Dihydrotanshinone I

Modify Date: 2024-01-02 09:38:58

Dihydrotanshinone I Structure
Dihydrotanshinone I structure
 Common Name Dihydrotanshinone I
CAS Number 87205-99-0 Molecular Weight 278.302
Density 1.3±0.1 g/cm3 Boiling Point 479.2±45.0 °C at 760 mmHg
Molecular Formula C18H14O3 Melting Point 214.0 to 218.0 °C
MSDS Chinese USA Flash Point 214.9±28.8 °C
Symbol GHS07 GHS09
GHS07, GHS09		 Signal Word Warning

 Use of Dihydrotanshinone I


Dihydrotanshinone I is a natural compound extracted from Salvia miltiorrhiza Bunge which has been widely used for treating cardiovascular diseases.

 Names

Name (1R)-1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione
Synonym More Synonyms

 Dihydrotanshinone I Biological Activity

Description Dihydrotanshinone I is a natural compound extracted from Salvia miltiorrhiza Bunge which has been widely used for treating cardiovascular diseases.
Related Catalog
In Vitro In lipopolysaccharide (LPS)-stimulated human umbilical vein endothelial cells (HUVECs), DHT (10 nM) decreases lectin-like ox-LDL receptor-1 (LOX-1) and NADPH oxidase 4 (NOX4) expression, reactive oxygen species (ROS) production, NF-κB nuclear translocation, ox-LDL endocytosis and monocytes adhesion[1]. Dihydrotanshinone I induces caspase dependent apoptosis induced in HCT116 cells. Dihydrotanshinone I induces concentration and ROS dependent caspase activation. Apoptosis induced by Dihydrotanshinone I is completely prevented by Z-VAD-fmk. Apoptosis induced by Dihydrotanshinone I is significantly inhibited by pretreatment of Z-LEHD-fmk but only is partially inhibited by Z-IETD-fmk. Apoptosis induced by Dihydrotanshinone I is significantly increased by caspase-2 knockdown[3].
In Vivo DHT (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice. DHT dramatically inhibits the enhanced expression of LOX-1, NOX4, and NF-κB in aorta[1]. Dihydrotanshinone I (1, 2, 4 mg/kg) treatment can improve cardiac function, reduce infarct size, ameliorate the variations in myocardial zymogram and histopathological disorders, decrease 20-HETE generation, and regulate apoptosis-related protein in myocardial ischemia-reperfusion rats[2].
Kinase Assay Cells are treated with various concentrations of Dihydrotanshinone I (3.13-20 µM) for 48 h. For the activity assay, Ac-DEVD-AMC (1 µg/µL), Ac-IETD-AMC (1 µg/µL) or Ac-LEDH-AMC (1 µg/µL) and cell lysate are added into Protease Assay Buffer in 96-well plate. Reaction mixtures with lysis buffer are used as negative controls. Cells treated with DMSO (0.1%) are treated as vehicle control. The reaction mixtures are incubated for 1 h at 37°C. The AMC liberated from the substrates is measured using spectrofluorometer of Victor 2 plate reader with an excitation wavelength of 380 nm and an emission wavelength of 430 nm.
Animal Admin Male ApoE-/- mice (6-8 weeks old) on C57BL/6J background and age-matched wild-type C57BL/6J controls housed in SPF-grade animal facilities with a 12 h light/dark cycle, at 23°C (±2°C). Starting from 6 weeks, the mice are fed with a HCD (54.35% raw grain, 20% lard, 0.15% cholesterol, 15% sucrose, 0.5% Sodium Cholate, 10% yolk powder) for 12 weeks. All ApoE-/- mice are dosed daily via intragastric gavage with 10 and 25 mg/kg Dihydrotanshinone I dissolved in 0.5% CMC-Na or administered 0.5% CMC-Na alone (vehicle control) (n=8 per group).
References

[1]. Zhao W, et al. Dihydrotanshinone I Attenuates Atherosclerosis in ApoE-Deficient Mice: Role of NOX4/NF-κB Mediated Lectin-Like Oxidized LDL Receptor-1 (LOX-1) of the Endothelium. Front Pharmacol. 2016 Nov 8;7:418. eCollection 2016.

[2]. Wei Y, et al. The cardioprotection of dihydrotanshinone I against myocardial ischemia-reperfusion injury via inhibition of arachidonic acid ω-hydroxylase. Can J Physiol Pharmacol. 2016 Dec;94(12):1267-1275. Epub 2016 Jun 24.

[3]. Wang L, et al. Dihydrotanshinone I induced apoptosis and autophagy through caspase dependent pathway in colon cancer. Phytomedicine. 2015 Nov 15;22(12):1079-87.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 479.2±45.0 °C at 760 mmHg
Melting Point 214.0 to 218.0 °C
Molecular Formula C18H14O3
Molecular Weight 278.302
Flash Point 214.9±28.8 °C
Exact Mass 278.094299
PSA 43.37000
LogP 3.90
Appearance of Characters red
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.671
Storage condition 2-8°C
Water Solubility ethanol: soluble1mg/mL, clear, orange to red

 Safety Information

Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning
Hazard Statements H302-H400
Precautionary Statements P273
Hazard Codes Xn,N
Risk Phrases 22-50
Safety Phrases 61
RIDADR UN 3077 9 / PGIII
RTECS SF8282630

 Articles6

More Articles
Dihydrotanshinone-I interferes with the RNA-binding activity of HuR affecting its post-transcriptional function.

Sci. Rep. 5 , 16478, (2015)

Post-transcriptional regulation is an essential determinant of gene expression programs in physiological and pathological conditions. HuR is a RNA-binding protein that orchestrates the stabilization a...

Comparison of neuroprotective effects of five major lipophilic diterpenoids from Danshen extract against experimentally induced transient cerebral ischemic damage.

Fitoterapia 83 , 1666-1674, (2012)

We observed neuroprotective effects of five major lipophilic diterpenes derived from Danshen (Radix Salvia miltiorrhiza) extract, such as cryptotanshinone (CTs), dihydrotanshinone I (DTsI), tanshinone...

Modeling gradient elution in countercurrent chromatography: efficient separation of tanshinones from Salvia miltiorrhiza Bunge.

J. Sep. Sci. 35 , 964-976, (2012)

Countercurrent chromatography (CCC) is a support-free liquid-liquid chromatography using centrifugal fields to hold the liquid stationary phase. CCC has been widely applied in the separation of variou...

 Synonyms

1,6-Dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione
1,2-dihydrotanshinone
Tanshinone I,dihydro
dihydrotanshinone 1
1,2-dihydrotanshinone I
15,16-dihydrotanshinone I
Phenanthro[1,2-b]furan-10,11-dione, 1,2-dihydro-1,6-dimethyl-
Dihydrotanshinone I
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