Xanthohumol

Catalog No.S7889

Xanthohumol Chemical Structure

Molecular Weight(MW): 354.4

Xanthohumol, a prenylated chalcone from hop, inhibits COX-1 and COX-2 activity and shows chemopreventive effects. Phase 1.

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Biological Activity

Description Xanthohumol, a prenylated chalcone from hop, inhibits COX-1 and COX-2 activity and shows chemopreventive effects. Phase 1.
Targets
COX-1 [1] COX-2 [1]
In vitro

Xanthohumol inhibits Cyp1A activity and induces QR activity in mouse hepatoma cell culture. Xanthohumol scavenges reactive oxygen species and inhibits superoxide anion radical and nitric oxide production. In addition, Xanthohumol prevents carcinogenesis via inhibition of DNA synthesis and induction of cell cycle arrest in S phase, apoptosis, and cell differentiation. [1] Xanthohumol shows potent anti-HIV-1 activity. [2]

In vivo In CETP-Tg mice, xanthohumol (p.o.) prevents cholesterol accumulation leading to atherosclerosis. [3] In TRAMP mice, xanthohumol (p.o.) induces a decrease in the average weight of the urogenital (UG) tract, delays advanced tumor progression and inhibits the growth of poorly differentiated prostate carcinoma. [4]

Protocol

Kinase Assay:[1]
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Inhibition of Cox Activity:

Inhibition of Cox-1 activity is measured by monitoring oxygen consumption during the conversion of arachidonic acid to PGs using a Clark-type O2-electrode. The reaction mixture contains ∼0.2 units Cox-1 in 100 μL of microsome fraction derived from ram seminal vesicles as a crude source of Cox-1 (specific activity 0.2–1 units/mg protein) or 0.23 units of recombinant human Cox-2 (specific activity 43 units/mg protein). For calculation, the rate of O2 consumption is compared with a DMSO control (100% activity). Piroxicam, a nonsteroidal anti-inflammatory drug, is used as positive inhibitory substance for Cox-1 activity with an IC50 of 0.35 ± 0.05 μM (n = 2). Alternatively, nimesulide, a Cox-2 specific inhibitor, inhibits Cox-2 activity by 52 ± 5.7% (n = 2) at a concentration of 50 μM.
Cell Research:[1]
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  • Cell lines: HL-60 cells
  • Concentrations: 12.5 μM
  • Incubation Time: 96 h
  • Method: HL-60 cells are maintained in RPMI 1640 supplemented with 10% FBS at 37°C in a 5% CO2 atmosphere. Log-phase cells with a population doubling time of 14–16 h are used for experiments. Serial 2-fold dilutions of compounds (dissolved in DMSO, final concentration 0.1%) in a final concentration range of 0.2–12.5 μM are prepared in 24-well plates using 1 ml of RPMI/well. Control wells obtain the same amount of solvent. Subsequently, 1 ml of the cell suspension is added to the wells. After 96 h, the experiment is evaluated. Cell numbers are counted using a Casy 1 TTC flow-cytometer. The proliferation of treated cells is expressed as a percentage in comparison with the solvent control.
    (Only for Reference)
Animal Research:[3] [4]
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  • Animal Models: CETP-Tg and C57BL/6N (wild-type) mice; TRAMP C57BL/6 mice
  • Formulation: 0.05% (w/w) xanthohumol powder in diet, or suspended in ethanol (2.5 mg/mL)
  • Dosages: 50 μg/mouse
  • Administration: p.o.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 70 mg/mL (197.51 mM)
Ethanol 70 mg/mL (197.51 mM)
Water Insoluble
In vivo Add solvents to the product individually and in order:
0.05% (w+w) xanthohumol powder in diet, or suspended in ethanol (2.5 mg+mL)
13mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 354.4
Formula

C21H22O5

CAS No. 6754-58-1
Storage powder
Synonyms N/A

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT02432651 Active, not recruiting Oxidative Stress Oregon State University March 2015 Phase 1
NCT01367431 Completed Metabolic Syndrome Oregon State University|Oregon Health and Science University|National Center for Complementary and Integrative Health (NCCIH) August 2011 --

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COX Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID