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| | Tanshinone IIA Basic information |
| Product Name: | Tanshinone IIA | | Synonyms: | AKOS NCG1-0066;3,8,8-TRIMETHYL-8,9,10,11-TETRAHYDROPHENANTHRO[1,2-B]FURAN-1,2-DIONE;TANSHINONE IIA 98+%;Tanshinone IIA, 97%, from Salvia miltiorrhiza Bunge;1,6,6-TRIMETHYL-6,7,8,9-TETRAHYDRO-PHENANTHRO[1,2-B]FURAN-10,11-DIONE;TANSHINONE IIA;TANSHINONES IIA;tanshiones | | CAS: | 568-72-9 | | MF: | C19H18O3 | | MW: | 294.34 | | EINECS: | | | Product Categories: | Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Plant Oils, Toxins, Phenolic Acids & Derivatives;The group of Danshen;Plant extract | | Mol File: | 568-72-9.mol |  |
| | 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) |
| | 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 |
| | Tanshinone IIA Preparation Products And Raw materials |
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