3542-72-1Relevant academic research and scientific papers
Lipid and Phenolic Constituents from Seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their Antioxidant Activity
Heinrich, Miriam,Lorenz, Peter,Daniels, Rolf,Stintzing, Florian C.,Kammerer, Dietmar R.
, (2017)
Seeds of Hypericum perforatum and H. tetrapterum were extracted with dichloromethane and methanol and investigated by chromatographic and mass spectrometric methods. Both species yielded a fatty oil fraction amounting to 30.5% and 18.0% of the seed weight, respectively. Linoleic acid (C18:2n-6) was shown to be the predominant fatty acid constituent. Moreover, xanthone derivatives, i.e. tetrahydroxyxanthones (THX), xanthone-glycosides and xanthone-sulfonates, were assigned in methanolic extracts. For structure elucidation, one representative xanthone, namely 1,3,6,7-THX, was synthesized and analyzed via HPLC-DAD/MSn and GC/MS. Total THX contents were quantitated applying a validated HPLC-DAD method, resulting in 1.25 g/kg (H. perforatum) and 0.27 g/kg (H. tetrapterum), respectively. Moreover, the free radical scavenging capacity of the methanol extracts was tested using the DPPH antioxidant assay. Both, H. perforatum (IC50 = 8.7 mg/l) and 1,3,6,7-THX (IC50 = 3.0 mg/l), exhibited good DPPH free radical scavenging activity compared to Trolox (IC50 = 6.6 mg/l).
A novel and efficient synthesis of norathyriol using Pd(II) as a catalyst
Qin, Qi-Xue,Yang, Jian,Yang, Bo
, p. 1633 - 1636 (2014)
A facile and simple procedure for the synthesis of norathyriol using Pd(II) as a catalyst via two steps under mild conditions is described. The major advantages of this method are the use of a commercially available catalyst, short reaction times, and the simplicity of the reaction and work-up. The overall yield of 36.6 % is acceptable.
XANTHONES FROM THE ROOTS OF Swertia iberica
Denisova, O. A.,Glyzin, V. I.,Patudin, A. V.,Fesenko, D. A.
, p. 145 - 149 (1980)
From the roots of Swertia iberica, together with the previously known swertiaperenin decussatin, gentiakochianin, and norswertianin, we have isolated two new xanthones - isogentiakochianin and swertiaiberin.On the basis of UV, IR, PMR, and mass spectroscopy, the structure of 1,3,8-trihydroxy-7-methoxyxanthone is proposed for isogentiakochianin, and that of 1,2,3-trihydroxy-7,8-dimethoxyxanthone for swertiaiberin.
Yeast-mediated xanthone synthesis through oxidative intramolecular cyclization
Fromentin, Yann,Grellier, Philippe,Buisson, Didier,Lallemand, Marie-Christine,Wansi, Jean Duplex
, p. 5054 - 5057,4 (2012)
Benzoylphloroglucinol derivatives are natural products showing diverse biological activities that could be modulated by structural modifications. For this purpose, we studied the biotransformation of guttiferone A and of maclurin using a combinatorial approach for screening active microorganism strains. We found a novel and unexpected yeast-catalyzed oxidation that has selectively given a new oxy-guttiferone A and norathyriol.
Design, synthesis, and biological evaluation of 1,3,6,7-tetrahydroxyxanthone derivatives as phosphoglycerate mutase 1 inhibitors
Jiang, Kaixuan,Gao, Biao,Yu, Jing,Jiang, Lulu,Niu, Ao,Jia, Yihe,Meng, Tao,Zhou, Lu,Wang, Jinxin
supporting information, (2021/02/09)
Phosphoglycerate mutase 1 (PGAM1) is a promising target for cancer treatment. Herein, we found that α-mangostin and γ-mangostin exhibited moderate PGAM1 inhibitory activities, with IC50 of 7.2 μM and 1.2 μM, respectively. Based on α-mangostin, a series of 1,3,6,7-tetrahydroxyxanthone derivatives were designed, synthesized and evaluated in vitro for PGAM1 inhibition. The significant structure–activity relationships (SAR) and a fresh binding mode of this kind of new compounds were also clearly described. This study provides valuable information for further optimization of PGAM1 inhibitors with 1,3,6,7-tetrahydroxyxanthone backbone or de novo design of novel inhibitor.
Preparing method of norathyriol using eco-friendly C-deglycosylation
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Paragraph 0032-0087, (2019/09/11)
The present invention relates to a method for preparing norathyriol using eco-friendly carbon deglycosylation. The method for preparing norathyriol using eco-friendly carbon deglycosylation comprises: a step of adding mangiferin, resorcinol, or a derivative thereof to a dilute aqueous solution, and heating and refluxing the same; a step of cooling the refluxed solution to room temperature, adding a basic solution, and mixing the mixture; a step of stirring the mixed solution, and then filtering, washing and drying the same; a step of adding the dried crude norathyriol to an organic solvent, and heating and stirring the same; and a step of filtering and washing the stirred solution and concentrating the same. The method in accordance with the present invention is an eco-friendly method which can replace the existing technology which requires the use of toxic materials, and can be used in a mass production method which is needed for research studies of raw materials and medicines using norathyriol.COPYRIGHT KIPO 2019
Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them
Liu, Jie,Zhang, Jianrun,Wang, Huailing,Liu, Zhijun,Zhang, Cao,Jiang, Zhenlei,Chen, Heru
, p. 50 - 61 (2017/04/06)
34 Xanthones were synthesized by microwave assisted technique. Their in?vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231?cell line growth with an IC50 of 0.46?±?0.03?μM. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.
A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers
Huang, Zheng,Lumb, Jean-Philip
, p. 11543 - 11547 (2016/11/17)
ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.
Discovery of novel xanthone derivatives as xanthine oxidase inhibitors
Hu, Lina,Hu, Honggang,Wu, Weifeng,Chai, Xiaoyun,Luo, Jianfei,Wu, Qiuye
scheme or table, p. 4013 - 4015 (2011/08/02)
Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. In this study, a series of xanthone derivatives were synthesized as effective and a new class of xanthine oxidase inhibitor. Compounds 8a, 8c, 8i, 8g and 8r showed good inhibition against xanthine oxidase. The presence of a cyano group at the para position of benzyl moiety turned out to be the preferred substitution pattern. Molecular modeling studies were performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors associated with the xanthone framework.
γ-Pyrone compounds. II: Synthesis and antiplatelet effects of tetraoxygenated xanthones
Lin,Liou,Ko,Teng
, p. 1109 - 1112 (2007/10/02)
Norathyriol and its analogues, 1,3,5,6-, 3,4,5,6-, 3,4,6,7- and 2,3,6,7- tetrahydroxyxanthone, were synthesized from benzophenone precursors by Friedel-Crafts acylation and subsequent base-catalyzed cyclization to eliminate methanol. Both 3,4,6,7- and 2,3,6,7-tetrahydroxyxanthone tetraacetate showed potent anti-platelet aggregation effects on arachidonic acid-induced platelet aggregation. 3,4,6,7-Tetrahydroxyxanthone tetraacetate and 1,3,5,6-tetrahydroxyxanthone showed potent and significant anti-platelet aggregation effects on collagen-induced platelet aggregation.
