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Wen-Jin Wu, Ru Yan, Ting Li, Ya-Ping Li, Rui-Na Zhou, Yi-Tao Wang
ETHNOPHARMACOLOGICAL RELEVANCE: Rhubarb (Rhei Rhizoma et Radix) is used for the treatment of digestive diseases in traditional medicinal practice in China. Recent studies also support its beneficial activities in alleviating ulcerative colitis (UC). AIM OF THE STUDY: This study aimed to characterize the oral pharmacokinetics of rhubarb anthraquinones, the main bioactive components of this herb, in the experimental chronic colitis rat model induced by dextran sulfate sodium (DSS) and to identify the factors causing the pharmacokinetic alterations...
February 14, 2017: Journal of Ethnopharmacology
Woo Nam, Sung Phil Kim, Seok Hyun Nam, Mendel Friedman
Anthraquinone (9,10-anthraquinone) and several hydroxy derivatives, including purpurin (1,2,4-trihydroxyanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), and chrysazin (1,8-dihydroxyanthraquinone), were evaluated for antioxidative and anti-inflammatory activities in chemical assays and mammalian cells (murine macrophage RAW 264.7 cells). Several tests were used to assess their activities: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical; ABTS radical cation; hydrogen peroxide scavenging; reduction of potassium ferricyanide; chelation of ferrous ions; inhibition of lipid peroxidation; inhibition of nitric oxide generation; scavenging of the intracellular hydroxyl radical; expression of NLRP3 polypeptide for inflammasome assembly; and quantitation of proinflammatory cytokine interleukin 1β (IL-1β) for inflammasome activation...
February 10, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Arijit Singha Hazari, Abhishek Mandal, Katharina Beyer, Alexa Paretzki, Wolfgang Kaim, Goutam Kumar Lahiri
Redox series [LnRu(μ-DPPP)RuLn](k), H2DPPP = 2,5-dihydro-3,6-di-2-pyridylpyrrolo(3,4-c)pyrrole-1,4-dione and L = 2,4-pentanedionato (acac(-)), 2,2'-bipyridine (bpy), and 2-phenylazopyridine (pap), have been studied by voltammetry (CV, DPV), EPR, and UV-vis-NIR spectroelectrochemistry, supported by TD-DFT calculations. Crystal structure analysis and (1)H NMR revealed oxidation states [(acac)2Ru(III)(μ-DPPP(2-))Ru(III)(acac)2] and [(bpy)2Ru(II)(μ-DPPP(2-))Ru(II)(bpy)2](2+) for the corresponding precursors, isolated as rac diastereomers...
February 16, 2017: Inorganic Chemistry
Ali K Ismael, Iain Grace, Colin J Lambert
Using a first principles approach combined with analysis of heuristic tight-binding models, we examine the connectivity dependence of two forms of quantum interference in single molecules. Based on general arguments, Fano resonances are shown to be insensitive to connectivity, while Mach-Zehnder-type interference features are shown to be connectivity dependent. This behaviour is found to occur in molecular wires containing anthraquinone units, in which the pendant carbonyl groups create Fano resonances, which coexist with multiple-path quantum interference features...
February 16, 2017: Physical Chemistry Chemical Physics: PCCP
Ali K Ismael, Alaa Al-Jobory, Iain Grace, Colin J Lambert
Crown-ether molecules are well known to selectively bind alkali atoms, so by incorporating these within wires, any change in electrical conductance of the wire upon binding leads to discriminating sensing. Using a density functional theory-based approach to quantum transport, we investigate the potential sensing capabilities of single-molecule junctions formed from crown ethers attached to anthraquinone units, which are in turn attached to gold electrodes via alkyl chains. We calculate the change in electrical conductance for binding of three different alkali ions (lithium, sodium, and potassium)...
February 14, 2017: Journal of Chemical Physics
Jesica A Dimmer, Susana C Núñez Montoya, Caterine S Mendoza, José L Cabrera
Seven anthraquinones were isolated from aerial parts of Heterophyllaea lycioides (Rusby) Sandwith (Rubiaceae), including three derivatives that have not been described before: a hetero-bianthraquinone identified as (R)-2-hydroxymethyl-2'methyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (lycionine), and two mono-chlorinated derivatives related to soranjidiol. One of them is a homo-bianthraquinone: (R)-7-chloro-2,2'-dimethyl-1,1',6,6'-tetrahydroxy-5,5' bianthraquinone (7-chlorobisoranjidiol), whereas the second halogenated derivative corresponds to a monomeric structure: 5-chloro-1,6-dihydroxy-2-methyl anthraquinone (5-chlorosoranjidiol)...
February 10, 2017: Phytochemistry
Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim
Monoamine oxidase (MAO) catalyzes the oxidation of monoamines that act as neurotransmitters. During a target-based screening of natural products using two isoforms of recombinant human MAO-A and MAO-B, purpurin (an anthraquinone derivative) was found to potently and selectively inhibit MAO-A, with an IC50 value of 2.50μM, and not to inhibit MAO-B. Alizarin (also an anthraquinone) inhibited MAO-A less potently with an IC50 value of 30.1μM. Furthermore, purpurin was a reversible and competitive inhibitor of MAO-A with a Ki value of 0...
January 31, 2017: Bioorganic & Medicinal Chemistry Letters
Jin Hyoung Cho, Jung-Il Chae, Jung-Hyun Shim
The Pin1 protein (or peptidyl-prolyl cis/trans isomerase) specifically catalyzes the cis/trans isomerization of phosphorylated serine/threonine-proline (Ser/Thr-Pro) bonds and plays an important role in many cellular events through the effects of conformational change in the function of c-Jun, its biological substrate. Pin1 expression is involved in essential cellular pathways that mediate cell proliferation, cell cycle progression, tumorigenesis and apoptosis by altering their stability and function, and it is overexpressed in various types of tumors...
March 2017: Oncology Reports
Monika Janeczko, Maciej Masłyk, Konrad Kubiński, Hieronim Golczyk
Emodin (1,3,8-trihydroxy-6-methyl-anthraquinone) is a natural secondary plant product, originally isolated from the rhizomes of Rheum palmatum. Many reports show its diuretic, vasorelaxant, anti-bacterial, anti-viral, anti-ulcerogenic, immunosuppressive, hepatoprotective, anti-inflammatory, and anti-cancer potential. Emodin is a pleiotropic molecule capable of interacting with several major molecular targets, e.g. NF-κB, AKT/mTOR, and STAT3. The compound can also act as an inhibitor of some protein kinases, with special affinity to protein kinase CK2...
February 8, 2017: Yeast
André T Gotardo, Mitsue Haraguchi, Paulo C F Raspantini, Maria L Z Dagli, Silvana L Górniak
Senna occidentalis is a toxic leguminous plant found in many tropical and subtropical regions of the world and causes poisoning mainly in confined animals. The seeds are the most toxic part of the plant and may be present in animal rations. The main toxic component of the S. occidentalis seed is a dianthrone, an anthraquinone-derived compound that affects mitochondrial function. This study evaluated the effects on egg production of low-level contamination of the S. occidentalis in the laying hens' diet. Forty-eight one-day-old pullets were randomly allocated into two treatment groups: control, birds that received no experimental treatment; and external and internal tegument (ET/IT), birds that received a diet containing 0...
February 6, 2017: Avian Pathology: Journal of the W.V.P.A
Li Kang, Luqin Si, Jing Rao, Dan Li, Ya Wu, Sanlan Wu, Minghui Wu, Sijie He, Wenwen Zhu, Yang Wu, Jiaqiang Xu, Gao Li, Jiangeng Huang
Hepatic adverse reaction associated with Polygoni Multiflori Radix (PMR) has been frequently reported in recent years. Highly-enriched anthraquinones (AQs) in PMR, such as emodin, chrysophanol and physcion, have been found to be hepatotoxic. In the present study, sandwich-cultured rat hepatocytes (SCRHs) were employed to investigate the effect of individual and combined AQs on the disposition of endogenous bile acids (BAs) and exogenous probe substrates including deuterium-labeled taurocholate (d5-TCA), glycochenodeoxycholic acid (d4-GCDCA) and 5 (and 6)-carboxy-2,7'dichlorofluorescein (CDF)...
February 1, 2017: Toxicology in Vitro: An International Journal Published in Association with BIBRA
Yaoyu Zhou, Jiachao Zhang, Lin Tang, Bo Peng, Guangming Zeng, Lin Luo, Jun Gao, Ya Pang, Yaocheng Deng, Fengfeng Zhang
A label-free electrochemical sensor, based on a classic lead ions (Pb(2+))-dependent GR-5DNAzyme as the catalytic unit, disodium-anthraquinone-2,6-disulfonate (AQDS) as DNA intercalator, and nanoporous gold (NPG) for signal amplification, was designed for sensitive and selective detection of Pb(2+). Firstly, NPG modified electrode surface were employed as a platform for the immobilization of thiolated probe DNA, and then, hybridized with DNAzyme catalytic beacons. The Pb(2+)-induced catalytic reaction makes the substrate strand break at the cleavage sitGe irreversibly, which disturbs the formation of DNA strands...
April 1, 2017: Talanta
Min Zhou, Huan-Huan Xing, Yan Yang, Yue-De Wang, Kun Zhou, Wei Dong, Gan-Peng Li, Wei-Yao Hu, Qiang Liu, Xue-Mei Li, Qiu-Fen Hu
Three previously unreported anthraquinones, fistulaquinones A-C (1-3), together with three known ones (4-6) were isolated from the twigs of Cassia fistula. Their structures were determined by means of extensive NMR and MS spectroscopic analyses. All the isolated compounds were tested for their anti-tobacco mosaic virus (anti-TMV) activity, and compound 3 showed significant activity with inhibition rate of 34.5% at 20 μM concentration, even more potent than positive control. Additionally, compounds 1-6 exhibited moderate cytotoxicity with IC50 values ranging from 2...
February 2, 2017: Journal of Asian Natural Products Research
Zhuan Zhang, Yu-Kang Gong, Qiang Zhou, Yu Hu, Hong-Min Ma, Yong-Sheng Chen, Yasuhiro Igarashi, Lifeng Pan, Gong-Li Tang
Ranking among the most effective anticancer drugs, anthracyclines represent an important family of aromatic polyketides generated by type II polyketide synthases (PKSs). After formation of polyketide cores, the post-PKS tailoring modifications endow the scaffold with various structural diversities and biological activities. Here we demonstrate an unprecedented four-enzyme-participated hydroxyl regioisomerization process involved in the biosynthesis of kosinostatin. First, KstA15 and KstA16 function together to catalyze a cryptic hydroxylation of the 4-hydroxyl-anthraquinone core, yielding a 1,4-dihydroxyl product, which undergoes a chemically challenging asymmetric reduction-dearomatization subsequently acted by KstA11; then, KstA10 catalyzes a region-specific reduction concomitant with dehydration to afford the 1-hydroxyl anthraquinone...
January 30, 2017: Proceedings of the National Academy of Sciences of the United States of America
Ting-Jian Zhang, Song-Ye Li, Wei-Yan Yuan, Qing-Xia Wu, Lin Wang, Su Yang, Qi Sun, Fan-Hao Meng
A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC50 values of 0.6μM and 0.8μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound 1h acted as a mixed-type xanthine oxidase inhibitor. SAR analysis showed that the benzaldehyde moiety played a more important role than the anthraquinone moiety for inhibition potency...
January 16, 2017: Bioorganic & Medicinal Chemistry Letters
Lauren Ford, Robert L Henderson, Christopher M Rayner, Richard S Blackburn
Madder (Rubia tinctorum L.) has been widely used as a red dye throughout history. Acid-sensitive colorants present in madder, such as glycosides (lucidin primeveroside, ruberythric acid, galiosin) and sensitive aglycons (lucidin), are degraded in the textile back extraction process; in previous literature these sensitive molecules are either absent or present in only low concentrations due to the use of acid in typical textile back extraction processes. Anthraquinone aglycons alizarin and purpurin are usually identified in analysis following harsh back extraction methods, such those using solvent mixtures with concentrated hydrochloric acid at high temperatures...
January 24, 2017: Journal of Chromatography. A
Derrick Watkins, Changjun Gong, Patrick Kellish, Dev P Arya
Nucleic acids adopt a broad array of hydrogen-bonded structures that enable their diverse roles in the cell; even the familiar DNA double helix displays subtle architectural nuances that are sequence dependent. While there have been many approaches for recognition of B-form nucleic acids, A-form DNA recognition has lagged behind. Here, using a tight binding fluorescein-neomycin (F-neo) conjugate that can probe the electrostatic environment of A-form DNA major groove, we developed a fluorescent displacement assay to be used as a screen for DNA duplex-binding compounds...
November 2, 2016: Bioorganic & Medicinal Chemistry
Zhonghui Huang, Xuhua Nong, Zhe Ren, Jie Wang, Xiaoyong Zhang, Shuhua Qi
Chemical investigation of the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502 resulted in the isolation of three new anthraquinones, aspergilols G-I (1-3), one new diphenyl ether, 4-carbglyceryl-3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (4), and one new benzaldehyde derivative, 2,4-dihydroxy-6-(4-methoxy-2-oxopentyl)-3-methylbenzaldehyde (5), along with 23 known phenolic compounds (6-28). The structures of new compounds were elucidated by extensive spectroscopic analysis. The absolute configuration of 3 was established by CD spectrum and the modified Mosher method...
January 16, 2017: Bioorganic & Medicinal Chemistry Letters
Ming-Hua Xie, Rong Shao, Xin-Guo Xi, Gui-Hua Hou, Rong-Feng Guan, Peng-Yu Dong, Qin-Fang Zhang, Xiu-Li Yang
A 3D metal-organic framework (ADA-Cd) constructed by diacrylate substituted anchracene sharing structural characters similar to some frequently employed anthraquinone type dye sensitizers was introduced as effective sensitizer for anatase TiO2 to achieve enhanced visible light photocatalytic performance. A facile mechanical mixing procedure was adopted to prepare the co-catalyst denoted as ADA-Cd/TiO2, which showed enhanced photodegradation ability as well as sustainability towards several dyes under visible light irradiation...
January 25, 2017: Chemistry: a European Journal
Jörgen Forss, Markus V Lindh, Jarone Pinhassi, Ulrika Welander
Textile dying processes often pollute wastewater with recalcitrant azo and anthraquinone dyes. Yet, there is little development of effective and affordable degradation systems for textile wastewater applicable in countries where water technologies remain poor. We determined biodegradation of actual textile wastewater in biofilters containing rice husks by spectrophotometry and liquid chromatography mass spectrometry. The indigenous microflora from the rice husks consistently performed >90% decolorization at a hydraulic retention time of 67 h...
2017: PloS One
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