Xanthohumol

Modify Date: 2024-01-01 18:57:34

Xanthohumol Structure
Xanthohumol structure
 Common Name Xanthohumol
CAS Number 6754-58-1 Molecular Weight 354.396
Density 1.2±0.1 g/cm3 Boiling Point 576.5±50.0 °C at 760 mmHg
Molecular Formula C21H22O5 Melting Point 157-159ºC
MSDS Chinese USA Flash Point 203.4±23.6 °C
Symbol GHS07 GHS09
GHS07, GHS09		 Signal Word Warning

 Use of Xanthohumol


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.

 Names

Name xanthohumol
Synonym More Synonyms

 Xanthohumol Biological Activity

Description 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.
Related Catalog
In Vitro Xanthohumol significantly attenuates ADP-induced blood platelet aggregation, and significantly reduces the expression of fibrinogen receptor (activated form of GPIIbIIIa) on platelets' surface[1]. Xanthohumol (5-50 nM) reduces the frequency of spontaneously occurring Ca2+ sparks and Ca2+ waves in control myocytes and in cells subjected to Ca2+ overload caused by: (1) exposure to low K+ solutions, (2) periods of high frequency electrical stimulation, (3) exposures to isoproterenol or (4) caffeine. Xanthohumol (50-100 nM) reduces the rate of relaxation of electrically- or caffeine-triggered Ca2+ transients, without suppressing ICa, but this effect is small and reversed by isoproterenol at physiological temperatures. Xanthohumol also suppresses the Ca2+ content of the SR, and its rate of recirculation[2]. Treatment of endothelial cells with Xanthohumol leads to increased AMPK phosphorylation and activity. Functional studies using biochemical approaches confirm that AMPK mediates Xanthohumol anti-angiogenic activity. AMPK activation by Xanthohumol is mediated by CAMMKβ, but not LKB1. Analysis of the downstream mechanisms shows that Xanthohumol-induced AMPK activation reduces nitric oxide (NO) levels in endothelial cells by decreasing eNOS phosphorylation. Finally, AKT pathway is inactivated by Xanthohumol as part of its anti-angiogenic activity, but independently from AMPK, suggesting that these two signaling pathways proceed autonomously[3]. Xanthohumol significantly reduces cell viability and induces apoptosis via pro-caspase-3/8 cleavage and poly(ADP ribose) polymerase (PARP) degradation. Pro-caspase-9 cleavage, Bcl2 family expression changes, mitochondrial dysfunction, and intracellular ROS generation also participate in Xanthohumol-induced glioma cell death. Xanthohumol's inhibition of the IGFBP2/AKT/Bcl2 pathway via miR-204-3p targeting plays a critical role in mediating glioma cell death[4].
Cell Assay In vitro cell proliferation/viability is measured by the MTT test at different time points. 1000 cells/well are plated into 96-multiwell plates in complete medium. Following adhesion, medium is replaced with fresh medium containing the different treatments or vehicle (DMSO in medium). Xanthohumol and EGCG are used in a concentration range from 2.5 to 40 μM, up to 96 hours. 3 hours before each time point, MTT reagent (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) is added to the wells and plates are incubated at 37°C. At the indicated time points, absorbance at 540 nm is then measured by a FLUOstar spectrophotometer.
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.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 576.5±50.0 °C at 760 mmHg
Melting Point 157-159ºC
Molecular Formula C21H22O5
Molecular Weight 354.396
Flash Point 203.4±23.6 °C
Exact Mass 354.146729
PSA 86.99000
LogP 5.17
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.641
Storage condition 2-8°C
Water Solubility ethanol: soluble10mg/mL

 Safety Information

Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning
Hazard Statements H317-H400
Precautionary Statements P273-P280
Hazard Codes N: Dangerous for the environment;
Risk Phrases R50/53
Safety Phrases 60-61
RIDADR UN 3077 9
RTECS UD5574117

 Articles34

More Articles
Xanthohumol modulates inflammation, oxidative stress, and angiogenesis in type 1 diabetic rat skin wound healing.

J. Nat. Prod. 76(11) , 2047-53, (2013)

Type 1 diabetes mellitus is responsible for metabolic dysfunction, accompanied by chronic inflammation, oxidative stress, and endothelium dysfunction, and is often associated with impaired wound heali...

Protective effects of arachidonic acid against palmitic acid-mediated lipotoxicity in HIT-T15 cells.

Mol. Cell Biochem. 364(1-2) , 19-28, (2012)

Saturated fatty acids have been considered major contributing factors in type 2 diabetes, whereas unsaturated fatty acids have beneficial effects for preventing the development of diabetes. However, t...

Search method for inhibitors of Staphyloxanthin production by methicillin-resistant Staphylococcus aureus.

Biol. Pharm. Bull. 35(1) , 48-53, (2012)

Staphyloxanthin, a yellow pigment produced by methicillin-resistant Staphylococcus aureus (MRSA), is a virulent factor escaping from the host immune system. A new screening method for inhibitors of st...

 Synonyms

(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
MFCD00210576
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Xanthohumol
2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
2-Propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
QR D1U1VR BQ DQ FO1 C2UY1&1
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
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