Tanshinone IIA Chemical Properties

Melting point:

196.0 to 200.0 °C

Boiling point:

480.7±44.0 °C(Predicted)

Density 

1.209±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

methanol: soluble5mg/mL, clear, red-orange to red

form 

powder, red

color 

Orange

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

InChIKey

HYXITZLLTYIPOF-UHFFFAOYSA-N

LogP

4.925 (est)

CAS DataBase Reference

568-72-9(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

SF8282695

HS Code 

29321900

Hazardous Substances Data

568-72-9(Hazardous Substances Data)

Tanshinone IIA Usage And Synthesis

Description

Tanshinone IIA mainly exists in the roots of Salvia miltiorrhiza Bge. Traditional Chinese medicine Danshen, slightly cold and bitter, is often used for activating blood circulation and eliminating stasis in Chinese medicine. It can also promote blood circulation, open the energy channels, calm the heart, cool the blood, relieve swelling, remove twinge in the heart and stomach, and remove carbuncle and erysipelas. It is classified as high grade in Shen Nong’s Herbal Classic. It has been used as a traditional Chinese medicine in clinical practice for thousands of years. And it is not only recorded in the leading medical works through the ages but also in CP and USP.

Description

Tanshinone IIA (TSA) is a major lipophilic component of extracts from the root of S. miltiorrhiza, used widely in Chinese herbal medicine. It has anti-inflammatory activity, inhibiting production of TNF-α, IL-1β, IL-6, NO, INFγ, and expression of iNOS, and IL-12. It blocks human aortic smooth muscle cell migration, inhibits MMP-9 activity, and interferes with PI3K/Akt and ERK1/2 signaling pathways. It is cytotoxic to various cancer cells including A549 lung cancer cells and leukemia cells.Reduction of TSA by NAD(P)H:quinone oxidoreductase (NQO1) generates an unstable intermediate resulting in reactive oxygenase species-mediated apoptotic cell death.

Chemical Properties

Orange powder

Physical properties

Appearance: brick-red crystalline powder. Melting point: 209–210?°C. Solubility: absorbs moisture easily, very soluble in hot water, slightly soluble in methanol or ethanol, and practically insoluble in chloroform

History

The study of the chemical composition of Salvia miltiorrhiza began in the 1930s. Japanese scholars first extracted three kinds of liposoluble components from Danshen. They are tanshinones I, II, and III.

Uses

Tanshinone IIA is a derivative of Tanshinone and acts as a potential inhibitor of tumor growth in vivo. Also maintains vasodilating activity in vivo.

Uses

antineoplastic, bone resorption inhibitor, antiproliferative, apoptosis inducer

Definition

ChEBI: 1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g]benzofuran-10,11-dione is an abietane diterpenoid.

Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 1522, 1989 DOI: 10.1021/ja00186a070

Biochem/physiol Actions

Phenanthrenequinone constituent of Chinese medicinal herb Danshen (Salvia miltiorrhiza). Anti-inflammatory. Antioxidant. Cytotoxic against a variety of cell lines, inlcuding human glioma cells.

Pharmacology

Long-term researches show that tanshinone exhibits a variety of pharmacological effects, such as the protection of the cardiovascular system, anti-infective effects, and antioxidant effects. As for the domestic pharmacological study of tanshinone IIA, it was first started in the Shanghai Institute of Chinese Medicine. Professor Ding Guangsheng discussed the cardiovascular effects of tanshinone IIA.?He found that intraperitoneal injection of tanshinone IIA sodium sulfonate (200?mg/kg) significantly prolonged the survival time of mice under hypoxia atmosphere, and an increase in cardiac output was observed in a dog under anesthesia with a one-time intravenous injection of 20? mg/kg . In recent years, the mechanism of tanshinone IIA is increasingly brought to further research. Tanshinone IIA can increase the activity of superoxide dismutase (SOD) and interfere with the pathological process of many diseases, especially in cardiovascular diseases. It can attenuate the damages from the reactive oxygen species to vascular endothelial cells, lower the risk of atherosclerosis, and reduce the formation of atheromatous plaque. tumor cells and the expression of various genes connected with the proliferation, differentiation, and apoptosis of tumor cells. It may also have something to do with the inhibition of telomerase activity in tumor cells, changes in antigen expression on tumor cell surface, etc.

Clinical Use

Tanshinone IIA is a diterpenoid quinone liposoluble ingredient of high content, and its chemical structure is the most representative in Danshen. In addition to tanshinone IIA sodium sulfonate, there are a variety of preparations of Salvia common ketone used clinically, such as tanshinone tablets, tanshinone capsules, tanshinone injection, Danshen Shuxin capsule, compound Danshen soft capsules, and compound Danshen particles.

Cytotoxicity

IC50 (μg/mL): 0.59 (A549), 0.81 (TOV-21G) and 1.9 (MIAPaCa-2), NS (MV-3)(Chang et al. 2013; Fronza et al. 2011).
IC50 (μg/mL): 2.97 (HeLa), 2.71 (KB-3-1),>2.94 (NCI-H460), 2.62 (PC3), 2.94(MCF-7), 1.62 (K562)(Wu et al. 2014)

References

1) Kang et al. (2000), Inhibition of interleukin-12 and interferon-gamma production in immune cells by tanshinones from Salvia miltiorrhiza; Immunopharmacology, 49 355 2) Sung et al. (1999), Tanshinone IIA, an ingredient of Salvia miltiorrhiza BUNGE, induces apoptosis in human leukemia cell lines through the activation of caspase-3; Exp. Mol. Med., 31 174 3) Park et al. (1999), Suppression of AP-1 Activity by Tanshinone and Cancer Cell Growth Inhibition; Bull. Korean Chem. Soc., 20 925

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