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S7576

Sigma-Aldrich

Shikonin

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H16O5
CAS Number:
54952-43-1
Molecular Weight:
288.30
MDL number:
MFCD00016668
UNSPSC Code:
12352200
PubChem Substance ID:
329824586
NACRES:
NA.25

Quality Level

200

Assay

≥98% (HPLC)

form

powder or solid

color

red to brown

solubility

methanol: 1 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

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

InChI key

NEZONWMXZKDMKF-UHFFFAOYSA-N

Related Categories

General description

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

Biochem/physiol Actions

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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hui-Ming Chen et al.
Cancer immunology, immunotherapy : CII, 61(11), 1989-2002 (2012-04-25)
Immunogenic cell death is characterized by damage-associated molecular patterns, which can enhance the maturation and antigen uptake of dendritic cells. Shikonin, an anti-inflammatory and antitumor phytochemical, was exploited here as an adjuvant for dendritic cell-based cancer vaccines via induction of
Jen-Tsung Yang et al.
PloS one, 9(4), e94180-e94180 (2014-04-10)
Shikonin is a quinone-containing natural product that induces the apoptotic death of some cancer cell lines in culture through increasing intracellular reactive oxygen species (ROS). Quinone-based drugs have shown potential in the clinic, making shikonin an interesting compound to study.
Chuanjie Guo et al.
Pharmacological research, 149, 104463-104463 (2019-09-26)
Shikonin is the major bioactive component extracted from the roots of Lithospermum erythrorhizon which is also known as "Zicao" in Traditional Chinese Medicine (TCM). Recent studies have shown that shikonin demonstrates various bioactivities related to the treatment of cancer, inflammation
Jian-Cai Tang et al.
Life sciences, 204, 71-77 (2018-05-09)
Mutant EGFR Non-small cell lung cancer has benefit from gefitinib, but it has limited effect for wild-type EGFR tumors. Shikonin, a natural naphthoquinone isolated from a traditional Chinese medicine, the plant Lithospermum erythrorhizon (zicao), not only can inhibit the tumor
Ching-Hsein Chen et al.
Annals of surgical oncology, 19(9), 3097-3106 (2012-03-27)
Shikonin is the main naphthoquinone compound of the root of Lithospermum erythrorhizon. Our previous study demonstrated that shikonin possesses anticancer activity in human hepatoma cells. However, the anticancer mechanism of shikonin in human glioma cells is unclear at present. In
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