PLUMBAGIN

PLUMBAGIN Basic information
Product Name:PLUMBAGIN
Synonyms:plumbagone;1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene;Plumbagin (natural);PLUMBAGIN PRACTICAL GRADE;Plumbagin, 99+%;PLUMBAGIN(RG);1,4-NAPHTHALENEDIONE,5-HYDROXY-2-METHYL;PLANT STEROLS KIT
CAS:481-42-5
MF:C11H8O3
MW:188.18
EINECS:207-569-6
Product Categories:Inhibitors;Anthraquinones, Hydroquinones and Quinones;chem-chemical
Mol File:481-42-5.mol
PLUMBAGIN Structure
PLUMBAGIN Chemical Properties
Melting point 76-78 °C(lit.)
Boiling point 283.17°C (rough estimate)
density 1.354
refractive index 1.6310 (estimate)
storage temp. -20°C
solubility very faint turbidity in hot Methanol
pka6.70±0.20(Predicted)
form Crystals or Crystalline Powder
color Orange
Merck 7538
Stability:Hygroscopic
LogP2.450 (est)
EPA Substance Registry System1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5)
Safety Information
Hazard Codes T
Risk Statements 25-34-36/37/38
Safety Statements 22-26-36/37/39-45-37/39-28A
RIDADR UN 2923 8/PG 2
WGK Germany 3
RTECS QL8500000
Hazard Note Toxic
HazardClass 6.1(a)
PackingGroup II
HS Code 29146990
ToxicityLD50 i.p. in mice: ~0.015 g/kg (Debray)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
PLUMBAGIN Usage And Synthesis
DescriptionPlumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.
Chemical PropertiesORANGE CRYSTALLINE POWDER OR CRYSTALS
Usesantibacterial, antifungal, tuberculostatic; antifeedant (worm)
UsesPlumbagin from Plumbago indica has been used:
  • as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblasts
  • as an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiae
  • as a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

DefinitionChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.
General DescriptionPlumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanica?roots.
Biochem/physiol ActionsPlumbagin exhibits various pharmacological activities including antimicrobial, anticancer, anti-atherosclerotic, antidiabetic, anti-inflammatory, hypolipidemic, and neuroprotective activities. It inhibits the signal transducer and activator of transcription 3 (STAT3) signaling and halts the proliferation of esophageal squamous cell carcinoma (ESCC). Plumbagin elicits protective antioxidative functionality in 4-nitroquinoline-N-oxide (NQNO) induced stress in lymphoma. Plumbagin in a nanoemulsion formulation has antiproliferative effect towards prostate cancer.
in vitroplumbagin exhibited effective cell growth inhibition via inducing cancer cells to undergo g2/m phase arrest and apoptosis. blockade of cell cycle was associated with increased levels of p21 and reduced amounts of cdc2, cdc25c and cyclinb1. plumbagin treatment also found to enhance the levels of inactivated phosphorylated cdc2 and cdc25c. blockade of p53 activity partially decreased plumbagin-induced apoptosis and g2/m arrest, indicating it might be operated by p53-dependent and independent pathway [1].
in vivoto determine whether plumbagin inhibited the in vivo tumor growth, a549 cells were injected into nude mice. tumor growth inhibition was most evident in mice treated with plumbagin at 2 mg/kg/day, where around 80% reductions in tumor size were observed, in contrast with mice treated with the vehicle. no sign of toxicity was observed in plumbagin-treated mice as judged by monitoring body weight [1].
IC 5011.69 μm for a549 cells
Purification MethodsIt crystallises in yellow needles from aqueous EtOH. It is soluble in organic solvents, it is steam volatile and it sublimes on heating in a vacuum. [Fieser & Dunn J Am Chem Soc 58 572 1936, Beilstein 8 III 2576, 8 IV 2376.]
references[1] hsu yl,cho cy,kuo pl,huang yt,lin cc. 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. j pharmacol exp ther.2006 aug;318(2):484-94.
DEOXYSHIKONIN bostrycin aquayamycin Shikalkin ISOBUTYRYLSHIKONIN 1H-NAPHTHO[2,3-C]PYRAN-3-ACETIC ACID, 3,4,5,10-TETRAHYDRO-9-HYDROXY-1-METHYL-5,10-DIOXO-(1S,3R)- ISOVALERYLSHIKONIN sakyomicin A RARECHEM BW GA 0197 PI 083 dihydrogranaticin Plumbagin methyl ether Medermycin diospyrin ACETYLSHIKONIN lactoquinomycin A RUBROSKYRIN (2-METHYL-N-BUTYRYL)SHIKONIN

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