Cryptotanshinone
Synonym(s):(R)-(−)-1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione;1,2,6,7,8,9-hexahydro-1,6,6-trimethyl- (R)-phenanthro(1,2-b)furan-10,11-dione;AMPK Signaling Activator VIII;Cryptotanshinon;Tanshinone C
- CAS NO.:35825-57-1
- Empirical Formula: C19H20O3
- Molecular Weight: 296.36
- MDL number: MFCD07636810
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 21:24:55
What is Cryptotanshinone?
Chemical properties
Orange powder
The Uses of Cryptotanshinone
Cryptotanshinone (CPT), a lipophilic diterpene derived from the roots of Salvia miltiorrhiza Bge and Salvia przewalskii Maxim, may be used to study its multiple bioactivities as an antibacterial, antidermatophytic, antioxidant, anti-inflammatory and anticancer agent. Cryptotanshinone may also be studied as a differentiation factor.
The Uses of Cryptotanshinone
inhibits angiogenesis
What are the applications of Application
A biochemical for proteomics research
What are the applications of Application
Cryptotanshinone is inhibitor of STAT3 and AChE
Definition
ChEBI: Cryptotanshinone is an abietane diterpenoid. It has a role as an anticoronaviral agent.
General Description
Cryptotanshinone, a cell-permeable diterpene quinone and naturally occurring herbal constituent of Salvia miltiorrhiza Bunge (Danshen), is shown to inhibit the constitutive STAT3 Tyr705 phosphorylation in DU145 prostate cancer cells (>90% inhibition in 1 h at 7 μM) independent of the IL-6/JAK/STAT3 signaling pathway, resulting in a blockage of STAT3 dimerization, nuclear translocation, and STAT3-dependent transcription activity (by ~80% in 24 h at 7 μM). Cryptotanshinone is also reported to deplete cellular ATP level (by 75% in 12 h at 20 μM in C2C12 myotubes), resulting in an indirect activation of cellular AMPK pathways and an enhancement of insulin-stimulated cellular glucose uptake in C2C12 myotubes and 3T3-L1 adipocytes (by ~1.3- and 1.9-fold, respectively). Cryptotanshinone is demonstrated to be an orally active hypoglycemic agent in ob/ob mice, db/db mice, and ZDF rats in vivo (600 mg/kg/day).
Biological Activity
Major tanshinone isolated from Salvia miltiorrhiza that exhibits multiple activities. Exhibits antitumor activity via inhibition STAT3 activity (IC 50 = 4.6 μ ). Displays antibacterial and anti-inflammatory activity and acts as an antidiabetes and antiobesity agent via activation of AMP-activated protein kinase (AMPK). Also improves cognitive impairment in Alzheimer's disease transgenic mice by inhibition of acetylcholinesterase (IC 50 = 4.09 μ ) and reduction in A β peptide generation.
Biochem/physiol Actions
Cryptotanshinone is an antibacterial and anti-inflammatory compound originally extracted from the roots of Salvia miltiorrhiaz (danshen). Cryptotanshinone has been found to inhibit HIF activation and to inhibit macrophage migration negatively regulate the PI3K pathway. It has demonstrated activity against several strains of Staphylococcus aureus.
Cytotoxicity
IC50 (μg/mL): 1.27 (A549), 1.39 (TOV-21G) (Chang et al. 2013)
storage
Room temperature
Properties of Cryptotanshinone
Melting point: | 192°C(lit.) |
Boiling point: | 459.0±45.0 °C(Predicted) |
Density | 1.23±0.1 g/cm3(Predicted) |
storage temp. | 2-8°C |
solubility | DMSO: ≥5mg/mL |
form | powder |
color | orange-brown |
optical activity | [α]/D -85.0±3.0°, c = 0.1 in chloroform |
λmax | 263nm(lit.) |
BRN | 5445400 |
CAS DataBase Reference | 35825-57-1(CAS DataBase Reference) |
Safety information for Cryptotanshinone
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 Environment GHS09 |
GHS Hazard Statements |
H301:Acute toxicity,oral H410:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P501:Dispose of contents/container to..… |
Computed Descriptors for Cryptotanshinone
InChIKey | IJSBKZLSTIFYIE-FPKDZHNTSA-N |
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