Xanthohumol

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

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	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.

Name	xanthohumol
Synonym	More Synonyms

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	Signaling Pathways >> Metabolic Enzyme/Protease >> Acyltransferase Signaling Pathways >> Immunology/Inflammation >> COX Research Areas >> Cancer Natural Products >> Flavonoids
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.

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

Xanthohumol MSDS(Chinese)

Symbol	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

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...

(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

BioBioPha
China
Product Name: Xanthohumol
Price: ￥Inquiry/20mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Xueping-Zheng

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Xanthohumol
Price: ￥788.0/20mg ￥2738.0/25mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Xanthohumol
Price: $250.0/100mg $450.0/250mg $900.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYLBUT-2-EN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

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