| Identification | Back Directory | [Name]
TAXIFOLIN 3-O-RHAMNOSIDE | [CAS]
29838-67-3 | [Synonyms]
Astilbin
Taxifolin 3-rhaMnoside
Taxifolin 3-o-rhamnoside
Dihydroquercetin 3-rhamnoside
Astilbin Taxifolin 3-O-rhaMnoside
Astilbin froM Engelhardtia roxburghiana
Astilbin, 98%, from Smilax glabra Roxb.
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chroMen-3-yl 6-deoxy-alpha-L-Mannopyranoside
(2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyloxy)]-2-(3,4-dihydroxy-phenyl)-2,3-dihydro-5,7-dihydroxy-4H-chromen-4-one
(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-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,3R)-
(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 | [EINECS(EC#)]
694-695-3 | [Molecular Formula]
C21H22O11 | [MDL Number]
MFCD01632717 | [MOL File]
29838-67-3.mol | [Molecular Weight]
450.4 |
| Chemical Properties | Back Directory | [Melting point ]
180 °C (decomp) | [Boiling point ]
801.1±65.0 °C(Predicted) | [density ]
1.74 | [storage temp. ]
2-8°C | [solubility ]
H2O: soluble1mg/mL, clear, colorless | [form ]
A crystalline solid | [pka]
7.34±0.60(Predicted) | [color ]
White to off-white | [Water Solubility ]
H2O: 1mg/mL, clear, colorless | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [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 Data | Back Directory | [Symbol(GHS) ]
GHS09 | [Signal word ]
Warning | [Hazard statements ]
H400 | [Precautionary statements ]
P273 | [Hazard Codes ]
N | [Risk Statements ]
50 | [Safety Statements ]
61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3 | [HS Code ]
29389090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
Astilbin is a flavonoid that has been found in S. glabra and has diverse biological activities.1,2,3 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.1 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.2 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.3 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, easily soluble in boiling water, almost insoluble in ether, derived from Smilax glabra, Smilax china, Engelhardtia roxburghiana Wall. | [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]
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]. | [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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