naphthoquinones and 1-1-diphenyl-2-picrylhydrazyl

naphthoquinones has been researched along with 1-1-diphenyl-2-picrylhydrazyl* in 14 studies

Other Studies

14 other study(ies) available for naphthoquinones and 1-1-diphenyl-2-picrylhydrazyl

ArticleYear
Neuroprotective Effect of 1,4-Naphthoquinones in an
    International journal of molecular sciences, 2021, Sep-14, Volume: 22, Issue:18

    Targeted screening using the MTT cell viability test with a mini-library of natural and synthetic 1,4-naphthoquinones and their derivatives was performed in order to increase the survival of Neuro-2a neuroblastoma cells in in vitro paraquat and 6-hydroxydopamine models of Parkinson's disease. As a result, 10 compounds were selected that could protect neuronal cells from the cytotoxic effects of both paraquat and 6-hydroxydopamine. The five most active compounds at low concentrations were found to significantly protect the activity of nonspecific esterase from the inhibitory effects of neurotoxins, defend cell biomembranes from lytic destruction in the presence of paraquat and 6-hydroxydopamine, and normalize the cell cycle. The protective effects of these compounds are associated with the suppression of oxidative stress, decreased expression of reactive oxygen species and nitric oxide formation in cells and normalization of mitochondrial function, and restoration of the mitochondrial membrane potential altered by neurotoxins. It was suggested that the neuroprotective activity of the studied 1,4-NQs is attributable to their pronounced antioxidant and free radical scavenging activity and their ability to reduce the amount of reactive oxygen species formed by paraquat and 6-hydroxydopamine action on neuronal cells. The significant correlation between the neuroprotective properties of 1,4-naphthoquinones and Quantitative Structure-Activity Relationship descriptors describing the physicochemical properties of these compounds means that the hydrophobicity, polarity, charge, and shape of the molecules can be of decisive importance in determining the biological activity of studied substances.

    Topics: Animals; Biphenyl Compounds; Cell Cycle; Cell Line; Cell Survival; Free Radical Scavengers; Membrane Potential, Mitochondrial; Mice; Models, Biological; Naphthoquinones; Neuroprotection; Neuroprotective Agents; Neurotoxins; Nitric Oxide; Oxidopamine; Paraquat; Picrates; Quantitative Structure-Activity Relationship; Reactive Oxygen Species; Reproducibility of Results

2021
Coelomic fluid of Echinometra mathaei: The new prospects for medicinal antioxidants.
    Fish & shellfish immunology, 2021, Volume: 117

    Topics: Animals; Antioxidants; Biphenyl Compounds; Naphthoquinones; Picrates; Pigments, Biological; Sea Urchins

2021
Molecular identification and phytochemical screening of endophytic fungi isolated from Lithospermum officinale L. roots: A new source of shikonin.
    Phytochemistry, 2019, Volume: 168

    Endophytic fungi are microorganisms located in the inter- or intracellular compartments of plant tissues but with no harmful effects. They are considered a potential source of biological compounds. The present study was conducted to investigate the molecular identification of endophytic fungi isolated from the roots of Lithospermum officinale and their potential production of shikonin. Phylogenetic analysis was performed based on the Internal Transcribed Spacer (ITS) region and the isolates were classified into five genera as follows: Alternaria, Chaetosphaeronema, Fusarium, Mucor, and Trichoderma. The study on the methanol extracts of endophytic fungi indicated that total polyphenol content had a positive relationship with antioxidant activities and the highest antioxidant activity belonged to the methanol extracts of Fusarium tricinctum and Alternaria altenata. Then, to investigate the ability of the fungal isolates to produce shikonin, a naphthoquinone compound with high biological activity, the extracts were subjected to HPLC. The results obtained from HPLC-mass spectrometry showed that shikonin could be produced only by F. tricinctum. Thus, F. tricinctum isolated from the roots of L. officinale can be presented as a new source of shikonin.

    Topics: Antioxidants; Biphenyl Compounds; Drug Evaluation, Preclinical; Endophytes; Lithospermum; Naphthoquinones; Phylogeny; Phytochemicals; Picrates; Plant Roots

2019
In vitro Antioxidant and Antimicrobial Effects of Ceratostigma plumbaginoides.
    Natural product communications, 2016, Volume: 11, Issue:10

    Bioactive compounds, including phenols, flavonoids, and tannins, were quantified in leaves, stems and roots of methanol, n-butanol, diethyl ether and n- hexane extracts of Ceratostigina plumbaginoides Bunge. (Plumbaginaceae) ornamental plants. The antioxidant capacity was measured by the DPPH and linoleic acid assays. The total bioactive compounds, as well as the antioxidant capacities, were the highest in the leaves compared with stems and roots. The -methanolic, n-butanol, diethyl ether and n-hexane leaf extracts varied in their antibacterial and antifungal activities. In general, the most sensitive bacterium to leaf extracts was Bacillus cereus and the most resistant was Staphyllococcus aureus, while the most sensitive fungus was Aspergillusflavus and the most resistant one was Penicillium ochrochloron. As the methanolic leaf extract was the most active, it was subjected to column chromatography and two compounds were isolated and identified as 1 (5-hydroxy-2-methyl-1,4-naphthoquinone / plumbagin) and 2 (3,3'-biplumbagin). Compounds 1 and 2 showed the highest antibacterial and antifungal activities compared with other extracts tested. The MIC and MBC values for the most active compound 1 were in the range of 0.001 - 0.09 and 0.004 - 0.21 mg mL⁻¹, while MIC and MFC were determined as 0.001 - 0.11 and 0.002 - 0.19 mg mL⁻¹, respectively. The isolated compounds and leaf extracts showed also equal or higher antimicrobial activities compared with antibiotics/commercial reagents which indicate that the plant might be useful for drug development. This is the first report on the antibacterial and antifungal activities, as well as the antioxidant properties of the tested plant parts and isolated compounds.

    Topics: Anti-Bacterial Agents; Anti-Infective Agents; Antifungal Agents; Antioxidants; Bacteria; Biphenyl Compounds; Fungi; Microbial Sensitivity Tests; Naphthoquinones; Picrates; Plant Extracts; Plant Leaves; Plumbaginaceae; Tannins

2016
Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa.
    Journal of natural products, 2016, Apr-22, Volume: 79, Issue:4

    Four new quinonoid naphthopyranones, ophioparmin (1), 4-methoxyhaemoventosins (2a and 2b), and 4-hydroxyhaemoventosin (3), together with anhydrofusarubin lactone (4) and haemoventosin (5) were isolated from the fruiting bodies of Ophioparma ventosa, a crustose lichen. Their structures were determined by spectroscopic analyses, and the absolute configurations of 1 and 2 were elucidated through experimental and calculated electronic circular dichroism analyses. Compounds 1, 2, and 5 exhibited moderate to strong antioxidant activities. The main pigment haemoventosin exhibited significant cytotoxicity toward a panel of nine cell lines.

    Topics: Antineoplastic Agents; Biphenyl Compounds; Circular Dichroism; Drug Screening Assays, Antitumor; Fruiting Bodies, Fungal; Humans; Inhibitory Concentration 50; Lichens; Molecular Structure; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Picrates; Pyrans

2016
Three new polyketides from marine-derived fungus Aspergillus glaucus HB1-19.
    Journal of Asian natural products research, 2013, Volume: 15, Issue:9

    Two new benzyl derivatives, aspergentisyl A (1) and aspergentisyl B (2), as well as one new naphthoquinone derivative, aspergiodiquinone (3), together with seven known prenylated benzaldehyde derivatives (4-10) were isolated from the marine-derived fungus Aspergillus glaucus HB1-19. The structures of these compounds were characterized based on 1D and 2D NMR spectra analyses and comparison with those reported in the literature. In addition, each isolate was tested for its 1,1-diphenyl-2-picrylhydrazyl radical-scavenging property and all these compounds except compound 3 exhibited strong radical-scavenging activity.

    Topics: Aspergillus; Benzyl Compounds; Biphenyl Compounds; Free Radical Scavengers; Marine Biology; Molecular Structure; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Picrates; Polyketides

2013
Anti-inflammatory, antimicrobial and antioxidant activities of Diospyros bipindensis (Gürke) extracts and its main constituents.
    Journal of ethnopharmacology, 2013, Mar-07, Volume: 146, Issue:1

    Diospyros bipindensis (Gürke) stem bark is used in Cameroon by Baka Pygmies for the treatment of respiratory disorders.. To assess the anti-inflammatory, antibacterial and antioxidant properties of constituents from the bark extracts through bioassay-guided fractionation.. The anti-inflammatory activity of extracts, fractions and pure compounds was assessed through the inhibition of the pro-inflammatory mediator nuclear factor-kappa B (NF-κB) transcriptional activity and nitric oxide (NO) production. DPPH, ABTS and ORAC assays were used for determining the antioxidant properties. The activity against Streptococcus pneumoniae, Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Klebsiella pneumoniae, was evaluated on the basis of the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) by the macrodilution method.. The water extract showed antimicrobial activity against S. pneumoniae (MIC: 300 μg/ml) and S. pyogenes (MIC: 300 μg/ml). The dichloromethane extract efficiently inhibited NF-κB transcriptional activity and NO production and exhibited significant antioxidant activity in the ORAC assay. An interesting activity was also found against S. pneumoniae (MIC: 200 μg/ml), S. aureus (MIC: 400 μg/ml) and S. pyogenes (MIC: 200 μg/ml). The phytochemical investigation of the dichloromethane extract afforded plumbagin, canaliculatin, ismailin, betulinic acid and 4-hydroxy-5-methyl-coumarin as the main constituents. Plumbagin and ismailin were found to be responsible for the main biological activities observed.. These results may provide a rational support for the traditional use of Diospyros bipindensis stem bark in the treatment of respiratory disorders, since the anti-inflammatory, antimicrobial and antioxidant compounds isolated from the dichloromethane extract were also present in the traditional water extract.

    Topics: Animals; Anti-Bacterial Agents; Anti-Inflammatory Agents; Antioxidants; Bacteria; Betulinic Acid; Biphenyl Compounds; Cell Line; Diospyros; HEK293 Cells; Humans; Mice; Microbial Sensitivity Tests; Naphthoquinones; NF-kappa B; Nitric Oxide; Pentacyclic Triterpenes; Picrates; Plant Bark; Plant Extracts; Triterpenes; Tumor Necrosis Factor-alpha

2013
Free radical scavenging activities of naturally occurring and synthetic analogues of sea urchin naphthazarin pigments.
    Natural product communications, 2012, Volume: 7, Issue:7

    Antioxidant activities of minor pigments of sea urchins (1-5) and synthetic naphthazarins (7-13) were evaluated and compared with echinochrome A (6) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assays. Structure-activity relationships showed that the antioxidant activities of the tested compounds depended on the number and positions of hydroxyl groups. Compounds bearing 3 or 2 hydroxyl groups on a naphthazarin core (5,8-dihydroxy-1,4-naphthoquinone) were the most active in both assays. Echinochrome A (6) (IC50 7.0 microM) and its monomethyl ethers 7 (IC50 15.0 microM) and 8 (IC50 15.0 microM) displayed stronger activities than Trolox (IC50 16.0 microM) in the DPPH and ABTS assays (TE = 3.41, 2.35, and 2.35 mM, respectively). Compounds with either one or without hydroxyl groups on a naphthazarin core displayed activities significantly lower than Trolox in both assays. These results suggest that hydroxylated naphthazarin pigments of sea urchins have a potential use as natural antioxidants.

    Topics: Animals; Antioxidants; Biphenyl Compounds; Free Radical Scavengers; Free Radicals; Molecular Structure; Naphthoquinones; Picrates; Sea Urchins

2012
Naphthoquinone-like polyketide isolated from Streptomyces sp. RI-77 and its predicted biosynthetic pathway.
    Journal of natural products, 2011, Dec-27, Volume: 74, Issue:12

    A novel naphthoquinone-like polyketide, JBIR-85 (1), with a unique skeleton and antioxidative activity was isolated from a culture of Streptomyces sp. RI-77. The planar structure of 1 was established on the basis of extensive NMR and MS analyses. The structure of 1 including the absolute configuration was established via X-ray crystallographic analysis. Since 1 exhibits a unique skeleton, we performed feeding experiments to reconfirm the structure and predict the biosynthetic pathway.

    Topics: Biphenyl Compounds; Crystallography, X-Ray; Free Radical Scavengers; Molecular Conformation; Molecular Structure; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Picrates; Polyketides; Streptomyces

2011
Antifungal and antioxidant activities of the phytomedicine pipsissewa, Chimaphila umbellata.
    Phytochemistry, 2008, Volume: 69, Issue:3

    Bioassay-guided fractionation of Chimaphila umbellata (L.) W. Bart (Pyrolaceae) ethanol extracts led to the identification of 2,7-dimethyl-1,4-naphthoquinone (chimaphilin) as the principal antifungal component. The structure of chimaphilin was confirmed by 1H and 13C NMR spectroscopy. The antifungal activity of chimaphilin was evaluated using the microdilution method with Saccharomyces cerevisiae (0.05mg/mL) and the dandruff-associated fungi Malassezia globosa (0.39mg/mL) and Malassezia restricta (0.55mg/mL). Pronounced antioxidant activity of C. umbellata crude extract was also identified using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, suggesting this phytomedicine has an antioxidant function in wound healing. A chemical-genetic profile was completed with chimaphilin using approximately 4700 S. cerevisiae gene deletion mutants. Cellular roles of deleted genes in the most susceptible mutants and secondary assays indicate that the targets for chimaphilin include pathways involved in cell wall biogenesis and transcription.

    Topics: Antifungal Agents; Antioxidants; Biphenyl Compounds; Dose-Response Relationship, Drug; Hydrazines; Magnetic Resonance Spectroscopy; Malassezia; Microbial Sensitivity Tests; Molecular Structure; Naphthoquinones; Picrates; Pyrolaceae; Saccharomyces cerevisiae; Structure-Activity Relationship

2008
Echinochrome, a naturally occurring iron chelator and free radical scavenger in artificial and natural membrane systems.
    Life sciences, 2005, Jan-07, Volume: 76, Issue:8

    Echinochrome, or 6-ethyl-2,3,5,7,8-pentahydroxy-1,4-naphthoquinone, possesses cardioprotective activity, and diminishes the myocardial ischemia/reperfusion injury that is known to be accompanied by free-radical oxidative damage and calcium overload. In this study, we investigated the lipophilicity of echinochrome, its ability to inhibit free-radical oxidation both in the bulk organic phase and in an artificial membrane system (liposomes), and to prevent the ferrous/ascorbate-induced leakage of calcium from the isolated sarcoplasmic reticulum (SR) of rabbit skeletal muscle. The experimentally-determined octanol/water partition coefficient (LogP) of echinochrome was +3.11, and the distribution coefficient (LogD) was +2.58 at pH 6.0 and -0.15 at pH 8.0. Echinochrome displayed high scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals with a stoichiometry of about 1:7. Echinochrome was more effective in inhibiting the phosphatidyl choline liposome peroxidation induced by Fe2+/ascorbate than that induced by hemin. The iron chelating ability of echinochrome was estimated spectrophotometrically. In isolated SR, echinochrome protected the ATP-dependent Ca2+-pump system from damage by Fe2+/ascorbate. It was concluded that iron chelation predominates in the overall antioxidant potential of echinochrome.

    Topics: Animals; Biphenyl Compounds; Calcium; Free Radical Scavengers; Hydrazines; Iron Chelating Agents; Lipid Peroxidation; Liposomes; Naphthoquinones; Octanols; Oxidation-Reduction; Picrates; Rabbits; Sarcoplasmic Reticulum; Solvents; Water

2005
Radical scavenging activity of Alkanna tinctoria root extracts and their main constituents, hydroxynaphthoquinones.
    Phytotherapy research : PTR, 2005, Volume: 19, Issue:2

    Alkannin and shikonin (A[sol ]S) are pharmaceutical substances with a wide spectrum of biological properties. Radical scavenging activity is involved in aging processes, antiinssammatory, anticancer and wound healing activities. Hence, in the present study the DPPH radical scavenging activity of alkannin and shikonin, both monomeric and oligomeric, and extracts of Alkanna tinctoria roots were studied and a structure-activity relationship was approximated. It was shown that both monomeric and oligomeric alkannin and shikonin and also A[sol ]S esters exhibited extremely high radical scavenging activity. The presence of the naphthoquinone moiety seems to be essential for that activity, while the side chain of A[sol ]S possibly plays a minor role. Esterification of A[sol ]S on the side chain hydroxyl group does not affect radical scavenging activity. Organic solvents and olive oil (extracted at room temperature) extracts of Alkanna tinctoria roots, which contain as active ingredients A[sol ]S esters, exhibited very good antiradical activity. Alkannin and shikonin and their esters and also extracts of Alkanna tinctoria roots could be used promisingly in pharmaceutical and cosmetic preparations for their radical scavenging activity and probably for their antiaging activity.

    Topics: Biphenyl Compounds; Boraginaceae; Free Radical Scavengers; Humans; Naphthoquinones; Phytotherapy; Picrates; Plant Extracts; Plant Roots; Structure-Activity Relationship

2005
Echinamines A and B, first aminated hydroxynaphthazarins from the sea urchin Scaphechinus mirabilis.
    Journal of natural products, 2005, Volume: 68, Issue:9

    Two new spinochromes, echinamines A (1) and B (2), were isolated from the sea urchin Scaphechinus mirabilis. Compounds 1 and 2 represent the first examples of natural polyhydroxynaphthazarins with a primary amine group. The structures of 1 and 2 were established by analysis of spectroscopic data and synthesis of their dimethyl ethers.

    Topics: Animals; Biphenyl Compounds; Japan; Molecular Structure; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Picrates; Sea Urchins

2005
Comparison of the antioxidant activities of extra virgin olive oils.
    Journal of agricultural and food chemistry, 2002, Dec-18, Volume: 50, Issue:26

    The phenol content and antioxidant activity of extra virgin olive oils (EVOOs) differing in their origins and degradation degrees were studied. The o-diphenolic compounds typical of olive oil, namely, the oleuropein derivatives hydroxytyrosol (3',4'-dihydroxyphenylethanol, 3',4'-DHPEA), the dialdehydic form of elenolic acid linked to 3',4'-DHPEA (3',4'-DHPEA-EDA), and an isomer of oleuropein aglycon (3',4'-DHPEA-EA), were analyzed by HPLC. The antioxidant activity was studied by (a) the xanthine oxidase (XOD)/xanthine system, which generates superoxide radical and hydrogen peroxide; (b) the diaphorase (DIA)/NADH/juglone system, which generates superoxide radical and semiquinonic radical; and (c) the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) test. Results showed that EVOOs with a low degradation level (as evaluated by acidity, peroxide number, and spectroscopic indices K(232), K(270), and deltaK according to the EU Regulation) had a higher content of 3',4'-DHPEA-EDA and a lower content of 3',4'-DHPEA than oils having intermediate and advanced degradation levels. EVOOs with a low degradation degree were 3-5 times more efficient as DPPH scavengers and 2 times more efficient as inhibitors of the XOD-catalyzed reaction than oils with intermediate and advanced degradation levels. The DIA-catalyzed reaction was inhibited by EVOOs having low or intermediate degradation levels but not by the most degraded oils.

    Topics: Antioxidants; Benzoquinones; Biphenyl Compounds; Chromatography, High Pressure Liquid; Dihydrolipoamide Dehydrogenase; Hydrogen Peroxide; Naphthoquinones; Olive Oil; Phenols; Picrates; Plant Oils; Superoxides; Xanthine; Xanthine Oxidase

2002