S7576

Shikonin

≥98% (HPLC)

• Synonyme(s) : (±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin
• Formule empirique (notation de Hill) : C₁₆H₁₆O₅
• CAS Number: 54952-43-1
• Poids moléculaire : 288.30
• Numéro MDL: MFCD00016668
• Code UNSPSC : 12352200
• ID de substance PubChem : 329824586
• Nomenclature NACRES : NA.25

Propriétés

• Niveau de qualité: 200
• Essai: ≥98% (HPLC)
• Forme: powder or solid
• Couleur: red to brown
• Solubilité: methanol: 1 mg/mL
• Application(s): metabolomics; vitamins, nutraceuticals, and natural products
• Température de stockage: 2-8°C
• Chaîne SMILES: C\C(C)=C\CC(O)C1=CC(=O)c2c(O)ccc(O)c2C1=O
• InChI: 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
• Clé InChI: NEZONWMXZKDMKF-UHFFFAOYSA-N

Description

Description générale

Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.

Application

Shikonin has been used:

• to enhance the anti-tumor activity of gefitinib on tyrosine kinase receptor epidermal growth factor receptor (EGFR) in wild-type lung cancer cells
• as an inhibitor of renal aerobic glycosis and a potential
• as an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunction
• to stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death

Actions biochimiques/physiologiques

Inhibits chemokine receptor function and suppresses HIV-1. Circumvents cancer drug resistance by induction of cell death through a necroptotic pathway. Treatment of cancer cells with shikonin suppressed glycolysis via the inhibition of pyruvate kinase M2 (PKM2).

Naphthoquinone isolated from Arnebia sp. Used as an anti-inflammatory treatment in traditional chinese medicine (TCM). Inhibits chemokine receptor function and suppresses HIV-1.† Circumvents cancer drug resistance by induction of cell death through a necroptotic pathway.† Treatment of cancer cells with shikonin suppressed glycolysis via the inhibition of pyruvate kinase M2 (PKM2).

Shikonin is a potent anti-fungal agent against C. albicans biofilms. It displays anti-oxidant and chemotherapeutic properties on human glioma cells.

Informations sur la sécurité

• Pictogrammes: GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H302,H400
• Conseils de prudence: P273 - P301 + P312 + P330
• Classification des risques: Acute Tox. 4 Oral - Aquatic Acute 1
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable