P7262

Plumbagin from Plumbago indica

• Synonym(s): 5-Hydroxy-2-methyl-1,4-naphthoquinone
• 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

Properties

• biological source: Plumbago indica
• Quality Level: 200
• 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

Description

General description

Plumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L.[1] It is a quinoid and is also derived from the roots of Plumbago zeylanica roots.[2]

Application

Plumbagin from Plumbago indica has been used:

• as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblasts[3]
• as an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiae[4]
• as a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples[5]

Biochem/physiol Actions

Exhibits cytotoxicity in rodent models of carcinogenesis and carcinoma; has antifungal, antiviral, and antibacterial action.

Plumbagin exhibits various pharmacological activities including antimicrobial, anticancer,[1] anti-atherosclerotic, antidiabetic, anti-inflammatory, hypolipidemic, and neuroprotective activities.[6] It inhibits the signal transducer and activator of transcription 3 (STAT3) signaling and halts the proliferation of esophageal squamous cell carcinoma (ESCC).[2] Plumbagin elicits protective antioxidative functionality in 4-nitroquinoline-N-oxide (NQNO) induced stress in lymphoma.[7] Plumbagin in a nanoemulsion formulation has antiproliferative effect towards prostate cancer.[6]

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301,H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• 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