Xanthohumol - CAS 6754-58-1
Catalog number: 6754-58-1
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C21H22O5
Molecular Weight:
354.4
COA:
Inquire
Targets:
Cox-2
Description:
An inhibitor of COX-1 and COX-2
Brife Description:
An inhibitor of COX-1 and COX-2
Appearance:
Yellow solid
Synonyms:
(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Solubility:
DMSO 70 mg/mL (197.51 mM); Ethanol 70 mg/mL (197.51 mM)
Storage:
3 years -20°C powder;6 months-80°C in solvent
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Melting Point:
157-159℃
InChIKey:
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
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+
Canonical SMILES:
CC(=CCC1=C(C=C(C(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)O)C
1.Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
Forino M1, Pace S2, Chianese G1, Santagostini L3, Werner M2, Weinigel C4, Rummler S4, Fico G5,6, Werz O2, Taglialatela-Scafati O1. J Nat Prod. 2016 Mar 25;79(3):590-7. doi: 10.1021/acs.jnatprod.5b01052. Epub 2016 Feb 26.
Humulus lupulus (hop plant) has long been used in traditional medicine as a sedative and antimicrobial agent. More recently, attention has been devoted to the phytoestrogenic activity of the plant extracts as well as to the anti-inflammatory and chemopreventive properties of the prenylated chalcones present. In this study, an Italian sample of H. lupulus cv. "Cascade" has been investigated and three new compounds [4-hydroxycolupulone (6), humudifucol (7) and cascadone (8)] have been purified and identified by means of NMR spectroscopy along with four known metabolites. Notably, humudifucol (7) is the first prenylated dimeric phlorotannin discovered in nature. Because structurally related phloroglucinols from natural sources were found previously to inhibit microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), the isolated compounds were evaluated for their bioactivity against these pro-inflammatory target proteins. The prenylated chalcone xanthohumol inhibited both enzymes at low μM concentrations.
2.Xanthohumol inhibits STAT3 activation pathway leading to growth suppression and apoptosis induction in human cholangiocarcinoma cells.
Dokduang H1, Yongvanit P1, Namwat N1, Pairojkul C2, Sangkhamanon S2, Yageta MS3, Murakami Y3, Loilome W1. Oncol Rep. 2016 Apr;35(4):2065-72. doi: 10.3892/or.2016.4584. Epub 2016 Jan 21.
STAT3 plays a significant role in the development of cholangiocarcinoma (CCA) associated with the liver fluke (Opisthorchis viverrini; Ov). Xanthohumol (XN), a prenylated flavonoid extracted from hops, has known anticancer activity and could potentially target STAT3. The present study determined the effect of XN on STAT3, as well as ascertained its usefulness against CCA. The CCA cell proliferation at 20 µM and 50 µM of XN was shown to inhibited, while 20 µM partially inhibited IL-6-induced STAT3 activation. At 50 µM, the inhibition was complete. The reduction in STAT3 activity at 20 and 50 µM was associated with a significant reduction of CCA cell growth and apoptosis. We also found that the administration of 50 µM XN orally in drinking water to nude mice inoculated with CCA led to a reduction in tumor growth in comparison with controls. In addition, apoptosis of cancer cells increased although there was no visible toxicity. The present study shows that XN can inhibit STAT3 activation both in vivo and in vitro due to suppression of the Akt-NFκB signaling pathway.
3.Xanthohumol improves dysfunctional glucose and lipid metabolism in diet-induced obese C57BL/6J mice.
Miranda CL1, Elias VD1, Hay JJ1, Choi J1, Reed RL1, Stevens JF2. Arch Biochem Biophys. 2016 Mar 11. pii: S0003-9861(16)30060-1. doi: 10.1016/j.abb.2016.03.008. [Epub ahead of print]
Xanthohumol (XN) is a prenylated flavonoid found in hops (Humulus lupulus) and beer. The dose-dependent effects of XN on glucose and lipid metabolism in a preclinical model of metabolic syndrome were the focus of our study. Forty-eight male C57BL/6J mice, 9 weeks of age, were randomly divided into three XN dose groups of 16 animals. The mice were fed a high-fat diet (60% kcal as fat) supplemented with XN at dose levels of 0, 30, or 60 mg/kg body weight/day, for 12 weeks. Dietary XN caused a dose-dependent decrease in body weight gain. Plasma levels of glucose, total triglycerides, total cholesterol, and MCP-1 were significantly decreased in mice on the 60 mg/kg/day treatment regimen. Treatment with XN at 60 mg/kg/day resulted in reduced plasma LDL-cholesterol (LDL-C), IL-6, insulin and leptin levels by 80%, 78%, 42%, and 41%, respectively, compared to the vehicle control group. Proprotein Convertase Subtilisin Kexin 9 (PCSK-9) levels were 44% lower in the 60 mg/kg dose group compared to the vehicle control group (p ≤ 0.
4.Xanthohumol-induced presynaptic reduction of glutamate release in the rat hippocampus.
Chang Y1, Lin TY2, Lu CW2, Huang SK3, Wang YC4, Wang SJ5. Food Funct. 2016 Jan 20;7(1):212-26. doi: 10.1039/c5fo01005e.
This study examined whether xanthohumol, a hop-derived prenylated flavonoid present in beer, affects glutamate release in the rat hippocampus. In the rat hippocampal nerve terminals (synaptosomes), xanthohumol inhibited the release of 4-aminopyridine (4-AP)-evoked glutamate and the elevation of cytosolic Ca(2+) concentration, whereas it had no effect on 4-AP-mediated depolarization. The inhibitory effect of xanthohumol on the evoked glutamate release was prevented by removing extracellular Ca(2+), using the Cav2.2 (N-type) and Cav2.1 (P/Q-type) channel blocker ω-CgTX MVIIC, the calmodulin antagonists W7 and calmidazolium, and the protein kinase A inhibitor H89; however, no such effect was observed when the G-protein inhibitor N-ethylmaleimide was used. In addition, immunocytochemical data demonstrated that GABAA receptors are present in the hippocampal synaptosomes and that the xanthohumol effect on evoked glutamate release was antagonized by the GABAA receptor antagonist SR95531.
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CAS 6754-58-1 Xanthohumol

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