Simplex Optimized LC Analysis of Plant Coumarins and Furanocoumarins

Paszkiewicz, Monika; Orlita, Aleksandra; Dziabas, Alicja; Gołębiowski, Marek; Łojkowska, Ewa; Szafranek, Janusz; Maliński, Edmund; Stepnowski, Piotr

doi:10.1365/s10337-008-0516-7

Cited by 4 publications

(3 citation statements)

References 15 publications

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“…Other phytochemical studies have confirmed the low level of scopoletin in R. graveolens : scopoletin has frequently been described to be a minor coumarin in R. graveolens (Steck et al. , 1971; Paszkiewicz et al. , 2008), and a recent report revealed that its concentration is below the HPLC‐UV quantification limit (<2.5 μg g −1 FW) (Adam et al.…”

Section: Discussionmentioning

confidence: 89%

A 2‐oxoglutarate‐dependent dioxygenase from Ruta graveolens L. exhibits p‐coumaroyl CoA 2′‐hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants

et al. 2012

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Coumarins are important compounds that contribute to the adaptation of plants to biotic or abiotic stresses. Among coumarins, umbelliferone occupies a pivotal position in the plant phenylpropanoid network. Previous studies indicated that umbelliferone is derived from the ortho-hydroxylation of p-coumaric acid by an unknown biochemical step to yield 2,4-dihydroxycinnamic acid, which then undergoes spontaneous lactonization. Based on a recent report of a gene encoding a 2-oxoglutarate-dependent dioxygenase from Arabidopsis thaliana that exhibited feruloyl CoA 6'-hydroxylase activity (Bourgaud et al., 2006), we combined a bioinformatic approach and a cDNA library screen to identify an orthologous ORF (Genbank accession number JF799117) from Ruta graveolens L. This ORF shares 59% amino acid identity with feruloyl CoA 6'-hydroxylase, was functionally expressed in Escherichia coli, and converted feruloyl CoA into scopoletin and p-coumaroyl CoA into umbelliferone with equal activity. Its bi-functionality was further confirmed in planta: transient expression of JF799117 in Nicotiana benthamiana yielded plants with leaves containing high levels of umbelliferone and scopoletin when compared to control plants, which contained barely detectable traces of these compounds. The expression of JF799117 was also tightly correlated to the amount of umbelliferone that was found in UV-elicited R. graveolens leaves. Therefore, JF799117 encodes a p-coumaroyl CoA 2'-hydroxylase in R. graveolens, which represents a previously uncharacterized step in the synthesis of umbelliferone in plants. Psoralen, which is an important furanocoumarin in R. graveolens, was found to be a competitive inhibitor of the enzyme, and it may exert this effect through negative feedback on the enzyme at an upstream position in the pathway.

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Section: Discussionmentioning

confidence: 89%

A 2‐oxoglutarate‐dependent dioxygenase from Ruta graveolens L. exhibits p‐coumaroyl CoA 2′‐hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants

et al. 2012

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“…Numerous analytical methods have been described for the major toxins and involve chromatography, mass spectrometry, and a few immunoassay -based methods [16,27,28] . When exposures are suspected, identifi cation of the plant material is often diffi cult at best.…”

Section: Investigations and Analysismentioning

confidence: 99%

Beyond Herbals: An Introduction to Poisonous Plants

Hammett‐Stabler

2010

Herbal Supplements

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“…Until now, the literatures about esculetin have been mainly focused on its extraction and pharmacology [7,8] . As far as the analytical method is concerned, the highperformance liquid chromatography was reported to the determination of esculetin [9,10] . Because of the great pharmacological and physiological activities of esculetin, it is urgent to develop an effective, simple analytical method to the evaluation and administration of esculetin.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Behavior of Esculetin on Glassy Carbon Electrode

Chen

Liang

et al. 2010

ECS Trans.

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The electrochemical behavior of esculetin was investigated by cyclic voltammetry on glassy carbon electrode. The experimental conditions, such as supporting electrolyte and pH value, were tested for the electrochemical characterization of esculetin. It was shown that, in acetate buffer, the electrochemical behavior of esculetin had good reversibility. The average peak potential of esculetin was linearly correlative with pH value of acetate buffer, indicating that proton was involved in the electrochemical process of esculetin. Furthermore, the peak current of esculetin had linear relationship with the potential scan rate, showing that esculetin presented surface confined on glassy carbon electrode. It was observed that the cathodic peak currents were linear to the concentration of esculetin in range of 5.0 × 10-6 to 4.6 × 10-5 mol L-1 (r = 0.9994, n = 10) and the detection limit was 3.8 × 10-7 mol L-1.

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Simplex Optimized LC Analysis of Plant Coumarins and Furanocoumarins

Cited by 4 publications

References 15 publications

A 2‐oxoglutarate‐dependent dioxygenase from Ruta graveolens L. exhibits p‐coumaroyl CoA 2′‐hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants

A 2‐oxoglutarate‐dependent dioxygenase from Ruta graveolens L. exhibits p‐coumaroyl CoA 2′‐hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants

Beyond Herbals: An Introduction to Poisonous Plants

Electrochemical Behavior of Esculetin on Glassy Carbon Electrode

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