Xanthohumol

Category	Cytomegalovirus (CMV)
CAS	6754-58-1
Description	Xanthohumol is a prenylated flavonoid isolated from Hops (Humulus lupulus L.), displaying anticancer and anti-angiogenic properties. It acts as an inhibitor of DGAT, COX-1 and COX-2.

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Product Information

Synonyms	(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-; (2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one; 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-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (E)-; Xantho Flav-Pure; Xantho-Flav; Xanthopure; (E)-2',4,4'-Trihydroxy-3'-prenyl-6'-methoxychalcone
IUPAC Name	(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Molecular Weight	354.40
Molecular Formula	C21H22O5
Canonical SMILES	CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
InChI	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+
InChIKey	ORXQGKIUCDPEAJ-YRNVUSSQSA-N
Boiling Point	576.5±50.0 °C at 760 mmHg
Melting Point	157-159°C
Flash Point	203.4±23.6 °C
Purity	>98%
Density	1.244 g/cm3
Solubility	Soluble in DMSO, Ethanol
Appearance	White Solid
Storage	Store at 2-8°C
Complexity	515
Exact Mass	354.14672380
Index Of Refraction	1.641
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. 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. 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. 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.
PSA	86.99000
Target	COX; Acyltransferase; Apoptosis; HSV; CMV; Influenza Virus
Vapor Pressure	0.0±1.7 mmHg at 25°C
XLogP3-AA	5.1