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Xanthones

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https://www.readbyqxmd.com/read/29155590/semisynthesis-and-biological-evaluation-of-xanthone-amphiphilics-as-selective-highly-potent-antifungal-agents-to-combat-fungal-resistance
#1
Shuimu Lin, Wan Ling Wendy Sin, Jun-Jie Koh, Fanghui Lim, Lin Wang, Derong Cao, Roger W Beuerman, Li Ren, Shouping Liu
New efficient antifungal agents are urgently needed to treat drug-resistant fungal infections. Here, we designed and synthesized a series of cationic xanthone amphiphilics as antifungal agents from natural α-mangostin to combat fungal resistance. The attachment of cationic residues on the xanthone scaffold of α-mangostin resulted in interesting antifungal agents with a novel mode of action. Two lead compounds (1 and 2) showed potent antifungal activity against a wide range of fungal pathogens, including drug-resistant C...
November 20, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29132213/a-novel-xanthone-dimer-derivative-with-antibacterial-activity-isolated-from-the-bark-of-garcinia-mangostana
#2
Weiyi Wang, Yanyan Liao, Xiaomei Huang, Chao Tang, Peng Cai
A novel xanthone dimer derivative, garmoxanthone (1), together with 10 known compounds (2-11), were isolated from bark of Garcinia mangostana. Their structures were established through spectroscopic methods. Garmoxanthone exhibited strong inhibitory activities against MRSA ATCC 43300 and MRSA CGMCC 1.12409 (with MIC values of both 3.9 μg/mL) and moderate activities against tested strains of Vibrio (with MIC values ranging from 15.6 to 31.2 μg/mL). Garmoxanthone is a unique xanthone dimer with linkage of a fused 5/6 ring system and its absolute configuration was elucidated on the basis of experimental and calculated electronic circular dichroism...
November 13, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29128163/depsidone-and-xanthones-from-garcinia-xanthochymus-with-hypoglycemic-activity-and-the-mechanism-of-promoting-glucose-uptake-in-l6-myotubes
#3
Yunfang Li, Ping Zhao, Yu Chen, Yanze Fu, Kuan Shi, Liu Liu, Hui Liu, Mingrui Xiong, Qing-Hua Liu, Guangzhong Yang, Yuxiu Xiao
Garcinia xanthochymus is a widely used folk medicine in southwestern China. Previous studies indicated it possesses potential anti-diabetic activities both in vitro (Fu et al., 2014; Nguyen et al., 2017) and in vivo (Shivanand et al., 2017). To discover bioactive ingredients from it and unveil their mechanism of action against diabetes, the present study was designed to isolate constituents from extract of G. xanthochymus, determine their structures, screen their activities and investigate mechanism of action of the active substances...
November 8, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/29126369/secondary-metabolites-from-endemic-species-iris-adriatica-trinajsti%C3%A4-ex-miti%C3%A4-iridaceae
#4
Danka Bukvički, Miroslav Novaković, Nurunajah Ab Ghani, Petar D Marin, Yoshinori Asakawa
This manuscript describes the first detailed chemical investigation of endemic species Iris adriatica, including isolation and structure elucidation. Chemical analyses of the rhizome CH2Cl2/MeOH (2:1) extract revealed fourteen secondary metabolites, mainly isoflavonoids. Among isoflavonoids, two groups have been found: nigricin-type and tectorigenin-type. Dominant group of the isolated compounds has been nigricin-type isoflavones: nigricin, nigricin-4'-(1-O-β-D-glucopyranoside) and nigricin-4'-(1-O-β-D-glucopyranosyl (1-6)-β-D-glucopyranoside) with 2...
November 10, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29116938/mangostanaxanthone-vii-a-new-cytotoxic-xanthone-from-garcinia-mangostana
#5
Sabrin R M Ibrahim, Gamal A Mohamed, Mahmoud A Elfaky, Mohamed F Zayed, Amal A El-Kholy, Osama H Abdelmageed, Samir A Ross
Garcinia mangostana L. (the queen of fruits, mangosteen, family Guttiferae) is a wealthy source of xanthones. The CHCl3 soluble fraction of the air-dried pericarps of G. mangostana provided a new xanthone: mangostanaxanthone VII (5), along with four known xanthones: mangostanaxanthones I (1) and II (2), gartanin (3) and γ-mangostin (4). The structural verification of these metabolites was achieved by different spectral techniques, including UV, IR, 1D and 2D NMR and HRESIMS. The new metabolite was assessed for cytotoxic potential, using sulforhodamine B (SRB) assay towards the A549 and MCF-7 cancer cell lines...
November 8, 2017: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
https://www.readbyqxmd.com/read/29116476/contribution-of-reactive-oxygen-species-to-the-anticancer-activity-of-aminoalkanol-derivatives-of-xanthone
#6
Daniel Sypniewski, Natalia Szkaradek, Tomasz Loch, Anna M Waszkielewicz, Agnieszka Gunia-Krzyżak, Daria Matczyńska, Dagna Sołtysik, Henryk Marona, Ilona Bednarek
Reactive oxygen species (ROS) are critically involved in the action of anticancer agents. In this study, we investigated the role of ROS in the anticancer mechanism of new aminoalkanol derivatives of xanthone. Most xanthones used in the study displayed significant pro-oxidant effects similar to those of gambogic acid, one of the most active anticancer xanthones. The pro-oxidant activity of our xanthones was shown both directly (by determination of ROS induction, effects on the levels of intracellular antioxidants, and expression of antioxidant enzymes) and indirectly by demonstrating that the overexpression of manganese superoxide dismutase decreases ROS-mediated cell senescence...
November 8, 2017: Investigational New Drugs
https://www.readbyqxmd.com/read/29110583/beta-mangostin-from-cratoxylum-arborescens-activates-the-intrinsic-apoptosis-pathway-through-reactive-oxygen-species-with-downregulation-of-the-hsp70-gene-in-the-hl60-cells-associated-with-a-g0-g1-cell-cycle-arrest
#7
Fatima Abdelmutaal Ahmed Omer, Najihah Binti Mohd Hashim, Mohamed Yousif Ibrahim, Firouzeh Dehghan, Maizatulakmal Yahayu, Hamed Karimian, Landa Zeenelabdin Ali Salim, Syam Mohan
Xanthones are phytochemical compounds found in a number of fruits and vegetables. Characteristically, they are noted to be made of diverse properties based on their biological, biochemical, and pharmacological actions. Accordingly, the apoptosis mechanisms induced by beta-mangostin, a xanthone compound isolated from Cratoxylum arborescens in the human promyelocytic leukemia cell line (HL60) in vitro, were examined in this study. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay was done to estimate the cytotoxicity effect of β-mangostin on the HL60 cell line...
November 2017: Tumour Biology: the Journal of the International Society for Oncodevelopmental Biology and Medicine
https://www.readbyqxmd.com/read/29096404/cyclopia-extracts-enhance-th1-th2-and-th17-type-t-cell-responses-and-induce-foxp3-cells-in-murine-cell-culture
#8
Shiho Murakami, Yutaka Miura, Makoto Hattori, Hiroshi Matsuda, Christiaan J Malherbe, Christo J F Muller, Elizabeth Joubert, Tadashi Yoshida
Cyclopia genistoides, one of the traditional South African medicinal plants, and other species of the same genus offer noteworthy phenolic profiles, in particular high levels of the anti-allergic xanthone mangiferin. Hot water and 40% ethanol-water (v/v) extracts, prepared from C. genistoides, Cyclopia subternata, and Cyclopia maculata, were tested for immune-regulating activity in vitro using murine splenocytes and mesenteric lymph node cells. The 40% ethanol-water extracts of C. genistoides and C. subternata significantly enhanced production of several types of cytokines, including IL-4, IL-17, and IFN-γ, by antigen-stimulated splenocytes...
November 2, 2017: Planta Medica
https://www.readbyqxmd.com/read/29078174/studies-on-the-chemical-and-intestinal-metabolic-profiles-of-polygalae-radix-by-using-uhplc-it-ms-n-and-uhplc-q-tof-ms-method-coupled-with-intestinal-bacteria-incubation-model-in-vitro
#9
Gui-Fang Feng, Shu Liu, Zi-Feng Pi, Feng-Rui Song, Zhi-Qiang Liu
Polygala Radix (PR) is one of the most commonly used traditional Chinese medicines (TCM), but its effective materials are still not very clear. In order to solve the existing problems, the chemical and intestinal metabolic profiles of PR were analyzed via intestinal bacteria incubation model. An integrated analysis method combined ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF MS) method and ultra-high performance liquid chromatography with ion-trap multi-stage tandem mass spectrometry (UHPLC-IT-MS(n)) method was established...
October 18, 2017: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/29077076/-click-chemistry-synthesis-of-novel-natural-product-like-caged-xanthones-bearing-a-1-2-3-triazole-moiety-with-improved-druglike-properties-as-orally-active-antitumor-agents
#10
Xiang Li, Yue Wu, Yanyan Wang, Qidong You, Xiaojin Zhang
DDO-6101, a natural-product-like caged xanthone discovered previously in our laboratory based on the pharmacophoric scaffold of the Garcinia natural product gambogic acid (GA), shows potent cytotoxicity in vitro, but poor efficacy in vivo due to its poor druglike properties. In order to improve the druglike properties and in vivo antitumor potency, a novel series of ten triazole-bearing caged xanthone derivatives of DDO-6101 has been efficiently synthesized by 'click chemistry' and evaluated for their in vitro antitumor activity and druglike properties...
October 27, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29076348/synthesis-and-evaluation-of-xanthone-derivatives-as-acid-sphingomyelinase-inhibitors-potential-treatment-for-uv-induced-skin-damage
#11
Kan Yang, Biao Gao, Xianjun Ming, Zhipeng Huang, Minghui Wang, Jibin Dong, Jinxin Wang
AIM: ASM, which hydrolyzes sphingomyelin into ceramide, is recognized as a therapeutic target for UV-induced skin damage. Direct inhibitors for this enzyme are rare. Here we synthesized several series of 1,3,6,7-tetrahydroxy-xanthone derivatives as novel ASM inhibitors. RESULTS: Several compounds were more potent than the lead compound, among which 5b was found competitively inhibiting the enzyme and dose-dependently reducing ceramide generation. Furthermore, 5b and 5c showed excellent protective effect to skin keratinocytes against UV...
October 2017: Future Medicinal Chemistry
https://www.readbyqxmd.com/read/29050237/modulation-of-the-nur77-bcl-2-apoptotic-pathway-by-p38%C3%AE-mapk
#12
Jie Liu, Guang-Hui Wang, Ying-Hui Duan, Yi Dai, Yuzhou Bao, Mengjie Hu, Yu-Qi Zhou, Mingyu Li, Fuquan Jiang, Hu Zhou, Xin-Sheng Yao, Xiao-Kun Zhang
Orphan nuclear receptor Nur77 promotes apoptosis by targeting mitochondria through interaction with Bcl-2, an event that converts Bcl-2 from a survival to killer. However, how the Nur77-Bcl-2 apoptotic pathway is regulated remains largely unknown. In this study, we examined the regulation of the Nur77-Bcl-2 pathway by CCE9, a xanthone compound. Our results demonstrated that the apoptotic effect of CCE9 depended on its induction of Nur77 expression, cytoplasmic localization, and mitochondrial targeting. The activation of the Nur77-Bcl-2 pathway by CCE9 was associated with its activation of p38α MAPK...
September 19, 2017: Oncotarget
https://www.readbyqxmd.com/read/29039600/synergism-between-%C3%AE-mangostin-and-trail-induces-apoptosis-in-squamous-cell-carcinoma-of-the-oral-cavity-through-the-mitochondrial-pathway
#13
Masakatsu Fukuda, Hide Sakashita, Hiroyasu Hayashi, Junya Shiono, Genki Miyake, Yusuke Komine, Fuyoko Taira, Hideaki Sakashita
Mangosteen (Garcinia mangostana) is a tree found in South-East Asia and the pericarp of its fruit has been used in folk medicine for the treatment of many human illnesses. Mangosteen fruit rinds contain a high concentration of xanthone, which is a type of polyphenol. One type of xanthone, α-mangostin, has been reported to exert chemopreventive effects against chemically-induced colon cancer through the decrease of c-Myc expression, suppressing tumor growth in a mouse model of mammary cancer. A recent study demonstrated the inhibitive effect of α-mangostin on the growth of prostate cancer...
October 12, 2017: Oncology Reports
https://www.readbyqxmd.com/read/29034186/medicinal-biological-and-phytochemical-properties-of-gentiana-species
#14
REVIEW
Fatemeh Mirzaee, Amirsaeed Hosseini, Hossein Bakhshi Jouybari, Ali Davoodi, Mohammad Azadbakht
Gentiana, a cosmopolitan and important genus of the Gentianaceae family, comprises 400 species distributed among the world. Based on the studies of Iranian traditional medicine texts, there are some promising bioactivities for this genus that is unknown in modern medicine and some of them are still the basis of new remedies. In traditional medicine texts, Gentiana's different exclusive forms of preparations are effective for treatment of some disorders such as menstrual over-bleeding, conjunctivitis, vitiligo, animals venom poisoning, injuries, infected wounds, pain and swelling of liver, spleen, stomach and sprains of muscles...
October 2017: Journal of Traditional and Complementary Medicine
https://www.readbyqxmd.com/read/29031558/resolution-and-identification-of-scalemic-caged-xanthones-from-the-leaf-extract-of-garcinia-propinqua-having-potent-cytotoxicities-against-colon-cancer-cells
#15
Teerayut Sriyatep, Cholpisut Tantapakul, Raymond J Andersen, Brian O Patrick, Stephen G Pyne, Chatchai Muanprasat, Sawinee Seemakhan, Suparerk Borwornpinyo, Surat Laphookhieo
A new scalemic 8,8a-dihydro caged xanthone (1) was isolated from the leaf extract of Garcinia propinqua. Five other known natural products, the three caged xanthones (2, 5 and 6) and the two neocaged xanthones, (3 and 4) were also isolated as scalemic mixtures. Their structures were characterized by spectroscopic methods. The enantiomeric ratios (er) of compounds 1-6 ranged from 1:0.7 to 1:0.9. These compounds were also resolved by semipreparative chiral HPLC. The absolute configurations of (+)-2 and (+)-3 were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation while the absolute configurations of the other compounds were determined by comparisons of their ECD spectra...
October 12, 2017: Fitoterapia
https://www.readbyqxmd.com/read/29027684/chemical-interaction-between-lilium-brownii-and-rhizoma-anemarrhenae-the-herbal-constituents-of-baihe-zhimu-decoction-by-liquid-chromatography-coupled-to-hybrid-triple-quadrupole-linear-ion-trap-mass-spectrometer
#16
Bo Yang, Zhirui Liu, Qian Wang, Peiyuan Xia
During the course of decoction, the components of herbal formula interact with each other, such that chemical extraction characteristics are altered. The crude drugs, Lilium brownii (Baihe) and Rhizoma Anemarrhenae (Zhimu), are the herbal constituents of Baihe Zhimu decoction, a traditional herbal formula. To investigate the chemical interaction between Baihe and Zhimu when decocting together, eight marker components in Baihe Zhimu decoction were simultaneously characterized and quantified in one run by a hybrid triple quadrupole linear ion trap mass spectrometer in the multiple reactions monitoring-information dependent acquisition-enhanced product ion (MRM-IDA-EPI) mode...
October 13, 2017: Biomedical Chromatography: BMC
https://www.readbyqxmd.com/read/29024899/mangiferin-ameliorates-fatty-liver-via-modulation-of-autophagy-and-inflammation-in-high-fat-diet-induced-mice
#17
Hu Wang, Yang-Yang Zhu, Li Wang, Tian Teng, Meng Zhou, Shu-Guang Wang, Yi-Zhu Tian, Lei Du, Xiao-Xing Yin, Ying Sun
Non-alcoholic fatty liver disease (NAFLD) is the most common liver disease globally. The progression of NAFLD is complex and associated with inflammation, oxidative stress, autophagy, endoplasmic reticulum stress, and insulin resistance. Mangiferin, a natural C-glucosyl xanthone, has been reported to show multiple biological activities. The aim of this study was to investigate the therapeutic effect of mangiferin on NAFLD and the underlying molecular mechanism. We established a mouse model of NAFLD using a high-fat diet (HFD), and injected the mice with different doses of mangiferin (15, 30, and 60mg/kg, intraperitoneal) for 12 weeks...
October 9, 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/29023411/scientific-study-of-gentiana-kurroo-royle
#18
REVIEW
Bhat Mohd Skinder, Bashir Ahmad Ganai, Abdul Hamid Wani
The present investigation was carried out to review and highlight the potential phytochemicals and medicinal phenomena of the critically endangered medicinal plant, Gentiana kurroo Royle of the western and north-western Himalayas. The medicinal plant is heavily exploited for root and rhizome. Due to its endemic nature and the high rate of exploitation from its natural habitat, this species had become critically endangered. The phytochemical screening of the plant revealed that the plant contains some vital phyto-constituents (iridoids, xanthones, C-glucoxanthone mangiferin, and C-glucoflavones) that have a medicinal value for various acute and chronic diseases...
October 12, 2017: Medicines (Basel, Switzerland)
https://www.readbyqxmd.com/read/29019929/chemical-and-biological-research-on-herbal-medicines-rich-in-xanthones
#19
REVIEW
Jingya Ruan, Chang Zheng, Yanxia Liu, Lu Qu, Haiyang Yu, Lifeng Han, Yi Zhang, Tao Wang
Xanthones, as some of the most active components and widely distributed in various herb medicines, have drawn more and more attention in recent years. So far, 168 species of herbal plants belong to 58 genera, 24 families have been reported to contain xanthones. Among them, Calophyllum, Cratoxylum, Cudrania, Garcinia, Gentiana, Hypericum and Swertia genera are plant resources with great development prospect. This paper summarizes the plant resources, bioactivity and the structure-activity relationships (SARs) of xanthones from references published over the last few decades, which may be useful for new drug research and development on xanthones...
October 11, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28963904/design-synthesis-and-biological-evaluation-of-1-3-dihydroxyxanthone-derivatives-effective-agents-against-acetylcholinesterase
#20
Cintia A Menéndez, Brunella Biscussi, Sebastián Accordino, A Paula Murray, Darío C Gerbino, Gustavo A Appignanesi
The present work concerns the rational design and development of new inhibitors of acetylcholinesterase (AChE) based on the privileged xanthone scaffold. In order to understand and rationalize the mode of action of these target structures a theoretical study was initially conducted. From the results of rational design, a new variety of amphiphilic xanthone derivatives were synthesized, structurally characterized and evaluated as potential anti-Alzheimer agents. The results showed that most of the synthesized compounds exhibited high AChE inhibitory activity at the micromolar range (IC50, 0...
September 22, 2017: Bioorganic Chemistry
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