Naturally Occurring Xanthones: Chemistry and Biology

Negi, Jagmohan S.; Bisht, V. K.; Singh, Pawan; Rawat, Mahiraj Singh; Joshi, Gopal Krishna

doi:10.1155/2013/621459

Cited by 164 publications

(134 citation statements)

References 106 publications

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“…With a number of pharmaceutical applications, xanthones ( Figure 5) are structurally related to flavanoids, and also commonly recovered from both plant and fungal sources [156]. With reference to endophytic fungi, a mangrovial strain of Penicillium sp.…”

Section: Xanthones and Quinonesmentioning

confidence: 99%

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

2015

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Abstract:It is known that plant-based ethnomedicine represented the foundation of modern pharmacology and that many pharmaceuticals are derived from compounds occurring in plant extracts. This track still stimulates a worldwide investigational activity aimed at identifying novel bioactive products of plant origin. However, the discovery that endophytic fungi are able to produce many plant-derived drugs has disclosed new horizons for their availability and production on a large scale by the pharmaceutical industry. In fact, following the path traced by the blockbuster drug taxol, an increasing number of valuable compounds originally characterized as secondary metabolites of plant species belonging to the Spermatophyta have been reported as fermentation products of endophytic fungal strains. Aspects concerning sources and bioactive properties of these compounds are reviewed in this paper.

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Section: Xanthones and Quinonesmentioning

confidence: 99%

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

2015

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“…secondary metabolism | gene cluster | cytoxicity | emodin | nataloe-emodin N aturally occurring anthraquinones and structurally related xanthones are particularly interesting families of secondary metabolites (SMs) that have long been exploited as vibrantly colored dyestuffs and for their excellent medicinal qualities (1)(2)(3). They have been largely used in both traditional Asian and modern Occidental medicines.…”

mentioning

confidence: 99%

“…Anthraquinones and xanthones contain an aromatic core that serves as a scaffold for the attachment of diverse functional groups, resulting in a wide variety of molecules with distinct biological and biochemical characteristics. This diversity is further increased by their assembly into homo-and heterodimers (3,5), with activities that are distinct from those exhibited by their respective monomeric components (6). Despite the large number of identified anthraquinones and xanthones and their potential applications, very few of their biosynthetic pathways are known.…”

mentioning

confidence: 99%

Elucidation of cladofulvin biosynthesis reveals a cytochrome P450 monooxygenase required for anthraquinone dimerization

Griffiths

Mesarich

Saccomanno

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

161

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Anthraquinones are a large family of secondary metabolites (SMs) that are extensively studied for their diverse biological activities. These activities are determined by functional group decorations and the formation of dimers from anthraquinone monomers. Despite their numerous medicinal qualities, very few anthraquinone biosynthetic pathways have been elucidated so far, including the enzymatic dimerization steps. In this study, we report the elucidation of the biosynthesis of cladofulvin, an asymmetrical homodimer of nataloe-emodin produced by the fungus Cladosporium fulvum. A gene cluster of 10 genes controls cladofulvin biosynthesis, which begins with the production of atrochrysone carboxylic acid by the polyketide synthase ClaG and the β-lactamase ClaF. This compound is decarboxylated by ClaH to yield emodin, which is then converted to chrysophanol hydroquinone by the reductase ClaC and the dehydratase ClaB. We show that the predicted cytochrome P450 ClaM catalyzes the dimerization of nataloe-emodin to cladofulvin. Remarkably, such dimerization dramatically increases nataloe-emodin cytotoxicity against mammalian cell lines. These findings shed light on the enzymatic mechanisms involved in anthraquinone dimerization. Future characterization of the ClaM enzyme should facilitate engineering the biosynthesis of novel, potent, dimeric anthraquinones and structurally related compound families.secondary metabolism | gene cluster | cytoxicity | emodin | nataloe-emodin

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“…The pharmacological properties of both natural and synthetic xanthones (e.g., anti-inflammatory, antimalarial, antioxidant, and antitumour activities) are associated to different substituents in different positions of their main core [7][8][9][10][11][12]. Aryl groups linked to xanthones are scarce in natural sources, but several publications reporting their synthesis and/or biomedical potential have been highlighted in literature and reviewed in [13].…”

Section: Introductionmentioning

confidence: 99%

2,3-Diarylxanthones as Potential Inhibitors of Arachidonic Acid Metabolic Pathways

et al. 2017

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Abstract-In response to an inflammatory stimulus, arachidonic acid (AA), the main polyunsaturated fatty acid present in the phospholipid layer of cell membranes, is released and metabolized to a series of eicosanoids. These bioactive lipid mediators of inflammation arise physiologically through the action of the enzymes 5-lipoxygenase (5-LOX) and cyclooxygenases (constitutive COX-1 and inducible COX-2). It is believed that dual inhibition of 5-LOX and COXs may have a higher beneficial impact in the treatment of inflammatory disorders rather than the inhibition of each enzyme. With this demand for new dual-acting antiinflammatory agents, a range of 2,3-diarylxanthones were tested through their ability to interact in the AA metabolism. In vitro anti-inflammatory activity was evaluated through the inhibition of 5-LOX-catalyzed leukotriene B 4 (LTB 4 ) formation in human neutrophils and inhibition of COX-1-and COX-2-catalyzed prostaglandin E 2 (PGE 2 ) formation in human whole blood. The results showed that some of the studied arylxanthones were able to prevent LTB 4 production in human neutrophils, in a concentration-dependent manner. The xanthone with a 2-catechol was the most active one (IC 50 ∼ 9 μM). The more effective arylxanthones in preventing COX-1-catalyzed PGE 2 production presented IC 50 values from 1 to 7 μM, exhibiting a structural feature with at least one non-substituted aryl group. All the studied arylxanthones were ineffective to prevent the formation of PGE 2 catalyzed by COX-2, up to the maximum concentration of 100 μM. The ability of the tested 2,3-diarylxanthones to interact with both 5-LOX and COX-1 pathways constitutes an important step in the research of novel dual-acting anti-inflammatory drugs.

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Naturally Occurring Xanthones: Chemistry and Biology

Cited by 164 publications

References 106 publications

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

Elucidation of cladofulvin biosynthesis reveals a cytochrome P450 monooxygenase required for anthraquinone dimerization

2,3-Diarylxanthones as Potential Inhibitors of Arachidonic Acid Metabolic Pathways

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