Xanthohumol

Alias: Xanthohumol;(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Cat No.:V1046 Purity: ≥98%
Xanthohumol, a naturally occuring prenylated chalcone compound isolated from hops (the female inflorescences of Humulus lupulus), is an inhibitor of COX-1 and COX-2 enzymatic activity and shows chemopreventive effects as well as anti-cancer and anti-angiogenic activities.
Xanthohumol Chemical Structure CAS No.: 6754-58-1
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Xanthohumol, a naturally occuring prenylated chalcone compound isolated from hops (the female inflorescences of Humulus lupulus), is an inhibitor of COX-1 and COX-2 enzymatic activity and shows chemopreventive effects as well as anti-cancer and anti-angiogenic activities. It binds to the N domain of VCP, suppressing function and impairing autophagosome maturation. It inhibits growth of a wide variety of human cancer cell lines by inhibiting proliferation and inducing apoptosis. Xanthohumol is one of the principal flavonoids isolated from hops, the inhibitor of diacylglycerol acetyltransferase (DGAT), COX-1 and COX-2, and shows anti-cancer and anti-angiogenic activities.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
ADP-induced blood platelet aggregation is markedly inhibited by xanthohumol, which also dramatically lowers fibrinogen receptor expression (the activated form of GPIIbIIIa) on the surface of platelets[1]. In control myocytes and in cells exposed to Ca2+ overload brought on by: (1) exposure to low K+ solutions; (2) periods of high frequency electrical stimulation; (3) exposures to isoproterenol; or (4) caffeine, xanthohumol (5-50 nM) decreases the frequency of spontaneously occurring Ca2+ sparks and Ca2+ waves. Without inhibiting ICa, xanthohumol (50–100 nM) lowers the rate of relaxation of electrically or caffeine-triggered Ca2+ transients; however, this action is negligible and isoproterenol reverses it at physiological temperatures. Additionally, xanthohumol reduces the SR's rate of recirculation and Ca2+ content[2]. When Xanthohumol is applied to endothelial cells, AMPK phosphorylation and activity rise. It has been confirmed by functional investigations employing biochemical methods that AMPK mediates the anti-angiogenic effect of xanthohumol. Xanthohumol activates AMPK through the action of CAMMKβ, not LKB1. By lowering eNOS phosphorylation, Xanthohumol-induced AMPK activation lowers nitric oxide (NO) levels in endothelial cells, according to an analysis of the downstream pathways. Lastly, Xanthohumol's anti-angiogenic action inactivates the AKT pathway apart from AMPK, indicating that these two signaling pathways operate independently of one another[3]. The formation of intracellular ROS contributes to the glioma cell death caused by xanthohumol. Glioma cell death is largely mediated by xanthohumol's suppression of the IGFBP2/AKT/Bcl2 pathway via miR-204-3p targeting[4].
ln Vivo
In CETP-Tg mice, xanthohumol (p.o.) prevents cholesterol accumulation leading to atherosclerosis. 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.
Animal Protocol
Dissolved in 0.05% (w/w) xanthohumol powder in diet, or suspended in ethanol (2.5 mg/mL); 50 mg/kg/day; p.o. administration
CETP-Tg and C57BL/6N (wild-type) mice; TRAMP C57BL/6 mice
References
[1]. Luzak B, et al. Xanthohumol from hop cones (Humulus lupulus L.) prevents ADP-induced platelet reactivity. Arch Physiol Biochem. 2016 Nov 18:1-7
[2]. Arnaiz-Cot JJ, et al. Xanthohumol modulates calcium signaling in rat ventricular myocytes: Possible Antiarrhythmic properties. J Pharmacol Exp Ther. 2016 Nov 4. pii: jpet.116.236588
[3]. Gallo C, et al. Hop derived flavonoid xanthohumol inhibits endothelial cell functions via AMPK activation. Oncotarget. 2016 Aug 1
[4]. Chen PH, et al. The miR-204-3p-targeted IGFBP2 pathway is involved in xanthohumol-induced glioma cell apoptotic death. Neuropharmacology. 2016 Nov;110(Pt A):362-75.
[5]. Inokoshi J, et al. Expression of two human acyl-CoA:diacylglycerol acyltransferase isozymes in yeast and selectivity of microbial inhibitors toward the isozymes. J Antibiot (Tokyo). 2009;62(1):51-54.
[6]. Buckwold VE, et al. Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral Res. 2004 Jan;61(1):57-62
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H22O5
Molecular Weight
354.4
CAS #
6754-58-1
SMILES
O(C([H])([H])[H])C1C([H])=C(C(=C(C=1C(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C([H])C=1[H])O[H])=O)O[H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H])O[H]
Synonyms
Xanthohumol;(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 70 mg/mL (197.5 mM)
Water:<1 mg/mL
Ethanol:70 mg/mL (197.5 mM)
Solubility (In Vivo)
0.05% (w+w) xanthohumol powder in diet, or suspended in ethanol (2.5 mg+mL): 13mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8217 mL 14.1084 mL 28.2167 mL
5 mM 0.5643 mL 2.8217 mL 5.6433 mL
10 mM 0.2822 mL 1.4108 mL 2.8217 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Biological Data
  • Xanthohumol

    Effect of xanthohumol on serum cholesterol and CETP activity.PLoS One.2012;7(11):e49415.
  • Xanthohumol

    Expression analyses in mice liver and ab. aorta.PLoS One.2012;7(11):e49415.
  • Xanthohumol

    Xanthohumol increased apoE protein expression in CETP-Tg mice after 18 weeks.



    Xanthohumol
    Changes in cholesterol accumulation over 18 weeks.PLoS One.2012;7(11):e49415.
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