin and expelled from the bore point of entry (a process called "pitching out"). This process has the dual function of killing and expelling the predator, but also to form a physical barrier around the wound through evaporation of the oleoresin turpentine which allows the resin acids to seal the wound (Croteau, 1985; Gijzen, 1993). Oleoresin is composed in roughly equal parts of volatile turpentine (a mixture of monoterpenes and sesquiterpenes) and rosin (also known as diterpene resin acids). The exact composition of turpentine and rosin varies from one conifer species to the next, as well as depending on the resin-producing tissue analyzed [Trapp01]. The main constituents of these fractions have been regrouped in the following pathways: superpathway of oleoresin turpentine biosynthesis and superpathway of diterpene resin acids biosynthesis.

Concerning this pathway:

Compared to monoterpenes, fewer sesquiterpene synthases from conifers have been identified and studied to date. Generally, the longer chain of (2E,6E)-farnesyl diphosphate compared to that of geranyl diphosphate, and the additional double bond, allows for a greater diversity of products being formed by those enzymes. Two coniferous enzymes γ-humulene synthase and delta-selinene synthase from Grand Fir (Abies grandis) produces each in excess of 30 different sesquiterpenes olefins. In contrast, (E)-alpha-bisabolene synthase catalyzes only the synthesis of (E)-alpha-bisabolene (Bohlmann, 1998). Importantly, this compound has been shown to be converted by methyl-jasmonate-induced suspension cell cultures of Grand Fir into todomatuic acid, a sesquiterpene derivative structurally similar to the insect juvenile hormone III (Bohlmann, 1998), and can disrupt insect reproduction and/or larval development [Trapp01].

See source in Plant Reactome, developed by Gramene.org. Plant Reactome version derives from MetaCyc pathway created by Chris Tissier of The Arabidopsis Information Resource on 2006-12-06.

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Bibliography

  1. Bohlmann, J, Crock, J, Jetter, R, Croteau, R; ''Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis)''; Proc Natl Acad Sci U S A 95(12);6756-61, 1998 PubMed Europe PMC Scholia
  2. Croteau, R, Johnson, MA; ''Biosynthesis of terpenoid wood extractives''; In Biosynthesis and biodegradation of wood components, ed. T. Higuichi, pp 379-439, 1985
  3. Gijzen, M, Lewinsohn, E, Croteau, R; ''Conifer monoterpenes: biochemistry and bark beetle chemical ecology''; In Bioactive volatile compounds from plants, eds R. Teranishi, R.G. Buttery, H. Sugisawa, pp. 8-22, Washington DC: Am. Chem. Soc., 1993
  4. Trapp, S, Croteau, R; ''Defensive resin biosynthesis in conifers''; Annu Rev Plant Physiol Plant Mol Biol 52;689-724, 2001 PubMed Europe PMC Scholia

History

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CompareRevisionActionTimeUserComment
118752view11:26, 1 June 2021EweitzReverted to version '10:52, 1 June 2021' by Eweitz
118751view11:14, 1 June 2021EweitzModified description
118738view10:52, 1 June 2021EweitzModified description
118730view10:40, 1 June 2021EweitzAdd literature references from MetaCyc, http://pathway.gramene.org/RICE/NEW-IMAGE?type=NIL&object=PWY-5425&redirect=T
118664view16:30, 31 May 2021EweitzReverted to version '15:37, 31 May 2021' by Eweitz
118663view16:13, 31 May 2021EweitzModified description
118662view15:37, 31 May 2021EweitzRefine interaction line positions
118661view15:32, 31 May 2021EweitzAdd alpha-longipinene output, fix graphics
118641view12:02, 31 May 2021EweitzOntology Term : 'metabolic pathway of secondary metabolites' added !
118640view11:59, 31 May 2021EweitzReverted to version '11:35, 31 May 2021' by Eweitz
118639view11:48, 31 May 2021EweitzModified description
118638view11:35, 31 May 2021EweitzModified description
118634view11:31, 31 May 2021EweitzReverted to version '11:19, 31 May 2021' by Eweitz
118631view11:19, 31 May 2021EweitzModified description
118630view11:19, 31 May 2021EweitzReverted to version '10:16, 29 May 2021' by Eweitz
118629view11:05, 31 May 2021EweitzModified description
118613view10:16, 29 May 2021EweitzModified description
118612view10:12, 29 May 2021EweitzModified description
118268view12:09, 26 May 2021EweitzModified title
82033view14:40, 8 September 2015Anweshafixing title, data source, & tagging incomplete pathways
80478view14:47, 25 June 2015AnweshaNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
Metabolite
(E)-alpha-bisaboleneMetaboliteCHEBI:49242 (ChEBI)
(E)-beta-caryophylleneMetaboliteCHEBI:10357 (ChEBI)
Farnesyl diphosphateMetaboliteCHEBI:17407 (ChEBI)
PPiMetaboliteCHEBI:29888 (ChEBI)
Terpene synthaseProtein4836390 (Reactome) Converts trans, trans-farnesyl diphosphate into (E)-beta-caryophyllene.
alpha-longipineneMetaboliteCHEBI:62753 (ChEBI)
delta-selineneMetaboliteCHEBI:49278 (ChEBI)
gamma-humuleneMetaboliteCHEBI:49290 (ChEBI)
longifoleneMetaboliteCHEBI:6530 (ChEBI)

Annotated Interactions

View all...
SourceTargetTypeDatabase referenceComment
(E)-alpha-bisaboleneArrow1121537 (Reactome)
(E)-beta-caryophylleneArrow1120850 (Reactome)
1119759 (Reactome) Trans, trans-farnesyl diphosphate is converted into delta-selinene by enzymatic activity of an unknown gene product.
1120246 (Reactome) Trans, trans-farnesyl diphosphate is converted into alpha-longipinene by enzymatic activity of an unknown gene product.
1120441 (Reactome) Trans, trans-farnesyl diphosphate is converted into longifolene by enzymatic activity of an unknown gene product.
1120850 (Reactome) Trans, trans-farnesyl diphosphate is converted into (E)-beta-caryophyllene by enzymatic activity of terpene synthase.
1120917 (Reactome) Trans, trans-farnesyl diphosphate is converted into gamma-humulene by enzymatic activity of an unknown gene product.
1121537 (Reactome) Trans, trans-farnesyl diphosphate is converted into (E)-alpha-bisabolene by enzymatic activity of an unknown gene product.
Farnesyl diphosphate1119759 (Reactome)
Farnesyl diphosphate1120246 (Reactome)
Farnesyl diphosphate1120850 (Reactome)
Farnesyl diphosphate1121537 (Reactome)
PPiArrow1119759 (Reactome)
PPiArrow1120246 (Reactome)
PPiArrow1120441 (Reactome)
PPiArrow1120850 (Reactome)
PPiArrow1120917 (Reactome)
PPiArrow1121537 (Reactome)
Terpene synthasemim-catalysis1120850 (Reactome)
alpha-longipineneArrow1120246 (Reactome)
delta-selineneArrow1119759 (Reactome)
gamma-humuleneArrow1120917 (Reactome)
longifoleneArrow1120441 (Reactome)
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