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Merck
모든 사진(3)

문서

S7576

Sigma-Aldrich

Shikonin

≥98% (HPLC)

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C16H16O5
CAS Number:
Molecular Weight:
288.30
MDL number:
UNSPSC 코드:
12352200
PubChem Substance ID:
NACRES:
NA.25

Quality Level

분석

≥98% (HPLC)

형태

powder or solid

색상

red to brown

solubility

methanol: 1 mg/mL

응용 분야

metabolomics
vitamins, nutraceuticals, and natural products

저장 온도

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

일반 설명

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

애플리케이션

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

생화학적/생리학적 작용

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.

픽토그램

Exclamation markEnvironment

신호어

Warning

유해 및 위험 성명서

예방조치 성명서

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


시험 성적서(COA)

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문서 라이브러리 방문

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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