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Information on EC 4.2.3.89 - (+)-beta-caryophyllene synthase
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4.2.3.89 (+)-beta-caryophyllene synthaseIUBMB Comments
A multifunctional enzyme which also converts the (+)-beta-caryophyllene to (+)-caryolan-1-ol (see EC 4.2.1.138, (+)-caryolan-1-ol synthase). cf. EC 4.2.3.57 (-)-beta-caryophyllene synthase.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
(E)-beta-caryophyllene synthase, BCS, beta-caryophyllene synthase, CsSesquiTPS6a, CsSesquiTPS6b, CsSesquiTPS6c, DcTPS1, E-(beta)-caryophyllene synthase, GcoA, More, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
GcoA
TPS1
additional information
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-beta-caryophyllene + diphosphate
-
-
-
-
(2E,6E)-farnesyl diphosphate = (+)-beta-caryophyllene + diphosphate
possible mechanism of sesquiterpene synthases from Piper nigrum, the reaction mechanism includes a 1,10-ring closure, overview
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(2Z,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (+)-beta-caryophyllene-forming]
A multifunctional enzyme which also converts the (+)-beta-caryophyllene to (+)-caryolan-1-ol (see EC 4.2.1.138, (+)-caryolan-1-ol synthase). cf. EC 4.2.3.57 (-)-beta-caryophyllene synthase.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication. Recombinant enzyme OkBCS converts farnesyl diphosphate to beta-caryophyllene as a major product (94%) and 6% alpha-humulene
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication, the reaction mechanism includes a 1,10-ring closure
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-beta-caryophyllene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-beta-caryophyllene + diphosphate
-
-
-
-
?
additional information
?
-
GC-MS analysis is used for compound identification
-
-
-
additional information
?
-
GC-MS analysis is used for compound identification
-
-
-
additional information
?
-
GC-MS analysis is used for compound identification
-
-
-
additional information
?
-
enzyme OkBCS is not active with geranyl diphosphate (GPP) as substrate, besides a weak hydrolysis activity converting GPP to geraniol, identification of substrates and products by GC-MS analysis
-
-
-
additional information
?
-
the recombinant enzyme catalyses the formation of a major product (E)-beta-caryophyllene (82%) and a minor product alpha-humulene (18%) from farnesyl diphosphate
-
-
-
additional information
?
-
the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS)
-
-
-
additional information
?
-
steady-state kinetic parameters are determined using malachite green phosphate assay
-
-
-
additional information
?
-
-
enzyme VGwECar2 catalyzes the cyclization of farnesyl diphosphate to both beta-caryophyllene and alpha-humulene, plus a small amount of germacrene D, GC-MS analysis
-
-
-
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS)
-
-
-
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
additional information
-
no activity is observed for Fe2+, Co2+, Zn2+, Ni2+, or Cu2+
Mg2+
required, interaction between Mg2+ atoms and binding residues, structure overview; required, interaction between Mg2+ atoms and binding residues, structure overview; required, interaction between Mg2+ atoms and binding residues, structure overview
Mg2+
-
more than 5 mM MgCl2 is required for maximum activity. The enzyme reaction is unable to proceed without MgCl2
Mn2+
-
38% activity (relative to the activity in the presence of Mg2+) is retained in the presence of 5 mM Mn2+
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000956
(2E,6E)-farnesyl diphosphate
-
at pH 7.5 and 30°C in the presence of 5 mM MgCl2
0.0211
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
0.1255
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
additional information
additional information
Michaelis-Menten steady-state kinetics
-
additional information
additional information
steady state kinetics
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.025
(2E,6E)-farnesyl diphosphate
-
at pH 7.5 and 30°C in the presence of 5 mM MgCl2
0.455
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
4.06
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
21.6
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
i.e. Citrus aurantium var. sinensis, pineapple sweet orange
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
unripe peppercorn is subjected to the Illumina transcriptome sequencing, young, unripe, and ripe fruits. GC/MS profiling of terpenes from immature black pepper fruit, accumulation of beta-caryophyllene, the major sesquiterpene in peppercorn, changes from 46% to 70% as fruits ripen
brenda
higher beta-caryophyllene contents in mature leaves compared to young leaves; higher beta-caryophyllene contents in mature leaves compared to young leaves
brenda
additional information
in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emit nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp
brenda
additional information
in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emit nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp
brenda
additional information
in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emit nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp; in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp
brenda
additional information
-
tissue expression analysis of enzyme TPS1. The highest expression of WtDcTPS1 gene occurs in the fruits, whereas the lowest transcript levels are observed in the flowers, fruit pericarp, and roots. The expression level of the WtDcTPS1 gene in the fruits of the wild type carrot accession 23727 is 40fold higher than that found in the roots, leaves, flowers, and pericarp
brenda
additional information
expression variation of OkBCS well corroborate with beta-caryophyllene levels in different tissues from five Ocimum species
brenda
additional information
isozyme expression patterns, overview; isozyme expression patterns, overview
brenda
additional information
isozyme expression patterns, overview; isozyme expression patterns, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
isozyme RtTPS1 contains no typical N-terminal transit peptide (62-64aa); isozyme RtTPS3 contains no typical N-terminal transit peptide (62-64aa)
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
the cyclization process catalyzed by PnTPSs follows a 1,10-closure mechanism assuming that the present PnTPSs have evolved from a common ancestor
evolution
the enzyme belongs to typical class of sesquiterpene synthases from angiosperms, clade TPS-a. Across five Ocimum species, OkBCS shows the highest expression in Ocimum kilimandscharicum followed by Ocimum americanum, Ocimum tenuiflorum, and Ocimum gratissimum while Ocimum basilicum hadve trace levels
evolution
the enzyme belongs to the terpene synthase (TPS) family; the enzyme belongs to the terpene synthase (TPS) family; the enzyme belongs to the terpene synthase (TPS) family
evolution
isozyme RtTPS1 contains all the conserved domains of the TPS family, including the RR(P)X8W, RXR, and DDXXD (X is any amino acid) motifs, and absolutely conserved arginine, cysteine and histidine residues in active-site; isozyme RtTPS3 contains all the conserved domains of the TPS family, including the RR(P)X8W, RXR, and DDXXD (X is any amino acid) motifs, and absolutely conserved arginine, cysteine and histidine residues in active-site
evolution
-
gene WtDcTPS1 exhibits highly conserved sequences of plant TPSs including the asparate-rich motif DDxxD and the RxR motif, both of which are involved in catalysis
evolution
the enzyme belongs to the terpene synthase family, TPS-a subfamily
evolution
-
in grapevine five genes are known to code for beta-caryophyllene synthases, but only one of them, VvGwECar2, is actually expressed in all plant tissues and therefore accounts for most of the volatile production in vegetative parts and berries, although in flowers two other genes, VvGwECar1 and VvPNECar2, seem to play a big role
metabolism
GC/MS profiling of terpenes from immature black pepper fruit, accumulation of beta-caryophyllene, the major sesquiterpene in peppercorn, changes from 46% to 70% as fruits ripen
metabolism
putative alpha-pinene and beta-caryophyllene biosynthesis pathway; putative alpha-pinene and beta-caryophyllene biosynthesis pathway
metabolism
beta-caryophyllene is produced via the mevalonate (MVA)-mediated pathway, overview
physiological function
agro-infiltration based transient expression manipulation with OkBCS overexpression and silencing confirms its role in beta-caryophyllene biosynthesis
physiological function
(E)-beta-caryophyllene synthase is a possible key enzyme of plant defence
physiological function
-
the TPS enzyme (VvGwECar2) is responsible for most of the production of E-(beta)-caryophyllene in grapevine (VvGwECar2). It might play a key role in the plant regulation machinery
additional information
three-dimensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket
additional information
three-dimensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket
additional information
three-dimensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket; three-dmensional structure homology modelling using the crystal structure of the delta-cadinene synthase from Gossypium. The functional C-terminal domain consists of 14 alpha-helices forming a central cavity and the amino terminal domain formed by two 10 antiparallel alpha-helices. The aspartate-rich motifs DDXXD (located on helix-alpha-13) and NSE/DTE motif (located helix alpha-20) are both involved in binding a trio of divalent magnesium ions, co-orientated to the catalytic pocket
additional information
isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with geranyl diphosphate, while RtTPS1 and RtTPS3 are also active with farnesyl diphosphate, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves; isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with GPP, while RtTPS1 and RtTPS3 are also active with FPP, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves
additional information
isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with geranyl diphosphate, while RtTPS1 and RtTPS3 are also active with farnesyl diphosphate, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves; isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with GPP, while RtTPS1 and RtTPS3 are also active with FPP, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves
additional information
-
monoterpene contents comparisons of different wild accessions of carrot. In cell-free extracts from carrot fruit pericarp of wild accession 23727, the monoterpenes contained are geraniol, sabinene, limonene, alpha-pinene, beta-pinene, beta-myrcene, and alpha-phellandrene and the sesquiterpenes are E-beta-caryophellene, E-beta-farnesene, and alpha-humelene
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
GCOA_STRGG
Streptomyces griseus subsp. griseus (strain JCM 4626 / NBRC 13350)
335
0
37906
Swiss-Prot
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A256E
site-directed mutagenesis of an alpha-helix residue disturbs the facing of the N-terminal loop
D319G
site-directed mutagenesis, the mutation prevents the interaction of this residue with one of the Mg2+ atoms
E41D
site-directed mutagenesis of an alpha-helix residue facing the N-terminal loop, the mutation can compensate the structural difference between enzymes CsSesquiTPS7 and CsSesquiTPS6b, both producing beta-caryophyllene and alpha-humulene
I260R
site-directed mutagenesis of an alpha-helix residue disturbs the facing of the N-terminal loop
T44P
site-directed mutagenesis of an alpha-helix residue facing the N-terminal loop, the mutation can compensate the structural difference between enzymes CsSesquiTPS7 and CsSesquiTPS6b, both producing beta-caryophyllene and alpha-humulene
additional information
additional information
gene OkBCS silencing in Ocimum kilimandscharicum plants via Agrobacterium tumefaciens strain GV3101 mediated transfection. beta-Caryophyllene and alpha-humulene levels decrease by about 20% in silenced plants compared to controls. The silencing effect is more prominent in systemic leaves with 95% reduction in OkBCS transcripts against 51% decrease in local leaves
additional information
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the enzyme from transgenic Arabidopsis thalina plants shows, in contrast with the behavior of the enzyme in vitro, no trace of germacrene D production. A low thujopsene production, also a higher selectivity for E-(beta)-caryophyllene production: the headspace of the modified plants is indeed dominated by alpha-humulene, thujopsene and E-(beta)-caryophyllene, in a 1:0.75:5 mass ratio (average). But a great variation in sesquiterpenes quantity among the different lines is observed, probably because of the difference in T-DNA copy number and expression. Overall, plants increase the E-(beta)-caryophyllene emission in the headspace collection by 8fold compared to Col-0 control plants. In grapevine VvGwECar2 overexpression result in higher E-(beta)-caryophyllene emissions. No differences in plant phenotypes or growth speed are observed
additional information
production of beta-caryophyllene by assembling a biosynthetic pathway in an engineered Escherichia coli strain of which phosphoglucose isomerase gene has been deleted. The 1-deoxy-D-xylulose 5-phosphate (DXP) or heterologous mevalonate (MVA) pathways are employed. Geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene), and beta-caryophyllene synthase genes are co-overexpressed in the engineered strain. The final genetically modified strain, YJM59, produces 220 mg/l of beta-caryophyllene in flask culture. Evaluation of fed-batch fermentation for the production of beta-caryophyllene. After induction for 60 h, the YJM59 strain produces beta-caryophyllene at a concentration of 1520 mg/l. The volumetric production fermented in the aerobic fed-batch is 0.34 mg/(l/h/OD600) and the conversion efficiency of glucose to beta-caryophyllene (gram to gram) is 1.69%. Method evaluation with beta-caryophyllene synthases from different origins, QHS1 from Artemisia annua is the most effective of the three enzymes, compared to TPS21 from Arabidopsis thaliana and TPS23 from Zea perennis. Substrate channeling
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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recombinant C-terminally His6-tagged enzyme from Escherichia coli TOP10 cells by nickel affinity chromatography to homogeneity
recombinant His-tagged enzyme TPS1 from Escherichia coli strain Rosetta 2(DE3) by nickel affinity chromatography, desalting gel filtration, and ultrafiltration
recombinant His-tagged isozyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography; recombinant His-tagged isozyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Streptomyces lividans strain TK21 and as N-terminally histidine-tagged enzyme in Escherichia coli BL21(DE3) cells
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gene CsSesquiTPS6b, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, the enzyme encoded by CsSesquiTPS6a produces exclusively beta-caryophyllene, while the enzyme encoded by CsSesquiTPS6b and CsSesquiTPS7 render higher amounts of beta-caryophyllene (about 73% or 75% of total, respectively) together with alpha-humulene (about 23% or 25% of total, respectively); gene CsSesquiTPS6b, DNA and amino acid sequence determination and analysis, the enzyme encoded by CsSesquiTPS6a produces exclusively beta-caryophyllene, while the enzyme encoded by CsSesquiTPS6b and CsSesquiTPS7 render higher amounts of beta-caryophyllene (about 73% or 75% of total, respectively) together with alpha-humulene (about 23% or 25% of total, respectively); gene CsSesquiTPS6c, DNA and amino acid sequence determination and analysis, the enzyme encoded by CsSesquiTPS6a produces exclusively beta-caryophyllene, while the enzyme encoded by CsSesquiTPS6b and CsSesquiTPS7 render higher amounts of beta-caryophyllene (about 73% or 75% of total, respectively) together with alpha-humulene (about 23% or 25% of total, respectively)
gene DcTPS1, cloned from wild Daucus carrota carota fruits (accession 23727), unrooted neighbor-joining phylogenetic tree, recombinant expression of C-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)
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gene OkBCS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, quantitative RT-PCR expression analysis, recombinant expression of C-terminally His6-tagged enzyme in Escherichia coli TOP10 cells, transient overexpression in Ocimum kilimandscharicum via Agrobacterium tumefaciens strain GV3101 mediated transfection
gene PlCAHS, DNA and amino acid sequence determination and analysis,sequence comparisons and phylogenetic analysis, real time quantitative PCR expression analysis, recombinant expression in Escherichia coli strain BL21(DE3)
gene TPS1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS), illumina transcriptome sequencing of unripe peppercorn identifiying sesquiterpene synthases (sesqui-TPSs), recombinant expression of His-tagged enzyme TPS1 in Escherichia coli strain Rosetta 2(DE3)
gene TPS1, sequence comparisons and phylogenetic tree, isozyme TPS1 RT-PCR expression analysis, recombinant expression of His-tagged isozyme in Escherichia coli strain BL21(DE3); gene TPS3, sequence comparisons and phylogenetic tree, isozyme TPS3 RT-PCR expression analysis, recombinant expression of His-tagged isozyme in Escherichia coli strain BL21(DE3)
gene tps23, recombinant overexpression in Escherichia coli strain YJM59, coexpression with geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene) from plasmid pACY-mvaE-mvaS-QHS1-GPPS2-G6PDH
gene VvGwECar2, recombinant overexpression in Escherichia coli strain BL21-CodonPlus(DE3)-RIPL, and transgenic recombinant overexpression under the control of cauliflower mosaic virus (CaMV) 35S promoter n the cytoplasm of Arabidopsis thaliana ecotype Col-0 and Vitis vinifera. In Arabidopsis thaliana, the stable enzyme expression changes the plant head space release, showing a higher selectivity for E-(beta)-caryophyllene, but also the production of thujopsene instead of germacrene D. Overall, plants increase the E-(beta)-caryophyllene emission in the headspace collection by 8fold compared to Col-0 control plants. In grapevine VvGwECar2 overexpression result in higher E-(beta)-caryophyllene emissions. Quantitative RT-PCR expression analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme PlCAHS transcript is significantly upregulated in leaves after treatment with spider mites and alamethicin (ALA) suggesting its ecological function in plant defence
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biofuel production
acute demand for high-density fuels has provided the impetus to pursue biosynthetic methods to produce b-caryophyllene from reproducible sources. Contribution by recombinant production of beta-caryophyllene by assembling a biosynthetic pathway in an engineered Escherichia coli strain
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nakano, C.; Horinouchi, S.; Ohnishi, Y.
Characterization of a novel sesquiterpene cyclase involved in (+)-caryolan-1-ol biosynthesis in Streptomyces griseus
J. Biol. Chem.
286
27980-27987
2011
Streptomyces griseus, Streptomyces griseus IFO 13350
brenda
Jin, Z.; Kwon, M.; Lee, A.R.; Ro, D.K.; Wungsintaweekul, J.; Kim, S.U.
Molecular cloning and functional characterization of three terpene synthases from unripe fruit of black pepper (Piper nigrum)
Arch. Biochem. Biophys.
638
35-40
2018
Piper nigrum (A0A1V0E492)
brenda
Jayaramaiah, R.H.; Anand, A.; Beedkar, S.D.; Dholakia, B.B.; Punekar, S.A.; Kalunke, R.M.; Gade, W.N.; Thulasiram, H.V.; Giri, A.P.
Functional characterization and transient expression manipulation of a new sesquiterpene synthase involved in beta-caryophyllene accumulation in Ocimum
Biochem. Biophys. Res. Commun.
473
265-271
2016
Ocimum kilimandscharicum (A0A0E3KJK7)
brenda
Alquezar, B.; Rodriguez, A.; de la Pena, M.; Pena, L.
Genomic analysis of terpene synthase family and functional characterization of seven sesquiterpene synthases from Citrus sinensis
Front. Plant Sci.
8
1481
2017
Citrus sinensis (A0A067G476), Citrus sinensis (A0A290U6M8), Citrus sinensis (A0A290U6M9)
brenda
He, S.M.; Wang, X.; Yang, S.C.; Dong, Y.; Zhao, Q.M.; Yang, J.L.; Cong, K.; Zhang, J.J.; Zhang, G.H.; Wang, Y.; Fan, W.
De novo transcriptome characterization of Rhodomyrtus tomentosa leaves and identification of genes involved in alpha/beta-pinene and beta-caryophyllene biosynthesis
Front. Plant Sci.
9
1231
2018
Rhodomyrtus tomentosa (A0A385J6X8), Rhodomyrtus tomentosa (A0A385J6Y9)
brenda
Yahyaa, M.; Tholl, D.; Cormier, G.; Jensen, R.; Simon, P.W.; Ibdah, M.
Identification and characterization of terpene synthases potentially involved in the formation of volatile terpenes in carrot (Daucus carota L.) Roots
J. Agric. Food Chem.
63
4870-4878
2015
Daucus carota subsp. carota
brenda
Li, F.; Fu, N.; Zhou, J.; Wang, G.
Functional characterization of (E)-beta-caryophyllene synthase from lima bean and its up-regulation by spider mites and alamethicin
J. Integr. Agric.
16
2231-2238
2017
Phaseolus lunatus (A0A2K8GLY5)
-
brenda
Salvagnin, U.; Carlin, S.; Angeli, S.; Vrhovsek, U.; Anfora, G.; Malnoy, M.; Martens, S.
Homologous and heterologous expression of grapevine E-(beta)-caryophyllene synthase (VvGwECar2)
Phytochemistry
131
76-83
2016
Vitis vinifera
brenda
Yang, J.; Li, Z.; Guo, L.; Du, J.; Bae, H.
Biosynthesis of beta-caryophyllene, a novel terpene-based high-density biofuel precursor, using engineered Escherichia coli
Renewable Energy
99
216-223
2016
Zea perennis (B2C4D8)
-
brenda
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