Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

Masters, Kye-Simeon; Bräse, Stefan

doi:10.1021/cr100446h

Cited by 365 publications

(265 citation statements)

References 422 publications

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“…36 Particularly, naturally occurring xanthones have been highlighted for their promising antimicrobial properties. 12,25 When tested against MRSA strains, several prenylated xanthones isolated from various species of the Clusiaceae family have shown interesting activity (minimum inhibitory concentration [MIC] values between 3.13 and 8.3 mg/ml). 10,14 Recently, we have reported the effect of xanthone 43 and thioxantone derivatives 30,31 in overcoming drug resistance mediated by ABC transporters, suggesting the potential of these families of compounds in new approaches in the field of chemotherapy.…”

Section: Introductionmentioning

confidence: 99%

Synergistic Effects Between Thioxanthones and Oxacillin Against Methicillin-ResistantStaphylococcus aureus

Bessa

Palmeira

Gomes

et al. 2015

Microbial Drug Resistance

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The extensive use of antimicrobials is leaving medicine with few effective therapeutic options to treat many infections due to the fact that many organisms developed resistance to commonly used drugs. It is therefore pertinent to search not only for new antimicrobials but also for compounds able to restore or potentiate the activity of existing antibiotics. We have screened a library consisting of 40 (thio)xanthone derivatives for antibacterial activity and possible synergistic effects when used in combination with antibiotics. Nine out of the 40 compounds exhibited antibacterial activity against Gram-positive bacteria. Two xanthone derivatives, 1-formyl-4-hydroxy-3-methoxy (7), 2-formyl-3-hydroxy-4-methoxyxanthone (8) and the thioxanthone derivative 1-((2-(diethylamino)ethyl)amino)-4-propoxythioxanthone (10) and its hydrochloride form 13, showed activity against a methicillin-resistant Staphylococcus aureus (MRSA) isolate with minimum inhibitory concentration (MIC) values lower than 256 μg/ml. Thioxanthone 10 demonstrated antibacterial activity and also synergy when combined with ampicillin and oxacillin against MRSA. Additionally, thioxanthone 1-(piperidin-1-yl)-4-propoxythioxanthone (9), despite not having antibacterial activity presented remarkable synergy with oxacillin against MRSA; the MIC of tioxanthone 9 and oxacillin when both were in combination were 128 and 8 μg/ml, respectively. Thioxanthones 9 and 10 were also found to be synergistic when both were combined. Subsequently, docking simulations between thioxanthones 9 and 10 and the allosteric domain of penicillin-binding protein 2A (PBP2A) were undertaken in AutoDock Vina. Both compounds had the ability to bind with an allosteric domain of PBP2A, which may explain their synergy with oxacillin. These two thioxanthone derivatives with different profiles may be promising tools for restoring the activity of oxacillin against MRSA.

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Section: Introductionmentioning

confidence: 99%

Synergistic Effects Between Thioxanthones and Oxacillin Against Methicillin-ResistantStaphylococcus aureus

Bessa

Palmeira

Gomes

et al. 2015

Microbial Drug Resistance

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“…diterpenes, triterpenes, steroids). 10,11 To date more than 1000 different secondary metabolites so-called 'lichen substances' are known in lichens. 12,13 Secondary metabolites are deposited usually as crystals on the surface of cortical and medullary hyphal cell walls.…”

Section: Phytochemistrymentioning

confidence: 99%

Parmeliaceae family: phytochemistry, pharmacological potential and phylogenetic features

et al. 2014

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Parmeliaceae is the largest family of lichenized fungi comprising about 2700 species distributed in about 80 genera. A wide array of secondary metabolites including depsides, depsidones, aliphatic acids, triterpenes, anthraquinones, secalonic acids, pulvinic acid derivatives and xanthones have been identified within this family. Many of these bioactive compounds such as usnic acid and atranorin are exclusively found in this family, being of great relevance for the systematics and phylogeny. Moreover, these compounds exert different biological roles including antimicrobial, antioxidant, cytotoxic, anti-inflammatory, analgesic and enzyme inhibitory actions. The current review focuses on the phytochemistry and main phylogenetic aspects of Parmeliaceae, and it discusses the pharmacological findings and mechanisms of action of their extracts and isolated compounds. The present work actually collects information related to more than 65 lichen species (from 21 different genuses and heterogeneous distribution) and 75 isolated metabolites. As reported, the best studied genus from a pharmacological point of view is Parmelia, followed by Usnea. At the species level, Cetraria islandica and Evernia prunastri attract remarkable interest in their bioactive activities and metabolite content. The major pharmacological activities investigated on extracts and compounds from Parmeliaceae spp. have been antimicrobial, anticancer and antioxidant potentials; and regarding isolated compounds, the aforementioned usnic acid and atranorin are among the most studied metabolites. Reviewed data suggest that some of these lichens and natural compounds are worthy of further investigation.

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“…Many derivatives exhibited noticeable biological properties, from which antitumor effects can be highlighted [1,2]. This family has been studied for over a century and several reviews, covering their natural sources [3][4][5], biological activities [6], chemical synthesis [7,8] and even biosynthesis [1,9], were published. Nonetheless, the field of xanthone chemistry is growing rapidly, due to several update publications, it is noteworthy that arylxanthones are not the focus of these articles.…”

Section: Introductionmentioning

confidence: 99%

Arylxanthones and arylacridones: a synthetic overview

Santos

Pinto

Silva

et al. 2016

Pure and Applied Chemistry

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Arylxanthones and arylacridones although not yet found in nature are becoming an important group of heterocyclic compounds due to their promising biological activities. Their central cores, xanthone and acridone, are recognized as interesting motifs for drug development mainly to be used in antitumour chemotherapy. The synthesis of this type of compounds is still scarce but several successful examples were recently published and a large variety of arylated xanthone and acridone derivatives were prepared. A systematic survey of the literature dedicated to their synthesis will be presented and discussed in this review.

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Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

Cited by 365 publications

References 422 publications

Synergistic Effects Between Thioxanthones and Oxacillin Against Methicillin-ResistantStaphylococcus aureus

Synergistic Effects Between Thioxanthones and Oxacillin Against Methicillin-ResistantStaphylococcus aureus

Parmeliaceae family: phytochemistry, pharmacological potential and phylogenetic features

Arylxanthones and arylacridones: a synthetic overview

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