Recent Insights into the Biosynthesis and Biological Activities of Natural Xanthones (original) (raw)
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Recent Insights into the biosynthesis and biological activites of natural Xanthones
This review focuses on recent advances in our understanding of the complex biosynthetic pathways and diverse biological activities of naturally occurring xanthones. The biosynthesis section covers studies published from 1989 to 2008 on xanthone production in plants and fungi, while the bioactivity review presents tabulated activities of more than 250 xanthones described in studies published from 2001 to 2008, together with structural information and indications of their wide-ranging potential uses as pharmacological tools. A large number of relevant papers have been published on these subjects (128 cited here), illustrating the diversity of the xanthones and their possible uses.
Naturally Occurring Xanthones: Chemistry and Biology
Journal of Applied Chemistry, 2013
Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants, fungi, ferns, and lichens. They have gradually risen to great importance because of their medicinal properties. This review focuses on the types, isolation, characterization, biological applications, and biosynthesis of naturally occurring xanthones isolated so far. Different physicochemical and instrumental methods such as liquid-solid and liquid-liquid extraction, TLC, flash chromatography, column chromatography, IR,1H NMR and13C NMR spectroscopy, GLC, HPLC, GC, and LCMS have been widely used for isolation and structural elucidation of xanthones. Hepatoprotective, anticarcinogenic, antileprosy, antimalarial, antioxidant, anticholinergic, mutagenicity, radioprotective, immunomodulatory, antibone resorption, antiparasitic, neuraminidase inhibitory, anticomplement, antibacterial, antifungal, algicidal, anti-HIV, cardioprot...
From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones
Molecules, 2021
This work reviews the contributions of the corresponding author (M.M.M.P.) and her research group to Medicinal Chemistry concerning the isolation from plant and marine sources of xanthone derivatives as well as their synthesis, biological/pharmacological activities, formulation and analytical applications. Although her group activity has been spread over several chemical families with relevance in Medicinal Chemistry, the main focus of the investigation and research has been in the xanthone family. Xanthone derivatives have a variety of activities with great potential for therapeutic applications due to their versatile framework. The group has contributed with several libraries of xanthones derivatives, with a variety of activities such as antitumor, anticoagulant, antiplatelet, anti-inflammatory, antimalarial, antimicrobial, hepatoprotective, antioxidant, and multidrug resistance reversal effects. Besides therapeutic applications, our group has also developed xanthone derivatives w...
Recent progress in biologically active xanthones
Journal of chemical and pharmaceutical research, 2016
Xanthone is a novel and pharmacologically important oxygen containing hetrocyclic ring exhibiting variety of potent biological activities. This fused tricyclic ring is derived naturally from the plants of Bonnetiaceae and Clusiaceae family as well as synthesized by employing various synthetic protocols. Their wide range of reported therapeutic attributes include α-glucosidase inhibition, anti-cancer, anti-oxidant, anti-asthmatic, anti-convulsant, xanthine oxidase inhibition and anti-microbial. Among these attributes, anti-cancer and anti-oxidant potential are comprehensively studied as evidenced by number of research papers. Although, there is no marketed formulation containing xanthone derivatives except some herbal formulations, their medicinal properties can not be neglected at all. Promising activities revealed by these compounds chains their use and places them ahead as potential drug candidates for the future studies. Therefore, the present review article is entirely an assemb...
Asian Journal of Pharmaceutical and Clinical Research, 2018
Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants such as fungi, ferns, and lichens. Synthetic analogs of xanthones have shown a large number of pharmacological properties such as antioxidant, anti-inflammatory, antidiabetics, antihistamine, antitumoral, antiulcer, and algicidal. Moreover, they also find usages in photodynamic therapy, laser technology, and dyes. This review lays stress on various solvents, catalyst and synthetic route for synthesis of xanthones, benzoxanthones analogs. The review has also focused on the classifications of xanthone as well as extensively studied biological properties of the xanthones and benzoxanthones analogs.
Xanthones as Potential Antioxidants
Current Medicinal Chemistry, 2013
Xanthones (dibenzo--pyrones) constitutes an important class of oxygenated heterocycles and occur as secondary metabolites in plants and microorganisms. They are known for various biological activities such as antioxidant, monoamine oxidase inhibitor, antihypertensive, hepatoprotective, antithrombotic, antifungal and anticancer. The tricyclic scaffold as well as the nature and/or position of the substituents present on it play an important role in displaying various biological activities. The unique structural scaffold and medicinal importance of xanthones have therefore attracted many Scientists in the past, to isolate or synthesize xanthones or their analogs as potential drug candidates. It would not be wrong to call them as close cousins to the polyphenol family that are known to possess strong antioxidant effects on the nervous system. The main two sources of xanthones are: Isolation from natural resources or synthesis. Though few reviews have been published in the past, mainly focusing on the anticancer activities of xanthone derivatives, but there is not a single review which is based on their antioxidant activities. We therefore have made efforts to briefly summarize natural and synthetic xanthones possessing antioxidant activity in this review.
Synthetic approaches to biologically active xanthones: an update
Chemical Papers, 2020
Many xanthone structures show promising biological activities. Accordingly, a breadth of synthetic strategies toward xanthone derivatives have been developed. This review surveys these methods published from 2013 to 2019, and in an integrated manner details the biological activities of key xanthone structures. The review highlights the synthesis of xanthones via the classical and the modified Grover, Shah, and Shah reaction; the use of ytterbium, palladium, ruthenium, copper catalysis; the use of chromen-4-ones as building blocks; the use of the Friedel-Crafts reaction; Ullmann-ether coupling; metal-free oxidative coupling; intermolecular and intramolecular couplings; xanthone synthesis via the intermolecular Diels-Alder reaction; a novel decarboxylative aminocatalytic strategy; use of the Michael reaction, and the use of the Knoevenagel-Michael, Michael/Michael, Michael/Henry cycloadditions; and [4+2] cycloaddition.
Bioactive xanthones from the roots of Hypericum perforatum (common St John's wort)
Journal of the Science of Food and Agriculture, 2011
Hypericaceae) are sold as phytopharmaceuticals and herbal supplements to treat mild to moderate depression and as food additives. Extensively cultivated in Europe, plants can be infected by anthracnose (Colletotrichum gloeosporioides), a virulent fungal pathogen that causes tissue necrosis and dramatically decreases crop value. Such infections triggered the production of new secondary metabolites, specifically xanthones, in cell culture experiments.
Biologically active xanthones from Codonopsis ovata
Five new xanthones, named coxanthones AeE (1e5), together with 21 known secondary metabolites (6 e26) that include seven xanthones, five flavonoids, two steroids and seven triterpenoids were isolated from the chemically unexplored whole plant Codonopsis ovata. The structures of new metabolites were elucidated by HRMS, interpretation of NMR spectra and other spectroscopic techniques. The absolute configuration of the stereogenic centre of coxanthone B (2) was determined by electronic circular di-chroism (ECD) spectroscopy. This is the first report of xanthones from the genus Codonopsis. All isolated metabolites were evaluated for cytotoxic activity by SRB assay against six human cancer cell lines A549 (lung), PC-3 (prostate), HCT-116 (colon), MCF-7 (breast), SF-295 (CNS), and MDAMB-435 (melanoma). Among the new compounds, coxanthone B (2) exhibited significant inhibitory activity against SF-295 and MDAMB-435 with IC 50 values of 7.0 and 15.0 mM, respectively. Coxanthone A (1) displayed cytotoxicity against A549 cell line at IC 50 value of 22.5 mM. Cytotoxic activity of 1-hydroxy-3,5-dimethoxyxanthone (7), swertiperenine (9) and 1,7,8-trihydroxy-3-methoxyxanthone (10) are reported here first time that exhibited the IC 50 values of 3.0, 5.0 and 21.0 mM against A549, MDAMB-435, and A549 cell lines, respectively. Kaempferol (13) showed most potent cytotoxic activity with an IC 50 values in the 1.0 e2.3 mM range against all tested cancer cell lines.