TAXIFOLIN 3-O-RHAMNOSIDE Chemical Properties

Melting point:

180 °C (decomp)

Boiling point:

801.1±65.0 °C(Predicted)

Density 

1.74

storage temp. 

Sealed in dry,2-8°C

solubility 

H2O: soluble1mg/mL, clear, colorless

pka

7.34±0.60(Predicted)

form 

A crystalline solid

color 

White to off-white

Water Solubility 

H2O: 1mg/mL, clear, colorless

InChIKey

ZROGCCBNZBKLEL-MQGABXIONA-N

SMILES

O([C@]1([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)[C@H]1C(C2=C(C=C(O)C=C2O[C@@H]1C1C=CC(O)=C(O)C=1)O)=O |&1:1,4,6,8,10,12,22,r|

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

29389090

TAXIFOLIN 3-O-RHAMNOSIDE Usage And Synthesis

Description

Astilbin is a flavonoid that has been found in S. glabra and has diverse biological activities. It inhibits cisplatin-induced increases in apoptosis and accumulation of reactive oxygen species (ROS) in HEK293 cells when used at a concentration of 200 μM. Astilbin (50 mg/kg) increases renal glutathione (GSH) levels and superoxide dismutase (SOD) and catalase activity and reduces serum creatinine and blood urea nitrogen (BUN) levels, renal IL-1β, IL-6, and TNF-α levels, apoptosis in kidney tissue, and kidney injury in a mouse model of cisplatin-induced nephrotoxicity. It reduces loss of dopaminergic neurons in the substantia nigra and increases striatal GSH levels and SOD activity in a mouse model of MPTP-induced Parkinson''s disease when administered at a dose of 50 mg/kg per day. Astilbin also reduces descent time in a pole test and increases traction test score in a mouse model of Parkinson''s disease, indicating reduced motor deficits. It reduces cell viability of MDA-MB-231 and MCF-7 cells (IC₅₀s = 167.9 and 191.6 μM, respectively), as well as inhibits migration and increases apoptosis when used at concentrations of 50 and 200 μM. Astilbin (20 mg/kg every other day for 14 days) reduces tumor growth in an MCF-7 mouse xenograft model.

Chemical Properties

White crystalline powder, soluble in boiling water, almost insoluble in ether, from Poria cocos, Sarsaparilla, yellow wolfberry Engelhardtia roxburghiana Wall. red velvet goat's foot.

Uses

Astilbin displays anti-depressant activity involving monoaminergic neurotransmitters an the BDNF signal pathway. Anti-oxidant.

Definition

ChEBI: A flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.

in vivo

IC 50

NRF2; NF-κB

References

[1] SI-WEI WANG . Astilbin ameliorates cisplatin-induced nephrotoxicity through reducing oxidative stress and inflammation[J]. Food and Chemical Toxicology, 2018, 114: Pages 227-236. DOI: 10.1016/j.fct.2018.02.041
[2] YING-LI ZHU . Neuroprotective effects of Astilbin on MPTP-induced Parkinson’s disease mice: Glial reaction, α-synuclein expression and oxidative stress[J]. International immunopharmacology, 2019, 66: Pages 19-27. DOI: 10.1016/j.intimp.2018.11.004
[3] XIAOQI SUN. Caspase-dependent mitochondrial apoptotic pathway is involved in astilbin-mediated cytotoxicity in breast carcinoma cells.[J]. Oncology reports, 2018, 40 4: 2278-2286. DOI: 10.3892/or.2018.6602

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