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P7262

Sigma-Aldrich

Plumbagin from Plumbago indica

Sinónimos:

5-Hydroxy-2-methyl-1,4-naphthoquinone

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About This Item

Fórmula empírica (notación de Hill):
C11H8O3
Número de CAS:
481-42-5
Peso molecular:
188.18
Número CE:
207-569-6
Número MDL:
MFCD00001682
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
24898833
NACRES:
NA.79

origen biológico

Plumbago indica

formulario

powder

color

faint orange to dark orange

mp

76-78 °C (lit.)

temp. de almacenamiento

−20°C

cadena SMILES

CC1=CC(C2=C(C1=O)C=CC=C2O)=O

InChI

1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3

Clave InChI

VCMMXZQDRFWYSE-UHFFFAOYSA-N

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Descripción general

Plumbagin 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.

Aplicación

Plumbagin 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

Acciones bioquímicas o fisiológicas

Plumbagin 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.
Exhibits cytotoxicity in rodent models of carcinogenesis and carcinoma; has antifungal, antiviral, and antibacterial action.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301,H315,H319,H335

Clasificaciones de peligro

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

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Subhash Padhye et al.
Medicinal research reviews, 32(6), 1131-1158 (2012-10-13)
Plumbagin is one of the simplest plant secondary metabolite of three major phylogenic families viz. Plumbaginaceae, Droseraceae, and Ebenceae, and exhibits highly potent biological activities, including antioxidant, antiinflammatory, anticancer, antibacterial, and antifungal activities. Recent investigations indicate that these activities arise
Sagar Uttarkar et al.
Molecular cancer therapeutics, 15(12), 2905-2915 (2016-10-22)
The transcription factor c-Myb is essential for the proliferation of hematopoietic cells and has been implicated in the development of leukemia and other human cancers. Pharmacologic inhibition of Myb is therefore emerging as a potential therapeutic strategy for these diseases.
Xiao-Juan Chen et al.
Saudi journal of biological sciences, 25(6), 1033-1039 (2018-09-04)
Cerebral ischemic damage and infarction are well documented in stroke, which is presenting a foremost health concern globally with very high mortality and morbidity rates. Mechanisms that are associated with excitotoxicity, inflammation and oxidative stress are found to be critically
Raghavendra Gowda et al.
Cancer letters, 385, 243-250 (2016-10-25)
Melanoma is a highly drug resistant cancer. To circumvent this problem, a class of synergistically acting drug combinations, which inhibit multiple key pathways in melanoma cells, could be used as one approach for long-term treatment of this deadly disease. A
Oleic acid and ergosterol supplementation mitigates oxidative stress in wine strains of Saccharomyces cerevisiae
Landolfo S, et al.
International Journal of Food Microbiology, 141(3), 229-235 (2010)
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