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
• UNSPSC Code: 12352204
• PubChem Substance ID: 24902121
• NACRES: NA.77
• MDL number: MFCD00210576

Eigenschaften

• Produktname: Xanthohumol from hop (Humulus lupulus), ≥96% (HPLC)
• biological source: plant (Humulus lupulus)
• Quality Segment: 200
• assay: ≥96% (HPLC)
• form: powder
• mp: 172 °C
• solubility: ethanol: 10 mg/mL
• storage temp.: 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+
• InChI key: ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Beschreibung

General description

Xanthohumol is a chalcone compound[1] present in the female inflorescence of hop (Humulus lupulus) plant. It is a food additive.[2]

Application

Xanthohumol from hop (Humulus lupulus) has been used:

• to treat glioblastoma cells to test its effect on inducing apoptosis[1]
• 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[3]

Biochem/physiol Actions

Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines. Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT) and human P450 enzymes. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions.

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.[1] 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.[3] 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.[2]

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves