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X0379

Sigma-Aldrich

Xanthohumol

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

product name

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

biological source

plant (Humulus lupulus)

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

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Feng Zhao et al.
Journal of natural products, 68(1), 43-49 (2005-02-01)
The ethyl acetate soluble fraction of hops (Humulus lupulus) showed potent inhibitory activity on the production of nitric oxide (NO) induced by a combination of LPS and IFN-gamma. Four known prenylflavonoids (1-4) and a new prenylflavonoid (5), hulupinic acid (6)
Sai Lou et al.
Planta medica, 80(2-3), 171-176 (2013-12-21)
Hepatitis C virus is a major cause of chronic liver disease worldwide. Xanthohumol, a prenylated flavonoid from hops, has various biological activities including an antiviral effect. It was previously characterized as a compound that inhibits bovine viral diarrhea virus, a
Michela Festa et al.
Journal of natural products, 74(12), 2505-2513 (2011-11-25)
The effect of the biologically active prenylated chalcone and potential anticancer agent xanthohumol (1) has been investigated on apoptosis of the T98G human malignant glioblastoma cell line. Compound 1 decreased the viability of T98G cells by induction of apoptosis in
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
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
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