A Short, Atom‐Economical Entry to Tetrahydroxanthenones.

Lesch, B.; Braese, Stefan

doi:10.1002/chin.200417133

Cited by 5 publications

(7 citation statements)

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“…According the concept of Evans et al [ 20 ] the xanthone nucleus could be considered as a “privileged structure”, taking into account its binding to multiple, unrelated classes of protein receptors as high affinity ligands. Following, several authors associated the “xanthone” to the “privileged structure concept” [ 21 , 22 , 23 , 24 , 25 ]. This ability of xanthones to interfere with a variety of biological targets is related with some special molecular features such as the presence of a heteroaromatic tricyclic ring system predominantly planar and rigid, a carbonyl group at the central ring able of several interactions, a biaryl ether group contributing to the electronic system, and the xanthone core that accommodates a vast variety of substituents at different positions.…”

Section: Introductionmentioning

confidence: 99%

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

et al. 2021

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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 with analytical applications as chiral selectors for liquid chromatography and for maritime application as antifouling agents for marine paints. Chemically, it has been challenging to afford green chemistry methods and achieve enantiomeric purity of chiral derivatives. In this review, the structures of the most significant compounds will be presented.

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Section: Introductionmentioning

confidence: 99%

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

et al. 2021

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“…Xanthones exhibit multiple pharmacological activities, including antimicrobial, antitumoral and anti-Alzheimer properties (Fotie & Bohle, 2006;El-Seedi et al, 2010;Wang et al, 2016a). Owing to their array of bioactivities and their interaction with multiple types of drug targets, they were referred to as 'privileged structures' (Lesch & Br€ ase, 2004;Wezeman et al, 2015). More recently, the polyprenylated caged xanthone derivatives have attracted attention for drug design and development as a result of their unique chemical structures and promising pharmacology (Chantarasriwong et al, 2009;Han & Xu, 2009;Anantachoke et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Exodermis and endodermis are the sites of xanthone biosynthesis in Hypericum perforatum roots

et al. 2017

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Xanthones are specialized metabolites with antimicrobial properties, which accumulate in roots of Hypericum perforatum. This medicinal plant provides widely taken remedies for depressive episodes and skin disorders. Owing to the array of pharmacological activities, xanthone derivatives attract attention for drug design. Little is known about the sites of biosynthesis and accumulation of xanthones in roots. Xanthone biosynthesis is localized at the transcript, protein, and product levels using in situ mRNA hybridization, indirect immunofluorescence detection, and high lateral and mass resolution mass spectrometry imaging (AP-SMALDI-FT-Orbitrap MSI), respectively. The carbon skeleton of xanthones is formed by benzophenone synthase (BPS), for which a cDNA was cloned from root cultures of H. perforatum var. angustifolium. Both the BPS protein and the BPS transcripts are localized to the exodermis and the endodermis of roots. The xanthone compounds as the BPS products are detected in the same tissues. The exodermis and the endodermis, which are the outermost and innermost cell layers of the root cortex, respectively, are not only highly specialized barriers for controlling the passage of water and solutes but also preformed lines of defence against soilborne pathogens and predators.

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“…Phytochemical study permitted to isolate the 1, 5,8-trihydroxy-4′,5′-dimethyl-2H-pyrano (2,3 : 3,2)-4-(3-methylbut-2-enyl) xanthone (TDP), which showed a significant diuretic effect in rats after a single-dose treatment [17,18]. Xanthones are polyphenolic compounds, and their structures are recognized for their importance in discovering new active compounds [20]. Indeed, several biological activities have been described for xanthones, including anti-inflammatory, antioxidant [21], cardioprotective [22], diuretic [17,23], and renal protective [24] effects.…”

Section: Introductionmentioning

confidence: 99%

Prolonged Diuretic and Renoprotective Effects of a Xanthone Obtained from Garcinia achachairu Rusby in Normotensive and Hypertensive Rats

Mariano

Boeing

Filho

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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The previous study showed that 1,5,8-trihydroxy-4′,5′-dimethyl-2H-pyrano(2,3 : 3,2)-4-(3-methylbut-2-enyl) xanthone (TDP) obtained from Garcinia achachairu Rusby (Clusiaceae) branches induces acute diuresis in normotensive (NTR) and spontaneously hypertensive rats (SHR) after 8 h of the experiment. In complementarity, the present study evaluated the prolonged diuretic and renoprotective effects of TDP in both NTR and SHR. The animals received, once a day, oral treatment with TDP (0.1 mg/kg), hydrochlorothiazide (10 mg/kg), or vehicle (VEH; 10 mL/kg). At the end of 7 days, the urine, blood, and kidney samples were collected for biochemical and histological analyzes. The urinary volume of both NTR and SHR after 7 days of treatment with the TDP was significantly increased, associated with augmented urinary electrolyte excretion levels. The treatments did not modify the urinary pH values nor the parameters analyzed in plasma (Na+, K+, Cl−, and Ca2+). Concerning the renal analyzes, when compared with the VEH-treated NTR group, while the activity of the enzymes catalase (CAT) and N-acetyl-β-D-glucosaminidase (NAG), as well as nitrite levels, were increased, the generation of lipid hydroperoxides and the activity of the enzyme myeloperoxidase (MPO) were unaltered. On the other hand, the activities of superoxide dismutase (SOD) and glutathione S-transferase (GST) and the levels of reduced glutathione (GSH) in kidney homogenates of the SHR group were decreased. However, TDP augmented the levels of GSH and GST activities and reduced the levels of nitrite and the activities of CAT and MPO, when compared with VEH-treated only SHR. Besides, the treatment with TDP alleviated the morphological changes of the renal corpuscle region of SHR. Together, these results revealed the prolonged diuretic effect of TDP and their renal protective effect by improving the antioxidative capacity.

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A Short, Atom‐Economical Entry to Tetrahydroxanthenones.

Cited by 5 publications

References 1 publication

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

Exodermis and endodermis are the sites of xanthone biosynthesis in Hypericum perforatum roots

Prolonged Diuretic and Renoprotective Effects of a Xanthone Obtained from Garcinia achachairu Rusby in Normotensive and Hypertensive Rats

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