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HomeProduct name listCryptotanshinone

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

Cryptotanshinone Structural

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)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
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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