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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

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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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