| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H20O3 |
| Molecular Weight | 296.3603 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
InChI
InChIKey=GVKKJJOMQCNPGB-JTQLQIEISA-N
InChI=1S/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/t10-/m0/s1
Cryptotanshinone is one of the major tanshinones isolated from the roots of the plant Salvia miltiorrhiza Bunge (Danshen). Danshen has been widely used in traditional Chinese medicine for treatment of a variety of diseases, including coronary artery disease, acute ischemic stroke, hyperlipidemia, chronic renal failure, chronic hepatitis, and Alzheimer's disease, showing no serious adverse effects. Recent studies have shown that cryptotanshinone not only possesses the potential for treatment and prevention of the above-mentioned diseases, but also is a potent anticancer agent. In vitro studies have demonstrated that cryptotanshinone inhibits cell proliferation in a
variety of cancer cell lines, including rhabdomyosarcoma, melanoma, cervical, colon, breast
and prostate cancer cells. It has been described that cryptotanshinone induced a G1/G0 cell cycle arrest in
rhabdomyosarcoma (Rh30) and prostate cancer (DU145) cells by downregulating expression
of cyclin D1 and phosphorylation of retinoblastoma protein (Rb), but induced a G2/
M cell cycle arrest in melanoma (B16) cells via upregulating expression of Cdc25c, cyclin A1 and cyclin B1. Cryptotanshinone inhibiting expression of Aurora
A kinase led to significant suppression of prostate cancer cells in vitro and in mice. Cryptotanshinone also induces cell death in cancer cells.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Intraperitoneal injection of Cryptotanshinone (0, 10, or 25 mg/kg) for 4 weeks significantly inhibited the growth of HCCC-9810 xenografts in athymic nude mice.
Route of Administration:
Intraperitoneal
Cryptotanshinone (7 uM) dramatically blocks STAT3 Tyr705 phosphorylation but not STAT3 Ser727 phosphorylation in DU145 cells, and significantly inhibits JAK2 phosphorylation with IC50 of ~5 uM without affecting the phosphorylation of upstream kinases c-Src and EGFR, suggesting the inhibition of STAT3 Tyr705 phosphorylation might due to a direct mechanism probably by binding to the SH2 domain of STAT3. Cryptotanshinone significantly inhibits the proliferation of DU145 prostate cancer cells harboring constitutively active STAT3 with GI50 of 7 uM by blocking STAT3 activity, which leads to the down-regulation of cyclin D1, Bcl-xL, and survivin, subsequently the accumulation in the G0-G1 phase. Cryptotanshinone exhibits less growth inhibitory effect on PC3, LNCaP and MDA-MB-468 cells.
SUBSTANCE RECORD
