Статті в журналах: "'.3-Dihydroxyflavone"

1

Engelmann, Mark D., Ryan Hutcheson, and I. Francis Cheng. "Stability of Ferric Complexes with 3-Hydroxyflavone (Flavonol), 5,7-Dihydroxyflavone (Chrysin), and 3‘,4‘-Dihydroxyflavone." Journal of Agricultural and Food Chemistry 53, no. 8 (April 2005): 2953–60. http://dx.doi.org/10.1021/jf048298q.

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Ramasamy, Kavitha. "3′, 4′-dihydroxyflavone ameliorates paclitaxel model of peripheral neuropathy in mice by modulating KATP channel, adenosine (A3) and GABAA (a2 subunit) receptors." Bioinformation 19, no. 6 (June 30, 2023): 794–63. http://dx.doi.org/10.6026/97320630019754.

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Paclitaxel is a widely used cancer chemotherapeutic agent for many solid tumors; but peripheral neuropathy is a major limitation for its clinical use. Studies have demonstrated the usefulness of flavone derivatives in chemotherapy induced peripheral neuropathy. The present study evaluates the anti-neuropathic effect of 3′, 4′-dihydroxyflavone on paclitaxel-induced peripheral neuropathy and the underlying mechanisms. Paclitaxel was administered to mice in a single dose of 10 mg/kg, i.p.The neuropathic behavioural parameters such as mechanical allodynia, cold allodynia and thermal hyperalgesia were assessed 24 h later. The test compound 3′, 4′-dihydroxyflavone (50,100 or 200 mg/kg,s.c) was administered 30 min prior to the assessment of behavioral parameters. The possible mechanisms involving KATP channels, adenosine and GABAA receptors were explored by employing suitable interacting drugs. Molecular docking studies to predict the binding interactions of 3′, 4′-dihydroxyflavone at the above targets were also carried out. The test compound 3′, 4′-dihydroxyflavoneexhibited a significant reduction in paw withdrawal response score in both mechanical and cold allodynia and also increased the tail flick response time in thermal hyperalgesia due to paclitaxel-induced neuropathy. The anti-neuropathic effect of 3′, 4′-dihydroxyflavonewas significantly reversed by pre-treatment with glibenclamide, caffeine or bicuculline revealing the involvement of KATP channels, adenosine and GABAA receptors respectively. Furthermore, the molecular docking studies indicated a favourable binding affinity and good H-bond interaction of 3′, 4′-dihydroxyflavone at these targets. The findings of the present study suggests that, 3′, 4′-dihydroxyflavone has anti-neuropathic effect against paclitaxel-induced peripheral neuropathy through mechanisms that involve KATP channels, adenosine (A3) and GABAA (α2 subunit) receptors.

3

Labarrière, Luc, Aurélien Moncomble, and Jean-Paul Cornard. "pH dependency of the structural and photophysical properties of the atypical 2′,3-dihydroxyflavone." RSC Advances 10, no. 58 (2020): 35017–30. http://dx.doi.org/10.1039/d0ra06833k.

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Nassira GHEMBAZA, Nabila BELYAGOUBI-BENHAMMOU, Amel ZITOUNI, Fethi TOUL, Serge MICHALET, and Fawzia ATIK- BEKKARA. "Rapid identification analysis of chemical constituents of Sedum villosum L. (Orpin.) by UHPLC-DAD-HRSM." Journal of Natural Product Research and Applications 1, no. 01 (September 17, 2021): 15–23. http://dx.doi.org/10.46325/jnpra.v1i01.2.

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In the present paper, we are interested, for the first time, to separate and identify two glycosyl the flavones from Sedum villosum L, family Crassulaceae collected in the flowering phase in Lakhdar Oued, village of Tlemcen (Algeria). The crude methanolic extract of the flowers part was fractionated on column chromatography, and eluted with dichloromethane/methanol each time with increasing polarity of methanol; 24 fractions were separated. One of these fractions named F16 showed more antioxidant activity to scavenge DPPH free radical with percentage inhibition of 94.849 %. F16 was separated by thin-layer chromatography (TLC) to give 10 compounds. We were chosen the sub-fractions F16.8, which has antioxidative activity of 77.02 %, provided two major molecules of glycosyl the flavones, analysed by ultra-highperformance liquid chromatography coupled to mass spectrometry (UHPLC-DAD-HRSM). Compound 1 was identified as 7, 3'-dihydroxyflavone-5-O-dihexosyl-4'-O-deoxyhexose and compound 2 was 7, 3'-dihydroxyflavone-5-O-hexose- 4'-O-deoxyhexose.

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Tasdemir, Deniz, Marcel Kaiser, Reto Brun, Vanessa Yardley, Thomas J. Schmidt, Fatma Tosun, and Peter Rüedi. "Antitrypanosomal and Antileishmanial Activities of Flavonoids and Their Analogues: In Vitro, In Vivo, Structure-Activity Relationship, and Quantitative Structure-Activity Relationship Studies." Antimicrobial Agents and Chemotherapy 50, no. 4 (April 2006): 1352–64. http://dx.doi.org/10.1128/aac.50.4.1352-1364.2006.

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ABSTRACT Trypanosomiasis and leishmaniasis are important parasitic diseases affecting millions of people in Africa, Asia, and South America. In a previous study, we identified several flavonoid glycosides as antiprotozoal principles from a Turkish plant. Here we surveyed a large set of flavonoid aglycones and glycosides, as well as a panel of other related compounds of phenolic and phenylpropanoid nature, for their in vitro activities against Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani. The cytotoxicities of more than 100 compounds for mammalian L6 cells were also assessed and compared to their antiparasitic activities. Several compounds were investigated in vivo for their antileishmanial and antitrypanosomal efficacies in mouse models. Overall, the best in vitro trypanocidal activity for T. brucei rhodesiense was exerted by 7,8-dihydroxyflavone (50% inhibitory concentration [IC50], 68 ng/ml), followed by 3-hydroxyflavone, rhamnetin, and 7,8,3′,4′-tetrahydroxyflavone (IC50s, 0.5 μg/ml) and catechol (IC50, 0.8 μg/ml). The activity against T. cruzi was moderate, and only chrysin dimethylether and 3-hydroxydaidzein had IC50s less than 5.0 μg/ml. The majority of the metabolites tested possessed remarkable leishmanicidal potential. Fisetin, 3-hydroxyflavone, luteolin, and quercetin were the most potent, giving IC50s of 0.6, 0.7, 0.8, and 1.0 μg/ml, respectively. 7,8-Dihydroxyflavone and quercetin appeared to ameliorate parasitic infections in mouse models. Generally, the test compounds lacked cytotoxicity in vitro and in vivo. By screening a large number of flavonoids and analogues, we were able to establish some general trends with respect to the structure-activity relationship, but it was not possible to draw clear and detailed quantitative structure-activity relationships for any of the bioactivities by two different approaches. However, our results can help in directing the rational design of 7,8-dihydroxyflavone and quercetin derivatives as potent and effective antiprotozoal agents.

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Datta, Bidyut Kanti, Tahamina Iasmin, and Mohammad A. Rashid. "Further Flavonoids from Polygonum viscosum Buch-Ham. ex D. Don. (Polygonoceae)." Dhaka University Journal of Pharmaceutical Sciences 15, no. 1 (August 8, 2016): 27–30. http://dx.doi.org/10.3329/dujps.v15i1.29189.

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Three additional flavonoids such as 5,7,4?-trihydroxy-3,8,3?-trimethoxy flavonol (1), 5,7-dihydroxyflavone (chrysin, 2) and 5,6,7-trihydroxyflavone (baicalein, 3) were obtained from the methanol extract of whole plant of Polygonum viscosum. The structure of the isolated compounds was established exclusively by ultraviolet (UV) spectroscopy, mass spectrometry (MS) and a series of Nuclear Magnetic Resonance (NMR) analysis.Dhaka Univ. J. Pharm. Sci. 15(1): 27-30, 2016 (June)

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Fatoki, Toluwase, Stanley Chukwuejim, Omodele Ibraheem, Christiana Oke, Blessing Ejimadu, Isaiah Olaoye, Oluwabukola Oyegbenro, et al. "Harmine and 7,8-dihydroxyflavone synergistically suitable for amyotrophic lateral sclerosis management: An in silico study." Research Results in Pharmacology 8, no. 3 (August 25, 2022): 49–61. http://dx.doi.org/10.3897/rrpharmacology.8.83332.

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Introduction: Amyotrophic lateral sclerosis (ALS) is a fatal neurological disease characterized by progressive degeneration of both upper and lower motor neurons, resulting in paralysis and eventually leads to death from respiratory failure typically within 3 to 5 years of symptom onset. The aim of this work was to predict the pharmacokinetics and identify unique protein targets that are associated with potential anti-ALS phytochemicals and FDA-approved drugs, by in silico approaches. Materials and methods: Standard computational tools (webserver and software) were used, and the methods used are clustering analysis, pharmacokinetics and molecular target predictions, and molecular docking simulation. Results and discussion: The results show that riluzole, β-asarone, cryptotanshinone, harmine and 7,8-dihydroxyflavone have similar pharmacokinetics properties. Riluzole and harmine show 95% probability of target on norepinephrine transporter. Huperzine-A and cryptotanshinone show 100% probability of target on acetylcholinesterase. 7,8-dihydroxyflavone shows 35% probability of target on several carbonic anhydrases, 40% probability of target on CYP19A1, and 100% probability of target on inhibitor of nuclear factor kappa B kinase beta subunit and neurotrophic tyrosine kinase receptor type 2, respectively. Harmine also shows 95% probability of target on dual specificity tyrosine-phosphorylation-regulated kinases, threonine-protein kinases (haspin and PIM3), adrenergic receptors, cyclin-dependent kinases (CDK5 and CDK9), monoamine oxidase A, casein kinase I delta, serotonin receptors, dual specificity protein kinases (CLK1, CLK2, and CLK4), and nischarin, respectively. Also, the results of gene expression network show possible involvement of CDK1, CDK2, CDK4, ERK1, ERK2 and MAPK14 signaling pathways. This study shows that riluzole and harmine have closely similar physicochemical and pharmacokinetics properties as well as molecular targets, such as norepinephrine transporter (SLC6A2). Harmine, huperzine-A and cryptotanshinone could modulate acetylcholinesterase (AChE), which is involved in ALS-pathogenesis. The impact of 7,8-dihydroxyflavone on several carbonic anhydrases (CA) I, II, VII, IX, XII, and XIV, as well as CYP19A1, could help in remediating the respiratory failure associated with ALS. Conclusion: Overall, harmine is found to be superior to riluzole, and the combination of harmine with 7,8-dihydroxyflavone can provide more effective treatment for ALS than the current regime. Further work is needed to validate the predicted therapeutic targets of harmine identified in this study on ALS model or clinical trials, using in silico, in vitro and in vivo techniques. Graphical abstract:

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Espíndola, Cecilia. "Some Nanocarrier’s Properties and Chemical Interaction Mechanisms with Flavones." Molecules 28, no. 6 (March 22, 2023): 2864. http://dx.doi.org/10.3390/molecules28062864.

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Flavones such as 7,8-dihydroxyflavone (tropoflavin), 5,6,7-trihydroxyflavone (baicalein), 3′,4′,5,6-tetrahydroxyflavone (luteolin), 3,3′,4′,5,5′,7-hexahydroxyflavone (myricetin), 4′,5,7-trihydroxyflavone (apigenin), and 5,7-dihydroxyflavone (chrysin) are important both for their presence in natural products and for their pharmacological applications. However, due to their chemical characteristics and their metabolic processes, they have low solubility and low bioavailability. Knowledge about the physicochemical properties of nanocarriers and the possible mechanisms of covalent and non-covalent interaction between nanoparticles (NPs) and drugs is essential for the design of nanocarriers to improve the bioavailability of molecules with pharmacological potential, such as tropoflavin, baicalein, luteolin, myricetin, apigenin, and chrysin. The parameters of characterization of some NPs of these flavones, such as size, polydispersity index (PDI), zeta potential, encapsulation efficiency (EE), and % release/time, utilized in biomedical applications and the covalent and non-covalent interactions existing between the polymeric NPs and the drug were analyzed. Similarly, the presence of functional groups in the functionalized carbon nanotubes (CNTs), as well as the effect of pH on the % adsorption of flavonoids on functionalized multi-walled carbon nanotubes (MWCNT-COOH), were analyzed. Non-covalent interaction mechanisms between polymeric NPs and flavones, and covalent interaction mechanisms that could exist between the NPs and the amino and hydroxyl functional groups, are proposed.

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Kim, Namkwon, Hyung-Seok Yoo, Yeon-Joo Ju, Myung Sook Oh, Kyung-Tae Lee, Kyung-Soo Inn, Nam-Jung Kim, and Jong Kil Lee. "Synthetic 3',4'-Dihydroxyflavone Exerts Anti-Neuroinflammatory Effects in BV2 Microglia and a Mouse Model." Biomolecules & Therapeutics 26, no. 2 (March 1, 2018): 210–17. http://dx.doi.org/10.4062/biomolther.2018.008.

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Šimunková, Miriama, and Michal Malček. "Dimethyl sulfoxide as a strongly coordinating solvent: 3′,4′-dihydroxyflavone-Cu(II)-DMSO system case study." Acta Chimica Slovaca 13, no. 2 (October 1, 2020): 38–48. http://dx.doi.org/10.2478/acs-2020-0022.

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Abstract Dimethyl sulfoxide (DMSO) is an aprotic organic solvent widely used in laboratory practice due to its ability to dissolve both polar and nonpolar compounds. However, DMSO is also commonly known as a strongly coordinating solvent, especially towards transition metal containing complexes. In this study, estimation of the coordination ability of DMSO towards the Cu(II) ion was attempted, employing a model system composed of 3′,4′-dihydroxyflavone-Cu(II) complex in the presence of explicit DMSO molecules, using the density functional theory (DFT). Nature of the Cu-DMSO chemical interaction (i.e. Cu-O bonding) was studied within the framework of quantum theory of atoms in molecules (QTAIM). Impact of DMSO coordination on the charge and spin distribution at Cu(II) ion was inspected using Mulliken population and QTAIM analysis.

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Sakalauskas, Andrius, Agne Janoniene, Gediminas Zvinys, Kamile Mikalauskaite, Mantas Ziaunys, and Vytautas Smirnovas. "Exploring the Formation of Polymers with Anti-Amyloid Properties within the 2′3′-Dihydroxyflavone Autoxidation Process." Antioxidants 11, no. 9 (August 30, 2022): 1711. http://dx.doi.org/10.3390/antiox11091711.

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Amyloid-β and α-synuclein aggregation into amyloid fibrils is linked to the onset and progression of Alzheimer’s and Parkinson’s diseases. While there are only a few disease-modifying drugs, it is essential to search for new, more effective ways to encounter these neurodegenerative diseases. Multiple research articles have shown that the autoxidation of flavone is a critical factor for activating the inhibitory potential against the protein aggregation. Despite this, the structure of the newly-formed inhibitors is unknown. In this research, we examined the autoxidation products of 2′,3′-dihydroxyflavone that were previously shown to possess one of the most prominent inhibitory effects against amyloid-β aggregation. Their analysis using HPLC suggested the formation of polymeric molecules that were isolated using a 3 kDa cut-off. These polymeric structures were indicated as the most potent inhibitors based on protein aggregation kinetics and AFM studies. This revelation was confirmed using MALDI-TOF and NMR. We also show that active molecules have a tendency to reduce the Amyloid-β and α-synuclein aggregates toxicity to SH-SY5Y cells.

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Cody, Vivian, Joseph Luft, Mary Mc Court, and Klaus Irmscher. "Conformational analysis of flavonoids: Crystal and molecular structure of 3?,5?-dibromo-3-methyl-6,4?-dihydroxyflavone (1:2) triphenylphosphine oxide complex." Structural Chemistry 2, no. 6 (October 1991): 601–6. http://dx.doi.org/10.1007/bf00673444.

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Egwuatu, Ifeanyi Anthony, Chiadikobi Lawrence Ozoemena, Emeka Williams Ugwuishi, Christian Chiemeka Ozor, Augustine Oviosun, and Favour Onwene. "Deciphering the Ameliorative Potential of 5, 7-dihydroxyflavone (Chrysin) on Doxorubicin-Induced Cardiotoxicity by Modulating Oxidative Stress in Rats." Scholars International Journal of Anatomy and Physiology 6, no. 11 (November 23, 2023): 181–90. http://dx.doi.org/10.36348/sijap.2023.v06i11.005.

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Doxorubicin-induced cardiotoxicity is the leading cause of morbidity and mortality among cancer survivors. The present study aimed to investigate the ameliorative effect of 5, 7-dihydroxyflavone (chrysin) against doxorubicin-induced cardiotoxicity in Wistar rats. Thirty-five adult male Wistar albino rats were randomly allocated into seven groups (n = 5 each) which consisted of normal control (group 1) receiving phosphate buffer saline (0.4 ml), positive control (Group 2) received 2mg\kg of doxorubicin (DOX) through an intraperitoneal route once weekly for 21 days, chrysin low dose and chrysin high dose (Group 3 and 4) received oral administration of chrysin 50&100mg/kg for 21 days, chrysin low dose and DOX, chrysin medium dose and DOX and chrysin high dose and DOX(group 5, 6, and 7) received 2mg/kg of DOX once weekly with 50, 100 and 150mg/kg of chrysin for 21 days. Significant elevations in cardiac troponin I (cTnI) and histological lesions, which corresponded with oxidative stress, inflammation, apoptotic indicators, and cardiotoxicity when compared to controls, were indicative of DOX-induced cardiotoxicity. Malondialdehyde (MDA), a sign of oxidative stress, SOD, CPK (creatinine phosphokinase), TBARS (thiobarbituric acid reactive substance), and CAT (catalase) were also elevated in the DOX group. The DOX group also had increased levels of cardiac inflammatory markers, including as interleukin-1 (IL-1), interleukin-6 (IL-6), and the apoptotic marker caspase-3. 5, 7-dihydroxyflavone (chrysin) significantly mitigated, but did not entirely reverse, the cardiotoxicity caused by DOX by reducing the histopathological scores of cardiomyopathies and lowering cTnI in comparison to the DOX group. Additionally, chrysin reduced MDA to substantially similar levels as the control. Following chrysin administration, significant decreases in IL-1, IL-6, and caspase-3 were also seen in comparison to the DOX-only group. All things considered, these findings point to chrysin's protective action against DOX-induced cardiotoxicity, which may have been rendered possible by oxidative stress, inflammatory, and apoptotic suppression.

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Gu, Jian-Qiao, Yuehong Wang, Scott G. Franzblau, Gloria Montenegro, and Barbara N. Timmermann. "Constituents of Quinchamalium majus with Potential Antitubercular Activity." Zeitschrift für Naturforschung C 59, no. 11-12 (December 1, 2004): 797–802. http://dx.doi.org/10.1515/znc-2004-11-1206.

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Antitubercular bioassay-guided fractionation of the dichloromethane extracts of the above-ground biomass and roots of Quinchamalium majus led to the identification of six known constituents, betulinic acid (1), daucosterol (2), 5,7-dihydroxyflavone (3), oleanolic acid (4), (D)-2S-pinocembrin (5), and ursolic acid (6), for the first time in this species. Their chemical structures were determined on the basis of spectroscopic evidence and chemical transformation methods. All of these compounds along with additional 11 analogues were evaluated for their antitubercular potential against Mycobacterium tuberculosis in a microplate alamar blue assay, and the primary structure-activity relationships (SARs) for 4 and 6 were discussed. In addition, all the isolates were tested for cytotoxicity against African green monkey Vero cells in order to evaluate for their selectivity potential.

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Jiang, Meng, Xing Su, Jianling Liu, Chunli Zheng, and Xiaogang Li. "Systems Pharmacology-Dissection of the Molecular Mechanisms of Dragon’s Blood in Improving Ischemic Stroke Prognosis." Evidence-Based Complementary and Alternative Medicine 2020 (May 18, 2020): 1–14. http://dx.doi.org/10.1155/2020/4858201.

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Ethnopharmacological Relevance. Dragon’s blood (DB) is a widely used traditional Chinese medicine that has many pharmacological effects, including antiplatelet aggregation, promoting epidermal growth, and anti-inflammatory and antioxidant activities. The main component of Longxuetongluo capsule and Dragon’s blood dropping pills is DB’s standard phenolic extract, which was used for ischemic stroke prognosis in China. Aim of Study. To dissect the molecular mechanisms of Dragon’s blood (DB) in improving ischemic stroke prognosis. Materials and Methods. (1) Based on system-pharmacology platform, the potential active compounds of DB are screened out according to ADME. (2) The ischemic stroke-related targets are predicted by utilizing these active compounds as probes, mapping the targets to the CTD database to establish a molecular-target-disease network. (3) To analyze the mechanism of DB treatment for the prognosis of ischemic stroke, we used the Metascape and DAVID databases to construct “ischemic stroke pathways”. (4) PC12 cells were used to explore the protective effect of loureirin B on oxygen-glucose deprivation/reperfusion (OGD/R) injury, and BV-2 cells were used to determine the anti-inflammation effect of 4′,7-dihydroxyflavone. Results. Finally, we obtained 38 active compounds and 58 stroke-related targets. Network and pathway analysis indicate that DB is effective in the treatment of ischemic stroke by enhancing cell survival and inhibiting inflammatory and antiplatelet activation. In in vitro experiments, the main component loureirin B promoted the expression of HO-1 and Bcl-2 via positive regulation of PI3K/AKT/CREB and Nrf2 signaling pathways in PC12 cells against OGD/R damage. And the anti-inﬂammatory activity of 4′,7-dihydroxyflavone was related to the inhibition of COX-2, TNF-α, and IL-6 in LPS-induced BV-2 cells. Conclusions. In our study, the results illustrated that DB in improving ischemic stroke prognosis may involve enhancing cell survival and antioxidant, anti-inflammation, and antiplatelet activities.

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Stompor, Monika, Marta Świtalska, and Joanna Wietrzyk. "Synthesis and biological evaluation of acyl derivatives of hydroxyflavones as potent antiproliferative agents against drug resistance cell lines." Zeitschrift für Naturforschung C 73, no. 1-2 (January 26, 2018): 87–93. http://dx.doi.org/10.1515/znc-2017-0093.

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AbstractThe synthesis of hydroxyflavone derivatives is described. The acyl derivatives of 3-, 6-, 7-hydroxyflavones (compounds2,4,6, respectively) and chrysin (5,7-dihydroxyflavone,7) were obtained in high yields and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MCF-7 (breast cancer), A549 (nonsmall cell lung cancer), MES-SA (uterine sarcoma), LoVo (colon cancer), drug-resistant human cancer cells (MES-SA/DX5, LoVo/DX) and also towards non-cancer cell line MCF-10A (normal breast epithelial cells). The flavones modified with acyl group showed higher antiproliferative activity than free hydroxyflavones. The highest activity was noted for 3-acetoxyflavone (2), which proved active against LoVo, LoVo/DX, and MES-SA cell lines (IC50from 4.7 μM to 7.8 μM, respectively). The highest ability to overcome the barrier of resistance (resistance index=0.82) against the drug-resistant MES-SA/DX5 cells compared to the parental drug-sensitive MES-SA cell line was found for 7-acetoxyflavone (6).

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CODY, V., J. LUFT, M. MC COURT, and K. IRMSCHER. "ChemInform Abstract: Conformational Analysis of Flavonoids: Crystal and Molecular Structure of 3′,5′-Dibromo-3-methyl-6,4′-dihydroxyflavone (1:2) Triphenylphosphine Oxide Complex." ChemInform 23, no. 4 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199204046.

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Jomová, Klaudia, Lenka Hudecova, Peter Lauro, Miriama Simunkova, Saleh H. Alwasel, Ibrahim M. Alhazza, and Marian Valko. "A Switch between Antioxidant and Prooxidant Properties of the Phenolic Compounds Myricetin, Morin, 3′,4′-Dihydroxyflavone, Taxifolin and 4-Hydroxy-Coumarin in the Presence of Copper(II) Ions: A Spectroscopic, Absorption Titration and DNA Damage Study." Molecules 24, no. 23 (November 27, 2019): 4335. http://dx.doi.org/10.3390/molecules24234335.

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The beneficial effects of polyphenols, predominantly in the context of oxidative stress-related diseases such as cancer, cardiovascular diseases and neurological conditions including Alzheimer’s and Parkinson’s diseases, have been documented by a number of papers and reviews. The antioxidant/prooxidant properties of phenolic compounds are related mainly to the number and positions of hydroxyl groups and to their redox metal (Cu, Fe) chelating capacity. In this work we studied structurally distinct phenolic molecules such as myricetin, morin, 3′,4′-dihydroxy-flavone, taxifolin and 4-hydroxycoumarin, either alone or as interacting with Cu2+ ions. EPR and UV-Vis spectroscopy confirmed that the effective binding of cupric ions to phenolic compounds requires the presence of the 3-OH and 4-CO groups on the flavonoid C ring and unsaturated C2-C3 bond of the C-ring, which permits through-conjugation with the B-ring. An ABTS assay revealed that radical scavenging activities of phenolic compounds are related to their number of hydroxyl groups, planarity of the molecular skeleton, extent of delocalization and they decrease in the order: myricetin > morin > 3′,4′-dihydroxyflavone ~ 4-hydroxy coumarin > taxifolin. Absorption titrations indicate that copper ions can modulate the DNA binding affinity of flavonoids via the formation of their Cu-chelates. Gel electrophoresis measurements indicated that the protective effect of the phenolic compounds decreases in the order: 3′,4′-dihydroxyflavone > 4-OH coumarin > morin > taxifolin ~ myricetin. This can be explained by the fact that myricetin, taxifolin and morin form stable Cu(II) complexes capable of causing DNA damage via interaction with DNA and ROS formation via the Fenton reaction. Application of ROS scavengers revealed the formation of singlet oxygen, superoxide and hydroxyl radicals and their concerted synergistic effect on the DNA. The overall results suggest that the most pronounced DNA damage has been observed for flavonoids containing higher number of hydroxyl groups (including 3-OH group of the C ring), such as myricetin (six hydroxyl groups), morin and taxifolin (five hydroxyl groups) in the presence of Cu(II) ions. The proposed mechanism of action by which Cu(II) complexes of myricetin, morin and taxifolin interact with DNA predispose these substances to act as potential anticancer agents. The anticancer activity of phenolic compounds can be explained by their moderate prooxidant properties, which can boost ROS formation and kill cancer cells. Alternatively, slight prooxidant properties may activate antioxidant systems, including antioxidant enzymes and low molecular antioxidants such as glutathione and thus act as preventive anticancer agents.

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Šimunková, Miriama, Marián Valko, Lukáš Bučinský, and Michal Malček. "Structure functionality relationship of flavonoids (myricetin, morin, taxifolin and 3′,4′-dihydroxyflavone). A computational study via the cupric ion probe." Journal of Molecular Structure 1222 (December 2020): 128923. http://dx.doi.org/10.1016/j.molstruc.2020.128923.

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Gabriela, Nuño, Alberto María Rosa, Zampini Iris Catiana, Cuello Soledad, Ordoñez Roxana Mabel, Sayago Jorge Esteban, Baroni Veronica, Wunderlin Daniel, and Isla María Ines. "The Effect of Zuccagnia punctata, an Argentine Medicinal Plant, on Virulence Factors from Candida Species." Natural Product Communications 9, no. 7 (July 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900712.

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Zuccagnia punctata Cav. has been used as a traditional medicine in Argentina for the treatment of bacterial and fungal infections. In this study, we evaluated the ability of Z. punctata extract (ZpE) and compounds isolated from it to inhibit the growth and virulence factors of Candida species. ZpE showed inhibitory activity against planktonic cells of all assayed Candida species with MIC values of 400 μg/mL and with MFC values between 400 and 1,200 μg/mL. The principal identified compounds by HPLC-MS/MS and UV-VIS were chalcones (2′,4′-dihydroxy-3′-methoxychalcone, 2′,4′- dihydroxychalcone), flavones (galangin, 3,7-dihydroxyflavone and chrysin) and flavanones (naringenin, 7-hydroxyflavanone and pinocembrine). These compounds were more effective as inhibitors than the extracts upon biofilm formation as well as on preformed Candida biofilm and yeast germ tube formation. Furthermore, ZpE and chalcones are able to inhibit exoenzymes, which are responsible for the invasion mechanisms of the pathogens. All these effects could moderate colonization, thereby suppressing the pathogen invasive potential. Our results indicate that ZpE and chalcones could be used in antifungal therapy.

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Chagas, Maria do Socorro S., Maria D. Behrens, Carla J. Moragas-Tellis, Gabriela X. M. Penedo, Adriana R. Silva, and Cassiano F. Gonçalves-de-Albuquerque. "Flavonols and Flavones as Potential anti-Inflammatory, Antioxidant, and Antibacterial Compounds." Oxidative Medicine and Cellular Longevity 2022 (September 6, 2022): 1–21. http://dx.doi.org/10.1155/2022/9966750.

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Plant preparations have been used to treat various diseases and discussed for centuries. Research has advanced to discover and identify the plant components with beneficial effects and reveal their underlying mechanisms. Flavonoids are phytoconstituents with anti-inflammatory, antimutagenic, anticarcinogenic, and antimicrobial properties. Herein, we listed and contextualized various aspects of the protective effects of the flavonols quercetin, isoquercetin, kaempferol, and myricetin and the flavones luteolin, apigenin, 3 ′ ,4 ′ -dihydroxyflavone, baicalein, scutellarein, lucenin-2, vicenin-2, diosmetin, nobiletin, tangeretin, and 5-O-methyl-scutellarein. We presented their structural characteristics and subclasses, importance, occurrence, and food sources. The bioactive compounds present in our diet, such as fruits and vegetables, may affect the health and disease state. Therefore, we discussed the role of these compounds in inflammation, oxidative mechanisms, and bacterial metabolism; moreover, we discussed their synergism with antibiotics for better disease outcomes. Indiscriminate use of antibiotics allows the emergence of multidrug-resistant bacterial strains; thus, bioactive compounds may be used for adjuvant treatment of infectious diseases caused by resistant and opportunistic bacteria via direct and indirect mechanisms. We also focused on the reported mechanisms and intracellular targets of flavonols and flavones, which support their therapeutic role in inflammatory and infectious diseases.

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Egwuatu, Ifeanyi Anthony, Emeka Godson Anyanwu, Augustine Oviosun, Abraham John Chukwuebuka, Chiadikobi Lawrence Ozoemena, Ekene Valentine Ugbor, and Maduadichie Arinze Godswill. "Ameliorative Effects of 5-7, Dihydroxy Flavone (Chrysin) on Hippocampus of Wistar Rats with Doxorubicin-induced Cognitive Impairment." Journal of Complementary and Alternative Medical Research 22, no. 2 (June 5, 2023): 49–61. http://dx.doi.org/10.9734/jocamr/2023/v22i2456.

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Concern is increasing regarding the effect of chemotherapy induced cognitive impairment on oncology patients. This sought to investigate the effect of 5-7, dihydroxyflavone on the hippocampus of wistar rats with Doxorubicin induced cognitive impairment. 30 male Wistar rats were procured and acclimatized for 14 days with feed and water, they were divided into six (6) experimental groups of five (5) animals each. Group 1 served as normal control. Group 2 was induced with 2mg/kg of DOX and was untreated. Group 3 received 150mg/kg of Chrysin. Groups 4, 5 and 6 were induced with 2mg/kg of doxorubicin and treated with Chrysin at doses of 50mg/kg, 100mg/kg, and 150mg/kg respectively. The study lasted for 21 days. The body weight of the animals were recorded three (3) times before and after induction and then recorded again at the end of the 21 days treatment. At the end of the experiment, there were significantly increase in body weight. The increase was more pronounce in group 1 and group 2. In the oxidative stress analysis and ELISA analysis on the levels of inflammatory cytokines (IL-1 & IL-6), there was a significant increase in the levels compared to the control group 1. In the neurobehavioural test, group 6 had a high spontaneous alternation percentage compared to other groups. The treatment with Chrysin significantly had an ameliorative effect on the treated animal groups and in group 3. The result from this work suggest that Chrysin extract had an ameliorative effect on cognitive impairment of the hippocampus.

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Mohos, Violetta, Eszter Fliszár-Nyúl, Gabriella Schilli, Csaba Hetényi, Beáta Lemli, Sándor Kunsági-Máté, Balázs Bognár, and Miklós Poór. "Interaction of Chrysin and Its Main Conjugated Metabolites Chrysin-7-Sulfate and Chrysin-7-Glucuronide with Serum Albumin." International Journal of Molecular Sciences 19, no. 12 (December 17, 2018): 4073. http://dx.doi.org/10.3390/ijms19124073.

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Chrysin (5,7-dihydroxyflavone) is a flavonoid aglycone, which is found in nature and in several dietary supplements. During the biotransformation of chrysin, its conjugated metabolites chrysin-7-sulfate (C7S) and chrysin-7-glucuronide (C7G) are formed. Despite the fact that these conjugates appear in the circulation at much higher concentrations than chrysin, their interactions with serum albumin have not been reported. In this study, the complex formation of chrysin, C7S, and C7G with human (HSA) and bovine (BSA) serum albumins was investigated employing fluorescence spectroscopic, ultrafiltration, and modeling studies. Our major observations/conclusions are as follows: (1) Compared to chrysin, C7S binds with a threefold higher affinity to HSA, while C7G binds with a threefold lower affinity; (2) the albumin-binding of chrysin, C7S, and C7G did not show any large species differences regarding HSA and BSA; (3) tested flavonoids likely occupy Sudlow’s Site I in HSA; (4) C7S causes significant displacement of Sudlow’s Site I ligands, exerting an even stronger displacing ability than the parent compound chrysin. Considering the above-listed observations, the high intake of chrysin (e.g., through the consumption of dietary supplements with high chrysin contents) may interfere with the albumin-binding of several drugs, mainly due to the strong interaction of C7S with HSA.

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Mehdi, Syed Hassan, Md Zafaryab, Sana Nafees, Asad Khan, Irfan Ahmad, Zubair Bin Hafeez, and Moshahid Alam Rizvi. "Chrysin Sensitizes Human Lung Cancer Cells to Tumour Necrosis Factor Related Apoptosis-Inducing Ligand (TRAIL) Mediated Apoptosis." Asian Pacific Journal of Cancer Biology 4, no. 2 (August 3, 2019): 27–33. http://dx.doi.org/10.31557/apjcb.2019.4.2.27-33.

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Background: Lung cancer is the primary cause of cancer deaths worldwide. Thus, the requisite for more coherent methods to lung cancer therapy is needed. Purpose: Chrysin (5, 7-dihydroxyflavone) is a naturally occurring flavonoid having a wide range of pharmacological properties and is commonly found in fruits, vegetables, honey and propolis. In our study, we have hypothesized that chrysin would have anticancer activity on L132 lung cancer cell line.Methods: The cytotoxic effects were assessed by MTT and NRU assay. DAPI was used to evaluate the cell death. The pro- or anti-apoptotic proteins were detected by Western Blot assay, and, besides, mRNA expression was analysed with RT-PCR. In silico study of chrysin was performed to identify suitable inhibitors against the protein function. Results: Results indicated that chrysin enhanced the inhibitory effects of TRAIL (Tumour Necrosis Factor Related Apoptosis-Inducing Ligand) in comparison to TNF-α (tumour necrosis factor) on cell viability in L132 lung cancer cells and altered nuclear morphology of cells was observed in DAPI (4’,6-diamidino-2-phenylindole) staining after 48 hrs treatment. Treatment with chrysin enhances TRAIL-induced apoptosis by increasing the expression of apoptosis-related proteins including caspase-3, 8, 9 and Bax, whereas the expression of Bcl-2 was decreased. Chrysin was docked with caspase-3, 8, 9, Bax, and Bcl-2 proteins to identify suitable inhibitors against the protein function.Conclusion: We concluded that chrysin sensitizes lung cancer cells to TRAIL-induced apoptosis and may be considered for future studies as a promising therapeutic candidate for human lung cancer.

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Wang, Yi, Junsen Cheng, Wei Jiang, and Shu Chen. "Metabolomics study of flavonoids in Coreopsis tinctoria of different origins by UPLC–MS/MS." PeerJ 10 (December 19, 2022): e14580. http://dx.doi.org/10.7717/peerj.14580.

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To analyze the flavonoids in Coreopsis tinctoria and compare the differences in flavonoids among C. tinctoria of different origins, the chemical composition of C. tinctoria capitulum was analyzed by ultra-high-performance liquid chromatography-tandem quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS), and the flavonoid metabolites were analyzed and identified based on their retention time, mass-to-charge ratio and fragment ions in the UPLC-QTOF-MS matrix. Capitulum samples of C. tinctoria were collected from three locations in the Xinjiang region at different altitudes. A total of 204 flavonoid compounds were identified, and 31 different flavonoid metabolites were then identified from flowers of C. tinctoria of different origins. Further analysis of these 31 significantly accumulated metabolites identified seven flavonoid metabolites, namely, homoplantaginin, kaempferol, quercetin, isorhamnetin, avicularin, quercetin 3-O-(6′-galloyl)-β-D-galactopyranoside and isorhamnetin 3-O-glucoside, with high accumulation only in sample collected from Tashkurgan Tajik (TX) and low expression in sample collected from Yutian County (YT) and Shaya County (SY). Moreover, 7,4′-dihydroxyflavone and 4,4′-dimethoxychalcone showed high accumulation only in SY, and afzelin was specifically highly accumulated in YT. In addition, the identified flavonoid metabolites were annotated using the Kyoto Encyclopedia of Genes and Genomes (KEGG) database, and key pathways that might regulate the biosynthesis of these flavonoid compounds were analyzed. These findings provide key information for research on flavonoids and their biosynthesis in C. tinctoria and will provide a theoretical basis for studying the herbal quality and origin of C. tinctoria.

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Ademuwagun, Ibitayo Abigail, Gbolahan Oladipupo Oduselu, Solomon Oladapo Rotimi, and Ezekiel Adebiyi. "Pharmacophore-Aided Virtual Screening and Molecular Dynamics Simulation Identifies TrkB Agonists for Treatment of CDKL5-Deficiency Disorders." Bioinformatics and Biology Insights 17 (January 2023): 117793222311582. http://dx.doi.org/10.1177/11779322231158254.

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Therapeutic intervention in cyclin-dependent kinase-like 5 (CDKL5) deficiency disorders (CDDs) has remained a concern over the years. Recent advances into the mechanistic interplay of signalling pathways has revealed the role of deficient tropomyosin receptor kinase B (TrkB)/phospholipase C γ1 signalling cascade in CDD. Novel findings showed that in vivo administration of a TrkB agonist, 7,8-dihydroxyflavone (7,8-DHF), resulted in a remarkable reversal in the molecular pathologic mechanisms underlying CDD. Owing to this discovery, this study aimed to identify more potent TrkB agonists than 7,8-DHF that could serve as alternatives or combinatorial drugs towards effective management of CDD. Using pharmacophore modelling and multiple database screening, we identified 691 compounds with identical pharmacophore features with 7,8-DHF. Virtual screening of these ligands resulted in identification of at least 6 compounds with better binding affinities than 7,8-DHF. The in silico pharmacokinetic and ADMET studies of the compounds also indicated better drug-like qualities than those of 7,8-DHF. Postdocking analyses and molecular dynamics simulations of the best hits, 6-hydroxy-10-(2-oxo-1-azatricyclo[7.3.1.05,13]trideca-3,5(13),6,8-tetraen-3-yl)-8-oxa-13,14,16-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1,3,6,9,11,15-hexaen-5-one (PubChem: 91637738) and 6-hydroxy-10-(8-methyl-2-oxo-1H-quinolin-3-yl)-8-oxa-13,14,16-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1,3,6,9,11,15-hexaen-5-one (PubChem ID: 91641310), revealed unique ligand interactions, validating the docking findings. We hereby recommend experimental validation of the best hits in CDKL5 knock out models before consideration as drugs in CDD management.

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Mathesius, Ulrike, Cathy Bayliss, Jeremy J. Weinman, Helmi R. M. Schlaman, Herman P. Spaink, Barry G. Rolfe, Margaret E. McCully, and Michael A. Djordjevic. "Flavonoids Synthesized in Cortical Cells During Nodule Initiation Are Early Developmental Markers in White Clover." Molecular Plant-Microbe Interactions® 11, no. 12 (December 1998): 1223–32. http://dx.doi.org/10.1094/mpmi.1998.11.12.1223.

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We examined the site-specific induction of the flavonoid pathway before and during nodule initiation in white clover with transgenic plants, fluorescence microscopy, and microspectrofluorometry to test if flavonoids play a role in nodule organogenesis. A chalcone synthase regulated β-glucuronidase (GUS) transgene (CHS3:gusA) was up-regulated from 3 h post inoculation (p.i.) until cell division (around 40 h p.i.) in inner cortex cells underlying the inoculation site. Intracellular fluorescence occurred in vacuoles of those inner cortex cells from 13 h p.i. until the fluorescent cells divided. Fluorescence emission spectra of contents of individual fluorescing cortex cells were measured in situ and compared with emission spectra of compounds purified from root extracts. The fluorescing compound located in cells of the inner cortex after Rhizobium leguminosarum bv. trifolii infection was identified as a water-soluble derivative of 7,4′-dihydroxyflavone. Nodule primordium cells contained a different fluorescent compound, identified as the isoflavonoid formononetin. CHS3:gusA expression and flavonoid accumulation were only induced in inner cortex cells by a nodulating Rhizo-bium strain and by clover-specific lipo-chitinoligosac-charides, but not by non-nodulating rhizobia. Fluorescence was also induced by compatible rhizobia in other legumes such as alfalfa, pea, and siratro in the cells that participate in nodule initiation. Our results show that fluorescent flavonoids are useful markers in nodule or-ganogenesis in clover and may have direct roles in nodule formation.

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Klebe, Damon, Mahima Tibrewal, Deep R. Sharma, Rachna Vanaparthy, Sunil Krishna, Merina Varghese, Bokun Cheng, et al. "Reduced Hippocampal Dendrite Branching, Spine Density and Neurocognitive Function in Premature Rabbits, and Reversal with Estrogen or TrkB Agonist Treatment." Cerebral Cortex 29, no. 12 (March 16, 2019): 4932–47. http://dx.doi.org/10.1093/cercor/bhz033.

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Abstract Preterm-born children suffer from neurological and behavioral disorders. Herein, we hypothesized that premature birth and non-maternal care of preterm newborns might disrupt neurobehavioral function, hippocampal dendritic arborization, and dendritic spine density. Additionally, we assessed whether 17β-estradiol (E2) replacement or the TrkB receptor agonist, 7,8-dihydroxyflavone (DHF), would reverse compromised dendritic development and cognitive function in preterm newborns. These hypotheses were tested by comparing preterm (E28.5) rabbit kits cared and gavage-fed by laboratory personnel and term-kits reared and breast-fed by their mother doe at an equivalent postconceptional age. Neurobehavioral tests showed that both premature-birth and formula-feeding with non-maternal care led to increased anxiety behavior, poor social interaction, and lack of novelty preference compared with term-kits. Dendritic branching and number of total or mushroom dendritic spines were reduced in the CA1 field of preterm-kits compared with term controls. While CDC42 and Rac1/2/3 expression levels were lower, RhoA-activity was higher in preterm-kits compared with term controls. Both E2 and DHF treatment reversed prematurity-induced reduction in spine density, reduced total RhoA-GTPase levels, and enhanced cognitive function. Hence, prematurity and non-maternal care result in cognitive deficits, and reduced dendritic arbors and spines in CA1. E2 replacement or DHF treatment might reverse changes in dendritic spines and improve neurodevelopment in premature infants.

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Chen, Yufeng, Jingchong Peng, Yueqi Wang, Daniel Wadhawan, Lijun Wu, Xiaojing Gao, Yi Sun, and Guobin Xia. "Development, Characterization, Stability and Bioaccessibility Improvement of 7,8-Dihydroxyflavone Loaded Zein/Sophorolipid/Polysaccharide Ternary Nanoparticles: Comparison of Sodium Alginate and Sodium Carboxymethyl Cellulose." Foods 10, no. 11 (October 29, 2021): 2629. http://dx.doi.org/10.3390/foods10112629.

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In this study, two polysaccharides [sodium alginate (ALG) and sodium carboxymethyl cellulose (CMC)] were selected to establish zein/sophorolipid/ALG (ALG/S/Z) and zein/sophorolipid/ALG (CMC/S/Z) nanoparticles to encapsulate 7,8-dihydroxyflavone (7,8-DHF), respectively. The results showed that polysaccharide types significantly affected performance of ternary nanoparticles, including CMC/S/Z possessed lower polydispersity index, particle size and turbidity, but higher zeta potential, encapsulation efficiency and loading capacity compared to ALG/S/Z. Compared to zein/sophorolipid nanoparticles (S/Z), both ALG/S/Z and CMC/S/Z had better stability against low pH (pH 3~4) and high ionic strengths (150~200 mM NaCl). Hydrophobic effects, electrostatic interactions and hydrogen bonding were confirmed in ternary nanoparticles fabrication via Fourier-transform infrared spectroscopy. Circular dichroism revealed that CMC and ALG had no evident impact on secondary structure of zein in S/Z, but changed surface morphology of S/Z as observed by scanning electron microscope. Encapsulated 7,8-DHF exhibited an amorphous state in ternary nanoparticles as detected by X-ray diffraction and differential scanning calorimetry. Furthermore, compared to S/Z, ALG/S/Z, and CMC/S/Z remarkably improved the storage stability and bioaccessibility of 7,8-DHF. CMC/S/Z possessed a greater storage stability for 7,8-DHF, however, ALG/S/Z exhibited a better in vitro bioaccessibility of 7,8-DHF. This research provides a theoretical reference for zein-based delivery system application.

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Balta, Cornel, Alina Ciceu, Hildegard Herman, Marcel Rosu, Oana Maria Boldura, and Anca Hermenean. "Dose-Dependent Antifibrotic Effect of Chrysin on Regression of Liver Fibrosis: The Role in Extracellular Matrix Remodeling." Dose-Response 16, no. 3 (July 1, 2018): 155932581878983. http://dx.doi.org/10.1177/1559325818789835.

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Liver fibrosis represents an overaccumulation of extracellular matrix (ECM). This study was designed to investigate the effect of chrysin on established ECM overproduction in carbon tetrachloride (CCl4) mouse liver fibrosis. Experimental fibrosis was induced by intraperitoneal injection of 2 mL/kg CCl4 twice a week, for 7 weeks. Mice were orally treated with 3 doses of chrysin (5,7-dihydroxyflavone). For the assessment of the spontaneous reversion of fibrosis, CCl4-treated mice were investigated after 2 weeks of recovery time. Silymarin was used as a standard of liver protection. In fibrotic livers, the results showed the upregulation of collagen I (Col I) and tissue inhibitors of metalloproteinase 1 (TIMP-1) and modulation of matrix metalloproteinases (MMPs), which led to an altered ECM enriched in Col, confirmed as well by electron microscopy investigations. Treatment with chrysin significantly reduced ultrastructural changes, downregulated Col I, and restored TIMP-1/MMP balance, whereas in the group observed for the spontaneous regression of fibrosis, they remained in the same pattern with fibrotic livers. In this study, we have shown chrysin efficacy to attenuate dose-dependent CCl4-stimulated liver ECM accumulation by regulation of MMP/TIMP imbalance and inhibition of Col production. We have shown the dose-dependent chrysin efficiency in attenuation of CCl4-induced liver ECM accumulation by regulation of MMP/TIMP imbalance and inhibition of Col production. Our findings suggest that chrysin oral administration may introduce a new strategy for treating liver fibrosis in humans.

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Galindo-Romero, Caridad, Beatriz Vidal-Villegas, Javier Asís-Martínez, Fernando Lucas-Ruiz, Alejandro Gallego-Ortega, and Manuel Vidal-Sanz. "7,8-Dihydroxiflavone Protects Adult Rat Axotomized Retinal Ganglion Cells through MAPK/ERK and PI3K/AKT Activation." International Journal of Molecular Sciences 22, no. 19 (October 8, 2021): 10896. http://dx.doi.org/10.3390/ijms221910896.

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We analyze the 7,8-dihydroxyflavone (DHF)/TrkB signaling activation of two main intracellular pathways, mitogen-activated protein kinase (MAPK)/ERK and phosphatidylinositol 3 kinase (PI3K)/AKT, in the neuroprotection of axotomized retinal ganglion cells (RGCs). Methods: Adult albino Sprague-Dawley rats received left intraorbital optic nerve transection (IONT) and were divided in two groups. One group received daily intraperitoneal DHF (5 mg/kg) and another vehicle (1%DMSO in 0.9%NaCl) from one day before IONT until processing. Additional intact rats were employed as control (n = 4). At 1, 3 or 7 days (d) after IONT, phosphorylated (p)AKT, p-MAPK, and non-phosphorylated AKT and MAPK expression levels were analyzed in the retina by Western blotting (n = 4/group). Radial sections were also immunodetected for the above-mentioned proteins, and for Brn3a and vimentin to identify RGCs and Müller cells (MCs), respectively (n = 3/group). Results: IONT induced increased levels of p-MAPK and MAPK at 3d in DHF- or vehicle-treated retinas and at 7d in DHF-treated retinas. IONT induced a fast decrease in AKT in retinas treated with DHF or vehicle, with higher levels of phosphorylation in DHF-treated retinas at 7d. In intact retinas and vehicle-treated groups, no p-MAPK or MAPK expression in RGCs was observed. In DHF- treated retinas p-MAPK and MAPK were expressed in the ganglion cell layer and in the RGC nuclei 3 and 7d after IONT. AKT was observed in intact and axotomized RGCs, but the signal intensity of p-AKT was stronger in DHF-treated retinas. Finally, MCs expressed higher quantities of both MAPK and AKT at 3d in both DHF- and vehicle-treated retinas, and at 7d the phosphorylation of p-MAPK was higher in DHF-treated groups. Conclusions: Phosphorylation and increased levels of AKT and MAPK through MCs and RGCs in retinas after DHF-treatment may be responsible for the increased and long-lasting RGC protection afforded by DHF after IONT.

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Lawson, CGR, BG Rolfe, and MA Djordjevic. "Rhizobium Inoculation Induces Condition-Dependent Changes in the Flavonoid Composition of Root Exudates From Trifolium subterraneum." Functional Plant Biology 23, no. 1 (1996): 93. http://dx.doi.org/10.1071/pp9960093.

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Rapid induction of chalcone synthase (predominantly CHSS) gene expression occurs within 6 h following the inoculation of Rhizobium leguminosarum bv. trifolii strain ANU843 on Trifolium subterraneum or wounding of plants (C. G. R. Lawson, M. A. Djordjevic, J. J. Weinman and B. G. Rolfe. 1994. Molecular Plant-Microbe Interactions 7, 498-507). Experiments were conducted under the same conditions to examine the time of onset of synthesis and excretion of flavonoids that might result from this early CHS expression. Flavonoids in root tissues and root exudates were examined by HPLC analysis and the ability of fractionated and unfractionated material to induce nodulation gene expression in Rhizobium measured. There were no detectable changes in nod-gene-inducing activity of individual HPLC fractions of root exudates of 1 day dark-grown roots after Rhizobium inoculation. In contrast, after 3 days exposure to Rhizobium, analysis of specific HPLC fractions showed the presence of an additional nod-gene-inducing compound which the data indicate was 4′,7-dihydroxyflavone. A different and additional nod gene inducer was found in inoculated 5 day samples of root exudate of light-grown plants indicating that light exposure changes the HPLC profiles as well as the nod-gene-inducing compound(s). Exudates collected from wounded plants were considerably different from those from Rhizobium-inoculated and uninoculated plants and contained no detectable nod gene inducers. The late detection (at day 3) of Rhizobium-induced flavonoid excretion may occur too late to be directly correlated with the observed expression of CHS 6 h after inoculation. In addition, the data suggest that although the CHS5 promotor responds to both wounding and Rhizobium inoculation, the biochemical consequences of CHS5 induction resulting from these treatments are different.

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Khan, Rehan, Abdul Quaiyoom Khan, Wajhul Qamar, Abdul Lateef, Farrah Ali, Muneeb U. Rehman, Mir Tahir, Swati Sharma, and Sarwat Sultana. "Chrysin abrogates cisplatin-induced oxidative stress, p53 expression, goblet cell disintegration and apoptotic responses in the jejunum of Wistar rats." British Journal of Nutrition 108, no. 9 (February 6, 2012): 1574–85. http://dx.doi.org/10.1017/s0007114511007239.

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Cisplatin (cis-diamminedichloroplatinum (II) (CDDP)) is a commonly used chemotherapeutic drug for the treatment of numerous forms of cancer, but it has pronounced adverse effects, namely nephrotoxicity, ototoxicity, neurotoxicity, hepatotoxicity, diarrhoea and nausea. CDDP-induced emesis and diarrhoea are also marked toxicities that may be due to intestinal injury. Chrysin (5,7-dihydroxyflavone), a natural flavone commonly found in many plants, possesses multiple biological activities, such as antioxidant and anti-inflammatory properties. In the present study, we investigated the protective effect of chrysin against CDDP-induced jejunal toxicity. The plausible mechanism of CDDP-induced jejunal toxicity includes oxidative stress, p53 and apoptosis via up-regulating the expression of caspase-6 and -3. Chrysin was administered to Wistar rats orally in maize oil. A single intraperitoneal injection of CDDP was given and the animals were killed after 24 h of CDDP injection. Chrysin ameliorated CDDP-induced lipid peroxidation, increase in xanthine oxidase activity, glutathione depletion, decrease in antioxidant (catalase, glutathione reductase, glutathione peroxidase and glucose-6-phosphate dehydrogenase) and phase-II detoxifying (glutathione-S-transferase and quinone reductase) enzyme activities. Chrysin attenuated CDDP-induced goblet cell disintegration, enhanced expression of p53 and apoptotic tissue damage. Histological findings further substantiated the protective effects of chrysin against CDDP-induced damage in the jejunum. The results of the present study demonstrate that oxidative stress and apoptosis are closely associated with CDDP-induced toxicity and chrysin shows the protective efficacy against CDDP-induced jejunum toxicity possibly via attenuating the oxidative stress and apoptotic tissue damage.

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Schlupper, Doreen, Sabine Giesa, and Rolf Gebhardt. "Influence of Biotransformation of Luteolin, Luteolin 7-O-Glucoside, 3′,4′-Dihydroxyflavone and Apigenin by Cultured Rat Hepatocytes on Antioxidative Capacity and Inhibition of EGF Receptor Tyrosine Kinase Activity." Planta Medica 72, no. 07 (April 2006): 596–603. http://dx.doi.org/10.1055/s-2006-931555.

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Zhang, Tianlu, Dong Zhou, Miaofen Chen, Hui Zou, Qi Tang, Ying Lu, and Yajie Zheng. "Effects of the Fibrous Root of Polygonatum cyrtonema Hua on Growth Performance, Meat Quality, Immunity, Antioxidant Capacity, and Intestinal Morphology of White-Feathered Broilers." Antibiotics 12, no. 11 (November 15, 2023): 1627. http://dx.doi.org/10.3390/antibiotics12111627.

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This study was designed to evaluate the effects of different doses of the fibrous roots of Polygonatum cyrtonema Hua on the growth performance, slaughter parameters, meat quality, immune function, cytokines, antioxidant capacity, and intestinal morphology of white-feathered broilers. Also, the mechanism to improve immune functions of broilers was explored through network pharmacology and molecular docking technology. A total of 360 AA-white-feathered broilers were randomly divided into six groups (not separated by sex), with six repetitions per group (n = 10). The groups were as follows: basal diet (CON group), basal diet supplemented with 300 mg/kg aureomycin (ANT group), basal diet supplemented with 2%, 3%, and 4% fibrous root raw powder (LD, MD, and HD group), or basal diet supplemented with 3% fibrous root processed powder (PR group), in a 42-day experiment. The dietary inclusion of P. cyrtonema fibrous roots increased slaughter performance (p < 0.05), reduced the fat rate (p < 0.05), improved intestinal morphology (p < 0.05), and improved the immune organ index to varying degrees. It also significantly improved pH reduction, drip loss, and pressure loss of breast muscle and leg muscle (p < 0.05). Furthermore, it significantly improved immune and antioxidant functions including decreased MDA content of serum (p < 0.01), increased GSH-Px content (p < 0.01), IgG, IgA, and C4 contents (p < 0.05), and increased expression of IL-2 and IFN-γ (p < 0.01). Additionally, the mechanism by which fibrous roots improve immune function in broilers was explored using network pharmacology and molecular docking technology. Network pharmacology and molecular docking revealed that flavonoids such as baicalein, 4′,5-Dihydroxyflavone, 5,7-dihydroxy-6,8-dimethyl-3-(4′-hydroxybenzyl)-chroman-4-one, and 5,7-dihydroxy-3-(2′-hydroxy-4′-methoxybenzyl)-6,8-dimethyl-chroman-4-one were key components that enhanced immune function through the MAPK1 and other key targets involved in regulating the MAPK signaling pathway. From the findings, it can be concluded that incorporating P. cyrtonema Hua fibrous root as a natural feed supplement and growth promoter in broiler diets had a positive impact on bird health and performance.

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Kamat, Siya, Madhuree Kumari, Kuttuvan Valappil Sajna, Sandeep Kumar Singh, Kaushalendra, Ajay Kumar, and C. Jayabaskaran. "Improved Chrysin Production by a Combination of Fermentation Factors and Elicitation from Chaetomium globosum." Microorganisms 11, no. 4 (April 12, 2023): 999. http://dx.doi.org/10.3390/microorganisms11040999.

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Flavonoids encompass a heterogeneous group of secondary metabolites with exceptional health benefits. Chrysin, a natural dihydroxyflavone, possesses numerous bioactive properties, such as anticancer, antioxidative, antidiabetic, anti-inflammatory, etc. However, using traditional sources of chrysin involves extracting honey from plants, which is non-scalable, unsustainable, and depends on several factors, including geography, climatic conditions, and the season, which limits its production at a larger scale. Recently, microbial production of desirable metabolites has garnered attention due to the cost-effectiveness, easy scale-up, sustainability, and low emission of waste. We previously reported for the first time the chrysin-producing marine endophytic fungus Chaetomium globosum, associated with a marine green alga. To extend our understanding of chrysin biosynthesis in C. globosum, in the present study, we have assessed the presence of flavonoid pathway intermediates in C. globosum extracts using LC-MS/MS. The presence of several key metabolites, such as dihydrokaempferol, chalcone, galangin, baicalein, chrysin, p-Coumaroyl-CoA, and p-Cinnamoyl-CoA, indicates the role of flavonoid biosynthesis machinery in the marine fungus. Further, we have aimed to enhance the production of chrysin with three different strategies: (1) optimizing the fermentation parameters, namely, growth medium, incubation time, pH, and temperature; (2) feeding key flavonoid pathway intermediates, i.e., phenylalanine and cinnamic acid; (3) elicitation with biotic elicitors, such as polysaccharide, yeast extract, and abiotic elicitors that include UV radiation, salinity, and metal stress. The combined effect of the optimized parameters resulted in a 97-fold increase in the chrysin yield, resulting in a fungal cell factory. This work reports the first approach for enhanced production of chrysin and can serve as a template for flavonoid production enhancement using marine endophytic fungi.

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Li, Chunhou, Xican Li, Jingyuan Zeng, Rongxin Cai, Shaoman Chen, Ban Chen, and Xiaojun Zhao. "Detection of Adulterated Naodesheng Tablet (Naodesheng Pian) via In-Depth Chemical Analysis and Subsequent Reconstruction of Its Pharmacopoeia Q-Markers." Molecules 29, no. 6 (March 20, 2024): 1392. http://dx.doi.org/10.3390/molecules29061392.

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Naodesheng Tablet (Naodesheng Pian), a traditional Chinese medicine formula for stroke treatment, is made up of five herbal medicines, i.e., Sanqi, Gegen, Honghua, Shanzha, and Chuanxiong. However, the current Pharmacopoeia quality-marker (Q-marker) system cannot detect possible adulteration. Our study tried to use a new strategy, i.e., standards-library-dependent ultra-high-performance liquid chromatography-quadrupole-Orbitrap mass spectrometry (UHPLC-Q-Orbitrap MS/MS) putative identification, to reconstruct the Q-marker system. Through the strategy, 30 isomers were successfully differentiated (such as 2′-hydroxygenistein, luteolin, and kaempferol; ginsenoside Rg2 and ginsenoside Rg3; ginsenoside Rf and ginsenoside Rg1). In particular, 11 compounds were unexpectedly found in Naodesheng, including 2′-hydroxygenistein, 7,4′-dihydroxyflavone, pectolinarigenin, 7-methoxy-4′-hydroxyisoflavone, scoparone, matrine, 3,3′,4′,5,6,7,8-heptamethoxyflavone, 5-hydroxyflavone, diosgenin, chloesteryl acetate, and (+)-4-cholesten-3-one. In total, 68 compounds were putatively identified and fully elucidated for their MS spectra. Subsequently, relevant compounds were further investigated using UV-vis scanning experiments, semi-quantitative analysis, and quantum chemical calculation. Finally, five adulterated Naodesheng Tablets were used for validation experiments. The experiment successfully detected five adulterated ones via a lower-version LC-MS analysis. On this basis, three new candidates (hydroxy safflor yellow A (HSYA), citric acid, and levistilide A), along with puerarin and notoginsenoside R1, are re-nominated as the Q-markers for LC-MS analysis. The LC-MS analysis of puerarin, notoginsenoside R1, HSYA, citric acid, and levistilide A can clearly detect adulteration regarding all five herbal medicines mentioned above. Therefore, the reconstructed Q-markers are described as a “perfect” quality control system to detect adulteration in Naodesheng and will offer a valuable recommendation for the Pharmacopoeia Commission.

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Bhosale, Pritam Bhagwan, Abuyaseer Abusaliya, Hun Hwan Kim, Sang Eun Ha, Min Yeong Park, Se Hyo Jeong, Preethi Vetrivel та ін. "Apigetrin Promotes TNFα-Induced Apoptosis, Necroptosis, G2/M Phase Cell Cycle Arrest, and ROS Generation through Inhibition of NF-κB Pathway in Hep3B Liver Cancer Cells". Cells 11, № 17 (1 вересня 2022): 2734. http://dx.doi.org/10.3390/cells11172734.

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Apigetrin (7-(β-D-glucopyranosyloxy)-4′,5-dihydroxyflavone), a glycoside bioactive dietary flavonoid derived from Taraxacum officinale and Teucrium gnaphalodes, is known to possess anticancer, antioxidant, and anti-inflammatory effects on numerous cancers. In the present study, we examined the effect of apigetrin in Hep3B hepatocellular cancer cell line (HCC). Apigetrin inhibited cell growth and proliferation of Hep3B cells, as confirmed by MTT and colony formation assay. We used apigetrin at concentrations of 0, 50, and 100 µM for later experiments. Of these concentrations, 100 µM of apigetrin showed a significant effect on cell inhibition. In apigetrin-treated Hep3B cells, cell cycle arrest occurred at the G2/M phase. Apoptosis and necroptosis of Hep3B cells treated with apigetrin were confirmed by Annexin V/propidium iodide (PI) staining and flow cytometry results. Morphological observation through 4′,6-diamidino-2-phenylindole (DAPI) staining showed intense blue fluorescence representing chromatin condensation. Hematoxylin staining showed necroptotic features such as formation of vacuoles and swelling of organelles. Apigetrin increased reactive oxygen species (ROS) levels in cells, based on fluorescence imaging. Furthermore, the underlying mechanism involved in the apoptosis and necroptosis was elucidated through western blotting. Apigetrin up-regulated TNFα, but down-regulated phosphorylation of p-p65, and IκB. Apigetrin inhibited the expression of Bcl-xl but increased Bax levels. Up-regulation of cleaved PARP and cleaved caspase 3 confirmed the induction of apoptosis in apigetrin-treated Hep3B cells. Additionally, necroptosis markers RIP3, p-RIP3, and p-MLKL were significantly elevated by apigetrin dose-dependently, suggesting necroptotic cell death. Taken together, our findings strongly imply that apigetrin can induce apoptosis and necroptosis of Hep3B hepatocellular cancer cells. Thus, apigetrin as a natural compound might have potential for treating liver cancer.

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McKhann, Heather I., Nancy L. Paiva, Richard A. Dixon, and Ann M. Hirsch. "Chalcone Synthase Transcripts Are Detected in Alfalfa Root Hairs Following Inoculation with Wild-Type Rhizobium meliloti." Molecular Plant-Microbe Interactions® 10, no. 1 (January 1997): 50–58. http://dx.doi.org/10.1094/mpmi.1997.10.1.50.

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Flavonoids are involved in a number of critical events in the interaction between nitrogen-fixing bacteria and legumes. To get a better understanding of the importance of flavonoids in the earliest stages of the alfalfa-Rhizobium meliloti symbiosis, we followed the expression of two chal-cone synthase (CHS) gene family members as well as of chalcone isomerase (CHI) and isoflavone reductase (IFR) genes. CHS transcripts increased 2 to 4 dpi (days post-inoculation) with wild-type rhizobia, but not after inoculation with the heterologous R. leguminosarum bv. trifolii or with an exopolysaccharide (exo) mutant of R. meliloti. CHS transcripts were detected in the root hairs and epidermal cells of the root hair zone, and infrequently in nodule pri-mordia. Insignificant CHI and IFR mRNA accumulation over control levels was observed in response to rhizobial inoculation. The slight increase in CHS transcript accumulation following wild-type R. meliloti inoculation was correlated with an observed increase in root flavonoid content as well as a change in the nod gene-inducing activity of the root exudate. The nod gene-inducing flavonoids exuded from wild-type rhizobia-inoculated roots were identified as 4′, 7-dihydroxyflavone and 4, 4′ dihydroxy-2′-methoxychalcone. Although there was a slight increase over the uninoculated controls in the level of medicarpin-3-O-glucoside 6″-O-malonate (MGM) in extracts of roots inoculated with rhizobia, IFR transcript accumulation was not significantly elevated over that of the controls. Moreover, no medicarpin aglycone was detected in the inoculated roots. Thus, although inoculation with wild-type rhizobia triggers some of the genes induced during an interaction between a host and a pathogen, the expression of these genes in the Rhizobium-legume interaction is at a very low level, suggesting that rhizobia have evolved a mechanism(s) to avoid triggering the host's defense responses.

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Kikuchi, Hidehiko, Kaori Harata, Sumiko Akiyoshi, Harishkumar Madhyastha, and Futoshi Kuribayashi. "3’, 4’-Dihydroxyflavone enhances all-trans retinoic acid-induced superoxide-generating activity through up-regulating transcription of gp91-phox in human monoblastic U937 cells, as opposed to flavone and other hydroxyflavone derivatives." Fundamental Toxicological Sciences 8, no. 2 (2021): 53–59. http://dx.doi.org/10.2131/fts.8.53.

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Bhusari, Sachin Shivling, Shreya Hiralal Waghmare, and Pravin Shridhar Wakte. "DEVELOPMENT AND VALIDATION OF Q-ABSORBANCE RATIO SPECTROPHOTOMETRIC METHOD FOR THE SIMULTANEOUS ESTIMATION OF RIFAMPICIN AND ITS BIOENHANCER; 3, 5'-DIHYDROXYFLAVONE-7-O-B-D-GALACTURONIDE-4'-O-B-D-GLUCOPYRANOSIDE; IN BULK AND FORMULATION." Journal of Pharmaceutical & Scientific Innovation 8, no. 5 (September 10, 2019): 182–88. http://dx.doi.org/10.7897/2277-4572.085152.

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Kuo, Chen-Miao, Tania N. Hill, and Barend C. B. Bezuidenhoudt. "Crystal structure of 7-benzyloxy-5,6-dihydroxyflavone, C22H16O5." Zeitschrift für Kristallographie - New Crystal Structures 230, no. 3 (September 1, 2015): 193–94. http://dx.doi.org/10.1515/ncrs-2014-0144.

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43

Wollenweber, Eckhard, Karin Mann, Munekazu Iinuma, Toshiyuki Tanaka, and Mizuo Mizuno. "2′,5′-Dihydroxyflavone and its 5′-Acetate — Novel Compounds from the Farinose Exudate of Primula." Zeitschrift für Naturforschung C 43, no. 3-4 (April 1, 1988): 305–7. http://dx.doi.org/10.1515/znc-1988-3-424.

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2′,5′-Dihydroxyflavone and its 5′-acetate were isolated from the farinose exudate of Primula japonica and P. pulverulenta. Their structures were elucidated by spectroscopic methods and confirmed by synthesis. Both flavones are novel natural products.

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Añón, M. T., A. Ubeda, and M. J. Alcaraz. "Protective Effects of Phenolic Compounds on CCl4-Induced Toxicity in Isolated Rat Hepatocytes." Zeitschrift für Naturforschung C 47, no. 3-4 (April 1, 1992): 275–79. http://dx.doi.org/10.1515/znc-1992-3-417.

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Abstract The protective effects of a series of phenolic compounds, phenolic acids and flavonoids on the cytotoxicity of CCl4 in rat hepatocytes were studied. A number of flavones, 7,8-dihydroxyflavone, luteolin and hypolaetin-8-glucoside, flavonols, morin, quercetin, robinetin and gossypin, phenolic acids, gallic, caffeic and chlorogenic acids, as well as the flavane ( + )-catechin significantly inhibited alanine amine transferase (ALT) release. Catechol groups are determinant for the protective activity of flavonoids and cinnamic acid derivatives, as well as the resorcinol or pyrogallol moieties in the B ring of flavonoids. In benzoic acid derivatives a pyrogallol group is required. This feature is associated with the inhibition of ALT spontaneous release.

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Kang, Myung-Su, Tae-Yong Choi, Hye Guk Ryu, Dohyun Lee, Seung-Hyun Lee, Se-Young Choi, and Kyong-Tai Kim. "Autism-like behavior caused by deletion of vaccinia-related kinase 3 is improved by TrkB stimulation." Journal of Experimental Medicine 214, no. 10 (September 12, 2017): 2947–66. http://dx.doi.org/10.1084/jem.20160974.

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Vaccinia-related kinases (VRKs) are multifaceted serine/threonine kinases that play essential roles in various aspects of cell signaling, cell cycle progression, apoptosis, and neuronal development and differentiation. However, the neuronal function of VRK3 is still unknown despite its etiological potential in human autism spectrum disorder (ASD). Here, we report that VRK3-deficient mice exhibit typical symptoms of autism-like behavior, including hyperactivity, stereotyped behaviors, reduced social interaction, and impaired context-dependent spatial memory. A significant decrease in dendritic spine number and arborization were identified in the hippocampus CA1 of VRK3-deficient mice. These mice also exhibited a reduced rectification of AMPA receptor–mediated current and changes in expression of synaptic and signaling proteins, including tyrosine receptor kinase B (TrkB), Arc, and CaMKIIα. Notably, TrkB stimulation with 7,8-dihydroxyflavone reversed the altered synaptic structure and function and successfully restored autism-like behavior in VRK3-deficient mice. These results reveal that VRK3 plays a critical role in neurodevelopmental disorders and suggest a potential therapeutic strategy for ASD.

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Zhang, Ji-chun, Wei Yao, Chao Dong, Chun Yang, Qian Ren, Min Ma, Mei Han, and Kenji Hashimoto. "Comparison of ketamine, 7,8-dihydroxyflavone, and ANA-12 antidepressant effects in the social defeat stress model of depression." Psychopharmacology 232, no. 23 (September 4, 2015): 4325–35. http://dx.doi.org/10.1007/s00213-015-4062-3.

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47

Silva, David, and Cecilia Nunez. "FLAVONOIDES E ÁCIDOS FENÓLICOS ISOLADOS DOS EXTRATOS METANÓLICOS DAS FOLHAS E GALHOS DE Macrolobium acaciifolium (FABACEAE)." Química Nova, 2024. http://dx.doi.org/10.21577/0100-4042.20240040.

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FLAVONOIDS AND PHENOLIC ACIDS ISOLATED FROM Macrolobium acaciifolium (FABACEAE) LEAVES AND BRANCHES METHANOLIC EXTRACTS. The phytochemical study of Macrolobium acaciifolium extracts allowed the isolation and identification of 18 substances, 15 of which are reported for the first time in this species. From the methanolic extract of the leaves, the flavonoids luteolin-3’-O-α-L-rhamnoside (1), neoastilbin (2), astilbin (3), neoisoastilbin (4), isoastilbin (5), quercetin-3-O-α-L-rhamnoside (6), quercetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), quercetin-3-O-glicoside (9) and kaempferol-7-O-rutinoside (10) were isolated. From the methanolic extract of branches, the flavonoids chrysoeriol (13), apigenin (14), 7,4’-dihydroxyflavone (16), eriodictyol (17) and luteolin (18), in addition to the phenolic acids 3,4-dihydroxybenzoic acid (11), 3-methoxy,4-hydroxybenzoate (12) and methyl 3,4-dihydroxybenzoate (15) were isolated. The structural identification of the compounds was established by proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) and correlated spectroscopy (COSY) analyses. In this paper, we also discuss about the anisotropic effects on H-1’’, H-2’’, H-5’’ and H-6’’ rhamnose of isomers dihydroflavonoids.

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Chen, Ting‐Xiao, Shou‐Kai Wang, Yu‐Qing Zhang, Wei Wang, Qi Wang, Jian‐Chun Yu, Sheng‐Chen Zhao, et al. "7,8‐dihydroxyflavone displayed antioxidant effect through activating HO‐1 expression and inhibiting caspase‐3/PARP activation in RAW264.7 cells." Journal of Biochemical and Molecular Toxicology, December 5, 2023. http://dx.doi.org/10.1002/jbt.23602.

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AbstractFlavonoids, which contain a benzo‐γ‐pyrone (C6–C3–C6) skeleton, have been reported to exhibit effective antioxidant ability. This study aimed to compare the antioxidant activities of 7,8‐dihydroxyflavone (7,8‐DHF) and 7‐hydroxyflavone (7‐HF) in H2O2, lipopolysaccharide (LPS), or tert‐butyl hydroperoxide (t‐BHP)‐induced RAW264.7 cells, respectively. The antioxidant capacities of 7,8‐DHF and 7‐HF were firstly evaluated by 2,2‐azinobis‐3‐ethyl‐benzothiazoline‐6‐sulphonic acid (ABTS), 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays. Then, reactive oxygen species (ROS), super oxide dismutase (SOD), and malondialdehyde (MDA) productions in H2O2, LPS, or t‐BHP‐induced RAW264.7 cells were tested and compared, respectively. Finally, the antioxidant mechanisms of 7‐HF and 7,8‐DHF were initially investigated by western blot. Our results showed that 7,8‐DHF possessed stronger free‐radical scavenging capacity than 7‐HF. Both 7,8‐DHF and 7‐HF suppressed MDA production and ROS accumulation, improved the activity of SOD in H2O2, LPS, or t‐BHP‐induced RAW264.7 cells, respectively. And 7,8‐DHF exerted a better antioxidant effect than 7‐HF, especially in t‐BHP‐induced oxidative stress. Mechanically, 7,8‐DHF prevented the activation of poly ADP‐ribosepolymerase and caspase‐3, meanwhile markedly upregulated the expression of HO‐1 protein in t‐BHP‐induced oxidative stress. These results suggested that 7,8‐DHF might serve as a potential pharmaceutical drug against oxidative stress injury.

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Aboul Naser, Asmaa F., Yomna R. Ahmed, Mona A. Mohammed, Mohamed Aboelmagd, Mona E. Aboutabl, Entesar E. S. Hassan, Wagdy K. B. Khalil, and Manal A. Hamed. "Inflammatory mediators, oxidative stress and genetic disturbance in rheumatoid arthritis rats supported by alfalfa seeds metabolomic constituents via blocking interleukin‐1receptor." Chemistry & Biodiversity, December 29, 2023. http://dx.doi.org/10.1002/cbdv.202301653.

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Rheumatoid arthritis (RA) is an autoimmune disease characterized by aggressive cartilage and bone erosion. This work aimed to evaluate the metabolomic profile of Medicago sativa L. (MS) seeds and explore its therapeutic impact against RA in rats. Arthritis was induced by complete Freund’s adjuvant (CFA) and its severity was assessed by the arthritis index. Treatment with MS seeds butanol fraction and interlukin‐1 receptor antagonist (IL‐1RA) were evaluated through measuring interlukin‐1 receptor (IL‐1R) type 1 gene expression, interlukin‐1 beta (IL‐1β), oxidative stress markers, C‐reactive protein (CRP), tumor necrosis factor‐alpha (TNF‐α), prostaglandin E2 (PGE2), caspase‐3 (Cas‐3), intracellular adhesion molecule‐1 (ICAM‐1), DNA fragmentation, and chromosomal damage. Total phenolics/ flavonoids content in the ethyl acetate, butanol fraction and crude extract of MS seeds were estimated. The major identified compounds were Quercetin, Trans‐taxifolin, gallic acid, 7,4'‐Dihydroxyflavone, Cinnamic acid, Kudzusaponin SA4, Isorhamnetin 3‐O‐beta‐D‐2'',3'',4''‐triacetylglucopyranoside, Apigenin, 5,7,4'‐Trihydroxy‐3'‐methoxyflavone, Desmethylxanthohumol, Pantothenic acid, Soyasapogenol E, Malvidin, Helilandin B, Stigmasterol, and Wairol. Treatment with MS seeds butanol fraction and IL‐1RA enhanced all the biochemical parameters and the histopathological features of the ankle joint. In conclusion, Trans‐taxifolin was isolated for the first time from the genus Medicago. MS butanol fraction seeds extract and IL‐1 RA were considered as anti‐rheumatic agents.

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CIRRIK, Selma, Gulay HACIOĞLU, Emine Gülçeri GÜLEÇ PEKER, Hatıce KESER, and Selcen ABIDIN. "Yaşa bağlı oksidatif stres ve nitrik oksid azalışında 7,8-dihidroksiflavonun etkisi." Pamukkale Medical Journal, June 13, 2022. http://dx.doi.org/10.31362/patd.1071847.

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Purpose: It has been reported that 7,8-dihydroxyflavone (7,8-DHF), known as a brain-derived neurotrophic factor (BDNF) receptor agonist, affects nitric oxide (NO) production as well as its antioxidant properties. Although favorable effects of 7,8-DHF have been reported in the central nervous system in aged rodents, its effects on non-neural tissues are not fully understood yet. In the literature, it has been stated that liver, kidney and heart tissues show age-related oxidative stress and NO dysregulation. In this study, the effects of 7,8-DHF on oxidative stress and NO production in liver, kidney and heart tissues in aged mice were investigated. Materials and methods: Male C57BL/6 mice were divided into 3 groups as young (5 months old, n=10), elderly (18 months old, n=10) and DHF-elderly (18 months old, n=7). The mice in DHF-elderly group were treated with 7,8-DHF (5 mg.kg-1.day-1, intraperitoneally) for 3 weeks. The malondialdehyde (MDA), reduced glutathione (GSH) and nitrite/nitrate (NOx) levels were measured in the liver, heart and kidney tissues of mice. Results: Hepatic MDA increase (p

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