Orientin
LUTEOLIN-8-C-GLUCOSIDE · lutexin · Polygonin · ORIENTINE · Luteolin 8-C-β-D-glucopyranoside · ORIENTIN · Aids026706 · Aids-026706
Identifikatoren & physikalische Daten
| CAS No. | 28608-75-5 |
|---|---|
| Summenformel | C21H20O11 |
| Durchschnittliche Molmasse | 448,4 g/mol |
| Monoisotopische Masse | 448,10056146 g/mol |
| SMILES | O=c1cc(-c2ccc(O)c(O)c2)oc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc(O)c12 |
| InChIKey | PLAPMLGJVGLZOV-VPRICQMDSA-N |
| PubChem CID | 5281675 |
| ChEMBL | CHEMBL520866 |
| ChEBI | CHEBI:7781 |
| EC No. | 608-227-2 |
| DTXSID | DTXSID60182790 |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 197 |
| H-Brücken-Donoren | 8 |
| H-Brücken-Akzeptoren | 11 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 32 |
| Formalladung | 0 |
| Komplexität | 729 |
| Lipide | Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211] |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 260-285°C |
| Siedepunkt | 816.1±65.0 °C(Predicted) |
| Dichte | 1.759±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C(protect from light) |
| Löslichkeit | 1 M NaOH: soluble1mg/mL, clear, yellow-orange |
| pKa (Säurekonstante) | 6.24±0.40(Predicted) |
| Aggregatzustand | powder |
| Farbe | yellow |
| Stabilität | Hygroscopic |
| Hauptanwendungen | metabolomicsvitamins, nutraceuticals, and natural products |
| InChIKey | PLAPMLGJVGLZOV-FYNBPVOANA-N |
| SMILES | C12OC(=CC(=O)C=1C(=CC(O)=C2[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)O)C1C=CC(O)=C(O)C=1 |&1:12,13,15,16,18,r| |
| LogP (Verteilungskoeffizient) | 1.580 (est) |
| FDA UNII | IAX93XCW6C |
| UNSPSC Code | 85151701 |
| NACRES | NA.25 |
| GHS-Piktogramm | GHS07 |
| Signalwort | Warning |
| GHS-Gefahrenhinweise | H302-H315-H319-H335 |
| GHS-Sicherheitshinweise | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
| Sicherheitshinweise (S) | 24/25 |
| Wassergefährdungsklasse (WGK) | 3 |
| RTECS-Nr. | DJ3009300 |
| Zollcode | 29389090 |
| Lagerklasse | 11 - Combustible Solids |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| RTECS-Nr. | DJ3009300 |
| Zollcode | 29389090 |
| Signalwort | Warning |
| GHS-Piktogramm | GHS07 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 11 - Combustible Solids |
| GHS-Gefahrenhinweise | H302-H315-H319-H335 |
| GHS-Sicherheitshinweise | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
Anwendungen & Verwendung
Description
Orientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; ) radicals with an IC50 value of 316.21 μg/ml. It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells. Orientin (5-40 μM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs). It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 μg/animal 12 hours after LPS administration.
Uses
Orientin is a flavone, a chemical flavonoid compound. Orientin have been investigated for its anti-oxidant, antihypertensive and antihyperlipidemic effects.