568-72-9 Usage
Description
Tanshinone IIA (TSA) is a major lipophilic component derived from the roots of Salvia miltiorrhiza Bge., commonly known as Danshen in traditional Chinese medicine. It is a brick-red crystalline powder with a melting point of 209-210°C and is very soluble in hot water, slightly soluble in methanol or ethanol, and practically insoluble in chloroform. Tanshinone IIA has been used for thousands of years in traditional Chinese medicine for its various therapeutic properties, including activating blood circulation, eliminating stasis, calming the heart, cooling the blood, relieving swelling, and treating carbuncle and erysipelas. It is also classified as a high-grade medicinal herb in Shen Nong's Herbal Classic and is recorded in various leading medical works, as well as in the Chinese Pharmacopeia (CP) and the United States Pharmacopeia (USP).
Uses
1. Anticancer Applications:
Tanshinone IIA is used as an antineoplastic agent, exhibiting potential inhibitory effects on tumor growth in vivo. It is particularly effective against various types of cancer cells, including A549 lung cancer cells and leukemia cells. It modulates several oncological signaling pathways and induces apoptosis in cancer cells, making it a promising candidate for cancer treatment.
2. Cardiovascular Applications:
Tanshinone IIA is used as a vasodilator, promoting blood circulation and maintaining vasodilating activity in vivo. This property makes it useful in treating cardiovascular diseases and improving blood flow.
3. Anti-inflammatory Applications:
Tanshinone IIA is used as an anti-inflammatory agent, inhibiting the production of various pro-inflammatory cytokines and mediators, such as TNF-α, IL-1β, IL-6, NO, INFγ, and the expression of iNOS and IL-12. It also blocks human aortic smooth muscle cell migration and inhibits MMP-9 activity, making it a potential therapeutic agent for inflammatory diseases.
4. Bone Resorption Inhibition:
Tanshinone IIA is used as a bone resorption inhibitor, potentially useful in the treatment of bone-related disorders and conditions, such as osteoporosis.
5. Antiproliferative Applications:
Tanshinone IIA is used as an antiproliferative agent, inhibiting the proliferation of various cancer cells and potentially useful in cancer therapy.
6. Apoptosis Induction:
Tanshinone IIA is used to induce apoptosis in cancer cells, promoting cell death and potentially enhancing the efficacy of cancer treatments.
Used in Pharmaceutical Industry:
Tanshinone IIA is used as an active pharmaceutical ingredient for the development of drugs targeting various diseases, including cancer, cardiovascular diseases, and inflammatory conditions.
Used in Traditional Chinese Medicine:
Tanshinone IIA is used as a key component in traditional Chinese medicine formulations, leveraging its diverse therapeutic properties for the treatment of various ailments and promoting overall health and well-being.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 568-72-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 8 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 568-72:
(5*5)+(4*6)+(3*8)+(2*7)+(1*2)=89
89 % 10 = 9
So 568-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3
568-72-9Relevant articles and documents
Total synthesis of tanshinone IIA
Huang, He,Song, Chuanjun,Wang, Zhen,Li, Mengyang,Chang, Junbiao
, (2020)
A novel synthetic route toward tanshinone IIA has been developed. Key steps involve a base mediated furan ring formation, and an acyloin condensation reaction to construct the ortho-quinone ring.
Site-selective Csp3-H aryloxylation of natural product Tanshinone IIA and its analogues
Liang, Bing,Yu, Shujuan,Li, Jie,Wang, Fan,Liang, Gaolin,Zhang, Ao,Ding, Chunyong
, p. 1822 - 1825 (2017/04/21)
A novel catalyst-free Csp3-H aryloxylation approach allowing for rapid installation of a wide range of aryloxyl groups regioselectively at the C-4 position of Tanshinone IIA under simple and mild conditions was developed. This unique protocol exhibited atom-/step-economy, low cost, high efficiency and robust functional-group tolerance, which will greatly facilitate to diversify the A-ring of the bioactive natural product.
Atomatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (+/-)-Royleanone
Danheiser, Rick L.,Casebier, David S.,Firooznia, Fariborz
, p. 8341 - 8350 (2007/10/02)
The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Chen is reported.The pivotal step in each synthesis involves the assembly of the key tricyclic intermediate via the application of a recently developed "second generation" photochemical aromatic annulation method for the construction of highly substituted aromatic systems.In the total synthesis of neocryptotanchinone, the synthesis of the requisite diazo ketone anulation substrate 7 was achieved using paladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds.The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily availabe siloxyalkyne 6 in benzene at room temperature.The desired tricyclic phenol 16 was produced in 58-65percent yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen.Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3).As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of (+/-)-royleanone (4) was also investigated.Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.