Tanshindiol C

• CAT Number: I042500
• CAS Number: 97465-71-9
• Molecular Formula: C18H16O5
• Molecular Weight: 312.32
• Purity: ≥95%
• Synonyms: (6R,7R)-6,7-dihydroxy-1,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
• InChI: InChI=1S/C18H16O5/c1-8-7-23-17-10-3-5-11-9(4-6-12(19)18(11,2)22)14(10)16(21)15(20)13(8)17/h3,5,7,12,19,22H,4,6H2,1-2H3/t12-,18-/m1/s1
• InChIKey: RTKDBIDPGKCZJS-KZULUSFZSA-N
• SMILES: CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCC(C4(C)O)O

Tanshindiol C is a S-adenosylmethionine-competitive EZH2 (Histone Methyltransferase) inhibitor with an IC50 of 0.55 μM for inhibiting the methyltransferase activity. Tanshindiol C is also an activator of both Nrf2 and Sirtuin 1 (Sirt1) in macrophages. Tanshindiol C possesses anti-cancer activity, and can be used for atherosclerosis research[1][2].
Tanshindiol C (1-10 μM; for 24 h) activates Nrf2 and upregulates Prdx1 expression and mRNA levels in macrophages. Tanshindiol C protects macrophages from oxidized low-density lipoprotein (oxLDL) induced foam cell formation via activation of Prdx1/ABCA1 signaling[1].
Tanshindiol C inhibits both wild-type and A667G mutant (Ki value of 176 nM) EZH2 activity with similar potencies[2].
Tanshindiol C inhibits growth of the cell lines such as Pfeiffer, U-2932 and Daudi (lymphoma), PC3 (prostate cancer), T98G and U87MG (glioma), and A549 (lung cancer), with GI50 values of 1.5 μM, 9.5 μM, 10.6 μM, 4 μM, 6 μM, 5.7 μM and 4.2 μM, respectively[2].
Tanshindiol C (1-5 μM; 72 hours) induces accumulation of Pfeiffer cells in sub-G1 phase, which indicates cells in late apoptosis and necrosis[2].
Tanshindiol C (1-3 μM; 72 hours) increases protein levels of the important apoptosis related protein markers, cleaved caspase-3, caspase-7 and poly ADP-ribose polymerase (PRAP) in the cells.Tanshindiol C significantly decreases the levels of H3K27me3 in cells[2].

Reference

[1]. Yuyu Yang, et al. Tanshindiol C inhibits oxidized low-density lipoprotein induced macrophage foam cell formation via a peroxiredoxin 1 dependent pathway. Biochim Biophys Acta Mol Basis Dis. 2018 Mar;1864(3):882-890.
 [Content Brief]

[2]. Jimin Woo, et al. Biological evaluation of tanshindiols as EZH2 histone methyltransferase inhibitors. Bioorg Med Chem Lett. 2014 Jun 1;24(11):2486-92.
 [Content Brief]