Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
curcuminoid synthase catalyzes the formation of diketide-CoA by condensing 4-coumaroyl-CoA and malonyl-CoA. The resulting diketide-CoA is hydrolyzed and converted to a beta-keto acid. Finally, curcuminoid synthase catalyzes a decarboxylative condensation of the beta-keto acid with another molecule of 4-coumaroyl-CoA, to synthesize curcuminoid
-
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
no head-to-tail synthesis, the reaction begins with the thioesterification of the thiol moiety of Cys-174 by a starter molecule, 4-coumaroyl-CoA. Decarboxylative condensation of the first extender substrate, malonyl-CoA, onto the thioester of 4-coumarate results in the formation of a diketide-CoA intermediate. Subsequent hydrolysis of the intermediate yields a beta-keto acid, which in turn acts as the second extender substrate. The beta-keto acid is then joined to the Cys-174-bound 4-coumarate by decarboxylative condensation to form bisdemethoxycurcumin
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
the reaction proceeds in three steps via formation of 4-coumaroyldiketide-CoA and 4-coumaroyl beta-keto acid, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2H-pyran-2-one + curcumin
very low activity
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
4-coumaroyl-CoA + 3-oxodecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)dodeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxododecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)tetradeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxooctanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)deca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + 3-oxotetradecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)hexadeca-1,4-dien-3-one + CoA + CO2 + H2O
-
-
-
-
?
4-coumaroyl-CoA + cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + cinnamoyl-4-coumaroyl-methane + 2 CO2
-
-
-
-
?
cinnamoyl-CoA + 2 malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 2 CO2
-
cinnamoyl-CoA reacts to form a triketide pyrone with a small amount of dicinnamoylmethane
-
?
cinnamoyl-CoA + 3-oxo-octanoate + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
-
-
-
?
cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
-
-
-
?
additional information
?
-
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
a minor product is a triketide pyrone formed from one 4-coumaroyl-CoA and two malonyl-CoAs. No formation of 5-(4-hydroxyphenyl)-3-oxo-pent-4-enoic acid and 4-hydroxybenzalacetone
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
curcuminoid synthase catalyzes the formation of diketide-CoA by condensing 4-coumaroyl-CoA and malonyl-CoA. The resulting diketide-CoA is hydrolyzed and converted to a beta-keto acid. Finally, curcuminoid synthase catalyzes a decarboxylative condensation of the beta-keto acid with another molecule of 4-coumaroyl-CoA, to synthesize curcuminoid
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
the reaction proceeds in three steps via formation of 4-coumaroyldiketide-CoA and 4-coumaroyl beta-keto acid, overview
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
-
the reaction proceeds in three steps via formation of feruloyldiketide-CoA and feruloyl beta-keto acid, overview
-
-
?
additional information
?
-
-
the curcuminoid synthase might also use feruloyl-CoA as substrate, via demethoxycurcumin, to curcumin, possible pathway overview
-
-
?
additional information
?
-
-
curcuminoid synthase activity shows a requirement for both 4-coumaroyl-CoA and feruloyl-CoA to be present in the activity assay in order for any product to be observed
-
-
?
additional information
?
-
enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
-
-
?
additional information
?
-
-
enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
-
-
?
additional information
?
-
-
the enzyme is capable of synthesizing gingerol-related compounds by condensing 4-coumaroyl-CoA with 3-oxooctanoic acid (a beta-keto acid), or with 3-oxoocarboxyl-N-acetylcysteamine thioester, a diketide-CoA analogue, in vitro. The enzyme is inactive with 3-oxoacyl derivatives of chain lengths beow C8 and above C14, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
-
-
-
-
?
additional information
?
-
-
the curcuminoid synthase might also use feruloyl-CoA as substrate, via demethoxycurcumin, to curcumin, possible pathway overview
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
purified recombinant His6-tagged enzyme, sitting drop vapour diffusion method, optimization of the crystallization conditions, mixing 0.0005 ml of protein solution, containing 10 mg/ml in 20 mM HEPES-NaOH, pH 7.0, 100 mM NaCl, and 2 mM DTT, with an equal volume of reservoir solution, containing 100 mM HEPES-NaOH, pH 7.8, 1995 mM ammonium sulfate, 3% dimethylsulfoxide, and 2 mM CoA, and equilibration against 0.1 ml reservoir solution, 20°C, cryoprotection in 100 mM HEPES-NaOH pH 7.8, 1330 mM ammonium sulfate, 2 mM CoA, 12% v/v glycerol and 14% w/v PEG 400, X-ray diffraction structure determination and analysis st 2.5 A resolution
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
analysis
engineering of an in vivo reporter assay for phenylalanine ammonia-lyase efficiency in Escherichia coli based on a plant type III polyketide biosynthetic pathway. The candidate phenylalanine ammonia-lyases are coexpressed with 4-coumarate:CoA ligase 4CL1 from Arabidopsis thaliana and curcuminoid synthase from Oryza sativa. A microplate-based assay is used to measure the titer of dicinnamoylmethane
synthesis
an engineered Escherichia coli strain expressing phenylalanine ammonia-lyase, 4-coumarate:CoA ligase 4CL1 from Arabidopsis thaliana and curcuminoid synthase from Oryza sativa leads to the production of dicinnamoylmethane at a high level of 0.36 g/l. Supplement of 2-fluoro-phenylalanine yields fluorinated dicinnamoylmethane derivatives, 6,6'-difluorodicinnamoylmethane and 6-fluoro-dicinnamoylmethane, of which the latter is a new curcuminoid
synthesis
an artificial pathway for curcuminoid production in Escherichia coli is constructed. Overexpression of curcuminoid synthase from Oryza sativa in Escherichia coli results in the production of the major curcuminoid, bisdemethoxycurcumin from p-coumaric acid. It is demonstrated that enhancement of the intracellular malonyl-CoA pool is essential for increasing the final production titer of bisdemethoxycurcumin. Expression of a recombinant pathway that allows the conversion of malonate to malonyl-CoA encoded by genes matB and matC results in a 25fold improvement of final bisdemethoxycurcumin titer
synthesis
engineering of a Pseudomonas putida strain to produce bisdemethoxycurcumin
synthesis
production of curcuminoids in engineered Escherichia coli. PAL (phenylalanine ammonia lyase) or TAL (tyrosine ammonia lyase), along with Os4CL (p-coumaroyl-CoA ligase) and CUS (curcumin synthase) genes, are introduced into Escherichia coli, and each strain produces dicinnamoylmethane or bisdemethoxycurcumin, respectively. In order to increase the production of curcuminoids in Escherichia coli, the shikimic acid biosynthesis pathway, which increases the substrates for curcuminoid biosynthesis, is engineered. Using the engineered strains, the production of bisdemethoxycurcumin increases from 0.32 to 4.63 mg/l, and that of dicinnamoylmethane from 1.24 to 6.95 mg/l
synthesis
production of curcuminoids in engineered Escherichia coli. Two curcuminoids (dicinnamoylmethane and bisdemethoxycurcumin) are synthesized from glucose in Escherichia coli. PAL (phenylalanine ammonia lyase) or TAL (tyrosine ammonia lyase), along with Os4CL (p-coumaroyl-CoA ligase) and CUS genes, are introduced into Escherichia coli, and each strain produces dicinnamoylmethane or bisdemethoxycurcumin, respectively. In order to increase the production of curcuminoids in Escherichia coli, the shikimic acid biosynthesis pathway, which increases the substrates for curcuminoid biosynthesis, is engineered. Using the engineered strains, the production of bisdemethoxycurcumin increases from 0.32 to 4.63 mg/l, and that of dicinnamoylmethane from 1.24 to 6.95 mg/l
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ramirez-Ahumada, M.d.e.l.C.; Timmermann, B.N.; Gang, D.R.
Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases
Phytochemistry
67
2017-2029
2006
Curcuma longa
brenda
Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S.
Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway
Microbiology
154
2620-2628
2008
Oryza sativa
brenda
Morita, H.; Wanibuchi, K.; Nii, H.; Kato, R.; Sugio, S.; Abe, I.
Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from Oryza sativa
Proc. Natl. Acad. Sci. USA
107
19778-19783
2010
Oryza sativa
brenda
Morita, H.; Wanibuchi, K.; Kato, R.; Sugio, S.; Abe, I.
Expression, purification and crystallization of a plant type III polyketide synthase that produces diarylheptanoids
Acta Crystallogr. Sect. F
66
948-950
2010
Oryza sativa
brenda
Katsuyama, Y.; Ohnishi, Y.; Horinouchi, S.
Production of dehydrogingerdione derivatives in Escherichia coli by exploiting a curcuminoid synthase from Oryza sativa and a beta-oxidation pathway from Saccharomyces cerevisiae
ChemBioChem
11
2034-2041
2010
Oryza sativa
brenda
Resmi, M.S.; Soniya, E.V.
Molecular cloning and differential expressions of two cDNA encoding Type III polyketide synthase in different tissues of Curcuma longa L
Gene
491
278-283
2012
Curcuma longa (G9F7X3), Curcuma longa
brenda
Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S.
In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa
J. Biol. Chem.
282
37702-37709
2007
Oryza sativa (Q8LIL0), Oryza sativa
brenda
Wang, S.; Zhang, S.; Zhou, T.; Zeng, J.; Zhan, J.
Design and application of an in vivo reporter assay for phenylalanine ammonia-lyase
Appl. Microbiol. Biotechnol.
97
7877-7885
2013
Oryza sativa (Q8LIL0), Oryza sativa
brenda
Fang, Z.; Jones, J.A.; Zhou, J.; Koffas, M.A.G.
Engineering Escherichia coli co-cultures for production of curcuminoids from glucose
Biotechnol. J.
13
e1700576
2018
Oryza sativa Japonica Group (Q8LIL0)
brenda
Kim, E.J.; Cha, M.N.; Kim, B.G.; Ahn, J.H.
Production of curcuminoids in engineered Escherichia coli
J. Microbiol. Biotechnol.
27
975-982
2017
Oryza sativa Japonica Group (Q8LIL0)
brenda
Incha, M.R.; Thompson, M.G.; Blake-Hedges, J.M.; Liu, Y.; Pearson, A.N.; Schmidt, M.; Gin, J.W.; Petzold, C.J.; Deutschbauer, A.M.; Keasling, J.D.
Leveraging host metabolism for bisdemethoxycurcumin production in Pseudomonas putida
Metab. Eng. Commun.
10
e00119
2020
Oryza sativa Japonica Group (Q8LIL0)
brenda