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article

Synthesis and evaluation of pharmacological properties of some new xanthone derivatives with piperazine moiety

A.M. Waszkielewicz, A. Gunia, N. Szkaradek, K. Pytka, more

Bioorganic & Medicinal Chemistry Letters > 2013 > 23 > 15 > 4419-4423

A series of new xanthone derivatives with piperazine moiety [1–7] was synthesized and evaluated for their pharmacological properties. They were subject to binding assays for α ₁ and β ₁ adrenergic as well as 5-HT _1A , 5-HT ₆ and 5-HT _7b serotoninergic receptors. Five of the tested compounds were also evaluated for their anticonvulsant properties. The compound...

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Neuromodulation of Acid‐Sensitive Ion Channels (ASICs) and Anti‐Inflammatory Potential by Lichenxanthone in Adult Zebrafish (Danio rerio): Experimental and Docking Studies

Hortência Ribeiro Liberato, Jéssica Bezerra Maciel, Antônio Wlisses Da Silva, Maria Eduarda Uchoa Bezerra, more

Chemistry & Biodiversity > 21 > 4 > n/a - n/a

The xanthone lichenxanthone did not show toxic effects (LC₅₀>1.0 mg/mL). lichenxanthone prevented nociceptive behavior induced by acidic saline, and its analgesic effect was blocked by amiloride, highlighting the involvement of neuromodulation of acid‐sensitive ion channels (ASICs). In the analysis of anti‐inflammatory activity, concentrations of 0.1 and 0.5 mg/mL of lichenxanthone reduced the...

article

Copper‐Catalyzed Intramolecular S_EAr Reaction–Oxidation under Aerobic Conditions: Synthesis of Styryl‐/Alkenyl‐Substituted Xanthone Derivatives

Sanjay Yadav, Prashant Kumar Sinha, Surisetti Suresh

European Journal of Organic Chemistry > 26 > 23 > n/a - n/a

Herein, we report a copper‐catalyzed intramolecular electrophilic aromatic substitution (S_EAr)−oxidation process to access a wide range of diversified xanthone derivatives using air as a sole oxidant. Specifically, this protocol affords hitherto unknown styryl‐/alkenyl‐substituted xanthone derivatives in moderate to high yields. The practicality of the method has been demonstrated by gram‐scale syntheses.

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A Comprehensive Review of the Phytochemical and Pharmacological Potential of an Evergreen Plant Garcinia cowa

Anirban Chouni, Santanu Paul

Chemistry & Biodiversity > 20 > 2 > n/a - n/a

Garcinia cowa of the Clusiaceae family, native to South‐East Asia used in traditional medicine. It has antipyretic, antimicrobial, and many other biological activities. In this review, a thorough study of this plant's chemical constituents and pharmacological and therapeutic effects was conducted from the research articles from PubMed, Science Direct, Google Scholar, and Scopus from 1977 to 2022....

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Six New Constituents from the Fruit of Hypericum patulum and Their Anti‐Inflammatory Activity

Jing‐Yi Xue, Wei Jiang, Li Li, Ding‐Yan Lu, more

Chemistry & Biodiversity > 20 > 1 > n/a - n/a

Four new xanthone glucosides, 3‐hydroxy‐2‐methoxyxanthone‐4‐O‐β‐D‐glucopyranoside (1), 4,8‐dihydroxy‐2‐methoxyxanthone‐3‐O‐β‐D‐glucopyranoside (2), 2‐methoxyxanthone‐5‐O‐β‐D‐glucopyranoside (3), 4‐hydroxy‐2‐methoxyxanthone‐3‐O‐β‐D‐glucopyranoside (4), a new phenolic acid, 4,4′‐dihydroxy‐3,3′‐imino‐di‐benzoic acid monomethyl ester (5), and a new isoquinoline, methyl 6‐hydroxy‐1‐oxo‐1,2,3,4‐tetrahydroisoquinoline‐4‐carboxylate...

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Promising anticonvulsant and/or analgesic compounds among 5‐chloro‐2‐ or 5‐chloro‐4‐methyl derivatives of xanthone coupled to aminoalkanol moieties—Design, synthesis and pharmacological evaluation

Gabriela Mazur, Katarzyna Pańczyk‐Straszak, Anna Rapacz, Jan Kiszela, more

Chemical Biology & Drug Design > 101 > 2 > 278 - 325

A series of 10 aminoalkanol derivatives of 5‐chloro‐2‐ or 5‐chloro‐4‐methylxanthone was synthetized and evaluated for anticonvulsant properties (MES test, mice, intraperitoneal) and compared with neurotoxicity rotarod test (NT, mice, i.p.). The best results both in terms of anticonvulsant activity and protective index value were obtained for 3: 5‐chloro‐2‐([4‐hydroxypiperidin‐1‐yl]methyl)‐9H‐xanthen‐9‐one...

article

Revisiting the synthesis of bis(2‐hydroxy‐3,5‐di‐t‐butylphenyl)methanone

Xin‐Jie Lin, Shih‐Peng Huang, Min‐Jie Huang, Chien‐Lung Wang, more

Journal of the Chinese Chemical Society > 69 > 10 > 1803 - 1809

Described is our effort toward establishing a practical and sustainable synthesis of bis(2‐hydroxy‐3,5‐di‐t‐butylphenyl)methanone. In it, we found the phenol‐aldehyde condensation could be efficiently catalyzed by sulfonic acid‐functionalized microporous carbon spheres (MCS‐SO₃H). Additionally, we developed practical and sustainable procedures for the synthesis of the title ligand by applying readily...

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Two New Xanthones from the Twigs of Calophyllum membranaceum and Their Anti‐Inflammatory Activities in HESC Cells

Si‐Yuan Li, Ya‐Hui Mi, Wei Shen, Xiao‐Long Hu, more

Chemistry & Biodiversity > 19 > 7 > n/a - n/a

Two new xanthones, calmemxanthone A (1) and calmemxanthone B (2), along with eleven known compounds were isolated from the dried twigs of Calophyllum membranaceum Gardn. et Champ. The structures of compounds 1 and 2 were established by analysis of spectra and mass spectrometry data. The absolute configuration of compound 1 was confirmed by electronic circular dichroism (ECD) spectral analysis. The...

article

Xanthones from Calophyllum Polyanthum Wallich ex Choisy with CYP1 Enzymes Inhibitory Activity

Ting‐Ting Cao, Ruo‐Yue Huang, Xu Li, Teng‐Yun Yang, more

Chemistry & Biodiversity > 19 > 6 > n/a - n/a

Three new xanthone compounds, 1,3,5‐trihydroxy‐2‐(2‐hydroxy‐3‐methylbut‐3‐enyl)‐4‐(3‐methylbut‐2‐enyl)xanthone (1), toxyloxanthone E (2), dehydrocycloguanandin B (3) along with 15 known xanthones (4–18) were isolated from the aerial parts of Calophyllum polyanthum Wall. ex Choisy. Their structures were fully characterised using spectroscopic data, as well as comparison with the previous literature...

article

Effect of Bis‐Dimethylamine Substitution on DNA Binding Property and Cytotoxic Activity of Polyhydroxyxanthone

Rui Shen, Yuhong Chen, Jianhua Wu, Lihua Zhao, more

Chemistry & Biodiversity > 19 > 5 > n/a - n/a

A bis‐dimethylamine substituted xanthone (Xan‐2) was obtained by cationic modification of the free C3 and C6 hydroxy groups of 1,3,6‐trihydroxyxanthone (Xan‐1) which was isolated from Polygala hongkongensis Hemsl.. The results of the spectroscopic analysis, melting profiles, electrophoretic migration, PCR assay and molecular docking indicated that the hydrophobic plane of Xan‐1 and Xan‐2 could intercalate...

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Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Ha Nguyen Thi Thu, Quan Pham Minh, Cuong Pham Van, Tuyen Nguyen Van, more

Chemistry & Biodiversity > 18 > 11 > n/a - n/a

A new racemic xanthone, garmckeanin A (1), and eight known analogs 2–9 were isolated from the ethyl acetate (AcOEt) extract of the Vietnamese Garcinia mckeaniana leaves. Their structures were determined by MS and NMR spectral analyses and compared with the literature. The AcOEt extract showed good cytotoxicity against cancer cell lines KB, Lu, Hep‐G2 and MCF7, with IC₅₀ values of 5.40–8.76 μg/mL,...

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Identification and characterization of xanthone biosynthetic genes contributing to the vivid red coloration of red‐flowered gentian

Nobuhiro Sasaki, Keiichirou Nemoto, Yuzo Nishizaki, Naoki Sugimoto, more

The Plant Journal > 107 > 6 > 1711 - 1723

Cultivated Japanese gentians traditionally produce vivid blue flowers because of the accumulation of delphinidin‐based polyacylated anthocyanins. However, recent breeding programs developed several red‐flowered cultivars, but the underlying mechanism for this red coloration was unknown. Thus, we characterized the pigments responsible for the red coloration in these cultivars. A high‐performance liquid...

article

Antioxidant Activity of a New Xanthone Derivative from Aspidistra Letreae: In Vitro and In Silico Studies

Duc Viet Ho, Hoai Thi Nguyen, Thien‐Y Vu, Ty Viet Pham, more

Chemistry & Biodiversity > 18 > 4 > n/a - n/a

A new xanthone derivative, aspidxanthone A (1), and three known compounds ((2S)‐1‐(β‐D‐galactopyranosyloxy)‐3‐(hexadecanoyloxy)propan‐2‐yl (9Z,12Z)‐octadeca‐9,12‐dienoate (2), (25S)‐spirostane‐1β,3α,5β‐triol (3), and asparenyldiol (4)) were isolated from the whole of the endemic species Aspidistra letreae in Vietnam. Their structures were elucidated by means of extensive spectroscopic analyses and...

article

Design, synthesis and activity against Staphylococcus epidermidis of 5‐chloro‐2‐ or 5‐chloro‐4‐methyl‐9H‐xanthen‐9‐one and some of its derivatives

Gabriela Mazur, Iwona Skiba‐Kurek, Elżbieta Karczewska, Katarzyna Pańczyk‐Straszak, more

Chemical Biology & Drug Design > 97 > 3 > 674 - 685

Ten new xanthone derivatives have been designed and synthesized for their potential antibacterial activity. All compounds have been screened against Staphylococcus epidermidis strains ATCC 12228 and clinical K/12/8915. The highest antibacterial activity was observed for compound 3: 5‐chloro‐2‐((4‐(2‐hydroxyethyl)piperazin‐1‐yl)methyl)‐9H‐xanthen‐9‐one dihydrochloride, exhibiting MIC of 0.8 µg/ml against...

article

Design of a Functional Chromene‐Type Kobayashi Precursor: Gram‐Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation

Yuan‐Ze Xu, Feng Sha, Xin‐Yan Wu

Chemistry – A European Journal > 27 > 3 > 1066 - 1071

The 2,2‐dimethyl‐2H‐chromene motif is widely found in many bioactive molecules, and is a privileged structure in the pharmaceutical arena. We have developed a concise and regioselective approach to chromenes and chromanes through an aryne‐based synthetic strategy. A practical, gram‐scale synthetic route to a chromene‐type aryne precursor was explored. Subsequently, cyclization under mild conditions...

article

Design, Synthesis and Biological Evaluation of Xanthone Derivatives for Possible Treatment of Alzheimer's Disease Based on Multi‐Target Strategy

Aihong Yang, Qiao Yu, Hui Ju, Lulu Song, more

Chemistry & Biodiversity > 17 > 10 > n/a - n/a

Four xanthone derivatives were synthesized and evaluated as acetylcholinesterase inhibitors (AChEIs) with metal chelating ability and antioxidant ability against Alzheimer's disease (AD). Most of them exhibited potential acetylcholinesterase (AChE), butylcholinesterase (BuChE) inhibitory, antioxidant and metal chelating properties. Among them, 1‐hydroxy‐3‐[2‐(pyrrolidin‐1‐yl)ethoxy]‐9H‐xanthen‐9‐one...

article

Xanthone‐enriched fraction of Garcinia mangostana and α‐mangostin improve the spatial learning and memory of chronic cerebral hypoperfusion rats

Ning Tiang, Mohamad Anuar Ahad, Vikneswaran Murugaiyah, Zurina Hassan

Journal of Pharmacy and Pharmacology > 72 > 11 > 1629 - 1644

Objectives Xanthones isolated from the pericarp of Garcinia mangostana has been reported to exhibit neuroprotective effect. Methods In this study, the effect of xanthone‐enriched fraction of Garcinia mangostana (XEFGM) and α‐mangostin (α‐MG) were investigated on cognitive functions of the chronic cerebral hypoperfusion (CCH) rats. Key findings HPLC analysis revealed that XEFGM contained 55.84%...

article

How Far Does Energy Migrate in DNA and Cause Damage? Evidence for Long‐Range Photodamage to DNA

Arthur Kuhlmann, Larissa Bihr, Hans‐Achim Wagenknecht

Angewandte Chemie International Edition > 59 > 40 > 17378 - 17382

A new DNA architecture addresses the question, how far energy migrates in DNA and forms cyclobutane pyrimidine dimers (CPDs) as photodamages causing skin cancer. The 3‐methoxyxanthone nucleoside allows site‐selective photoenergy injection into DNA. The designated CPD site lacks the phosphodiester bond and can be placed in defined distances. The CPD formation links two oligonucleotides together and...

article

Frontispiece: How Far Does Energy Migrate in DNA and Cause Damage? Evidence for Long‐Range Photodamage to DNA

Arthur Kuhlmann, Larissa Bihr, Hans‐Achim Wagenknecht

Angewandte Chemie International Edition > 59 > 40 > n/a - n/a

DNA Lesions In their Communication on page 17378, H.‐A. Wagenknecht et al. report a new DNA architecture to address the question how far energy migrates in DNA and forms cyclobutane pyrimidine dimers as photodamages causing skin cancer.

article

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

Tao Xie, Chaoying Zheng, Kuanwei Chen, Haibing He, more

Angewandte Chemie > 132 > 11 > 4390 - 4394

A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD‐594, a complex polycyclic xanthone natural product from Streptomyces sp. TA‐0256, in a longest linear sequence (LLS) of 20 steps. The trans‐9,10‐dihydrophenanthrene‐9,10‐diol fragment (B‐C‐D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu‐mediated...

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Search results

Synthesis and evaluation of pharmacological properties of some new xanthone derivatives with piperazine moiety

Neuromodulation of Acid‐Sensitive Ion Channels (ASICs) and Anti‐Inflammatory Potential by Lichenxanthone in Adult Zebrafish (Danio rerio): Experimental and Docking Studies

Copper‐Catalyzed Intramolecular S_EAr Reaction–Oxidation under Aerobic Conditions: Synthesis of Styryl‐/Alkenyl‐Substituted Xanthone Derivatives

A Comprehensive Review of the Phytochemical and Pharmacological Potential of an Evergreen Plant Garcinia cowa

Six New Constituents from the Fruit of Hypericum patulum and Their Anti‐Inflammatory Activity

Promising anticonvulsant and/or analgesic compounds among 5‐chloro‐2‐ or 5‐chloro‐4‐methyl derivatives of xanthone coupled to aminoalkanol moieties—Design, synthesis and pharmacological evaluation

Revisiting the synthesis of bis(2‐hydroxy‐3,5‐di‐t‐butylphenyl)methanone

Two New Xanthones from the Twigs of Calophyllum membranaceum and Their Anti‐Inflammatory Activities in HESC Cells

Xanthones from Calophyllum Polyanthum Wallich ex Choisy with CYP1 Enzymes Inhibitory Activity

Effect of Bis‐Dimethylamine Substitution on DNA Binding Property and Cytotoxic Activity of Polyhydroxyxanthone

Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Identification and characterization of xanthone biosynthetic genes contributing to the vivid red coloration of red‐flowered gentian

Antioxidant Activity of a New Xanthone Derivative from Aspidistra Letreae: In Vitro and In Silico Studies

Design, synthesis and activity against Staphylococcus epidermidis of 5‐chloro‐2‐ or 5‐chloro‐4‐methyl‐9H‐xanthen‐9‐one and some of its derivatives

Design of a Functional Chromene‐Type Kobayashi Precursor: Gram‐Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation

Design, Synthesis and Biological Evaluation of Xanthone Derivatives for Possible Treatment of Alzheimer's Disease Based on Multi‐Target Strategy

Xanthone‐enriched fraction of Garcinia mangostana and α‐mangostin improve the spatial learning and memory of chronic cerebral hypoperfusion rats

How Far Does Energy Migrate in DNA and Cause Damage? Evidence for Long‐Range Photodamage to DNA

Frontispiece: How Far Does Energy Migrate in DNA and Cause Damage? Evidence for Long‐Range Photodamage to DNA

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

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