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X0379

Xanthohumol

Name: Xanthohumol
Brand: SIGMA

powder, ≥96% (HPLC)

Synonym(s):

(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

Empirical Formula (Hill Notation):

C₂₁H₂₂O₅

CAS Number:

6754-58-1

Molecular Weight:

354.40

UNSPSC Code:

12352204

PubChem Substance ID:

24902121

NACRES:

NA.77

MDL number:

MFCD00210576

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Properties

Product Name

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

Description

General description

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

Application

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 Actions

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.

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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