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481-42-5

481-42-5 | 5-Hydroxy-2-methylnaphthalene-1,4-dione

CAS No: 481-42-5 Catalog No: AG003TTF MDL No:MFCD00001682

Product Description

Catalog Number:
AG003TTF
Chemical Name:
5-Hydroxy-2-methylnaphthalene-1,4-dione
CAS Number:
481-42-5
Molecular Formula:
C11H8O3
Molecular Weight:
188.1794
MDL Number:
MFCD00001682
IUPAC Name:
5-hydroxy-2-methylnaphthalene-1,4-dione
InChI:
InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChI Key:
VCMMXZQDRFWYSE-UHFFFAOYSA-N
SMILES:
CC1=CC(=O)c2c(C1=O)cccc2O
EC Number:
207-569-6
UNII:
YAS4TBQ4OQ

Properties

Complexity:
317  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
188.047g/mol
Formal Charge:
0
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
188.182g/mol
Monoisotopic Mass:
188.047g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
54.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3  

Literature

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Plumbagin inhibits tumour angiogenesis and tumour growth through the Ras signalling pathway following activation of the VEGF receptor-2. British journal of pharmacology 20120201
Ascorbate and thiol antioxidants abolish sensitivity of yeast Saccharomyces cerevisiae to disulfiram. Cell biology and toxicology 20120201
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Expression patterns of glutathione transferase gene (GstI) in maize seedlings under juglone-induced oxidative stress. International journal of molecular sciences 20110101
Modeling natural anti-inflammatory compounds by molecular topology. International journal of molecular sciences 20110101
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Plumbagin inhibits proliferative and inflammatory responses of T cells independent of ROS generation but by modulating intracellular thiols. Journal of cellular biochemistry 20100801
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Plumbagin enhances TRAIL-mediated apoptosis through up-regulation of death receptor in human melanoma A375 cells. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20100801
The prolyl isomerase Pin1 induces LC-3 expression and mediates tamoxifen resistance in breast cancer. The Journal of biological chemistry 20100730
Plumbagin activates ERK1/2 and Akt via superoxide, Src and PI3-kinase in 3T3-L1 cells. European journal of pharmacology 20100725
Inhibition of mycobacterial growth by plumbagin derivatives. Chemical biology & drug design 20100701
Glucose 6-phosphate accumulation in mycobacteria: implications for a novel F420-dependent anti-oxidant defense system. The Journal of biological chemistry 20100618
Role of Pin1 in neointima formation: down-regulation of Nrf2-dependent heme oxygenase-1 expression by Pin1. Free radical biology & medicine 20100615
5-Hydroxy-1,4-naphthoquinone (juglone) and 2-hydroxy-1,4-naphthoquinone (lawsone) influence on jack bean urease activity: Elucidation of the difference in inhibition activity. Bioorganic chemistry 20100601
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Progresses in TCM metal-based antitumour agents. Anti-cancer agents in medicinal chemistry 20100601
Plumbagin induces ROS-mediated apoptosis in human promyelocytic leukemia cells in vivo. Leukemia research 20100501
Enhanced plumbagin production from in vitro cultures of Drosera burmanii using elicitation. Biotechnology letters 20100501
Bioactivity-guided isolation of mosquitocidal constituents from the rhizomes of Plumbago capensis Thunb. Bioorganic & medicinal chemistry letters 20100501
1,4-Naphthoquinones as inducers of oxidative damage and stress signaling in HaCaT human keratinocytes. Archives of biochemistry and biophysics 20100415
Caenorhabditis elegans lifespan extension caused by treatment with an orally active ROS-generator is dependent on DAF-16 and SIR-2.1. Biogerontology 20100401
Effect of hydroxy substituent on the prooxidant action of naphthoquinone compounds. Toxicology in vitro : an international journal published in association with BIBRA 20100401
Preparation, in vitro characterization, pharmacokinetic, and pharmacodynamic evaluation of chitosan-based plumbagin microspheres in mice bearing B16F1 melanoma. Drug delivery 20100401
Development of sensitivity-improved fluorescence-linked immunosorbent assay using a fluorescent single-domain antibody against the bioactive naphthoquinone, plumbagin. Analytical and bioanalytical chemistry 20100401
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol. Bioorganic & medicinal chemistry 20100401
Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol. Bioorganic & medicinal chemistry 20100401
Polar and antioxidant fraction of Plumbago europaea L., a spontaneous plant of Sardinia. Natural product research 20100401
Bioassay-guided isolation of anti-inflammatory and antinociceptive compound from Plumbago zeylanica leaf. Pharmaceutical biology 20100401
Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative. Chemico-biological interactions 20100330
Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana. Journal of experimental botany 20100301
Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia. Journal of neurochemistry 20100301
The prolyl isomerase Pin1 enhances HER-2 expression and cellular transformation via its interaction with mitogen-activated protein kinase/extracellular signal-regulated kinase kinase 1. Molecular cancer therapeutics 20100301
A two-tiered compensatory response to loss of DNA repair modulates aging and stress response pathways. Aging 20100301
Simultaneous detection of pro- and antioxidative effects in the variants of the deoxyribose degradation assay. Journal of agricultural and food chemistry 20100224
Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B. The Journal of organic chemistry 20100205
Plumbagin inhibits TPA-induced MMP-2 and u-PA expressions by reducing binding activities of NF-kappaB and AP-1 via ERK signaling pathway in A549 human lung cancer cells. Molecular and cellular biochemistry 20100201
Antifungal constituents isolated from the seeds of Aegle marmelos. Phytochemistry 20100201
Design of a new electrogenerated polyquinone film substituted with glutathione. Towards direct electrochemical biosensors. Talanta 20100115
The Pin 1 inhibitor juglone attenuates kidney fibrogenesis via Pin 1-independent mechanisms in the unilateral ureteral occlusion model. Fibrogenesis & tissue repair 20100101
5-hydroxy-2-methyl-1,4-naphthoquinone, a vitamin K3 analogue, suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase, SHP-1: potential role in chemosensitization. Molecular cancer research : MCR 20100101
Allyl isothiocyanate that induces GST and UGT expression confers oxidative stress resistance on C. elegans, as demonstrated by nematode biosensor. PloS one 20100101
Quality control standards for the roots of three plumbago species. Indian journal of pharmaceutical sciences 20100101
Iron and its complexation by phenolic cellular metabolites: from oxidative stress to chemical weapons. Plant signaling & behavior 20100101
A systematic investigation of Escherichia coli central carbon metabolism in response to superoxide stress. BMC systems biology 20100101
An update on the therapeutic role of alkylglycerols. Marine drugs 20100101
Dietary, metabolic, and potentially environmental modulation of the lysine acetylation machinery. International journal of cell biology 20100101
A role of ygfZ in the Escherichia coli response to plumbagin challenge. Journal of biomedical science 20100101
Pinning down viral proteins: a new prototype for virus-host cell interaction. Frontiers in microbiology 20100101
Cameroonian medicinal plants: pharmacology and derived natural products. Frontiers in pharmacology 20100101
Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in its copper chemistry. Dalton transactions (Cambridge, England : 2003) 20091228
High levels of thioredoxin reductase 1 modulate drug-specific cytotoxic efficacy. Free radical biology & medicine 20091201
Antiovulatory and estrogenic activity of Plumbago rosea leaves in female albino rats. Indian journal of pharmacology 20091201
Histopathology and cholinergic assessment of Pterocarya fraxinifolia on chicken embryo. Interdisciplinary toxicology 20091201
Novel role of Pin1 induction in type II collagen-mediated rheumatoid arthritis. Journal of immunology (Baltimore, Md. : 1950) 20091115
4-(8-Hydr-oxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphth-yl)butanoic acid. Acta crystallographica. Section E, Structure reports online 20091101
The rotamase Pin1 is up-regulated, hypophosphorylated and required for cell cycle progression in head and neck squamous cell carcinomas. Oral oncology 20091001
Diospyrone, crassiflorone and plumbagin: three antimycobacterial and antigonorrhoeal naphthoquinones from two Diospyros spp. International journal of antimicrobial agents 20091001
Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells. Cell biology international 20091001
In vitro antifilarial activity of glutathione S-transferase inhibitors. Parasitology research 20091001
Plumbagin inhibits invasion and migration of liver cancer HepG2 cells by decreasing productions of matrix metalloproteinase-2 and urokinase- plasminogen activator. Hepatology research : the official journal of the Japan Society of Hepatology 20091001
Defective responses to oxidative stress in protein l-isoaspartyl repair-deficient Caenorhabditis elegans. Mechanisms of ageing and development 20091001
The peptidyl-prolyl isomerase Pin1 determines parathyroid hormone mRNA levels and stability in rat models of secondary hyperparathyroidism. The Journal of clinical investigation 20091001
Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin. The Journal of biological chemistry 20090904
Plumbagin induces cell death through a copper-redox cycle mechanism in human cancer cells. Mutagenesis 20090901
Pin1 affects Tau phosphorylation in response to Abeta oligomers. Molecular and cellular neurosciences 20090901
Superoxide protects Escherichia coli from bleomycin mediated lethality. Journal of inorganic biochemistry 20090901
Pin1 as an anticancer drug target. Drug news & perspectives 20090901
Prolyl isomerase Pin1 acts as a switch to control the degree of substrate ubiquitylation. Nature cell biology 20090801
Enhancement of vascular endothelial growth factor-mediated angiogenesis in tamoxifen-resistant breast cancer cells: role of Pin1 overexpression. Molecular cancer therapeutics 20090801
(+/-)-catechin: chemical weapon, antioxidant, or stress regulator? Journal of chemical ecology 20090801
Plant antimicrobial agents and their effects on plant and human pathogens. International journal of molecular sciences 20090801
Synthesis and insect antifeedant activity of plumbagin derivatives with the amino acid moiety. Journal of agricultural and food chemistry 20090722
No selenium required: reactions catalyzed by mammalian thioredoxin reductase that are independent of a selenocysteine residue. Biochemistry 20090707
Juglone derivatives as antitubercular agents: a rationale for the activity profile. European journal of medicinal chemistry 20090701
Anti-inflammatory effects of plumbagin are mediated by inhibition of NF-kappaB activation in lymphocytes. International immunopharmacology 20090701
The comparative toxicity to soil invertebrates of natural chemicals and their synthetic analogues. Chemosphere 20090701
Spatial distribution, kinetics, signaling and cytokine production during homeostasis driven proliferation of CD4+ T cells. Molecular immunology 20090701
The mitochondrial ribosomal protein of the large subunit, Afo1p, determines cellular longevity through mitochondrial back-signaling via TOR1. Aging 20090701
In vitro screening for anthelmintic and antitumour activity of ethnomedicinal plants from Thailand. Journal of ethnopharmacology 20090625
Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I. The Journal of organic chemistry 20090605
Inhibition of insulin-stimulated hydrogen peroxide production prevents stimulation of sodium transport in A6 cell monolayers. American journal of physiology. Renal physiology 20090601
Increased age reduces DAF-16 and SKN-1 signaling and the hormetic response of Caenorhabditis elegans to the xenobiotic juglone. Mechanisms of ageing and development 20090601
Peptidyl-prolyl isomerase Pin1 markedly enhances the oncogenic activity of the rel proteins in the nuclear factor-kappaB family. Cancer research 20090601
[Effect of juglone on the ultrastructure of human liver cancer BEL-7402 cells]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20090601
Towards a molecular-level understanding of the reactivity differences for radical anions of juglone and plumbagin: an electrochemical and spectroelectrochemical approach. Organic & biomolecular chemistry 20090507
The prolyl isomerase Pin1 interacts with a ribosomal protein S6 kinase to enhance insulin-induced AP-1 activity and cellular transformation. Carcinogenesis 20090401
Two novel phospholipid hydroperoxide glutathione peroxidase genes of Paragonimus westermani induced by oxidative stress. Parasitology 20090401
Molecular events in the activation of B cells and macrophages by a non-microbial TLR4 agonist, G1-4A from Tinospora cordifolia. Immunology letters 20090324
Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells. Toxicology in vitro : an international journal published in association with BIBRA 20090301
Construction and expression of specificity-improved single-chain variable fragments against the bioactive naphthoquinone, plumbagin. Biological & pharmaceutical bulletin 20090301
Feeding a ROS-generator to Caenorhabditis elegans leads to increased expression of small heat shock protein HSP-16.2 and hormesis. Genes & nutrition 20090301
Milieu-dependent pro- and antioxidant activity of juglone may explain linear and nonlinear effects on seedling development. Journal of chemical ecology 20090301
[Recent advance in the study of novel anti-tumor targets and drugs--aurora kinase and Pin1]. Yao xue xue bao = Acta pharmaceutica Sinica 20090301
Crystal structure and catalysis of the selenoprotein thioredoxin reductase 1. The Journal of biological chemistry 20090206
Deletion of the mitochondrial superoxide dismutase sod-2 extends lifespan in Caenorhabditis elegans. PLoS genetics 20090201
Quinone-enhanced sonochemical production of nitric oxide from s-nitrosoglutathione. Ultrasonics sonochemistry 20090101
Characterization of an NADH oxidase of the flavin-dependent disulfide reductase family from Methanocaldococcus jannaschii. Microbiology (Reading, England) 20090101
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases. BMC medical genomics 20090101
Use of folding modulators to improve heterologous protein production in Escherichia coli. Microbial cell factories 20090101
Antimicrobial activity of Drosophyllum lusitanicum, an endemic Mediterranean insectivorous plant. Natural product research 20090101
Taking ecological function seriously: soil microbial communities can obviate allelopathic effects of released metabolites. PloS one 20090101
Modular evolution of glutathione peroxidase genes in association with different biochemical properties of their encoded proteins in invertebrate animals. BMC evolutionary biology 20090101
Emodin targets the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: enzymatic inhibition assay with crystal structural and thermodynamic characterization. BMC microbiology 20090101
Co-ordinated stage-dependent enhancement of Plasmodium falciparum antioxidant enzymes and heat shock protein expression in parasites growing in oxidatively stressed or G6PD-deficient red blood cells. Malaria journal 20090101
Tricyclic pyrone compounds prevent aggregation and reverse cellular phenotypes caused by expression of mutant huntingtin protein in striatal neurons. BMC neuroscience 20090101
Determination of psoralen and plumbagin from its polyherbal oil formulations by an HPTLC densitometric method. Journal of AOAC International 20090101
Plumbagin, isolated from Plumbago zeylanica, induces cell death through apoptosis in human pancreatic cancer cells. Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.] 20090101
Plumbagin-induced apoptosis of human breast cancer cells is mediated by inactivation of NF-kappaB and Bcl-2. Journal of cellular biochemistry 20081215
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Journal of medicinal chemistry 20081113
Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. Cancer research 20081101
Effects of electron transfer mediators on the bioreduction of lepidocrocite (gamma-FeOOH) by Shewanella putrefaciens CN32. Environmental science & technology 20080915
Plumbagin-induced apoptosis in human prostate cancer cells is associated with modulation of cellular redox status and generation of reactive oxygen species. Pharmaceutical research 20080901
Cancer is a preventable disease that requires major lifestyle changes. Pharmaceutical research 20080901
[Study on qualitative and quantitatire methods for Ceratostigma willmottianum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901
Juglone inactivates cysteine-rich proteins required for progression through mitosis. The Journal of biological chemistry 20080801
5-Hydr-oxy-8-nitro-1,4-naphthoquinone. Acta crystallographica. Section E, Structure reports online 20080801
The natural naphthoquinone plumbagin exhibits antiproliferative activity and disrupts the microtubule network through tubulin binding. Biochemistry 20080729
Natural product juglone targets three key enzymes from Helicobacter pylori: inhibition assay with crystal structure characterization. Acta pharmacologica Sinica 20080701
Investigation of Indian diospyros species for antiplasmodial properties. Evidence-based complementary and alternative medicine : eCAM 20080601
Thymic stromal lymphopoietin expression in allergic pulmonary inflammation is Pin1-dependent. The Journal of allergy and clinical immunology 20080501
Crystallization and preliminary characterization of a novel haem-binding protein of Streptomyces reticuli. Acta crystallographica. Section F, Structural biology and crystallization communications 20080501
Impact of lactic acid bacteria on oxidative DNA damage in human derived colon cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080401
Estrogen-dependent cell signaling and apoptosis in BRCA1-blocked BG1 ovarian cancer cells in response to plumbagin and other chemotherapeutic agents. Annals of oncology : official journal of the European Society for Medical Oncology 20080401
Solubilization of hydrophobic drugs by methoxy poly(ethylene glycol)-block-polycaprolactone diblock copolymer micelles: theoretical and experimental data and correlations. Journal of pharmaceutical sciences 20080301
Topoisomerase inhibitors as anti-arthritic agents. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20080301
Oxidative stress in Caenorhabditis elegans: protective effects of the Omega class glutathione transferase (GSTO-1). FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080201
Acaricidal activity and function of mite indicator using plumbagin and its derivatives isolated from Diospyros kaki Thunb. roots (Ebenaceae). Journal of microbiology and biotechnology 20080201
Development of an enzyme-linked immunosorbent assay (ELISA) using highly-specific monoclonal antibodies against plumbagin. Analytica chimica acta 20080121
Plumbagin induces cell cycle arrest and apoptosis through reactive oxygen species/c-Jun N-terminal kinase pathways in human melanoma A375.S2 cells. Cancer letters 20080118
Radiosensitizing effects of plumbagin in cervical cancer cells is through modulation of apoptotic pathway. Molecular carcinogenesis 20080101
Plumbagin recovery from field specimens of Drosophyllum lusitanicum (L.) link. Phytochemical analysis : PCA 20080101
Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in swiss albino mice. Metal-based drugs 20080101
Merger of ayurveda and tissue culture-based functional genomics: inspirations from systems biology. Journal of translational medicine 20080101
Cell death by SecTRAPs: thioredoxin reductase as a prooxidant killer of cells. PloS one 20080101
Anticancer mechanism of plumbagin, a natural compound, on non-small cell lung cancer cells. Anticancer research 20080101
A multicopy suppressor screening approach as a means to identify antibiotic resistance determinant candidates in Yersinia pestis. BMC microbiology 20080101
A classification model to predict synergism/antagonism of cytotoxic mixtures using protein-drug docking scores. BMC pharmacology 20080101
Genome-wide transcriptional response of an avian pathogenic Escherichia coli (APEC) pst mutant. BMC genomics 20080101
Identification and characterization of sigma, a novel component of the Staphylococcus aureus stress and virulence responses. PloS one 20080101
Prolyl isomerase Pin1 is highly expressed in Her2-positive breast cancer and regulates erbB2 protein stability. Molecular cancer 20080101
Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae. PloS one 20080101
Fingerprinting of Plumbagin in lic>Drosera burmannii Vahl using High Performance Thin Layer Chromatography. Indian journal of pharmaceutical sciences 20080101
A Reverse Phase HPLC-UV and HPTLC Methods for Determination of Plumbagin in Plumbago indica and Plumbago zeylanica. Indian journal of pharmaceutical sciences 20080101
Effects of the flavonoids kaempferol and fisetin on thermotolerance, oxidative stress and FoxO transcription factor DAF-16 in the model organism Caenorhabditis elegans. Archives of toxicology 20071201
Induction of multiple antibiotic resistance in Bacteroides fragilis by benzene and benzene-derived active compounds of commonly used analgesics, antiseptics and cleaning agents. The Journal of antimicrobial chemotherapy 20071201
The naphthoquinones, vitamin K3 and its structural analogue plumbagin, are substrates of the multidrug resistance linked ATP binding cassette drug transporter ABCG2. Molecular cancer therapeutics 20071201
[Insecticidal activity and active components of alcohol extract from Juglans mandshurica Maxim leaves]. Ying yong sheng tai xue bao = The journal of applied ecology 20071201
A critical role for Pin1 in allergic pulmonary eosinophilia in rats. The Journal of allergy and clinical immunology 20071101
Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071001
The influence of water quality on the toxicity and degradation of juglone (5-hydroxy 1,4-naphthoquinone). Environmental technology 20071001
Induction of apoptosis by plumbagin through reactive oxygen species-mediated inhibition of topoisomerase II. Toxicology and applied pharmacology 20070915
Polyunsaturated fatty acids modulate NOX 4 anion superoxide production in human fibroblasts. The Biochemical journal 20070815
Mycobacterium smegmatis mc2 155 fbiC and MSMEG_2392 are involved in triphenylmethane dye decolorization and coenzyme F420 biosynthesis. Microbiology (Reading, England) 20070801
In vitro antifungal activity of extract and plumbagin from the stem bark of Diospyros crassiflora Hiern (Ebenaceae). Phytotherapy research : PTR 20070701
Phytotoxic effects of 21 plant secondary metabolites on Arabidopsis thaliana germination and root growth. Journal of chemical ecology 20070701
Thioredoxin glutathione reductase from Schistosoma mansoni: an essential parasite enzyme and a key drug target. PLoS medicine 20070601
[Naphthoquinones and their pharmacological properties]. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20070601
[Chemical constituents from aerial parts of Plumbago zeylanica Linn]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20070501
Naphthoquinones as broad spectrum biocides for treatment of ship's ballast water: toxicity to phytoplankton and bacteria. Water research 20070301
Screening of natural product biocides for control of non-indigenous species. Environmental technology 20070301
A polyketide synthase of Plumbago indica that catalyzes the formation of hexaketide pyrones. The FEBS journal 20070101
Pin1 modulates the type 1 immune response. PloS one 20070101
Occurrence and fate of the phytotoxin juglone in alley soils under black walnut trees. Journal of environmental quality 20070101
Dynamic rerouting of the carbohydrate flux is key to counteracting oxidative stress. Journal of biology 20070101
Trypanothione reductase: a viable chemotherapeutic target for antitrypanosomal and antileishmanial drug design. Drug target insights 20070101
Plumbagin induces G2-M arrest and autophagy by inhibiting the AKT/mammalian target of rapamycin pathway in breast cancer cells. Molecular cancer therapeutics 20061201
DNA microarrays in herbal drug research. Evidence-based complementary and alternative medicine : eCAM 20061201
Therapeutic Strategies in Huntington's Disease. Journal of clinical neurology (Seoul, Korea) 20061201
Measurement and pharmacokinetic study of plumbagin in a conscious freely moving rat using liquid chromatography/tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20061121
[Determination of plumbagin in different parts of Plumbago zeylanica by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061001
Using of liquid chromatography coupled with diode array detector for determination of naphthoquinones in plants and for investigation of influence of pH of cultivation medium on content of plumbagin in Dionaea muscipula. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060914
Antiprotozoal and cytotoxic naphthalene derivatives from Diospyros assimilis. Phytochemistry 20060901
Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) induces apoptosis and cell cycle arrest in A549 cells through p53 accumulation via c-Jun NH2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. The Journal of pharmacology and experimental therapeutics 20060801
Mono and dimeric naphthalene derivatives from the roots of Diospyros assimilis. Natural product research 20060720
The peptidylprolyl cis/trans-isomerase Pin1 modulates stress-induced dephosphorylation of Tau in neurons. Implication in a pathological mechanism related to Alzheimer disease. The Journal of biological chemistry 20060714
Electrocoagulation of quinone pigments. Molecules (Basel, Switzerland) 20060714
Effects of quinones and flavonoids on the reduction of all-trans retinal to all-trans retinol in pig heart. European journal of pharmacology 20060701
UV/Vis spectra and solubility of some naphthoquinones, and the extraction behavior of plumbagin from Plumbago scandens roots in supercritical CO2. Analytical and bioanalytical chemistry 20060701
Acute irritant contact dermatitis due to Juglans regia. Contact dermatitis 20060701
Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. The Journal of biological chemistry 20060623
The development of a reagentless lactate biosensor based on a novel conducting polymer. Bioelectrochemistry (Amsterdam, Netherlands) 20060501
Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori. Journal of ethnopharmacology 20060421
Transformation of carbon tetrachloride by bisulfide treated goethite, hematite, magnetite, and kaolinite. Chemosphere 20060401
[Effects of plumbagin on the human acute promyelocytic leukemia cells in vitro]. Zhongguo shi yan xue ye xue za zhi 20060401
Interactions of nitroaromatic compounds with the mammalian selenoprotein thioredoxin reductase and the relation to induction of apoptosis in human cancer cells. The Journal of biological chemistry 20060303
Immunology and homeopathy. 2. Cells of the immune system and inflammation. Evidence-based complementary and alternative medicine : eCAM 20060301
Long-term starvation and ageing induce AGE-1/PI 3-kinase-dependent translocation of DAF-16/FOXO to the cytoplasm. BMC biology 20060101
Use of natural dye-casein complexes: effect of proteolytic treatment. Preparative biochemistry & biotechnology 20060101
Dyeing of wool fibres with natural dyes: effect of proteolytic enzymes. Preparative biochemistry & biotechnology 20060101
[Tolerance of the yeast Yarrowia lipolytica to oxidative stress]. Mikrobiologiia 20060101
Ethnopharmacological evaluation of radal (leaves of Lomatia hirsuta) and isolation of 2-methoxyjuglone. BMC complementary and alternative medicine 20060101
An NF-kappaB and slug regulatory loop active in early vertebrate mesoderm. PloS one 20060101
The whcE gene of Corynebacterium glutamicum is important for survival following heat and oxidative stress. Biochemical and biophysical research communications 20051125
Investigation into the resistance of lactoperoxidase tolerant Escherichia coli mutants to different forms of oxidative stress. FEMS microbiology letters 20051115
The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts. Toxicology and applied pharmacology 20051115
High-performance liquid chromatography for quantification of plumbagin, an anti-Helicobacter pylori compound of Plumbago zeylanica L. Journal of chromatography. A 20051111
Identification of a novel two-component system SenS/SenR modulating the production of the catalase-peroxidase CpeB and the haem-binding protein HbpS in Streptomyces reticuli. Microbiology (Reading, England) 20051101
Candida albicans-conditioned medium protects yeast cells from oxidative stress: a possible link between quorum sensing and oxidative stress resistance. Eukaryotic cell 20051001
Transformation of carbon tetrachloride by thiol reductants in the presence of quinone compounds. Environmental science & technology 20051001
Determination and identification of plumbagin from the roots of Plumbago zeylanica L. by liquid chromatography with tandem mass spectrometry. Journal of chromatography. A 20050812
Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L. Journal of agricultural and food chemistry 20050810
Induction of phenotypes resembling CuZn-superoxide dismutase deletion in wild-type yeast cells: an in vivo assay for the role of superoxide in the toxicity of redox-cycling compounds. Chemical research in toxicology 20050801
Effect of quinones on microtubule polymerization: a link between oxidative stress and cytoskeletal alterations in Alzheimer's disease. Biochimica et biophysica acta 20050610
Bacillus subtilis paraquat resistance is directed by sigmaM, an extracytoplasmic function sigma factor, and is conferred by YqjL and BcrC. Journal of bacteriology 20050501
Feeding response to host and nonhost compounds by males and females of the spruce bark beetle Ips typographus in a tunneling microassay. Journal of chemical ecology 20050401
Unique stress response to the lactoperoxidase-thiocyanate enzyme system in Escherichia coli. Research in microbiology 20050301
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria. Journal of agricultural and food chemistry 20050223
Phosphorylation modulates the alpha-helical structure and polymerization of a peptide from the third tau microtubule-binding repeat. Biochimica et biophysica acta 20050118
Peroxiredoxin-linked detoxification of hydroperoxides in Toxoplasma gondii. The Journal of biological chemistry 20050107
Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity. Photochemistry and photobiology 20050101
Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone. The Journal of pharmacy and pharmacology 20050101
Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation. BMC neuroscience 20050101
An extract from teak (Tectona grandis) bark inhibited Listeria monocytogenes and methicillin resistant Staphylococcus aureus. Letters in applied microbiology 20050101
Secondary metabolites in in vitro cultured plants of the genus Drosera. Phytochemical analysis : PCA 20050101
Isolation of secondary metabolites from roots of Plumbago auriculata Lam. by countercurrent chromatography. Phytochemical analysis : PCA 20050101
Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC neuroscience 20050101
In vivo micronucleus assay and GST activity in assessing genotoxicity of plumbagin in Swiss albino mice. Drug and chemical toxicology 20050101
Metabolism and disposition of juglone in male F344 rats. Xenobiotica; the fate of foreign compounds in biological systems 20050101
A fluorescence-based rapid screening assay for cytotoxic compounds. Biochemical and biophysical research communications 20041224
Separation methods of quinonoid constituents of plants used in Oriental traditional medicines. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20041205
Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide. Phytotherapy research : PTR 20041101
Antimicrobial activity and chemical investigation of Brazilian Drosera. Memorias do Instituto Oswaldo Cruz 20041101
NO reductase from Bacillus azotoformans is a bifunctional enzyme accepting electrons from menaquinol and a specific endogenous membrane-bound cytochrome c551. Biochemistry 20041026
Co-induction of methyltransferase Rv0560c by naphthoquinones and fibric acids suggests attenuation of isoprenoid quinone action in Mycobacterium tuberculosis. Canadian journal of microbiology 20041001
Quinones as antimycobacterial agents. Bioorganic & medicinal chemistry 20040915
Plumbagin quantification in roots of Plumbago scandens L. obtained by different extraction techniques. Anais da Academia Brasileira de Ciencias 20040901
Proteome-level differences between auxinic-herbicide-susceptible and -resistant wild mustard (Sinapis arvensis L.). Journal of agricultural and food chemistry 20040811
Plumbagin induces reactive oxygen species, which mediate apoptosis in human cervical cancer cells. Molecular carcinogenesis 20040801
Degradation of juglone by Pleurotus sajor-caju. Mycological research 20040801
Oxy2 as a transcriptional activator gene for copper uptake in Cryptococcus neoformans. Medical mycology 20040801
Isolation of long-lived mutants in Caenorhabditis elegans using selection for resistance to juglone. Free radical biology & medicine 20040715
Superoxide dismutase mimetics elevate superoxide dismutase activity in vivo but do not retard aging in the nematode Caenorhabditis elegans. Free radical biology & medicine 20040715
Cytotoxic constituents from Plumbago zeylanica. Fitoterapia 20040701
Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. Journal of natural products 20040701
Antitermitic quinones from Diospyros sylvatica. Phytochemistry 20040501
Role of NAD(P)H:quinone oxidoreductase encoded by drgA gene in reduction of exogenous quinones in cyanobacterium Synechocystis sp. PCC 6803 cells. Biochemistry. Biokhimiia 20040201
Juglone disrupts root plasma membrane H+-ATPase activity and impairs water uptake, root respiration, and growth in soybean (Glycine max) and corn (Zea mays). Journal of chemical ecology 20040201
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. The Journal of biological chemistry 20040109
Antisense blocking of BRCA1 enhances sensitivity to plumbagin but not tamoxifen in BG-1 ovarian cancer cells. Molecular carcinogenesis 20040101
Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chemical research in toxicology 20040101
N-methyl-N'-nitro-N-nitrosoguanidine-induced senescence-like growth arrest in colon cancer cells is associated with loss of adenomatous polyposis coli protein, microtubule organization, and telomeric DNA. Molecular cancer 20040101
Direct oxidation of 2',7'-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production. Free radical biology & medicine 20040101
Medicinal herb extract and a single-compound drug confer similar complex pharmacogenomic activities in mcf-7 cells. Journal of biomedical science 20040101
Multisite phosphorylation of Pin1-associated mitotic phosphoproteins revealed by monoclonal antibodies MPM-2 and CC-3. BMC cell biology 20040101
Source of tryptone in growth medium affects oxidative stress resistance in Escherichia coli. Journal of applied microbiology 20040101
Antioxidant properties of Plumbago zeylanica, an Indian medicinal plant and its active ingredient, plumbagin. Redox report : communications in free radical research 20040101
Expression of the small heat-shock protein Hsp16-2 in Caenorhabditis elegans is suppressed by Ginkgo biloba extract EGb 761. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20031201
Ultrasound-mediated release of iron from ferritin. Ultrasound in medicine & biology 20031201
Antimicrobial activity in vitro of plumbagin isolated from Plumbago species. Memorias do Instituto Oswaldo Cruz 20031001
Auxin action in a cell-free system. Current biology : CB 20030819
Effects of plumbagin on platelet aggregation and platelet-neutrophil interactions. Planta medica 20030701
Regional and habitat differences in 7-methyljuglone content of Finnish Drosera rotundifolia. Phytochemistry 20030601
A photochemical study of cells loaded with 2',7'-dichlorofluorescin: implications for the detection of reactive oxygen species generated during UVA irradiation. Free radical biology & medicine 20030415
Enhanced production of plumbagin in immobilized cells of Plumbago rosea by elicitation and in situ adsorption. Journal of biotechnology 20030306
Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica. Phytochemistry 20030201
Functional analysis of the glutathione S-transferase 3 from Onchocerca volvulus (Ov-GST-3): a parasite GST confers increased resistance to oxidative stress in Caenorhabditis elegans. Journal of molecular biology 20030103
In vitro mass multiplication and production of roots in Plumbago rosea. Planta medica 20030101
The prolyl isomerase Pin1 in breast development and cancer. Breast cancer research : BCR 20030101
Comparison of the antioxidant activities of extra virgin olive oils. Journal of agricultural and food chemistry 20021218
Antimicrobial activities of naphthazarins from Arnebia euchroma. Journal of natural products 20021201
Pin1: a therapeutic target in Alzheimer neurodegeneration. Journal of molecular neuroscience : MN 20021201
Temperature sensitive liposomes of plumbagin: characterization and in vivo evaluation in mice bearing melanoma B16F1. Journal of drug targeting 20021201
Purification and characterization of NAD(P)H quinone reductase from the latex of Hevea brasiliensis Müll.-Arg. (Euphorbiaceae). Phytochemistry 20020901
Long-patch base excision repair of apurinic/apyrimidinic site DNA is decreased in mouse embryonic fibroblast cell lines treated with plumbagin: involvement of cyclin-dependent kinase inhibitor p21Waf-1/Cip-1. Oncogene 20020829
Increasing plasmalogen levels protects human endothelial cells during hypoxia. American journal of physiology. Heart and circulatory physiology 20020801
Addition of hydrogen sulfide to juglone. Environmental science & technology 20020615
Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin. Phytochemistry 20020301
Multiple stressors in Caenorhabditis elegans induce stress hormesis and extended longevity. The journals of gerontology. Series A, Biological sciences and medical sciences 20020301
Synthesis of plumbagin derivatives and their inhibitory activities against Ehrlich ascites carcinoma in vivo and Leishmania donovani Promastigotes in vitro. Phytotherapy research : PTR 20020301
Inhibitory effects of quinones on RNase H activity associated with HIV-1 reverse transcriptase. Phytotherapy research : PTR 20020301
Main constituents of a commercial Drosera fluid extract and their antagonist activity at muscarinic M3 receptors in guinea-pig ileum. Die Pharmazie 20020301
DNA synthesis in the imaginal wing discs of the American bollworm Helicoverpa armigera (Hübner). Journal of biosciences 20020301
Electrochemical properties of natural organic matter (NOM), fractions of NOM, and model biogeochemical electron shuttles. Environmental science & technology 20020215
Mitochondrial NADH dehydrogenase from Plasmodium falciparum and Plasmodium berghei. Experimental parasitology 20020101
[Respiratory activity and naphthoquinone synthesis in the fungus Fusarium decemcellulare exposed to oxidative stress]. Mikrobiologiia 20020101
Thiol metabolism of the trypanosomatids as potential drug targets. IUBMB life 20020101
Effects of various environmental conditions on the transformation of chlorinated solvents by Methanosarcina thermophila cell exudates. Biotechnology and bioengineering 20011220
Effects of natural organic matter, anthropogenic surfactants, and model quinones on the reduction of contaminants by zero-valent iron. Water research 20011201
Interaction of camel lens zeta-crystallin with quinones: portrait of a substrate by fluorescence spectroscopy. Archives of biochemistry and biophysics 20011115
Phosphorylation and cell cycle-dependent regulation of Na+/H+ exchanger regulatory factor-1 by Cdc2 kinase. The Journal of biological chemistry 20011109
Mutagenicity of nitric oxide-releasing compounds in Escherichia coli: effect of superoxide generation and evidence for two mutagenic mechanisms. Mutation research 20011018
Plasmid-mediated dimethoate degradation in Pseudomonas aeruginosa MCMB-427. Letters in applied microbiology 20011001
Stress-related polyketide metabolism of Dioncophyllaceae and Ancistrocladaceae. Journal of experimental botany 20011001
Production of pyridoxal phosphate by a mutant strain of Schizosaccharomyces pombe. Bioscience, biotechnology, and biochemistry 20010801
Alkaloids, diarylheptanoid and naphthalene carboxylic acid ester from Rhoiptelea chiliantha. Chemical & pharmaceutical bulletin 20010601
Functional replacement of the essential ESS1 in yeast by the plant parvulin DlPar13. The Journal of biological chemistry 20010427
Functional conservation of phosphorylation-specific prolyl isomerases in plants. The Journal of biological chemistry 20010427
Stimulation of topoisomerase II-mediated DNA damage via a mechanism involving protein thiolation. Biochemistry 20010320
2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity. Journal of medicinal chemistry 20010215
A stress-responsive glyoxalase I from the parasitic nematode Onchocerca volvulus. The Biochemical journal 20010201
Hyperpigmentation and contact dermatitis due to Juglans regia. Contact dermatitis 20010201
[Adaptation of the phytopathogenic fungus Fusarium decemcellulare to oxidative stress]. Mikrobiologiia 20010101
Effects of plant-derived naphthoquinones on the growth of Pleurotus sajor-caju and degradation of the compounds by fungal cultures. Journal of basic microbiology 20010101
Ascorbate-independent electron transfer between cytochrome b561 and a 27 kDa ascorbate peroxidase of bean hypocotyls. Protoplasma 20010101
[Collection of Arabidopsis thaliana mutants with altered sensitivity to oxidative stress inductors]. Izvestiia Akademii nauk. Seriia biologicheskaia 20010101
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Identification of a stress-responsive Onchocerca volvulus glutathione S-transferase (Ov-GST-3) by RT-PCR differential display. Molecular and biochemical parasitology 20000701
Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chemico-biological interactions 20000103
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