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P7262

Sigma-Aldrich

Plumbagin from Plumbago indica

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H8O3
Numéro CAS:
481-42-5
Poids moléculaire :
188.18
Numéro CE :
207-569-6
Numéro MDL:
MFCD00001682
Code UNSPSC :
12352205
ID de substance PubChem :
24898833
Nomenclature NACRES :
NA.79

Source biologique

Plumbago indica

Forme

powder

Couleur

faint orange to dark orange

Pf

76-78 °C (lit.)

Température de stockage

−20°C

Chaîne 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

Clé InChI

VCMMXZQDRFWYSE-UHFFFAOYSA-N

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Description générale

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.

Application

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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