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IUBMB CommentsThe enzyme is a component of the herbivore-induced indirect defense system. The product, (E,E)-geranyllinalool, is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT), which is released by many plants in response to damage.
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(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
reaction of EC 4.2.3.48
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(2E,6E)-farnesyl diphosphate + H2O
trans-nerolidol + diphosphate
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?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
additional information
?
-
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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-
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?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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-
-
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
preferred substrate
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?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
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-
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
no activity with geranyl diphosphate or farnesyl diphosphate
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?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
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-
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
no activity with geranyl diphosphate or farnesyl diphosphate
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-
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
KJ755868
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-
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?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
-
additional products are + linalool + (E)-nerolidol. Products are precursors of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
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?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
KJ755870
enzyme is 55fold more efficient with geranylgeranyl diphosphate than with farnesyl diphosphate. Reaction with farnesyl diphosphate yields nerolidol
single major product
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?
additional information
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the partially purified LnTPS3 protein catalyzes the formation of geranyllinalool from geranylgeranyl diphosphate (GGPP) and trans-nerolidol from eeFPP, GC-MS analysis of reaction products. In absence of functional LnTPS3, no trans-geranyllinalool and trans-nerolidol synthase activities are detected. No activity with geranyl diphosphate
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?
additional information
?
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the partially purified LnTPS3 protein catalyzes the formation of geranyllinalool from geranylgeranyl diphosphate (GGPP) and trans-nerolidol from eeFPP, GC-MS analysis of reaction products. In absence of functional LnTPS3, no trans-geranyllinalool and trans-nerolidol synthase activities are detected. No activity with geranyl diphosphate
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additional information
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enzyme NaGLS is not active with geranyl diphosphate and farnesyl diphosphate, GC-MS analysis of compounds
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additional information
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enzyme NaGLS is not active with geranyl diphosphate and farnesyl diphosphate, GC-MS analysis of compounds
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additional information
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enzyme SlTPS46 shows no activity with geranyl diphospate, GC-MS analysis of compounds
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additional information
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enzyme SlTPS46 shows no activity with geranyl diphospate, GC-MS analysis of compounds
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(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
reaction of EC 4.2.3.48
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-
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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-
-
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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-
-
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
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-
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?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
-
-
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
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-
?
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0.0637
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
0.0187 - 0.0434
geranylgeranyl diphosphate
0.0187
geranylgeranyl diphosphate
pH and temperature not specified in the publication
0.0187
geranylgeranyl diphosphate
KJ755870
pH 7.0, temperature not specified in the publication
0.0305
geranylgeranyl diphosphate
recombinant enzyme, pH 7.0, 30°C
0.0315
geranylgeranyl diphosphate
pH and temperature not specified in the publication
0.0315
geranylgeranyl diphosphate
KJ755868
pH 7.0, temperature not specified in the publication
0.0434
geranylgeranyl diphosphate
recombinant enzyme, pH 7.0, 30°C
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evolution
SlGLS, NaGLS, AtGLSs, and several other GLSs come from different eudicot families and constitute a separate branch of the TPS-e/f clade that diverged from kaurene synthases, also in the TPS-e/f clade, before the gymnosperm-angiosperm split. The early divergence of this branch and the GLS activity of genes in this branch in diverse eudicot families suggest that GLS activity encoded by these genes predates the angiosperm-gymnosperm split
evolution
SlGLS, NaGLS, AtGLSs, and several other GLSs come from different eudicot families and constitute a separate branch of the TPS-e/f clade that diverged from kaurene synthases, also in the TPS-e/f clade, before the gymnosperm-angiosperm split. The early divergence of this branch and the GLS activity of genes in this branch in diverse eudicot families suggest that GLS activity encoded by these genes predates the angiosperm-gymnosperm split
evolution
geranyllinalool synthase activity is the likely ancestral function in angiosperms of genes belonging to an ancient TPS-e/f subclade that diverged from the kaurene synthase gene lineages before the split of angiosperms and gymnosperms. The geranyllinalool synthase subclade diverged from the rest of the TPS genes in clade e/f before the split of the gymnosperm and angiosperm lineages, enzymes encoded by genes in this subclade have only been characterized from eudicot species. Laurus nobilis also has a gene belonging to the geranyllinalool synthase subclade of TPS clade e/f and the enzyme encoded by this gene is an active geranyllinalool synthase. Geranyllinalool might have been one of the first specialized metabolites to have evolved from early stages in the evolution of the TPS gene family in plants. Phylogenetic analysis, unrooted tree
malfunction
the tps4 knockout mutant completely lacks induced emission of 4,8,12-trimethyl-1,3,7,11-tridecatetraene but is capable of beta-ionone and alpha-farnesene production, demonstrating that TPS4 is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene formation
malfunction
transgenic Arabidopsis lines carrying T-DNA insertions in the TPS04 locus are deficient in (E,E)-geranyllinalool and 4,8,12-trimethyl-1,3,7,11-tridecatetraene synthesis
malfunction
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the tps4 knockout mutant completely lacks induced emission of 4,8,12-trimethyl-1,3,7,11-tridecatetraene but is capable of beta-ionone and alpha-farnesene production, demonstrating that TPS4 is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene formation
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malfunction
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transgenic Arabidopsis lines carrying T-DNA insertions in the TPS04 locus are deficient in (E,E)-geranyllinalool and 4,8,12-trimethyl-1,3,7,11-tridecatetraene synthesis
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metabolism
the terpene synthase (TPS) catalyzes a two-step reaction in which carbocation formation of the C20 precursor geranylgeranyl diphosphate (GGPP) is followed by an allylic rearrangement that results in the production of the tertiary alcohol geranyllinalool, which is the precursor for biosynthesis of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT
metabolism
the terpene synthase (TPS) catalyzes a two-step reaction in which carbocation formation of the C20 precursor geranylgeranyl diphosphate (GGPP) is followed by an allylic rearrangement that results in the production of the tertiary alcohol geranyllinalool, which is the precursor for biosynthesis of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT
physiological function
the enzyme is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) formation. Induced TMTT production in Arabidopsis is a by-product of activated jasmonic acid signaling, rather than an effective defense response that contributes to resistance against Pseudomonas syringae
physiological function
contrary to wild-type, transgenic Lotus japonicus plants expressing isoform TPS2 produce (E,E)-geranyllinalool and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. Transgenic Nicotiana tabacum expressing isoform TPS2 produces (E,E)-geranyllinalool but not (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. In olfactory assays, the generalist predatory mite Neoseiulus californicus but not the specialist Phytoseiulus persimilis is attracted to uninfested, transgenic Lotus japonicus plants expressing TPS2 over wild-type plants. The specialist Phytoseiulus persimilis is more strongly attracted by the transgenic plants infested with spider mites than by infested wild-type plants
physiological function
GC-MS analysis of terpene volatiles induced by alamethicin treatment, overview
physiological function
GC-MS analysis of terpene volatiles induced by alamethicin treatment, overview
physiological function
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the enzyme is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) formation. Induced TMTT production in Arabidopsis is a by-product of activated jasmonic acid signaling, rather than an effective defense response that contributes to resistance against Pseudomonas syringae
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additional information
volatile profiles in leaves, flowers, fruits, and roots in male and female Laurus nobilis plants, overview. The biggest gender differences are observed in the flowers, where female flowers have predominantly monoterpenes as well as eugenol and methyleugenol, whereas male flowers contain mostly sesquiterpenes and benzaldehyde
additional information
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volatile profiles in leaves, flowers, fruits, and roots in male and female Laurus nobilis plants, overview. The biggest gender differences are observed in the flowers, where female flowers have predominantly monoterpenes as well as eugenol and methyleugenol, whereas male flowers contain mostly sesquiterpenes and benzaldehyde
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enzyme is not expressed in any tissue under normal growth but is induced in leaves by alamethicin and methyl jasmonate treatments
KJ755870
highly coordinated herbivore-induced expression of geranyllinalool synthase with CYP82G1 (At3g25180, a cytochrome P450 monooxygenase of the Arabidopsis CYP82 family, is responsible for the breakdown of the C20-precursor (E,E)-geranyllinalool to the insect-induced C16-homoterpene (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene (TMTT)) in leaves depending on the F-box protein COI-1
in leaves, expression is induced by methyl jasmonate
KJ755868
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
NaGLS is expressed constitutively, but the gene NaTPS46 can be induced in leaves with methyl jasmonate
no induction of the enzyme by the defense-suppressing mite line Tetranycus evansi Vicosa-1
suppression of the enzyme by methyl salicylate
TPS46 shows induction by alamethicin and methyljasmonate treatment, induction by defense-inducing spider mite line Tetranycus urticae Santpoort-2
transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
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transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
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Lee, S.; Badieyan, S.; Bevan, D.R.; Herde, M.; Gatz, C.; Tholl, D.
Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
Arabidopsis thaliana (Q93YV0)
brenda
Attaran, E.; Rostas, M.; Zeier, J.
Pseudomonas syringae elicits emission of the terpenoid (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene in Arabidopsis leaves via jasmonate signaling and expression of the terpene synthase TPS4
Mol. Plant Microbe Interact.
21
1482-1497
2008
Arabidopsis thaliana (Q93YV0), Arabidopsis thaliana, Arabidopsis thaliana Heynh. (Q93YV0)
brenda
Herde, M.; Grtner, K.; Kllner, T.G.; Fode, B.; Boland, W.; Gershenzon, J.; Gatz, C.; Tholl, D.
Identification and regulation of TPS04/GES, an Arabidopsis geranyllinalool synthase catalyzing the first step in the formation of the insect-induced volatile C16-homoterpene TMTT
Plant Cell
20
1152-1168
2008
Arabidopsis thaliana (Q93YV0), Arabidopsis thaliana, Arabidopsis thaliana Columbia ecotype (Q93YV0)
brenda
Brillada, C.; Nishihara, M.; Shimoda, T.; Garms, S.; Boland, W.; Maffei, M.E.; Arimura, G.
Metabolic engineering of the C16 homoterpene TMTT in Lotus japonicus through overexpression of (E,E)-geranyllinalool synthase attracts generalist and specialist predators in different manners
New Phytol.
200
1200-1211
2013
Phaseolus lunatus (U5KL21)
brenda
Falara, V.; Alba, J.M.; Kant, M.R.; Schuurink, R.C.; Pichersky, E.
Geranyllinalool synthases in Solanaceae and other angiosperms constitute an ancient branch of diterpene synthases that are involved in the synthesis of defensive compounds
Plant Physiol.
166
428-441
2014
Nicotiana attenuata (KJ755868), Nicotiana attenuata, Solanum lycopersicum (KJ755870), Solanum lycopersicum
brenda
Falara, V.; Alba, J.; Kant, M.; Schuurink, R.; Pichersky, E.
Geranyllinalool synthases in Solanaceae and other angiosperms constitute an ancient branch of diterpene synthases involved in the synthesis of defensive compounds
Plant Physiol.
166
428-441
2014
Nicotiana attenuata (A0A088DC07), Nicotiana attenuata, Solanum lycopersicum (K4BE78), Solanum lycopersicum
brenda
Yahyaa, M.; Matsuba, Y.; Brandt, W.; Doron-Faigenboim, A.; Bar, E.; McClain, A.; Davidovich-Rikanati, R.; Lewinsohn, E.; Pichersky, E.; Ibdah, M.
Identification, functional characterization, and evolution of terpene synthases from a basal dicot
Plant Physiol.
169
1683-1697
2015
Laurus nobilis (A0A0H4U599), Laurus nobilis
brenda