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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

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)
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
Plumbagin-Loaded Nanoemulsion Drug Delivery Formulation and Evaluation of Antiproliferative Effect on Prostate Cancer Cells
Chrastina A, et al.
BioMed Research International, 2018 (2018)
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)
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
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