X0379

Xanthohumol

powder, ≥96% (HPLC)

• Synonym(e): (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone, 2′,4,4′-Trihydroxy-6′-methoxy-3′-prenylchalcone
• Empirische Formel (Hill-System): C₂₁H₂₂O₅
• CAS-Nummer: 6754-58-1
• Molekulargewicht: 354.40
• MDL-Nummer: MFCD00210576
• UNSPSC-Code: 12352204
• PubChem Substanz-ID: 24902121
• NACRES: NA.77

Eigenschaften

• product name: Xanthohumol from hop (Humulus lupulus), ≥96% (HPLC)
• Biologische Quelle: plant (Humulus lupulus)
• Assay: ≥96% (HPLC)
• Form: powder
• mp (Schmelzpunkt): 172 °C
• Löslichkeit: ethanol: 10 mg/mL
• Lagertemp.: 2-8°C
• SMILES String: COc1cc(O)c(C\C=C(/C)C)c(O)c1C(=O)\C=C\c2ccc(O)cc2
• InChI: 1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
• InChIKey: ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Beschreibung

Allgemeine Beschreibung

Xanthohumol is a chalcone compound present in the female inflorescence of hop (Humulus lupulus) plant. It is a food additive.

Anwendung

Xanthohumol from hop (Humulus lupulus) has been used:

• to treat glioblastoma cells to test its effect on inducing apoptosis
• to test its protective effect in renal ischemia/reperfusion (I/R) injury
• as a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system

Biochem./physiol. Wirkung

Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines. Xanthohumol protected HepG2 cells against benzo[a]pyrene and related carcinogens. It also protected against reactive oxygen species (ROS), not by a direct anti-oxidant effect, but instead mediated by induction of cellular defense mechanisms against oxidative stress.Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT) and human P450 enzymes. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions.

Xanthohumol induces apoptosis in glioma cancer by modulating microRNA based network. It exhibits anti-inflammatory property by inhibiting janus kinases (JAKs), signal transducer and activator of transcription proteins (STATs). Xanthohumol elicits antiviral functionality against bovine viral diarrhea virus (BVDV) and anti-hepatitis C virus in vitro. It also induces autophagy and has antiplatelet and neuroprotective effects. Xanthohumol also regulates various metabolic processes including the inhibition of triglyceride formation, atherosclerotic plaque and adipogenesis.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves