Kinsenoside
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Grundinformationen
- CAS
151870-74-5- Standard-SMILES
O=C1C[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)CO1- InChIKey
MQEPWBMWFIVRPS-ZGSHZZHUSA-N- Summenformel
- C10H16O8
- Durchschnittliche Molmasse
- 264,23 g/mol
- Monoisotopische Masse
- 264,08451747
Namen und Bezeichner
- Bevorzugter Name
- Kinsenoside
- IUPAC
- (3R)-5-Oxooxolan-3-yl beta-D-glucopyranoside
- Englischer Name
- Kinsenoside
- Summenformel
- C10H16O8
- Molmasse
- 264.23
Namen und Synonyme
(4R)-4-(beta-D-Glucopyranosyloxy)dihydro-2(3H)-furanone2(3H)-Furanone, 4-(β-D-glucopyranosyloxy)dihydro-, (4R)-Kinsenoside(+)-Kinsenoside(4R)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-one(R)-4-(((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)dihydrofuran-2(3H)-oneKeap1-Nrf2,Inhibitor,pulposus,disc,degeneration,Kinsenoside,inhibit,cells,nucleus,Nrf2,Apoptosis,intervertebral
Datenbank-Bezeichner
- CAS
151870-74-5- PubChem CID
- 10422896
- DTXSID
DTXSID20164895- ChEMBL
CHEMBL4781365- ChEBI
CHEBI:188580- EC Number
- 112-687-5
- Nikkaji
- J1.053.183G
Eigenschaften
Physikochemische Eigenschaften
- Siedepunkt
- 570.2 · 570.2±50.0 °C(Predicted)
- Dichte
- 1.59 · 1.59±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- Löslichkeit
- 14 · DMF:14.0(Max Conc. mg/mL);52.98(Max Conc. mM)DMSO:33.0(Max Conc. mg/mL);124.89(Max Conc. mM)PBS (pH 7.2):10.0(Max Conc. mg/mL);37.85(Max Conc. mM)
- Aggregatzustand
- A crystalline solid
- pka
- 12.81 · 12.81±0.70(Predicted)
- Farbe
- White to light yellow
- InChI
- InChI=1/C10H16O8/c11-2-5-7(13)8(14)9(15)10(18-5)17-4-1-6(12)16-3-4/h4-5,7-11,13-15H,1-3H2/t4-,5-,7-,8+,9-,10-/s3
- InChIKey
- MQEPWBMWFIVRPS-MUOXDHKLNA-N
- SMILES
- O1C[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)CC1=O |&1:2,4,6,9,11,13,r|
Chemie und Industrie
Anwendungen
BeschreibungKinsenoside is a glycoside originally isolated from A. formosanus that has diverse biological activities, including antihyperlipidemic, immunosuppressive, and anti-inflammatory properties. It increases lipolysis mediated by adipose triglyceride lipase and increases hydrolysis of triglycerides in C3H10T1/2 adipocytes. It also increases phosphorylation of peroxisome proliferator-activated receptor α (PPARα) and CREB as well as protein levels of SIRT1, PGC-1α, and carnitine palmitoyltransferase I. Kinsenoside downregulates the expression and phosphorylation of VEGF receptor 2 (VEGFR2) and inhibits crosstalk between the JAK2/STAT3 and PI3K/AKT signaling pathways in dendritic cells in vitro. It decreases the production of IFN-γ, IL-17, and TNF-α and increases the production of IL-10 in splenocytes isolated from mice with collagen-induced arthritis (CIA). Kinsenoside (300 mg/kg per day) decreases the expression of IL-1β, TNF-α, and matrix metalloproteinase-9 (MMP-9) and increases the expression of IL-10 in inflamed joints in a mouse model of collagen-induced arthritis and prevents paw edema and reduces the severity of arthritis.
VerwendenKinsenoside is an anti-hyperlipidemic agent isolated from the plant Anoect chilus.
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