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Chemical Structure| 482-36-0 Chemical Structure| 482-36-0

Structure of Hyperoside
CAS No.: 482-36-0

Chemical Structure| 482-36-0

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Hyperoside, a natural product isolated and purified from the herb of Hypericum perforatum L., with neuro-protective, anti-inflammatory and antioxidative effects, promotes ECV304 cell proliferation, may cause herb-drug interactions when co-administrated with CYP2D substrates and serve as a protective agent by alleviating microglia activation in disorders such as Parkinson's disease.

Synonyms: Quercetin-3-O-galactoside; NSC 407304; Quercetin 3-D-galactoside

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Product Citations

Product Citations

Liezel Gouws ; Helena Dorathea Janse van Rensburg ; Gisella Terre' ; Blanche ; Mietha Magdalena Van der Walt ;

Abstract: Rooibos (Aspalathus linearis) and Honeybush (Cyclopia intermedia) are popular tisanes in South Africa and are of growing interest due to the wide variety of flavonoids and other phytochemicals they contain. Despite their history as herbal teas and traditional medicines, the chemical constituents of these tisanes have yet to be studied for their effects on adenosine receptors. Flavonoids have previously shown promising affinity toward the adenosine receptors. A series of 30 commercially available constituents of Rooibos and Honeybush were investigated via radioligand binding studies to determine their adenosine A1 and A2A receptor affinity at both rat and human subtypes in order to establish structure-activity relationships and identify novel adenosine receptor ligands. In addition, in silico evaluations of the 30 test compounds were also performed to investigate their physiochemical and pharmacokinetic properties. The most promising constituent was kaempferol (28) which showed sub-micromolar affinity towards the rat A1 subtype (rA1Ki = 0.7287 μM; hA1Ki = 9.88 µM) and acted as an antagonist toward adenosine rA1 receptors. Additionally, quercetin (2), chrysoeriol (8), luteolin (9), eriodyctiol (12), and naringenin (27) also showed adenosine A1 and/or A2A receptor affinity. It was observed that a flavonol scaffold is preferred to flavone and flavanone scaffolds, and within the flavonols, C4’-OH substitution on ring B is preferred to C3’,4’-diOH substitution. These phytochemicals, specifically kaempferol (28), may be considered lead-like and valuable in designing novel ligands, based on in vitro and in silico evaluation.

Keywords: Rooibos ; Honeybush ; adenosine A1 receptor ; adenosine A2A receptor ; structure-activity relationships

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Product Details of Hyperoside

CAS No. :482-36-0
Formula : C21H20O12
M.W : 464.38
SMILES Code : O=C1C(O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)=C(C3=CC=C(O)C(O)=C3)OC4=CC(O)=CC(O)=C14
Synonyms :
Quercetin-3-O-galactoside; NSC 407304; Quercetin 3-D-galactoside
MDL No. :MFCD00016933
InChI Key :OVSQVDMCBVZWGM-DTGCRPNFSA-N
Pubchem ID :5281643

Safety of Hyperoside

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Related Pathways of Hyperoside

pyroptosis

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human rheumatoid arthritis fibroblast-like synoviocytes (RA FLSs) 10, 50, 100 µmol/L 48 hours To investigate the effect of Hyperoside on LPS-induced proliferation and migration of RA FLSs. Results showed that Hyperoside dose-dependently inhibited LPS-induced proliferation and migration of RA FLSs, and reduced the production of TNF-α, IL-6, IL-1β, and MMP-9. PMC4857551
BV-2 cells 1 μg/ml ctDNA 3-6 hours To evaluate the inhibitory effect of Hyperoside on the production of pro-inflammatory factors TNF, IL6, and IFNB in ctDNA-stimulated BV-2 cells. Results showed that Hyperoside dose-dependently reduced the levels of these pro-inflammatory factors. PMC11097432
BV-2 cells 20 ng/ml LPS 12-24 hours To validate the inhibitory effect of Hyperoside on the production of pro-inflammatory factors TNF, IL6, and CCL2 in LPS-stimulated BV-2 cells. Results showed that Hyperoside dose-dependently reduced the levels of these pro-inflammatory factors. PMC11097432
HT22 cells 20–80 μM 24 hours To evaluate the protective effect of HYP on Aβ aggregate-induced cell death, results showed that HYP increased cell viability in a dose-dependent manner. PMC9975698

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/c nude mice CBRH-7919 tumor xenograft model Tail vein injection 6.0 mg/kg Every 2 days for 25 days To evaluate the antitumor efficacy of DLD/HYP-Lip in vivo. Results showed that DLD/HYP-Lip significantly inhibited tumor growth with a tumor inhibition rate of 88.79%. PMC8091078
APP/PS1 double transgenic Alzheimer’s disease mice APP/PS1 double transgenic Alzheimer’s disease model Intranasal administration 20, 40, 80 mg/kg Every 3 days for 8 weeks To evaluate the improvement of cognitive function and motor ability by HYP, results showed that HYP improved motor deficit, spatial memory and learning ability of APP/PS1 mice, and reduced the level of Aβ plaques and GFAP in the cortex and hippocampus. PMC9975698
DBA/1 mice Collagen-induced arthritis (CIA) model Intraperitoneal injection 25, 50 mg/kg/d Once daily for 3 weeks To investigate the therapeutic effect of Hyperoside on CIA mice. Results showed that Hyperoside significantly decreased clinical scores and alleviated synovial hyperplasia, inflammatory cell infiltration, and cartilage damage. PMC4857551
Balb/c mice Light damage-induced retinal degeneration model Intraperitoneal injection 100 mg/kg Twice daily for 7 days To evaluate the protective effects of hyperoside on retinal structure and function post-light damage. Results showed that hyperoside partially preserved retinal structure, attenuated functional decline, and reduced neuroinflammatory responses and microglial activation. PMC11097432

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.15mL

0.43mL

0.22mL

10.77mL

2.15mL

1.08mL

21.53mL

4.31mL

2.15mL

References

 

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