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(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + beta-elemene + beta-selinene + alpha-selinene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
2 neryl diphosphate
limonene + terpinolene + 2 diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
geranyl diphosphate
myrcene + (E)-beta-ocimene + (Z)-beta-ocimene + diphosphate
-
-
-
-
?
additional information
?
-
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
in GC-MS analysis, beta-elemene is identified as product. beta-Elemene is the Cope rearrangement product of germacrene A that is formed upon injection into the hot injection port of the GC-MS
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
in GC-MS analysis, beta-elemene is identified as product. beta-Elemene is the Cope rearrangement product of germacrene A that is formed upon injection into the hot injection port of the GC-MS
-
?
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
-
sole product
-
?
(2E,6E)-farnesyl diphosphate
germacrene A + diphosphate
-
sole product
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
GC-MS product analysis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
reaction product solubilization and analysis in pentane, determination of germacrene A configuration
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
the product germacerene A is released after reaction to be further processing by oxidations and/or glucosylations and cyclization by a germacrane cyclase
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
GC-MS product analysis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
reaction product analysis by GC-MS and NMR
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
98% of total product is (+)-(10R)-germacrene A, 2% is alpha-humulene in feeding experiments in vivo, chiral GC-MS product analysis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
chiral GC-MS product analysis
-
?
additional information
?
-
(+)-germacrene A synthesis is a step in isoprenoid biosynthesis, overview
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is a step in isoprenoid biosynthesis, overview
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
-
no activity with geranyl diphosphate
-
-
?
additional information
?
-
no substrates: geranyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no substrates: geranyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
no substrates: geranyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
sesquiterpene hydrocarbon profile of leaf extracts, overview
-
-
?
additional information
?
-
-
sesquiterpene hydrocarbon profile of leaf extracts, overview
-
-
?
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(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + beta-elemene + beta-selinene + alpha-selinene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
additional information
?
-
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-(R)-germacrene A + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
the product germacerene A is released after reaction to be further processing by oxidations and/or glucosylations and cyclization by a germacrane cyclase
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-(10R)-germacrene A + diphosphate
-
98% of total product is (+)-(10R)-germacrene A, 2% is alpha-humulene in feeding experiments in vivo
-
?
additional information
?
-
(+)-germacrene A synthesis is a step in isoprenoid biosynthesis, overview
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is a step in isoprenoid biosynthesis, overview
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
-
(+)-germacrene A synthesis is the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
-
-
?
additional information
?
-
sesquiterpene hydrocarbon profile of leaf extracts, overview
-
-
?
additional information
?
-
-
sesquiterpene hydrocarbon profile of leaf extracts, overview
-
-
?
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0.00074 - 0.0148
(2E,6E)-farnesyl diphosphate
0.0025 - 14.9
2-trans,6-trans-farnesyl diphosphate
additional information
additional information
-
0.00074
(2E,6E)-farnesyl diphosphate
-
0.00082
(2E,6E)-farnesyl diphosphate
-
0.00106
(2E,6E)-farnesyl diphosphate
thioredoxin-fusion protein
0.0078
(2E,6E)-farnesyl diphosphate
isoform GAS1, at pH 7.0 and 23°C
0.0148
(2E,6E)-farnesyl diphosphate
isoform GAS2, at pH 7.0 and 23°C
0.0025
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant enzyme
0.0032
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 30°C
0.0034
2-trans,6-trans-farnesyl diphosphate
-
in 10 mM Tris-HCl, 10 mM MgCl2, 1 mM mercaptoethanol
0.0047
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant T433A
0.0066
2-trans,6-trans-farnesyl diphosphate
-
pH 7.0, 30°C
0.0069
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 30°C
0.0076
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant T433A/A435T
0.0106
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant S434A
0.011
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant wild-type enzyme
0.0251
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant A435T
11
2-trans,6-trans-farnesyl diphosphate
-
pH 7.5-8.0, 25°C
14.9
2-trans,6-trans-farnesyl diphosphate
-
pH 7.5-8.0, 37°C
additional information
additional information
-
-
additional information
additional information
-
-
additional information
additional information
-
-
-
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0.13 - 0.28
(2E,6E)-farnesyl diphosphate
0.00035 - 4.4
2-trans,6-trans-farnesyl diphosphate
0.13
(2E,6E)-farnesyl diphosphate
isoform GAS1, at pH 7.0 and 23°C
0.28
(2E,6E)-farnesyl diphosphate
isoform GAS2, at pH 7.0 and 23°C
0.00035
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant T433A
0.00037
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant T433A/A435T
0.016
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant wild-type enzyme
0.017
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant S434A
0.044
2-trans,6-trans-farnesyl diphosphate
pH 7.0, 25°C, recombinant mutant A435T
4.4
2-trans,6-trans-farnesyl diphosphate
-
determined by incubating purified enzyme with various concentrations of 1 to 100 microM 2-trans,6-trans-farnesyl diphosphate
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normal and etiolated
brenda
head core tissue
brenda
-
-
brenda
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems. In flowers the highest expression wais observed in the biosynthetically most active stages of flower development
brenda
-
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems. In flowers the highest expression wais observed in the biosynthetically most active stages of flower development
-
brenda
-
-
brenda
-
brenda
-
-
brenda
head leaves, very low expression in green leaves
brenda
-
brenda
-
expression levels decline near the onset of flowering
brenda
-
brenda
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems
brenda
-
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems
-
brenda
-
high enzyme activity
brenda
-
brenda
-
-
brenda
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems
brenda
-
GAS expression in flowers is more than 4fold higher than in leaves and 25fold higher than in stems
-
brenda
especially in outer tissue, highest expression level of the long isozyme
brenda
highest expression level of the short isozyme in outer and inner tissues
brenda
-
brenda
-
brenda
high expression of GAS in glandular trichomes, which also contain the highest concentration of parthenolide
brenda
-
high expression of GAS in glandular trichomes, which also contain the highest concentration of parthenolide
-
brenda
additional information
both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
-
both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
nearly no expression of the short isozyme in head leaves and in green leaves, both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
nearly no expression of the short isozyme in head leaves and in green leaves, both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
-
nearly no expression of the short isozyme in head leaves and in green leaves, both isozymes are expressed in all tissues but in varying levels, overview
brenda
additional information
expressed in all aerial tissues, the highest expression is observed in tissues that contain high concentrations of parthenolide
brenda
additional information
-
expressed in all aerial tissues, the highest expression is observed in tissues that contain high concentrations of parthenolide
brenda
additional information
-
expressed in all aerial tissues, the highest expression is observed in tissues that contain high concentrations of parthenolide
-
brenda
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Bertea, C.M.; Voster, A.; Verstappen, F.W.; Maffei, M.; Beekwilder, J.; Bouwmeester, H.J.
Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library
Arch. Biochem. Biophys.
448
3-12
2006
Artemisia annua (Q1PDD2), Artemisia annua
brenda
Chang, Y.J.; Jin, J.; Nam, H.Y.; Kim, S.U.
Point mutation of (+)-germacrene A synthase from Ixeris dentata
Biotechnol. Lett.
27
285-288
2005
Ixeridium dentatum (Q6YN71), Ixeridium dentatum
brenda
Kim, M.Y.; Chang, Y.J.; Bang, M.H.; Baek, N.I.; Jin, J.; Lee, C.H.; Kim, S.U.
cDNA isolation and characterization of (+)-germacrene A synthase from Ixeris dentata form. albiflora Hara
J. Plant Biol.
48
178-186
2005
Ixeridium dentatum
-
brenda
Prosser, I.; Phillips, A.L.; Gittings, S.; Lewis, M.J.; Hooper, A.M.; Pickett, J.A.; Beale, M.H.
(+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis
Phytochemistry
60
691-702
2002
Solidago canadensis (Q9AR67), Solidago canadensis
brenda
de Kraker, J.W.; Franssen, M.C.; de Groot, A.; Konig, W.A.; Bouwmeester, H.J.
(+)-Germacrene A biosynthesis. The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory
Plant Physiol.
117
1381-1392
1998
Cichorium intybus
brenda
Bouwmeester, H.J.; Kodde, J.; Verstappen, F.W.; Altug, I.G.; de Kraker, J.W.; Wallaart, T.E.
Isolation and characterization of two germacrene A synthase cDNA clones from chicory
Plant Physiol.
129
134-144
2002
Cichorium intybus (Q8LSC2), Cichorium intybus (Q8LSC3), Cichorium intybus
brenda
Ren, J.; Liu, Y.; Yang, L.; Ni, R.; You, S.
Molecular cloning and bacterial expression of germacrene A synthase cDNA from Crepidiastrum sonchifolium
Chem. Res. Chin. Univ.
22
606-611
2006
Crepidiastrum sonchifolium (A7RA92)
-
brenda
Agger, S.A.; Lopez-Gallego, F.; Hoye, T.R.; Schmidt-Dannert, C.
Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120
J. Bacteriol.
190
6084-6096
2008
Nostoc sp.
brenda
Goepfert, J.C.; Macnevin, G.; Ro, D.K.; Spring, O.
Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes
BMC Plant Biol.
9
86
2009
Helianthus annuus (B0FGA9), Helianthus annuus (Q4U3F7)
brenda
Agger, S.; Lopez-Gallego, F.; Schmidt-Dannert, C.
Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus
Mol. Microbiol.
72
1181-1195
2009
Coprinopsis cinerea
brenda
Majdi, M.; Liu, Q.; Karimzadeh, G.; Malboobi, M.A.; Beekwilder, J.; Cankar, K.; Vos, R.; Todorovic, S.; Simonovic, A.; Bouwmeester, H.
Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.)
Phytochemistry
72
1739-1750
2011
Tanacetum parthenium (F8UL80), Tanacetum parthenium, Tanacetum parthenium L. Schulz Bip. (F8UL80)
brenda
Benabdelkader, T.; Guitton, Y.; Pasquier, B.; Magnard, J.L.; Jullien, F.; Kameli, A.; Legendre, L.
Functional characterization of terpene synthases and chemotypic variation in three lavender species of section Stoechas
Physiol. Plant.
153
43-57
2015
Lavandula pedunculata (T1RRI5), Lavandula pedunculata, Lavandula viridis (T1RRJ6)
brenda
Nguyen, T.D.; Faraldos, J.A.; Vardakou, M.; Salmon, M.; OMaille, P.E.; Ro, D.K.
Discovery of germacrene A synthases in Barnadesia spinosa The first committed step in sesquiterpene lactone biosynthesis in the basal member of the Asteraceae
Biochem. Biophys. Res. Commun.
479
622-627
2016
Barnadesia spinosa (A0A0U1XNG2), Barnadesia spinosa (A0A0U1XRI2), Barnadesia spinosa
brenda
Pazouki, L.; Memari, H.R.; Kaennaste, A.; Bichele, R.; Niinemets, U.E.
Germacrene A synthase in yarrow (Achillea millefolium) is an enzyme with mixed substrate specificity gene cloning, functional characterization and expression analysis
Front. Plant Sci.
6
111
2015
Achillea millefolium
brenda
Ferro, A.M.; Ramos, P.; Guerra, A.; Parreira, P.; Bras, T.; Guerreiro, O.; Jeronimo, E.; Capel, C.; Capel, J.; Yuste-Lisbona, F.J.; Duarte, M.F.; Lozano, R.; Oliveira, M.M.; Goncalves, S.
Haplotype analysis of the germacrene A synthase gene and association with cynaropicrin content and biological activities in Cynara cardunculus
Mol. Genet. Genomics
293
417-433
2018
Cynara cardunculus (I1TE91), Cynara cardunculus
brenda
Majdi, M.; Abdollahi, M.R.; Maroufi, A.
Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium
Plant Cell Rep.
34
1909-1918
2015
Tanacetum parthenium (F8UL80), Tanacetum parthenium
brenda