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X0379

Sigma-Aldrich

Xanthohumol

powder, ≥96% (HPLC)

Sinónimos:

(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

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About This Item

Fórmula empírica (notación de Hill):
C21H22O5
Número de CAS:
6754-58-1
Peso molecular:
354.40
Número MDL:
MFCD00210576
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
24902121
NACRES:
NA.77

Nombre del producto

Xanthohumol from hop (Humulus lupulus), ≥96% (HPLC)

origen biológico

plant (Humulus lupulus)

Nivel de calidad

200

Ensayo

≥96% (HPLC)

Formulario

powder

mp

172 °C

solubilidad

ethanol: 10 mg/mL

temp. de almacenamiento

2-8°C

cadena SMILES

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+

Clave InChI

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

Descripción general

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

Aplicación

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

Acciones bioquímicas o fisiológicas

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. 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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000383492
0000367928
0000336301
0000326172
0000332603

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Peng-Hsu Chen et al.
Neuropharmacology, 110(Pt A), 362-375 (2016-08-04)
Xanthohumol (XN), a prenylated chalcone extracted from hop plant Humulus lupulus L. (Cannabaceae), has potential for cancer therapy, including gliomas. Micro (mi)RNAs are small noncoding RNAs that control gene expression. Several miRNAs have been identified to participate in regulating glioma
Andreas Hartkorn et al.
Journal of natural products, 72(10), 1741-1747 (2009-09-18)
Therapeutic effects of dietary flavonoids have been attributed mainly to their antioxidant capacity. Xanthohumol (1), a prominent flavonoid of the hop plant, Humulus lupulus, was investigated for its antioxidant potential and for its effect on NF-kappaB activation. To examine the
Ming Liu et al.
Molecules (Basel, Switzerland), 20(1), 754-779 (2015-01-13)
The female inflorescences of hops (Humulus lupulus L.), a well-known bittering agent used in the brewing industry, have long been used in traditional medicines. Xanthohumol (XN) is one of the bioactive substances contributing to its medical applications. Among foodstuffs XN
Susanne Vogel et al.
European journal of medicinal chemistry, 45(6), 2206-2213 (2010-02-16)
Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were
Xanthohumol from Humulus lupulus L. induces glioma cell autophagy via inhibiting Akt/mTOR/S6K pathway
Lu WJ, et al.
Journal of functional foods, 18, 538-549 (2015)
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