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Article ; Online: A peroxisomal heterodimeric enzyme is involved in benzaldehyde synthesis in plants

Xing-Qi Huang / Renqiuguo Li / Jianxin Fu / Natalia Dudareva

Nature Communications, Vol 13, Iss 1, Pp 1-

2022 Volume 15

Abstract: Benzaldehyde is a simple aromatic aldehyde that attracts pollinators, has antifungal properties and contributes to flavor in many plants. Here the authors show that benzaldehyde is synthesized in petunia via the benzoic acid β-oxidative pathway by a ... ...

Abstract	Benzaldehyde is a simple aromatic aldehyde that attracts pollinators, has antifungal properties and contributes to flavor in many plants. Here the authors show that benzaldehyde is synthesized in petunia via the benzoic acid β-oxidative pathway by a peroxisomal heterodimeric enzyme consisting of α and β subunits.
Keywords	Science ; Q
Language	English
Publishing date	2022-03-01T00:00:00Z
Publisher	Nature Portfolio
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: A Familiar Ring to It: Biosynthesis of Plant Benzoic Acids

Widhalm, Joshua R / Natalia Dudareva

Molecular plant. 2015 Jan. 05, v. 8, no. 1

2015

Abstract: Plant benzoic acids (BAs) are building blocks or important structural elements for numerous primary and specialized metabolites, including plant hormones, cofactors, defense compounds, and attractants for pollinators and seed dispersers. Many natural ... ...

Abstract	Plant benzoic acids (BAs) are building blocks or important structural elements for numerous primary and specialized metabolites, including plant hormones, cofactors, defense compounds, and attractants for pollinators and seed dispersers. Many natural products derived from plant BAs or containing benzoyl/benzyl moieties are also of medicinal or nutritional value to humans. Biosynthesis of BAs in plants is a network involving parallel and intersecting pathways spread across multiple subcellular compartments. In this review, a current overview on the metabolism of plant BAs is presented with a focus on the recent progress made on isolation and functional characterization of genes encoding biosynthetic enzymes and intracellular transporters. In addition, approaches for deciphering the complex interactions between pathways of the BAs network are discussed.
Keywords	attractants ; benzoic acids ; biosynthesis ; enzymes ; genes ; metabolites ; nutritive value ; plant hormones ; pollinators ; transporters
Language	English
Dates of publication	2015-0105
Size	p. 83-97.
Publishing place	Elsevier Inc.
Document type	Article
ZDB-ID	2393618-6
ISSN	1752-9867 ; 1674-2052
ISSN (online)	1752-9867
ISSN	1674-2052
DOI	10.1016/j.molp.2014.12.001
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Completion of the cytosolic post-chorismate phenylalanine biosynthetic pathway in plants

Yichun Qian / Joseph H. Lynch / Longyun Guo / David Rhodes / John A. Morgan / Natalia Dudareva

Nature Communications, Vol 10, Iss 1, Pp 1-

2019 Volume 15

Abstract: Phenylalanine is mostly synthesized in plant plastids, but cytosolic transamination of phenylpyruvate also contributes. Here the authors show that a cytosolic chorismate mutase and a prephenate dehydratase encoded by an isoform of the plastidial ADT3 ... ...

Abstract	Phenylalanine is mostly synthesized in plant plastids, but cytosolic transamination of phenylpyruvate also contributes. Here the authors show that a cytosolic chorismate mutase and a prephenate dehydratase encoded by an isoform of the plastidial ADT3 enzyme, produce phenylpyruvate in the cytosol.
Keywords	Science ; Q
Language	English
Publishing date	2019-01-01T00:00:00Z
Publisher	Nature Publishing Group
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Completion of the cytosolic post-chorismate phenylalanine biosynthetic pathway in plants

Yichun Qian / Joseph H. Lynch / Longyun Guo / David Rhodes / John A. Morgan / Natalia Dudareva

Nature Communications, Vol 10, Iss 1, Pp 1-

2019 Volume 15

Abstract	Phenylalanine is mostly synthesized in plant plastids, but cytosolic transamination of phenylpyruvate also contributes. Here the authors show that a cytosolic chorismate mutase and a prephenate dehydratase encoded by an isoform of the plastidial ADT3 enzyme, produce phenylpyruvate in the cytosol.
Keywords	Science ; Q
Language	English
Publishing date	2019-01-01T00:00:00Z
Publisher	Nature Portfolio
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Plant volatiles: going âinâ but not âoutâ of trichome cavities

Tissier, Alain / John A. Morgan / Natalia Dudareva

Trends in plant science. 2017,

2017

Abstract: Plant glandular trichomes are able to secrete and store large amounts of volatile organic compounds (VOCs). VOCs typically accumulate in dedicated extracellular spaces, which can be either subcuticular as in the Lamiaceae or Asteraceae or intercellular ... ...

Abstract	Plant glandular trichomes are able to secrete and store large amounts of volatile organic compounds (VOCs). VOCs typically accumulate in dedicated extracellular spaces, which can be either subcuticular as in the Lamiaceae or Asteraceae or intercellular as in the Solanaceae. Volatiles are retained at high concentrations in these storage cavities with limited release into the atmosphere and without re-entering the secretory cells, where they would be toxic. This implies the existence of mechanisms allowing transport of VOCs to the cavity but preventing their diffusion out once they have been delivered. The cuticle and cell wall lining the cavity are likely to play key roles in retaining volatiles but their exact composition and potential molecular players involved are largely unknown.
Keywords	Asteraceae ; cell walls ; Lamiaceae ; Solanaceae ; toxicity ; trichomes ; volatile organic compounds
Language	English
Size	p. .
Publishing place	Elsevier Ltd
Document type	Article
Note	Pre-press version
ZDB-ID	1305448-x
ISSN	1878-4372 ; 1360-1385
ISSN (online)	1878-4372
ISSN	1360-1385
DOI	10.1016/j.tplants.2017.09.001
Database	NAL-Catalogue (AGRICOLA)

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Article: Plant Volatiles: Going ‘In’ but not ‘Out’ of Trichome Cavities

Tissier, Alain / John A. Morgan / Natalia Dudareva

Trends in plant science. 2017 Nov., v. 22, no. 11

2017

Abstract: Plant glandular trichomes are able to secrete and store large amounts of volatile organic compounds (VOCs). VOCs typically accumulate in dedicated extracellular spaces, which can be either subcuticular, as in the Lamiaceae or Asteraceae, or intercellular, ...

Abstract	Plant glandular trichomes are able to secrete and store large amounts of volatile organic compounds (VOCs). VOCs typically accumulate in dedicated extracellular spaces, which can be either subcuticular, as in the Lamiaceae or Asteraceae, or intercellular, as in the Solanaceae. Volatiles are retained at high concentrations in these storage cavities with limited release into the atmosphere and without re-entering the secretory cells, where they would be toxic. This implies the existence of mechanisms allowing transport of VOCs to the cavity but preventing their diffusion out once they have been delivered. The cuticle and cell wall lining the cavity are likely to have key roles in retaining volatiles, but their exact composition and the potential molecular players involved are largely unknown.
Keywords	Asteraceae ; Lamiaceae ; Solanaceae ; cell walls ; toxicity ; trichomes ; volatile organic compounds
Language	English
Dates of publication	2017-11
Size	p. 930-938.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	1305448-x
ISSN	1878-4372 ; 1360-1385
ISSN (online)	1878-4372
ISSN	1360-1385
DOI	10.1016/j.tplants.2017.09.001
Database	NAL-Catalogue (AGRICOLA)

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Article: Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase

Yahyaa, Mosaab / Anna Berim / Bhagwat Nawade / Muhammad Ibdah / Mwafaq Ibdah / Natalia Dudareva

Phytochemistry. 2019 Mar., v. 159

2019

Abstract: Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce ... ...

Abstract	Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce considerable amounts of the phenylpropenes methyleugenol and methylisoeugenol. Notably, methyleugenol is most abundant in young leaves, while methylisoeugenol is the dominant phenylpropene in mature leaf tissue. The goal of the present study was to shed light on the biochemistry and molecular biology of these compounds' biosynthesis and accumulation. Using the available genomic and transcriptomic data, we isolated a cDNA encoding eugenol/isoeugenol synthase (DcE(I)GS1), an NADPH-dependent enzyme that converts coniferyl acetate to eugenol. This enzyme exhibits dual product specificity and yields propenylphenol isoeugenol alongside allylphenol eugenol. Furthermore, we identified a cDNA encoding S-adenosyl-L-methionine:eugenol/isoeugenol O-methyltransferase 1 (DcE(I)OMT1) that produces methyleugenol and methylisoeugenol via methylation of the para-OH-group of their respective precursors. Both DcE(I)GS1 and DcE(I)OMT1 were expressed in seeds, roots, young and mature leaves, and the DcE(I)OMT1 transcript levels were the highest in leaves. The DcE(I)GS1 protein is 67% identical to anise t-anol/isoeugenol synthase and displays an apparent Km of 247 μM for coniferyl acetate. The catalytic efficiency of DcEOMT1 with eugenol is more than five-fold higher than that with isoeugenol, with Km values of 40 μM for eugenol, and of 115 μM for isoeugenol. This work expands the current knowledge of the enzymes involved in phenylpropene biosynthesis and would enable studies into structural elements defining the regioselectivity of phenylpropene synthases.
Keywords	acetates ; anise ; biosynthesis ; carrots ; catalytic activity ; complementary DNA ; cultivars ; Daucus carota subsp. sativus ; eugenol ; genomics ; leaves ; methylation ; methyltransferases ; molecular biology ; odors ; regioselectivity ; roots ; seeds ; terpenoids ; transcriptomics
Language	English
Dates of publication	2019-03
Size	p. 179-189.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2018.12.020
Database	NAL-Catalogue (AGRICOLA)

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Article: Dynamic modeling of subcellular phenylpropanoid metabolism in Arabidopsis lignifying cells

Guo, Longyun / Clint Chapple / John A. Morgan / Natalia Dudareva / Peng Wang / Rohit Jaini

International Metabolic Engineering Society Metabolic engineering. 2018 Sept., v. 49

2018

Abstract: Lignin is a polymer that significantly inhibits saccharification of plant feedstocks. Adjusting the composition or reducing the total lignin content have both been demonstrated to result in an increase in sugar yield from biomass. However, because lignin ...

Abstract	Lignin is a polymer that significantly inhibits saccharification of plant feedstocks. Adjusting the composition or reducing the total lignin content have both been demonstrated to result in an increase in sugar yield from biomass. However, because lignin is essential for plant growth, it cannot be manipulated with impunity. Thus, it is important to understand the control of carbon flux towards lignin biosynthesis such that optimal modifications to it can be made precisely. Phenylalanine (Phe) is the common precursor for all lignin subunits and it is commonly accepted that all biosynthetic steps, spanning multiple subcellular compartments, are known, yet an in vivo model of how flux towards lignin is controlled is lacking. To address this deficiency, we formulated and parameterized a kinetic model based on data from feeding Arabidopsis thaliana basal lignifying stems with ring labeled [13C6]-Phe. Several candidate models were compared by an information theoretic approach to select the one that best matched the experimental observations. Here we present a dynamic model of phenylpropanoid metabolism across several subcellular compartments that describes the allocation of carbon towards lignin biosynthesis in wild-type Arabidopsis stems. Flux control coefficients for the enzymes in the pathway starting from arogenate dehydratase through 4-coumarate: CoA ligase were calculated and show that the plastidial cationic amino-acid transporter has the highest impact on flux.
Keywords	Arabidopsis thaliana ; biomass ; biosynthesis ; carbon ; dynamic models ; enzymes ; feedstocks ; kinetics ; lignin ; phenylalanine ; plant growth ; saccharification ; stems ; sugars
Language	English
Dates of publication	2018-09
Size	p. 36-46.
Publishing place	Elsevier Inc.
Document type	Article
ZDB-ID	1470383-x
ISSN	1096-7184 ; 1096-7176
ISSN (online)	1096-7184
ISSN	1096-7176
DOI	10.1016/j.ymben.2018.07.003
Database	NAL-Catalogue (AGRICOLA)

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Article: Targeted Metabolomics of the Phenylpropanoid Pathway in Arabidopsis thaliana using Reversed Phase Liquid Chromatography Coupled with Tandem Mass Spectrometry

Jaini, Rohit / Peng Wang / Natalia Dudareva / Clint Chapple / John A. Morgan

Phytochemical analysis. 2017 July, v. 28, no. 4

2017

Abstract: INTRODUCTION: The phenylpropanoid pathway is a source of a diverse group of compounds derived from phenylalanine, many of which are involved in lignin biosynthesis and serve as precursors for the production of valuable compounds, such as coumarins, ... ...

Abstract	INTRODUCTION: The phenylpropanoid pathway is a source of a diverse group of compounds derived from phenylalanine, many of which are involved in lignin biosynthesis and serve as precursors for the production of valuable compounds, such as coumarins, flavonoids, and lignans. Consequently, recent efforts have been invested in mechanistically understanding monolignol biosynthesis, making the quantification of these metabolites vital. OBJECTIVE: To develop an improved and comprehensive analytical method for (i) extensively profiling, and (ii) accurately quantifiying intermediates of the monolignol biosynthetic network, using Arabidopsis thaliana as a model system. METHOD: A liquid chromatographyâtandem mass spectrometry with electrospray ionization was developed to quantify phenylpropanoid metabolites in Arabidopsis wildtype and cinnamoyl CoA reductase1 (CCR1) deficient lines (ccr1). RESULTS: Vortexing at high temperatures (65Â°C) enhanced release of phenylpropanoids, specifically the more hydrophobic compounds. A pH of 5.3 and ammonium acetate buffer concentration of 2.5 mM resulted in an optimal analyte response across standards. Ion suppression was estimated using standard spike recovery studies for accurate quantitation. The optimized method was used to profile Arabidopsis wildtype and ccr1 stems. An increase in hydroxycinnamic acid derivatives and a decrease in the hydroxycinnamyl aldehydes and alcohols in ccr1 lines, supports a shift of flux from lignin synthesis to other secondary metabolites and phenylpropanoid derivatives. CONCLUSIONS: Compared to existing targeted profiling techniques, our method is capable of quantifying a wider range of intermediates (15 out of 22 in WT Arabidopsis stems) at low in vivo concentrations (~50 pmol/gâFW for certain compounds), while requiring minimal sample preparation. Copyright Â© 2017 John Wiley & Sons, Ltd.
Keywords	Arabidopsis thaliana ; CCR1 receptor ; alcohols ; aldehydes ; ammonium acetate ; biosynthesis ; coumaric acids ; coumarins ; flavonoids ; hydrophobicity ; ionization ; lignans ; lignin ; liquid chromatography ; metabolomics ; models ; pH ; phenylalanine ; phenylpropanoids ; secondary metabolites ; stems ; tandem mass spectrometry ; temperature
Language	English
Dates of publication	2017-07
Size	p. 267-276.
Publishing place	John Wiley & Sons, Ltd
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	1073576-8
ISSN	1099-1565 ; 0958-0344
ISSN (online)	1099-1565
ISSN	0958-0344
DOI	10.1002/pca.2672
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: A 13C isotope labeling method for the measurement of lignin metabolic flux in Arabidopsis stems

Peng Wang / Longyun Guo / Rohit Jaini / Antje Klempien / Rachel M. McCoy / John A. Morgan / Natalia Dudareva / Clint Chapple

Plant Methods, Vol 14, Iss 1, Pp 1-

2018 Volume 15

Abstract: Abstract Background Metabolic fluxes represent the functional phenotypes of biochemical pathways and are essential to reveal the distribution of precursors among metabolic networks. Although analysis of metabolic fluxes, facilitated by stable isotope ... ...

Abstract	Abstract Background Metabolic fluxes represent the functional phenotypes of biochemical pathways and are essential to reveal the distribution of precursors among metabolic networks. Although analysis of metabolic fluxes, facilitated by stable isotope labeling and mass spectrometry detection, has been applied in the studies of plant metabolism, we lack experimental measurements for carbon flux towards lignin, one of the most abundant polymers in nature. Results We developed a feeding strategy of excised Arabidopsis stems with 13C labeled phenylalanine (Phe) for the analysis of lignin biosynthetic flux. We optimized the feeding methods and found the stems continued to grow and lignify. Consistent with lignification profiles along the stems, higher levels of phenylpropanoids and activities of lignin biosynthetic enzymes were detected in the base of the stem. In the feeding experiments, 13C labeled Phe was quickly accumulated and used for the synthesis of phenylpropanoid intermediates and lignin. The intermediates displayed two different patterns of labeling kinetics during the feeding period. Analysis of lignin showed rapid incorporation of label into all three subunits in the polymers. Conclusions Our feeding results demonstrate the effectiveness of the stem feeding system and suggest a potential application for the investigations of other aspects in plant metabolism. The supply of exogenous Phe leading to a higher lignin deposition rate indicates the availability of Phe is a determining factor for lignification rates.
Keywords	Stable isotope labeling ; Stem feeding ; Lignin ; Phenylpropanoids ; Plant culture ; SB1-1110 ; Biology (General) ; QH301-705.5
Language	English
Publishing date	2018-06-01T00:00:00Z
Publisher	BMC
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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