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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

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Consulter la Bibliothèque de documents

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
Increased production of plumbagin in Plumbago indica root cultures by gamma ray irradiation
Jaisi A, et al.
Pharmaceutical biology, 51(8), 1047-1051 (2013)
Kanjoormana Aryan Manu et al.
Molecular cancer, 10, 107-107 (2011-09-02)
Increasing evidence indicates that the interaction between the CXC chemokine receptor-4 (CXCR4) and its ligand CXCL12 is critical in the process of metastasis that accounts for more than 90% of cancer-related deaths. Thus, novel agents that can downregulate the CXCR4/CXCL12
Yousef Alharbi et al.
Scientific reports, 9(1), 11471-11471 (2019-08-09)
The Na+/K+-ATPase (NKA) complex is the master regulator of membrane potential and a target for anti-cancer therapies. Here, we investigate the effect of drug-induced oxidative stress on NKA activity. The natural product, plumbagin increases oxygen radicals through inhibition of oxidative
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
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