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P7262

Sigma-Aldrich

Plumbagin from Plumbago indica

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H8O3
CAS Number:
481-42-5
Molecular Weight:
188.18
EC Number:
207-569-6
MDL number:
MFCD00001682
UNSPSC Code:
12352205
PubChem Substance ID:
24898833
NACRES:
NA.79

biological source

Plumbago indica

form

powder

color

faint orange to dark orange

mp

76-78 °C (lit.)

storage temp.

−20°C

SMILES string

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

InChI key

VCMMXZQDRFWYSE-UHFFFAOYSA-N

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General description

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

Biochem/physiol Actions

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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María Marcén et al.
International journal of food microbiology, 241, 198-205 (2016-10-30)
Heat treatments are widely used by the food industry to inactivate microorganisms, however their mode of action on microbial cells is not fully known. In the last years, it has been proposed that the generation of oxidative species could be
In vitro callus induction and estimation of plumbagin content from Plumbago auriculata Lam.
Deshpande J, et al.
Indian Journal of Experimental Biology, 52(11), 122-1127 (2014)
Plumbagin inhibits the proliferation and survival of esophageal cancer cells by blocking STAT3-PLK1-AKT signaling
Cao YY, et al.
Cell Death & Disease, 9(2), 17-17 (2018)
Plumbagin-Loaded Nanoemulsion Drug Delivery Formulation and Evaluation of Antiproliferative Effect on Prostate Cancer Cells
Chrastina A, et al.
BioMed Research International, 2018 (2018)
Audrey Courboulin et al.
The European respiratory journal, 40(3), 618-629 (2012-04-13)
Like cancer, pulmonary arterial hypertension (PAH) is characterised by a pro-proliferative and anti-apoptotic phenotype. In PAH, pulmonary artery smooth muscle cell (PASMC) proliferation is enhanced and apoptosis suppressed. The sustainability of this phenotype requires the activation of pro-survival transcription factors
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