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S7576

Sigma-Aldrich

Shikonin

≥98% (HPLC)

Synonym(e):

(±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin

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About This Item

Empirische Formel (Hill-System):
C16H16O5
CAS-Nummer:
54952-43-1
Molekulargewicht:
288.30
MDL-Nummer:
MFCD00016668
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329824586
NACRES:
NA.25

Assay

≥98% (HPLC)

Form

powder or solid

Farbe

red to brown

Löslichkeit

methanol: 1 mg/mL

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

2-8°C

SMILES String

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

InChIKey

NEZONWMXZKDMKF-UHFFFAOYSA-N

Verwandte Kategorien

Allgemeine Beschreibung

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

Anwendung

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

Biochem./physiol. Wirkung

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.

Piktogramme

Exclamation markEnvironment
GHS07,GHS09

Signalwort

Warning

H-Sätze

H302,H400

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Acute 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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3PO

Konstantinos N Kontogiannopoulos et al.
International journal of pharmaceutics, 422(1-2), 381-389 (2011-10-08)
The interest of drug delivery has focused on the creation of new formulations with improved properties, taking much attention to the drug release from the carrier. Liposomes have already been commercialized, while dendrimers and hyperbranched polymers are emerging as potentially
Xin Chen et al.
Phytotherapy research : PTR, 16(3), 199-209 (2002-08-08)
The naphthoquinone pigment, shikonin, isolated from Lithospermum erythrorhizon Sieb. et Zucc.(Boraginaceae) and its derivatives are the active components isolated from the Chinese herbal therapeutic, Zicao. Historically, Zicao root extracts have been used to treat macular eruption, measles, sore-throat, carbuncles and
Yongwei Wang et al.
Biochemical pharmacology, 88(3), 322-333 (2014-02-14)
Although gemcitabine is currently the best chemotherapeutic agent available for the treatment of advanced pancreatic cancer, eventual failure of response is a significant clinical problem. Therefore, novel therapeutic approaches against this disease are highly needed. The aim of this study
Ke Gong et al.
Free radical biology & medicine, 51(12), 2259-2271 (2011-10-21)
Although shikonin, a naphthoquinone derivative, has showed anti-cancer activity, its precise molecular anti-tumor mechanism remains to be elucidated. In this study, we investigated the effects of shikonin on human hepatocellular carcinoma (HCC) in vitro and in vivo. Our results showed
Rubing Wang et al.
Expert opinion on therapeutic patents, 22(9), 977-997 (2012-07-28)
Shikonin and its derivatives are the main components of red pigment extracts from Lithospermum erythrorhizon, whose medicinal properties have been confirmed for a long history, and have aroused great interest as the hallmark molecules responsible for their significant biological activities
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