Shikonin

Names

[ Name ]:
Shikonin

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

Biological Activity

[Description]:

(Rac)-Shikonin (Shikonin) possesses anti-tumor activity. (Rac)-Shikonin (Shikonin) circumvents cancer drug resistance by induction of a necroptotic death[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Shikonin shows a similar potency toward drug-sensitive cancer cell lines (MCF-7 and HEK293) and their drug-resistant lines overexpressing P-glycoprotein, Bcl-2, or Bcl-xL, which account for most of the clinical cancer drug resistance[2].

[References]

[1]. U Sankawa, Antitumor activity of shikonin and its derivatives. Chem Pharm Bull (Tokyo). 1977 Sep;25(9):2392-5.

[2]. Weidong Han, et al. Shikonin circumvents cancer drug resistance by induction of a necroptotic death. Mol Cancer Ther. 2007 May;6(5):1641-9.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
567.4±50.0 °C at 760 mmHg

[ Melting Point ]:
149 °C

[ Molecular Formula ]:
C₁₆H₁₆O₅

[ Molecular Weight ]:
288.295

[ Flash Point ]:
311.0±26.6 °C

[ Exact Mass ]:
288.099762

[ PSA ]:
94.83000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.642

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
Xn

[ RIDADR ]:
UN 3077 9 / PGIII

Articles

Inhibitory effect of Shikonin on Candida albicans growth.

Biol. Pharm. Bull. 35(11) , 1956-63, (2012)

Our study showed that Shikonin (SK) could provide an action against almost all Candida albicans isolates tested. More importantly, to some Fluconazole (FCZ)-resistant Candida albicans, the action of S...

Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm.

J. Med. Microbiol. 60(Pt 12) , 1827-34, (2011)

The objective of this study was to screen for novel quorum-sensing inhibitors (QSIs) from traditional Chinese medicines (TCMs) that inhibit bacterial biofilm formation. Six of 46 active components fou...

Optimization of shikonin homogenate extraction from Arnebia euchroma using response surface methodology.

Molecules 18(1) , 466-81, (2013)

An efficient homogenate extraction technique was employed for extracting shikonin from Arnebia euchroma. The homogenate extraction procedure was optimized and compared with other conventional extracti...