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Coumarins and Coumarin Derivatives: From Chemistry to Drug
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Coumarins and Coumarin Derivatives: From Chemistry to Drug

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 April 2019) | Viewed by 36104

Special Issue Editors

Dr. Salvatore Genovese

E-Mail Website
Guest Editor
Dipartimento di Farmacia, University of G. d'Annunzio Chieti and Pescara, Chieti, Italy
Interests: phytochemistry; natural products; coumarin; chemical synthesis; HPLC, oxyprenylated, plant secondary metabolites identification and quantification; anti-inflammatory and anticancer activity
Special Issues, Collections and Topics in MDPI journals
Dr. Serena Fiorito

E-Mail Website
Guest Editor
Department of Pharmacy, ‘G. d’Annunzio’ Chieti-Pescara University, Via dei Vestini 31, 66100 Chieti, Italy
Interests: pharmaceutical analysis; chemical synthesis; medicinal chemistry; phytochemistry; plant natural compounds; plant extraction; HPLC; GC/MS
Special Issues, Collections and Topics in MDPI journals
Dr. Vito Alessandro Taddeo

E-Mail Website
Guest Editor
University of G. d'Annunzio Chieti and Pescara, Chieti, Italy
Interests: coumarin and coumarine derivatives; chemical characterizations; biological activities; plant secondary metabolites

Special Issue Information

Dear Colleagues,

Plant secondary metabolites have played an important role in human welfare due to their great therapeutic potential. Among them, coumarins and coumarin derivatives have gained popularity because of their health benefits; and structurally, coumarin derivatives resamble vitamin K, an important element involved in the synthesis of a numbers of clotting factors. Coumarins belong to the heterocyclic class of organic compounds, naturally present in a large variety of plant families. Since the discovery of the first coumarin, more than 200 years ago, a huge of number of coumarins and analogues have been either isolated or synthesized. Numerous biological activities, including the antimicrobial, the anti-inflammatory, the anti-cancer and the antioxidant properties have been demostratred. In light of these premises, this Special Issue aims to collect contributions on the potential of coumarins and coumarin derivatives to enhance the positive influence in human welfare. Chemical characterizations of plant extracts together with the evaluation of biological activities (cytotoxicity against microorganisms and human cell lines, antimicrobial, antifungal, antioxidant, anti-inflammatory effects) of the mixture, as well as of the single compounds, are required.

Prof. Genovese Salvatore
Dr. Serena Fiorito
Dr. Vito Alessandro Taddeo
Guest Editors

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Keywords

  • Coumarin and coumarine derivatives
  • chemical characterizations
  • biological activities
  • plant secondary metabolites

Published Papers (7 papers)

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Research

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7 pages, 647 KiB  
Article
Furocoumarin Content of Fennel—Below the Safety Threshold
by Diána Kerekes, Attila Csorba, Beáta Gosztola, Éva Németh-Zámbori, Tivadar Kiss and Dezső Csupor
Molecules 2019, 24(15), 2844; https://doi.org/10.3390/molecules24152844 - 05 Aug 2019
Cited by 12 | Viewed by 3797
Abstract
Furocoumarins are known for their phototoxic and potential carcinogenic effects. These types of compounds have previously been reported from fennel (Foeniculum vulgare Mill.), a widely used medicinal plant and spice; however, no reliable quantitative data are available on the occurrence of these [...] Read more.
Furocoumarins are known for their phototoxic and potential carcinogenic effects. These types of compounds have previously been reported from fennel (Foeniculum vulgare Mill.), a widely used medicinal plant and spice; however, no reliable quantitative data are available on the occurrence of these compounds in fennel fruits. For the first time, we report a comprehensive analysis of fennel fruit samples of different origins, representing a wide range of accessions for their furocoumarin content. Psoralene, 5-methoxypsoralene (bergapten), and imperatorin contents of 33 fennel samples were analyzed using a sensitive liquid chromatography-mass spectrometry (LC-MS) method. When applied at the highest therapeutic dose described in the monograph issued by the European Medicines Agency, the furocoumarin content of the fruits ranged up to 1.22 μg/d, which is below the most restrictive recommendations. Based on our findings, fennel consumption can be considered as safe, at least based on its low furocoumarin content. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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19 pages, 4064 KiB  
Article
The Effect of Furanocoumarin Derivatives on Induction of Apoptosis and Multidrug Resistance in Human Leukemic Cells
by Tomasz Kubrak, Marcin Czop, Przemysław Kołodziej, Marta Ziaja-Sołtys, Jacek Bogucki, Anna Makuch-Kocka, David Aebisher, Janusz Kocki and Anna Bogucka-Kocka
Molecules 2019, 24(9), 1824; https://doi.org/10.3390/molecules24091824 - 12 May 2019
Cited by 11 | Viewed by 3394
Abstract
Background: The insensitivity of cancer cells to therapeutic agents is considered to be the main cause of failure of therapy and mortality of patients with cancer. A particularly important problem in these patients is the phenomenon of multidrug resistance, consisting of abnormal, elevated [...] Read more.
Background: The insensitivity of cancer cells to therapeutic agents is considered to be the main cause of failure of therapy and mortality of patients with cancer. A particularly important problem in these patients is the phenomenon of multidrug resistance, consisting of abnormal, elevated expression of transport proteins (ABC family). The aim of this research included determination of IC50 values of selected furanocoumarins in the presence and absence of mitoxantrone in leukemia cells and analysis of changes in apoptosis using anexinV/IP and Casp3/IP after 24 h exposure of cell lines to selected coumarins in the presence and absence of mitoxantrone in IC50 concentrations. Methods: Research was conducted on 3 cell lines derived from the human hematopoietic system: HL-60, HL-60/MX1 and HL-60/MX2. After exposure to coumarin compounds, cells were subjected to cytometric analysis to determine the induction of apoptosis by two methods: the Annexin V test with propidium iodide and the PhiPhiLux-G1D2 reagent containing caspase 3 antibodies. Results: All of the furanocoumarin derivatives studied were found to induce apoptosis in leukemia cell lines. Conclusions: Our results clearly show that the furanocoumarin derivatives are therapeutic substances with antitumor activity inducing apoptosis in human leukemia cells with phenotypes of resistance. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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8 pages, 554 KiB  
Communication
HPLC Analysis and Skin Whitening Effects of Umbelliprenin-containing Extracts of Anethum Graveolens, Pimpinella Anisum, and Ferulago Campestris
by Vito Alessandro Taddeo, Francesco Epifano, Francesca Preziuso, Serena Fiorito, Nicolas Caron, Arnaud Rives, Philippe de Medina, Marc Poirot, Sandrine Silvente-Poirot and Salvatore Genovese
Molecules 2019, 24(3), 501; https://doi.org/10.3390/molecules24030501 - 30 Jan 2019
Cited by 16 | Viewed by 3681
Abstract
Umbelliprenin has recently been shown to have great potential as a skin whitening agent. Wishing to investigate the same effect in plant species known to biosynthesize this coumarin, three plants belonging to the Apiaceae family, namely Anethum graveolens L. (dill), Pimpinella anisum L. [...] Read more.
Umbelliprenin has recently been shown to have great potential as a skin whitening agent. Wishing to investigate the same effect in plant species known to biosynthesize this coumarin, three plants belonging to the Apiaceae family, namely Anethum graveolens L. (dill), Pimpinella anisum L. (anise), and Ferulago campestris (Besser) Grecescu (field ferula) were screened by HPLC analysis for their respective content of umbelliprenin in extracts obtained with different solvent mixtures and by maceration and ultrasound-assisted processes. EtOH was shown to be the best solvent, providing umbelliprenin yields ranging from 1.7% to 14.4% (with respect to the total amount of extract obtained). Extracts with the highest content of this farnesyloxycoumarin were then assayed as modulators of melanogenesis in cultured murine Melan A cells employing the same umbelliprenin obtained by chemical synthesis as the reference. A parallelism between the content of the coumarin and the recorded depigmenting effect (60% for the EtOH extract of F. campestris as the best value) was revealed for all plants extracts when applied at a dose of 100 μg/mL. Our results demonstrate that the same potential of umbelliprenin can be ascribed also to umbelliprenin-enriched plant extracts which reinforces enforce the widespread use of phyto-preparations for cosmetic purposes (e.g., A. graveolens). Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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12 pages, 1413 KiB  
Article
Effects of Osthol Isolated from Cnidium monnieri Fruit on Urate Transporter 1
by Yuusuke Tashiro, Ryo Sakai, Tomoko Hirose-Sugiura, Yukio Kato, Hirotaka Matsuo, Tappei Takada, Hiroshi Suzuki and Toshiaki Makino
Molecules 2018, 23(11), 2837; https://doi.org/10.3390/molecules23112837 - 01 Nov 2018
Cited by 13 | Viewed by 5410
Abstract
(1) Background: Crude drugs used in traditional Japanese Kampo medicine or folk medicine are major sources of new chemical entities for drug discovery. We screened the inhibitory potential of these crude drugs against urate transporter 1 (URAT1) to discover new drugs for hyperuricemia. [...] Read more.
(1) Background: Crude drugs used in traditional Japanese Kampo medicine or folk medicine are major sources of new chemical entities for drug discovery. We screened the inhibitory potential of these crude drugs against urate transporter 1 (URAT1) to discover new drugs for hyperuricemia. (2) Methods: We prepared the MeOH extracts of 107 different crude drugs, and screened their inhibitory effects on URAT1 by measuring the uptake of uric acid by HEK293/PDZK1 cells transiently transfected with URAT1. (3) Results: We found that the extract of the dried mature fruit of Cnidium monnieri inhibited urate uptake via URAT1. We isolated and identified osthol as the active ingredient from this extract. Osthol noncompetitively inhibited URAT1 with an IC50 of 78.8 µM. We evaluated the effects of other coumarins and found that the prenyl group, which binds at the 8-position of coumarins, plays an important role in the inhibition of URAT1. (4) Conclusions: Cnidium monnieri fruit may be useful for the treatment of hyperuricemia or gout in traditional medicine, and its active ingredient, osthol, is expected to be a leading compound for the development of new drugs for hyperuricemia. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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Review

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25 pages, 2798 KiB  
Review
Botanical Sources, Chemistry, Analysis, and Biological Activity of Furanocoumarins of Pharmaceutical Interest
by Renato Bruni, Davide Barreca, Michele Protti, Virginia Brighenti, Laura Righetti, Lisa Anceschi, Laura Mercolini, Stefania Benvenuti, Giuseppe Gattuso and Federica Pellati
Molecules 2019, 24(11), 2163; https://doi.org/10.3390/molecules24112163 - 08 Jun 2019
Cited by 78 | Viewed by 8642
Abstract
The aim of this work is to provide a critical review of plant furanocoumarins from different points of view, including their chemistry and biosynthetic pathways to their extraction, analysis, and synthesis, to the main biological activities found for these active compounds, in order [...] Read more.
The aim of this work is to provide a critical review of plant furanocoumarins from different points of view, including their chemistry and biosynthetic pathways to their extraction, analysis, and synthesis, to the main biological activities found for these active compounds, in order to highlight their potential within pharmaceutical science. The limits and the possible improvements needed for research involving these molecules are also highlighted and discussed. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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38 pages, 11682 KiB  
Review
Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds
by Ana I. Koleva, Nevena I. Petkova-Yankova and Rositca D. Nikolova
Molecules 2019, 24(11), 2030; https://doi.org/10.3390/molecules24112030 - 28 May 2019
Cited by 16 | Viewed by 4390
Abstract
Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their [...] Read more.
Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their chemical properties as acceptors in conjugate addition reactions, [2+2] and [3+2] cycloaddition reactions are discussed. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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17 pages, 2486 KiB  
Review
Coumarins and P450s, Studies Reported to-Date
by Maryam Foroozesh, Jayalakshmi Sridhar, Navneet Goyal and Jiawang Liu
Molecules 2019, 24(8), 1620; https://doi.org/10.3390/molecules24081620 - 24 Apr 2019
Cited by 32 | Viewed by 5476
Abstract
Cytochrome P450 enzymes (CYPs) are important phase I enzymes involved in the metabolism of endogenous and xenobiotic compounds mainly through mono-oxygenation reactions into more polar and easier to excrete species. In addition to their role in detoxification, they play important roles in the [...] Read more.
Cytochrome P450 enzymes (CYPs) are important phase I enzymes involved in the metabolism of endogenous and xenobiotic compounds mainly through mono-oxygenation reactions into more polar and easier to excrete species. In addition to their role in detoxification, they play important roles in the biosynthesis of endogenous compounds and the bioactivation of xenobiotics. Coumarins, phytochemicals abundant in food and commonly used in fragrances and cosmetics, have been shown to interact with P450 enzymes as substrates and/or inhibitors. In this review, these interactions and their significance in pharmacology and toxicology are discussed in detail. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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