Astilbin

Modify Date: 2024-01-02 14:44:46

Astilbin Structure
Astilbin structure
 Common Name Astilbin
CAS Number 29838-67-3 Molecular Weight 450.393
Density 1.7±0.1 g/cm3 Boiling Point 801.1±65.0 °C at 760 mmHg
Molecular Formula C21H22O11 Melting Point N/A
MSDS Chinese USA Flash Point 282.9±27.8 °C
Symbol GHS09
GHS09		 Signal Word Warning

 Use of Astilbin


Astilbin, a flavonoid compound, is isolated from the rhizome of Smilax glabra. Astilbin enhances NRF2 activation. Astilbin also suppresses TNF-α expression and NF-κB activation.

 Names

Name astilbin
Synonym More Synonyms

 Astilbin Biological Activity

Description Astilbin, a flavonoid compound, is isolated from the rhizome of Smilax glabra. Astilbin enhances NRF2 activation. Astilbin also suppresses TNF-α expression and NF-κB activation.
Related Catalog
Target

NRF2

TNF-α

NF-κB
In Vitro Astilbin is a common dietary flavonoid that can be found in various kinds of herbs and foods such as Smilax Glabra, Sarcandra glabra, grape and red wine. Astilbin markedly inhibits cisplatin-induced cell apoptosis and recovers cell growth. Astilbin significantly decreases reactive oxygen species (ROS) accumulation and alleviates ROS-induced activation of p53, MAPKs and AKT signaling cascades, which in turn attenuates cisplatin-induced HEK-293 cell apoptosis. Astilbin effectively enhances NRF2 activation and transcription of its targeting antioxidant genes to reduce ROS accumulation in cisplatin-induced HEK-293 cells. Astilbin obviously suppresses tumor necrosis factor alpha (TNF-α) expression and NF-κB activation, and also inhibits the expression of induced nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). To measure the effects of Astilbin on the growth of CDDP-treated renal cells, HEK-293 cells are treated with CDDP (100 μM) and/or Astilbin (200 μM). Astilbin treatment significantly improvescell growth in CDDP-induced HEK-293 cells[1].
In Vivo To explore whether Astilbin improves CDDP-induced nephrotoxicity in vivo, an acute cisplatin nephrotoxic mouse model is established. Single injection of CDDP with 8 mg/kg dose results in notable weight loss compared with control group. However, the phenomenon is significantly alleviated by Astilbin at dose of 50 mg/kg. The mice fed Astilbin alone do not show any obvious alteration in body weight. Similarly, serum creatinine (SCr) and blood urea nitrogen (BUN) are higher in CDDP-treated mice than in control group. Treatment with Astilbin also decreases SCr and BUN levels. To examine the protective effect of Astilbin on CDDP-induced renal histopathological damage, the mouse kidney sections are stained with H&E. The mice in control group and Astilbin treated group have normal kidney morphology, while kidneys in CDDP group show severe damage with tubular degeneration, necrosis and cystic dilatation of the tubules with focal hemorrhages. Administration of Astilbin mitigated kidney injury, resulting in lower histopathological score compared to CDDP group. The apoptosis of renal cells is also detected using TUNEL staining to determine whether Astilbin treatment decreased renal cell apoptosis in CDDP-induced acute nephrotoxic mice[1].
Cell Assay HEK-293 cells are seeded into 96-well plate with a density of 5 × 104 cells/well and subsequently treated with CDDP, Astilbin (0, 10, 30, 50, 100, 200 and 300 μM) or CDDP+Astilbin for 24 h. After treatments, 20 μL of 5 mg/mL MTT is added to each well. The cells are incubated for additional 4 h at 37°C. Then cell supernatant is abandoned and 100 μL of formanzan is added to each well. The plate is shaken at room temperature for 15 min. Spectrophotometric absorbance is measured by Synergy Microplate Reader at 570 nm[1].
Animal Admin Mice[1] Male C57BL/6 mice (20-24 g, 8 weeks of age) are used. After acclimation for one week, the experimental mice are randomly divided into 4 groups with 10 animals per group: control group, CDDP group, CDDP+Astilbin group and Astilbin group. The control group and CDDP group are orally administered saline for 10 days; the CDDP+Astilbin group and Astilbin group are orally administered 50 mg/kg Astilbin for 10 days. The CDDP group and CDDP+Astilbin group receive a single intraperitoneal injection of CDDP on the 7th day of the experiment, while control group and Astilbin group receive saline injection on the same day[1].
References

[1]. Wang SW, et al. Astilbin ameliorates cisplatin-induced nephrotoxicity through reducing oxidative stress and inflammation. Food Chem Toxicol. 2018 Apr;114:227-236.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 801.1±65.0 °C at 760 mmHg
Molecular Formula C21H22O11
Molecular Weight 450.393
Flash Point 282.9±27.8 °C
Exact Mass 450.116211
PSA 186.37000
LogP 2.97
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.748
Storage condition 2-8°C
Water Solubility H2O: soluble1mg/mL, clear, colorless

 Safety Information

Symbol GHS09
GHS09
Signal Word Warning
Hazard Statements H400
Precautionary Statements P273
Hazard Codes N
Risk Phrases 50
Safety Phrases 61
RIDADR UN 3077 9 / PGIII

 Synthetic Route

(2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-(((2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)chroman-4-one structure

(2R,3R)-5,7-bis...

CAS#:294203-79-5

~91%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: SUNTORY LIMITED Patent: EP1260517 A1, 2002 ; Location in patent: Example 6 ;
(2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol structure

(2R-trans)-2-[3...

CAS#:20728-73-8

~%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: Tetrahedron, , vol. 60, # 6 p. 1365 - 1373
1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose structure

1-O-acetyl-2,3,...

CAS#:80152-99-4

~%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: Tetrahedron, , vol. 60, # 6 p. 1365 - 1373
6-deoxy-2,3,4-tri-O-benzyl-α-L-mannopyranosyl fluoride structure

6-deoxy-2,3,4-t...

CAS#:104495-20-7

~%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: Tetrahedron, , vol. 60, # 6 p. 1365 - 1373
(2R,3S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-(((2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)chromane structure

(2R,3S)-5,7-bis...

CAS#:294203-76-2

~%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: Tetrahedron, , vol. 60, # 6 p. 1365 - 1373
(2R,3S,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-(((2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)chroman-4-ol structure

(2R,3S,4S)-5,7-...

CAS#:294203-78-4

~%

Astilbin Structure

Astilbin

CAS#:29838-67-3
Literature: Tetrahedron, , vol. 60, # 6 p. 1365 - 1373

 Articles27

More Articles
Isolation and characterization of two flavonoids, engeletin and astilbin, from the leaves of Engelhardia roxburghiana and their potential anti-inflammatory properties.

J. Agric. Food Chem. 59(9) , 4562-9, (2011)

Engeletin, a flavonoid compound, was isolated from the leaves of Engelhardia roxburghiana for the first time, along with astilbin, another flavonoid. The chemical structures of engeletin and astilbin ...
ACE inhibition by astilbin isolated from Erythroxylum gonocladum (Mart.) O.E. Schulz.

Phytomedicine 17(5) , 383-7, (2010)

Erythroxylum species have several traditional uses in different countries, including the treatment of hypertension. The ethanol extract from E. gonocladum aerial parts, a species endemic to the Brazil...
Chemical constituents comparison between Rhizoma Smilacis Glabrae and Rhizoma Smilacis Chinae by HPLC-DAD-MS/MS.

Nat. Prod. Res. 27(3) , 277-81, (2013)

Rhizoma Smilacis Glabrae (RSG) and Rhizoma Smilacis Chinae (RSC) are two herbal materials that belong to the same genera and are both listed in the Chinese Pharmacopoeia. Chemical constituents in the ...

 Synonyms

4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-
Astilbin Dihydroquercetin 3-rhamnoside Taxifolin 3-rhamnoside
4H-1-Benzopyran-4-one, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-
Taxifolin 3-rhamnoside
Neoisoastilbin
Astilbin
(2R-trans)-3-((6-Deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R-trans)-
Taxifolin 3-O-rhamnoside
Astilbin from Engelhardtia roxburghiana
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-α-L-mannopyranoside
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Price: ￥880/10 mM * 1 mL in DMSO

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Related Compounds: More...
Astilbin
54081-48-0
astilbin
54081-47-9
Chemsrc provides Astilbin(CAS#:29838-67-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Astilbin are included as well.>> amp version: Astilbin

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