Dihydrotanshinone
Dihydrotanshinone is found in Salvia that exhibits neuromodulatory, anticancer, anti-inflammatory, anti-allergic, anti-diabetic, antithrombotic, vasodilatory, antihypertensive, and anti-angiogenic activities. Dihydrotanshinone binds to the P-site of acetylcholinesterase (AChE), inhibiting its activity and showing potential benefit as a treatment for Alzheimer’s disease. Dihydrotanshinone also inhibits fatty acid synthase, mineralocorticoid receptors, and glucocorticoid receptors, suppressing expression of the Na+/K+ ATPase, G6Pase, and PEPCK; it also increases activation of AMPK. In colorectal cancer cells, dihydrotanshinone upregulates expression of ATF-3 and induces apoptosis, inhibiting proliferation. This compound also inhibits activation of AP-1 and NF-κB in vitro and suppresses passive cutaneous anaphylaxis in vivo by decreasing production of allergic mediators IL-4 and TNF-α. Dihydrotanshinone inhibits collagen-induced thromboxane B2 (TxB2) production and platelet aggregation in vitro. Additionally, dihydrotanshinone induces vascular relaxation in coronary artery rings in a Ca2+-dependent manner. This compound also inhibits migration, invasion, and tube formation in cellular and animal models of angiogenesis.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/1887333
| Cas No. |
87205-99-0 |
|---|---|
| Purity |
≥90% |
| Formula |
C18H14O3 |
| Formula Wt. |
278.30 |
| IUPAC Name |
(1R)-1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione |
| Melting Point |
233-234°C |
| Solubility |
Soluble in chloroform and acetone |
| Appearance |
Red Crystal |
Cheung J, Beri V, Shiomi K, et al. Acetylcholinesterase Complexes with the Natural Product Inhibitors Dihydrotanshinone I and Territrem B: Binding Site Assignment from Inhibitor Competition and Validation Through Crystal Structure Determination. J Mol Neurosci. 2014 Feb 27. [Epub ahead of print]. PMID: 24573600.
Suk FM, Jou WJ, Lin RJ, et al. 15,16-Dihydrotanshinone I-induced apoptosis in human colorectal cancer cells: involvement of ATF3. Anticancer Res. 2013 Aug;33(8):3225-31. PMID: 23898083.
Jang TS, Zhang H, Kim G, et al. Bioassay-guided isolation of fatty acid synthase inhibitory diterpenoids from the roots of Salvia miltiorrhiza Bunge. Arch Pharm Res. 2012 Mar;35(3):481-6. PMID: 22477195.
Trinh HT, Chae SJ, Joh EH, et al. Tanshinones isolated from the rhizome of Salvia miltiorrhiza inhibit passive cutaneous anaphylaxis reaction in mice. J Ethnopharmacol. 2010 Oct 28;132(1):344-8. PMID: 20732401.
Liu Q, Zhang Y, Lin Z, et al. Danshen extract 15,16-dihydrotanshinone I functions as a potential modulator against metabolic syndrome through multi-target pathways. J Steroid Biochem Mol Biol. 2010 Jun;120(4-5):155-63. PMID: 20380878.
Lam FF, Yeung JH, Chan KM, et al. Dihydrotanshinone, a lipophilic component of Salvia miltiorrhiza (danshen), relaxes rat coronary artery by inhibition of calcium channels. J Ethnopharmacol. 2008 Sep 26;119(2):318-21. PMID: 18682284.
Park JW, Lee SH, Yang MK, et al. 15,16-dihydrotanshinone I, a major component from Salvia miltiorrhiza Bunge (Dansham), inhibits rabbit platelet aggregation by suppressing intracellular calcium mobilization. Arch Pharm Res. 2008 Jan;31(1):47-53. PMID: 18277607.
Bian W, Chen F, Bai L, et al. Dihydrotanshinone I inhibits angiogenesis both in vitro and in vivo. Acta Biochim Biophys Sin (Shanghai). 2008 Jan;40(1):1-6. PMID: 18180848.
