Coumarins in Plants: Molecular Diversity, Biosynthesis, Evolution, Transport, Regulation and Bioactivity

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (15 April 2020) | Viewed by 6821

Special Issue Editors


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Guest Editor
Université de Lorraine – INRAE Laboratoire Agronomie et Environnement (LAE), UMR 1121. F54000 Nancy, France
Interests: plant specialized metabolism; phytochemistry; plant ecophysiology; crop protection; bioactive compounds
Special Issues, Collections and Topics in MDPI journals

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Co-Guest Editor
Université de Lorraine—INRA Laboratoire Agronomie et Environnement (LAE), UMR 1121. F54000 Nancy, France
Interests: plant-specialized metabolism; coumarins; evolution track; plant adaptation; biocontrol

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Co-Guest Editor
Université de Lorraine—INRA Laboratoire Agronomie et Environnement (LAE), UMR 1121. F54000 Nancy, France
Interests: iron homeostasis; enzymatic characterization; furanocoumarins; dioxygenases; cytochrome P450

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Co-Guest Editor
Université de Lorraine—INRA Laboratoire Agronomie et Environnement (LAE), UMR 1121. F54000 Nancy, France
Interests: plant-specialized metabolism; prenyltransferase; prenylated aromatics; molecular evolution; synthetic biology; coumarin transport

Special Issue Information

Dear Colleagues,

Coumarins are specialized metabolites ubiquitously distributed in the plant kingdom. Their core structure is a 1,2-benzopyrone, which consists of a benzene ring fused to a pyrone ring. Depending on diverse modifications and/or substitutions, they can be classified into two categories: (i) simple coumarins displaying hydroxylations, alkoxylations, alkylations, or glycosylations and (ii) complex coumarins with additional heterocycles leading, notably, to furanocoumarins, pyranocoumarins, or phenylcoumarins.

Coumarins are reported to have many physiological functions. They are involved in defenses against pathogens and insects but also in protection against abiotic stresses. More recently, they were described to play a role in iron uptake and root bacterial community structuratures. In addition, coumarins are considered as bioactive compounds with therapeutic interests in AIDS and several cancers.

Coumarin biosynthesis is mainly a branch of the phenylpropanoid pathway. The molecular characterization of its synthesis has progressed considerably in the last decade. Among the enzymes characterized, several alpha ketoglutarate dependant dioxygenases have been described to mediate the orthohydroxylation of hydroxycinnamoyl-CoA and lead to the synthesis of the coumarin core molecule. Other enzymes such as methyltransferases, prenyltransferases, and cytochrome P450s and, more recently, COSY genes were also reported. Despite these advances, many steps need to be more deeply investigated in order to fully understand the synthesis and chemical diversity of coumarins.

This Special Issue will be dedicated to the study of simple and complex coumarins including chemical structure diversity; characterization of their biosynthetic pathways with transport, regulation, and evolutional aspects; and the elucidation of physiological and biological functions. All works including research papers and reviews related to these items will be considered for publication.

Dr. Romain Larbat
Prof. Alain Hehn
Dr. Alexandre Olry
Dr. Ryosuke Munakata
Guest Editors

Manuscript Submission Information

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Keywords

  • simple and complex coumarins
  • chemical structure diversity
  • metabolic pathway
  • transport
  • molecular evolution
  • physiological function
  • iron homeostasis
  • bioactivity

Published Papers (2 papers)

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Research

16 pages, 2934 KiB  
Article
Allelochemical Activity of Eugenol-Derived Coumarins on Lactuca sativa L.
by Kamilla Pacheco Govêa, Rafaella Sueko Tomita Pereira, Mateus Donizetti Oliveira de Assis, Pâmela Ingrid Alves, Guilherme Andrade Brancaglion, André Eidi Toyota, José Vaz Cardoso Machado, Diogo Teixeira Carvalho, Thiago Corrêa de Souza, Luiz Alberto Beijo, Luciene de Oliveira Ribeiro Trindade and Sandro Barbosa
Plants 2020, 9(4), 533; https://doi.org/10.3390/plants9040533 - 20 Apr 2020
Cited by 17 | Viewed by 3224
Abstract
Coumarins are widely distributed substances in plant species that promote phytotoxic effects, allowing them to be exploited as herbicides less harmful to the environment, since many invasive species have demonstrated resistance to commercially available products. The derived coumarins used in this study had [...] Read more.
Coumarins are widely distributed substances in plant species that promote phytotoxic effects, allowing them to be exploited as herbicides less harmful to the environment, since many invasive species have demonstrated resistance to commercially available products. The derived coumarins used in this study had not been tested in plant models and their effect on plants was unknown. The objective of this study was to evaluate the phytotoxic action of these coumarins in bioassays with Lactuca sativa L., in order to select the most responsive substance whose toxicity was best elucidated by chromosomal complement and enzymatic antioxidant metabolism studies. From the phytotoxicity assays, coumarin 8-methoxy-2-oxo-6-(prop-2-en-1-yl)-2H-chromene-3-carboxylic acid (A1), reported here for the first time, was selected as the most responsive and caused a reduction in the following parameters: number of normal seedlings, fresh biomass, root length and shoot length. Subsequent studies demonstrated that this coumarin is cytogenotoxic due to damage caused to the cell cycle and the occurrence of chromosomal abnormalities. However, it did not interfere with antioxidant enzyme activity and did not cause lipid peroxidation. The changes caused by coumarin A1 described herein can contribute to better understanding the allelochemical actions of coumarins and the potential use of these substances in the production of natural herbicides. Full article
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10 pages, 1702 KiB  
Article
Separation of New Coumarin Glycosides from Toddalia asiatica Using Offline Two-Dimensional High-Performance Liquid Chromatography
by Yan Li, Shi-Wei Sun, Xiao-Yi Zhang, Yang Liu, Xiao-Hong Liu, Shuang Zhang, Wei Wang, Jin Wang and Wei Wang
Plants 2020, 9(4), 428; https://doi.org/10.3390/plants9040428 - 31 Mar 2020
Cited by 7 | Viewed by 2546
Abstract
Coumarins and flavonoids are the major constituents of Toddalia asiatica. The separation and purification of ingredients from T. asiatica is an important procedure to acquire high-purity compounds for subsequent pharmacological investigation to discover leading compounds. In the present work, an offline [...] Read more.
Coumarins and flavonoids are the major constituents of Toddalia asiatica. The separation and purification of ingredients from T. asiatica is an important procedure to acquire high-purity compounds for subsequent pharmacological investigation to discover leading compounds. In the present work, an offline two-dimensional high-performance liquid chromatography (HPLC) method was successfully established for the separation of high-purity glycosides from T. asiatica. Based on the separation results obtained with two different chromatographic stationary phases, a phenyl-bonded silica-based reversed-phase column was employed as the first HPLC preparation, and three fractions were obtained from the sample. Then, the fractions were isolated and purified on an octadecyl-bonded silica-based reversed-phase column to obtain high-purity compounds in the second HPLC separation. As a result, three coumarin glycosides, including two undescribed and one known, along with one known flavonoid glycoside with more than 98% purity were isolated from the sample. The structures of the isolated compounds were elucidated on the basis of extensive spectroscopic evidence derived from optical rotation, mass spectrometry, and nuclear magnetic resonance experiments. Two-dimensional HPLC with different stationary phases has the potential to be an efficient method for the separation of high-purity compounds from T. asiatica. Full article
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