Synthesis of C-glucosylated octaketide anthraquinones in Nicotiana benthamiana using a multispecies-based biosynthetic pathway

Johan Andersen-Ranberg; Kenneth Thermann Kongstad; Majse Nafisi; Dan Stærk; Finn T. Okkels; Uffe H. Mortensen; Birger Lindberg Møller; Rasmus J.N. Frandsen; Rubini Maya Kannangara

doi:10.1002/cbic.201700331

Synthesis of C-glucosylated octaketide anthraquinones in Nicotiana benthamiana using a multispecies-based biosynthetic pathway

Johan Andersen-Ranberg, Kenneth Thermann Kongstad, Majse Nafisi, Dan Stærk, Finn T. Okkels, Uffe H. Mortensen, Birger Lindberg Møller, Rasmus J.N. Frandsen, Rubini Maya Kannangara

Section for Plant Biochemistry

11 Citations (Scopus)

Abstract

Carminic acid is a C-glucosylated octaketide anthraquinone and the main constituent of the natural dye carmine (E120), possessing unique coloring, stability, and solubility properties. Despite being used since ancient times, longstanding efforts to elucidate its route of biosynthesis have been unsuccessful. Herein, a novel combination of enzymes derived from a plant (Aloe arborescens, Aa), a bacterium (Streptomyces sp. R1128, St), and an insect (Dactylopius coccus, Dc) that allows for the biosynthesis of the C-glucosylated anthraquinone, dcII, a precursor for carminic acid, is reported. The pathway, which consists of AaOKS, StZhuI, StZhuJ, and DcUGT2, presents an alternative biosynthetic approach for the production of polyketides by using a type III polyketide synthase (PKS) and tailoring enzymes originating from a type II PKS system. The current study showcases the power of using transient expression in Nicotiana benthamiana for efficient and rapid identification of functional biosynthetic pathways, including both soluble and membrane-bound enzymes.

Original language	English
Journal	ChemBioChem
Volume	18
Issue number	19
Pages (from-to)	1893-1897
Number of pages	5
ISSN	1439-4227
DOIs	https://doi.org/10.1002/cbic.201700331
Publication status	Published - 5 Oct 2017

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@article{66d441bf123f492f8c302800128d652f,

title = "Synthesis of C-glucosylated octaketide anthraquinones in Nicotiana benthamiana using a multispecies-based biosynthetic pathway",

abstract = "Carminic acid is a C-glucosylated octaketide anthraquinone and the main constituent of the natural dye carmine (E120), possessing unique coloring, stability, and solubility properties. Despite being used since ancient times, longstanding efforts to elucidate its route of biosynthesis have been unsuccessful. Herein, a novel combination of enzymes derived from a plant (Aloe arborescens, Aa), a bacterium (Streptomyces sp. R1128, St), and an insect (Dactylopius coccus, Dc) that allows for the biosynthesis of the C-glucosylated anthraquinone, dcII, a precursor for carminic acid, is reported. The pathway, which consists of AaOKS, StZhuI, StZhuJ, and DcUGT2, presents an alternative biosynthetic approach for the production of polyketides by using a type III polyketide synthase (PKS) and tailoring enzymes originating from a type II PKS system. The current study showcases the power of using transient expression in Nicotiana benthamiana for efficient and rapid identification of functional biosynthetic pathways, including both soluble and membrane-bound enzymes.",

author = "Johan Andersen-Ranberg and Kongstad, {Kenneth Thermann} and Majse Nafisi and Dan St{\ae}rk and Okkels, {Finn T.} and Mortensen, {Uffe H.} and M{\o}ller, {Birger Lindberg} and Frandsen, {Rasmus J.N.} and Kannangara, {Rubini Maya}",

year = "2017",

month = oct,

day = "5",

doi = "10.1002/cbic.201700331",

language = "English",

volume = "18",

pages = "1893--1897",

journal = "ChemBioChem",

issn = "1439-4227",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "19",

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TY - JOUR

T1 - Synthesis of C-glucosylated octaketide anthraquinones in Nicotiana benthamiana using a multispecies-based biosynthetic pathway

AU - Andersen-Ranberg, Johan

AU - Kongstad, Kenneth Thermann

AU - Nafisi, Majse

AU - Stærk, Dan

AU - Okkels, Finn T.

AU - Mortensen, Uffe H.

AU - Møller, Birger Lindberg

AU - Frandsen, Rasmus J.N.

AU - Kannangara, Rubini Maya

PY - 2017/10/5

Y1 - 2017/10/5

N2 - Carminic acid is a C-glucosylated octaketide anthraquinone and the main constituent of the natural dye carmine (E120), possessing unique coloring, stability, and solubility properties. Despite being used since ancient times, longstanding efforts to elucidate its route of biosynthesis have been unsuccessful. Herein, a novel combination of enzymes derived from a plant (Aloe arborescens, Aa), a bacterium (Streptomyces sp. R1128, St), and an insect (Dactylopius coccus, Dc) that allows for the biosynthesis of the C-glucosylated anthraquinone, dcII, a precursor for carminic acid, is reported. The pathway, which consists of AaOKS, StZhuI, StZhuJ, and DcUGT2, presents an alternative biosynthetic approach for the production of polyketides by using a type III polyketide synthase (PKS) and tailoring enzymes originating from a type II PKS system. The current study showcases the power of using transient expression in Nicotiana benthamiana for efficient and rapid identification of functional biosynthetic pathways, including both soluble and membrane-bound enzymes.

AB - Carminic acid is a C-glucosylated octaketide anthraquinone and the main constituent of the natural dye carmine (E120), possessing unique coloring, stability, and solubility properties. Despite being used since ancient times, longstanding efforts to elucidate its route of biosynthesis have been unsuccessful. Herein, a novel combination of enzymes derived from a plant (Aloe arborescens, Aa), a bacterium (Streptomyces sp. R1128, St), and an insect (Dactylopius coccus, Dc) that allows for the biosynthesis of the C-glucosylated anthraquinone, dcII, a precursor for carminic acid, is reported. The pathway, which consists of AaOKS, StZhuI, StZhuJ, and DcUGT2, presents an alternative biosynthetic approach for the production of polyketides by using a type III polyketide synthase (PKS) and tailoring enzymes originating from a type II PKS system. The current study showcases the power of using transient expression in Nicotiana benthamiana for efficient and rapid identification of functional biosynthetic pathways, including both soluble and membrane-bound enzymes.

U2 - 10.1002/cbic.201700331

DO - 10.1002/cbic.201700331

M3 - Journal article

C2 - 28719729

SN - 1439-4227

VL - 18

SP - 1893

EP - 1897

JO - ChemBioChem

JF - ChemBioChem

IS - 19

ER -

Synthesis of C-glucosylated octaketide anthraquinones in Nicotiana benthamiana using a multispecies-based biosynthetic pathway

Abstract

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