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Shikonin

$392

  • Brand : BIOFRON

  • Catalogue Number : BD-P0231

  • Specification : 98.0%(HPLC e.e.40%)

  • CAS number : 517-89-5

  • Formula : C16H16O5

  • Molecular Weight : 288.3

  • PUBCHEM ID : 479503

  • Volume : 20mg

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Catalogue Number

BD-P0231

Analysis Method

Specification

98.0%(HPLC e.e.40%)

Storage

-20℃

Molecular Weight

288.3

Appearance

Powder

Botanical Source

This product is isolated and purified from the roots of Lithosperraum erythrorhizon Sieb. et Zucc.

Structure Type

Category

SMILES

CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C

Synonyms

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone/1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-/1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-/Shikonin/5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone/(+)-Alkannin/5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

IUPAC Name

Applications

Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2. PUMID/DOI:21516121 Oncogene, 2011, 30(42):4297-306. We recently reported that shikonin and its analogs were a class of necroptotic inducers that could bypass cancer drug resistance. However, the molecular targets of shikonin are not known. Here, we showed that shikonin and its analogs are inhibitors of tumor-specific pyruvate kinase-M2 (PKM2), among which shikonin and its enantiomeric isomer alkannin were the most potent and showed promising selectivity, that is, shikonin and alkannin at concentrations that resulted in over 50% inhibition of PKM2 activity did not inhibit PKM1 and pyruvate kinase-L (PKL). Shikonin and alkannin significantly inhibited the glycolytic rate, as manifested by cellular lactate production and glucose consumption in drug-sensitive and resistant cancer cell lines (MCF-7, MCF-7/Adr, MCF-7/Bcl-2, MCF-7/Bcl-x(L) and A549) that primarily express PKM2.

Density

1.4±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

311.0±26.6 °C

Boiling Point

567.4±50.0 °C at 760 mmHg

Melting Point

147ºC

InChl

InChl Key

NEZONWMXZKDMKF-SNVBAGLBSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:517-89-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31867609

Abstract

Increased glycolysis is involved in the proliferation and migration of vascular smooth muscle cells (VSMCs). Pyruvate kinase isoform M2 (PKM2), a key rate-limiting enzyme in glycolysis, accelerates the proliferation and migration of tumor cells. Although the intracellular mechanisms associated with oxidized low-density lipoprotein (oxLDL)-stimulated VSMC proliferation and migration have been extensively explored, it is still unclear whether oxLDL promotes the proliferation and migration of VSMCs by enhancing PKM2-dependent glycolysis. In the present study, we detected PKM2 expression and pyruvate kinase activity in oxLDL-treated VSMCs and explored the regulation of PKM2 in oxLDL-treated VSMCs and apoE-/- mice. The results showed that PKM2 expression in VSMCs was higher in the intima than in the media in plaques from atherosclerotic rabbits. Moreover, PKM2 level in VSMCs was increased during atherosclerosis progression in apoE-/- mice. Both PKM2 expression and pyruvate kinase activity were found to be upregulated by oxLDL stimulation in VSMCs. Shikonin (SKN), a specific inhibitor of PKM2, was found to inhibit the oxLDL-induced proliferation and migration in VSMCs, in addition to delaying the atherosclerosis progression in apoE-/- mice. More importantly, oxLDL increased glucose uptake, ATP and lactate production, and the extracellular acidification rate in VSMCs, which could be reversed by SKN. Meanwhile, oxygen consumption rate was unchanged after oxLDL stimulation, suggesting that glycolysis is the main contributor to the energy supply in oxLDL-treated VSMCs. Our results suggest that oxLDL induces VSMC proliferation and migration by upregulating PKM2-dependent glycolysis, thereby contributing to the atherosclerosis progression. Thus, targeting PKM2-dependent glycolysis might provide a novel therapeutic approach for the treatment of atherosclerosis.

© The Author(s) 2019. Published by Oxford University Press on behalf of the Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.

KEYWORDS

PKM2; atherosclerosis; glycolysis; oxidized low-density lipoprotein; vascular smooth muscle cell

Title

PKM2-dependent glycolysis promotes the proliferation and migration of vascular smooth muscle cells during atherosclerosis.

Author

Zhao X1, Tan F2, Cao X2, Cao Z1, Li B1, Shen Z1, Tian Y1,2,3.

Publish date

2020 Jan 2;

PMID

31841980

Abstract

Shikonin, shikonofuran and their derivatives are the main bioactive components of Zicao, a traditional Chinese medicine prepared with the dried roots of Lithospermum erythrorhizon, Arnebia euchroma or Arnebia guttata. To establish an efficient and sensitive method for studying material basis of Zicao, different scan modes of ultra-high performance liquid chromatography quadrupole time of flight tandem mass spectrometry (UHPLC-QTOF-MS/MS) and UHPLC triple quadrupole linear ion trap mass spectrometry (QTRAP-MS/MS) were incorporated to make full use of the sensitivity of multiple reaction monitoring (MRM) and overcome its disadvantages. A total of 73 shikonins and shikonofurans compounds were detected in Zicao utilizing various scanning modes. Thereafter the characteristic chemical profile for shikonins and shikonofurans was established based on UHPLC-QTRAP-MS/MS, which was subsequently used to study the spectrum-effect relationship by correlating the relative quantity of compounds and the anti-tumor activity. As a result, 27 compounds were screened as the main active components inhibiting HeLa cells by othogonal partial least square (OPLS). Among them, shikonin, acetylshikonin have been reported to inhibit HeLa cells previously, and β, β-dimethylacrylshikonin has been reported to be active component by other method. Those results showed that chemical characteristic profile combined with chemometric methods was efficient and reliable for discovery of material basis in TCM, especially trace active compounds.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Characteristic chemical profile; Chemometrics; Shikonin/Shikonofuran; Spectrum-effect relationship; UHPLC-QTRAP-MS/MS; Zicao

Title

Spectrum-effect relationship for anti-tumor activity of shikonins and shikonofurans in medicinal Zicao by UHPLC-MS/MS and chemometric approaches.

Author

Liao M1, Yan P2, Liu X2, Du Z2, Jia S2, Aybek R3, Li A4, Kaisa S5, Jiang H6.

Publish date

2020 Jan 1;

PMID

31704839

Abstract

BACKGROUND/AIM:
Colon cancer is the second most common deadliest malignancy in the world and better understanding of its underlying mechanisms is needed to improve clinical management. Natural plant extracts are gaining attention in the development of new therapeutic strategies against various cancer types. Shikonin is a naturally extracted naphthoquinone pigment with effects against cancer, including colon cancer.

MATERIALS AND METHODS:
In this study, we conducted a series of in vitro experiments to show the effects of Shikonin on colon cancer cell apoptosis. A colon cancer cell line with overexpression of peroxiredoxin V (PrxV) was constructed and the relationship of PrxV expression with Shikonin-induced cell apoptosis was investigated.

RESULTS:
Shikonin induced colon cancer cell apoptosis via regulation of mammalian target of rapamycin signaling. Shikonin-induced cell apoptosis was abrogated by overexpression of PrxV.

CONCLUSION:
According to the results obtained in this study, targeting PrxV may provide new insight for the successful management of colon cancer by inducing cell apoptosis.

Copyright© 2019, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.

KEYWORDS

Peroxiredoxin V; ROS; Shikonin; colon cancer; mTOR

Title

Shikonin-induced Apoptosis of Colon Cancer Cells Is Reduced by Peroxiredoxin V Expression.

Author

Chandimali N1, Sun HN2, Kong LZ1, Zhen X1, Liu R1, Kwon T3, Lee DS4,5,6.

Publish date

2019 Nov