P7262

Plumbagin aus Plumbago indica

• Synonym(e): 5-Hydroxy-2-methyl-1,4-naphthoquinone
• Empirische Formel (Hill-System): C₁₁H₈O₃
• CAS-Nummer: 481-42-5
• Molekulargewicht: 188.18
• EG-Nummer: 207-569-6
• MDL-Nummer: MFCD00001682
• UNSPSC-Code: 12352205
• PubChem Substanz-ID: 24898833
• NACRES: NA.79

Eigenschaften

• Biologische Quelle: Plumbago indica
• Form: powder
• Farbe: faint orange to dark orange
• mp (Schmelzpunkt): 76-78 °C (lit.)
• Lagertemp.: −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
• InChIKey: VCMMXZQDRFWYSE-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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]

Anwendung

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. Wirkung

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]

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301,H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 1
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges