Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway

Katsuyama, Yoshihiko; Matsuzawa, Miku; Funa, Nobutaka; Horinouchi, Sueharu

doi:10.1099/mic.0.2008/018721-0

Cited by 84 publications

(101 citation statements)

References 28 publications

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“…p-Coumaroyl-CoA (6), cinnamoyl-CoA (10), and feruloyl-CoA (5) were synthesized according to the procedures reported by Blecher [9]. Cinnamoyldiketide-N-acetylcysteamine (NAC), cinnamoyl-p-coumaroylmethane (12), dicinnamoylmethane (11), and cinnamoylferuloylmethane (9) were synthesized according to the previously reported method [10,11].…”

Section: Methodsmentioning

confidence: 99%

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Katsuyama

Kita²,

Horinouchi

2009

FEBS Letters

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Edited by Ulf-Ingo Flügge Keywords:Polyketide synthase Curcumin Demethoxycurcumin Bisdemethoxycurcumin Curcuma longa a b s t r a c t Curcuminoids are pharmaceutically important compounds isolated from the herb Curcuma longa. Two additional type III polyketide synthases, named CURS2 and CURS3, that are capable of curcuminoid synthesis were identified and characterized. In vitro analysis revealed that CURS2 preferred feruloyl-CoA as a starter substrate and CURS3 preferred both feruloyl-CoA and p-coumaroyl-CoA. These results suggested that CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin. The availability of the substrates and the expression levels of the three different enzymes capable of curcuminoid synthesis with different substrate specificities might influence the composition of curcuminoids in the turmeric and in different cultivars.

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Section: Methodsmentioning

confidence: 99%

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Katsuyama

Kita²,

Horinouchi

2009

FEBS Letters

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“…The production of plant-specific curcuminoids has been reconstituted in E. coli by coexpressing CUS with phenylalanine ammonia-lyase from Rhodotorula rubra and 4-coumarate:CoA ligase (4CL) from Lithospermum erythrorhizon (50). Furthermore, the engineered strain was utilized to produce a series of unnatural curcuminoids by providing a variety of carboxylate precursors (Fig.…”

Section: Biosynthesis Of Novel Molecules By Type III Pkss Through Prementioning

confidence: 99%

Type III polyketide synthases in natural product biosynthesis

et al. 2012

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SummaryPolyketides represent an important class of biologically active and structurally diverse compounds in nature. They are synthesized from acyl-coenzyme A substrates by polyketide synthases (PKSs). PKSs are classified into three groups: types I, II, and III. This article introduces recent studies on type III PKSs identified from plants, bacteria, and fungi, and describes the catalytic functions of these enzymes in detail. Plant type III PKSs have been widely studied, as exemplified by chalcone synthase, which plays an important role in the synthesis of plant metabolites. Bacterial type III PKSs fall into five groups, many of which were identified from Streptomyces, a genus that has been well known for its production of bioactive molecules and genetic alterability. Although it was believed that type III PKSs exist exclusively in plants and bacteria, recent fungal genome sequencing projects and biochemical studies revealed the presence of type III PKSs in filamentous fungi, which provides a new chance to study fungal secondary metabolism and synthesize ''unnatural'' natural products. Type III PKSs have been used for the biosynthesis of novel molecules through precursordirected and structure-based mutagenesis approaches.2012 IUBMB IUBMB Life, 64(4): [285][286][287][288][289][290][291][292][293][294][295] 2012

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“…The supplementation of amino acids to the medium led to the production of bisdemethoxycurcumin and other two curcuminoids, cinnamoyl-pcoumaroylmethane and dicinnamoylmethane. The direct supplementation of carboxylic acids, as ferulic acid for instance, led to other curcuminoids including curcumin and demethoxycurcumin [6]. By adding two different unnatural carboxylic acids simultaneously (analogs of p-coumaric acid), Katsuyama and coworkers also produced unnatural curcuminoids [7].…”

Section: Introductionmentioning

confidence: 99%

“…Katsuyama et al [6] were the first to produce curcuminoids using an artificial pathway in E. coli. They used phenylalanine ammonia lyase (PAL) from Rhodotorula rubra with tyrosine ammonia lyase (TAL) activity to convert the amino acids phenylalanine and tyrosine directly to cinnamic acid and p-coumaric acid.…”

Section: Introductionmentioning

confidence: 99%

Production of curcuminoids from tyrosine by a metabolically engineered Escherichia coli using caffeic acid as an intermediate

Rodrigues

Araújo

Prather

et al. 2015

Biotechnology Journal

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Curcuminoids are phenylpropanoids with high pharmaceutical potential. Herein, we report an engineered artificial pathway in Escherichia coli to produce natural curcuminoids through caffeic acid. Arabidopsis thaliana 4-coumaroyl-CoA ligase (4CL1) and Curcuma longa diketide-CoA synthase (DCS) and curcumin synthase (CURS1) were used to produce curcuminoids and 70 mg/L of curcumin was obtained from ferulic acid. Bisdemethoxycurcumin and demethoxycurcumin were also produced, but in lower concentrations, by feeding p-coumaric acid or a mixture of p-coumaric acid and ferulic acid, respectively. Additionally, curcuminoids were produced from tyrosine through the caffeic acid pathway. To produce caffeic acid, tyrosine ammonia lyase (TAL) from Rhodotorula glutinis and 4-coumarate 3-hydroxylase (C3H) from Saccharothrix espanaensis were used. Caffeoyl-CoA 3-O-methyltransferase (CCoAOMT) from Medicago sativa was used to convert caffeoyl-CoA to feruloyl-CoA.Using caffeic acid, p-coumaric acid or tyrosine as a substrate, 3.9 mg/L, 0.3 mg/L and 0.2 mg/L of curcumin were produced, respectively. This is the first time DCS and CURS1 were used in vivo to produce curcuminoids and that curcumin was produced by feeding tyrosine. We have shown that curcumin can be produced using a pathway through caffeic acid. This alternative pathway represents a step forward in the heterologous production of curcumin using E. coli.

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Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway

Cited by 84 publications

References 28 publications

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Type III polyketide synthases in natural product biosynthesis

Production of curcuminoids from tyrosine by a metabolically engineered Escherichia coli using caffeic acid as an intermediate

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