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Xanthohumol

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https://www.readbyqxmd.com/read/29330372/non-estrogenic-xanthohumol-derivatives-mitigate-insulin-resistance-and-cognitive-impairment-in-high-fat-diet-induced-obese-mice
#1
Cristobal L Miranda, Lance A Johnson, Oriane de Montgolfier, Valerie D Elias, Lea S Ullrich, Joshua J Hay, Ines L Paraiso, Jaewoo Choi, Ralph L Reed, Johana S Revel, Chrissa Kioussi, Gerd Bobe, Urszula T Iwaniec, Russell T Turner, Benita S Katzenellenbogen, John A Katzenellenbogen, Paul R Blakemore, Adrian F Gombart, Claudia S Maier, Jacob Raber, Jan F Stevens
Xanthohumol (XN), a prenylated flavonoid from hops, improves dysfunctional glucose and lipid metabolism in animal models of metabolic syndrome (MetS). However, its metabolic transformation into the estrogenic metabolite, 8-prenylnaringenin (8-PN), poses a potential health concern for its use in humans. To address this concern, we evaluated two hydrogenated derivatives, α,β-dihydro-XN (DXN) and tetrahydro-XN (TXN), which showed negligible affinity for estrogen receptors α and β, and which cannot be metabolically converted into 8-PN...
January 12, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29322620/rice-protein-matrix-enhances-circulating-levels-of-xanthohumol-following-acute-oral-intake-of-spent-hops-in-humans
#2
Annalouise O'Connor, Veera Konda, Ralph L Reed, J Mark Christensen, Jan F Stevens, Nikhat Contractor
SCOPE: Xanthohumol (XN), a prenylated flavonoid found in hops, exhibits anti-inflammatory and antioxidant properties. However, poor bioavailability may limit therapeutic applications. As food components are known to modulate polyphenol absorption, the objective was to determine whether a protein matrix could enhance the bioavailability of XN post oral consumption in humans. METHODS AND RESULTS: This was a randomized, double-blind, cross-over study in healthy participants (n = 6) evaluating XN and its major metabolites [isoxanthohumol (IX), 6- and 8-prenylnaringenin (6-PN, 8-PN)] for 6 hours following consumption of 12...
January 11, 2018: Molecular Nutrition & Food Research
https://www.readbyqxmd.com/read/29305606/xanthohumol-protects-morphology-and-function-in-a-mouse-model-of-retinal-degeneration
#3
Nathaniel F Henneman, Stephanie L Foster, Micah A Chrenek, Jana T Sellers, Charles B Wright, Robin H Schmidt, John M Nickerson, Jeffrey H Boatright
Purpose: To investigate whether treatment with xanthohumol (XN), the principal prenylated chalconoid from Humulus lupulus (hops), is protective in a mouse model of light-induced retinal degeneration (LIRD). Methods: Mice (129S2/SvPasCrl) were intraperitoneally injected with vehicle or XN prior to toxic light exposure and every 3 days thereafter. Retinal function was assessed by electroretinograms at 1, 2, and 4 weeks following toxic light exposure. Visual acuity was tested by optokinetic tracking 1 week and 4 weeks after toxic light exposure...
January 1, 2018: Investigative Ophthalmology & Visual Science
https://www.readbyqxmd.com/read/29237346/arachidonic-acid-reverses-xanthohumol-induced-insufficiency-in-a-human-first-trimester-extravillous-trophoblast-cell-line-htr-8-svneo-cells
#4
Ana Correia-Branco, Elisa Keating, Fátima Martel
We previously described a negative effect of xanthohumol (XN) upon placentation-related processes. We aimed to better characterize this effect by investigating the effect of XN upon the uptake of arachidonic acid (ARA), a crucial nutrient during pregnancy, by the HTR-8/SVneo human first-trimester extravillous trophoblast cell line and its relationship with the negative effect of XN upon placentation-related processes. Uptake of 14C-ARA (100 nM) was time dependent and inhibited by short-term (26 minutes) or long-term (24 hours) exposure to XN...
January 1, 2017: Reproductive Sciences
https://www.readbyqxmd.com/read/29169265/a-new-formylated-chalcone-from-humulus-lupulus-with-protective-effect-on-huvecs-injury-by-angiotensin-ii
#5
Nenling Zhang, Birong Tian, Shuang Zhao, Xu Zhang, Di Pan, Xiangchun Shen, Yanyan Zhang
One new formylated chalcone, 3'- formyl xanthohumol (1) was isolated from the EtOAc-soluble partition of the cones of Humulus lupulus, along with two other known chalcones, namely dehydrocycloxanthohumol (2) and xanthohumol (3). The structure of compound 1 was elucidated on the basis of its 1D, 2D NMR and MS data. The structures of the known compounds were identified by comparison of their spectroscopic data with those reported by the literatures. The isolates were tested for their protective effects on human umbilical vein endothelial cells (HUVECs) injured by angiotensin II (Ang II), all the three compounds protected against the cell injury at the concentration of 20 μΜ, and compound 3 showed the most potent activity by improving cell viability from 53...
November 24, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29166278/interactions-between-plant-derived-oestrogenic-substances-and-the-mycoestrogen-zearalenone-in-a-bioassay-with-mcf-7-cells
#6
Sabine Hessenberger, K Botzi, C Degrassi, P Kovalsky, C Schwab, D Schatzmayr, G Schatzmayr, J Fink-Gremmels
Human and animal diets may contain several non-steroidal oestrogenic compounds which originate either from plants (phytoestrogens) or from fungi that infect plants (mycoestrogens such as zearalenone (ZEN)). Phytoestrogens may compete with ZEN in binding to the oestrogen receptor β and thereby may counteract the oestrogenic activity of ZEN. Using a modified version of the E-screen assay, plant-derived oestrogenic substances were tested for their proliferative or anti-proliferative effect on oestrogen-dependent MCF-7 cells...
September 26, 2017: Polish Journal of Veterinary Sciences
https://www.readbyqxmd.com/read/29152142/antiproliferative-and-apoptotic-effects-of-xanthohumol-in-cholangiocarcinoma
#7
Daniel Walden, Selvi Kunnimalaiyaan, Kevin Sokolowski, T Gamblin Clark, Muthusamy Kunnimalaiyaan
Cholangiocarcinoma remains the second most prevalent hepatic neoplasm in the United States with a 5-year survival rate of less than 10%. Currently, no systemic therapy has demonstrated efficacy. Therefore, an urgent need for the identification of molecularly targeted compound(s) remains. The Notch signaling pathway has been shown to be dysregulated in cholangiocarcinoma, exhibiting hyperactivity while also possibly mediating chemotherapeutic resistance. We analyzed the effects of xanthohumol, a prenylated chalcone, on cholangiocarcinoma proliferation utilizing human cholangiocarcinoma cell lines CCLP1, SG-231 and CC-SW-1 while gaining insight into the associated mechanism...
October 20, 2017: Oncotarget
https://www.readbyqxmd.com/read/29148787/acid-base-properties-of-xanthohumol-a-computational-and-experimental-investigation
#8
Marta Arczewska, Daniel M Kamiński, Barbara Gieroba, Mariusz Gagoś
UV-vis spectrophotometry has been applied to determine acid dissociation constants of the prenylated chalcone xanthohumol. The pKa values were compared with those derived from pH-metric titrations. The order of the deprotonation site in the xanthohumol molecule was estimated by quantum mechanical calculations as 2'-OH, 4'-OH, and 4-OH. Furthermore, the electronic and spectroscopic properties of xanthohumol have been investigated on the basis of the time-dependent density functional theory (TDDFT). The TDDFT method, combined with a hybrid exchange-correlation functional using the B3LYP and CAM-B3LYP levels of theory in conjunction with the SMD solvation model, was used to optimize all geometries and predict the excitation energies of the neutral form and ionized species of the chalcone depending on pH value...
November 17, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/29138867/effect-of-xanthohumol-on-th1-th2-balance-in-a-breast-cancer-mouse-model
#9
Wenchao Zhang, Yanlong Pan, Panhong Gou, Cheng Zhou, Lianqing Ma, Qiming Liu, Yuping Du, Jinbo Yang, Qin Wang
Xanthohumol (XN), a prenylflavonoid found in the hop plant, Humulus lupulus, exhibits a variety of biological activities. Numerous studies have reported that XN inhibits the growth of many types of cancer cells, but the effects of XN on tumor immunity have not yet been studied. We explored the effect of XN on Th1/Th2 balance and the underlying mechanism based on a BALB/c-4T1 breast cancer mouse model. The results showed that XN significantly slowed down tumor growth and inhibited expression of antitumor proliferation protein Ki-67 as well as breast cancer-specific marker cancer antigen 15-3 (CA15-3)...
November 13, 2017: Oncology Reports
https://www.readbyqxmd.com/read/29129239/an-iso-%C3%AE-acid-rich-extract-from-hops-humulus-lupulus-attenuates-acute-alcohol-induced-liver-steatosis-in-mice
#10
Marianne Hege, Finn Jung, Cathrin Sellmann, Chengjun Jin, Doreen Ziegenhardt, Claus Hellerbrand, Ina Bergheim
OBJECTIVE: Results of in vitro and in vivo studies suggest that consumption of beer is less harmful for the liver than consumption of spirits. It also has been suggested that secondary plant compounds derived from hops such as xanthohumol or iso-α-acids may have beneficial effects on the development of liver diseases of various etiologies. The aim of this study was to determine whether iso-α-acids consumed in doses achieved by "normal" beer consumption have beneficial effects on health...
January 2018: Nutrition
https://www.readbyqxmd.com/read/29121426/xanthohumol-inhibits-angiogenesis-by-suppressing-nuclear-factor-%C3%AE%C2%BAb-activation-in-pancreatic-cancer
#11
Kenta Saito, Yoichi Matsuo, Hiroyuki Imafuji, Tomotaka Okubo, Yuzo Maeda, Takafumi Sato, Tomoya Shamoto, Ken Tsuboi, Mamoru Morimoto, Hiroki Takahashi, Hideyuki Ishiguro, Shuji Takiguchi
Xantohumol, a prenylated chalcone from hops (Humulus lupulus L.), has been shown to inhibit proliferation in some cancers. However, little is known regarding the effects of xanthohumol in pancreatic cancer. We have previously reported that activation of the transcription factor nuclear factor-κB (NF-κB) plays a key role in angiogenesis in pancreatic cancer. In this study, we investigated whether xanthohumol inhibited angiogenesis by blocking NF-κB activation in pancreatic cancer in vitro and in vivo. We initially confirmed that xanthohumol significantly inhibited proliferation and NF-κB activation in pancreatic cancer cell lines...
November 9, 2017: Cancer Science
https://www.readbyqxmd.com/read/29063320/study-of-sedative-tea-phytocomplex-within-the-framework-of-studies-aimed-at-creation-of-a-rectal-dosage-form-with-antihistaminic-effect
#12
V F Kulikovskii, E T Zhilyakova, O O Novikov, D I Pisarev, N V Prokushchenko, L L Ivanova
We designed a new complex drug with antiallergic effect containing, in addition to the main component loratadine, a phytocomplex for an extra therapeutic effect. A collection of plants with sedative activity is chosen and the optimal agent for extraction of bioactive compounds (40% ethanol) and optimal degree of plant fragmentation are determined. Chemical composition of the sedative tea is evaluated by reverse phase HPLC. The marker components of the species are detected: xanthohumol and isoxanthohumol - Humulus lupulus cone components, Mentha piperita rosmarinic acid, and scutellareine, Menyanthes trifolia element - quercetin-3-rutinoside, and caffeic acid...
October 2017: Bulletin of Experimental Biology and Medicine
https://www.readbyqxmd.com/read/29048380/hop-phytochemicals-and-their-potential-role-in-metabolic-syndrome-prevention-and-therapy
#13
REVIEW
Pavel Dostálek, Marcel Karabín, Lukáš Jelínek
Historically, hop cones (Humulus lupulus) have been used since ancient times as a remedy for many ailments and, as a source of polyphenols and bitter acids, is very effective in the treatment of metabolic syndrome (MS). Hop flavonoids, particularly xanthohumol (XN), are substances with hypoglycemic, antihyperlipidemic, and antiobesity activities. Iso-α-acids (IAA) and matured hop bitter acids (MHBA) improve health by influencing lipid metabolism, glucose tolerance, and body weight. The modulatory effect of IAA and MHBA on lipid metabolism may also be responsible for a loss in body weight...
October 19, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28984993/total-synthesis-of-13-c-2-13-c-3-and-13-c-5-isotopomers-of-xanthohumol-the-principal-prenylflavonoid-from-hops
#14
Duncan C Ellinwood, Mohamed F El-Mansy, Layhna S Plagmann, Jan F Stevens, Claudia S Maier, Adrian F Gombart, Paul R Blakemore
Xanthohumol [(E)-6´-methoxy-3´-(3-methylbuten-2-yl)-2´,4´,4´´-trihydroxychalcone], the principal prenylated flavonoid from hops, has a complex bioactivity profile and (13) C-labelled isotopomers of this compound are of potential use as molecular probes and as analytical standards to study metabolism and mode-of-action. 1,3-[(13) C]2 -Xanthohumol was prepared by an adaptation of the total synthesis of Khupse and Erhardt in 7 steps and 5.7% overall yield from phloroglucinol by a route incorporating a cascade Claisen-Cope rearrangement to install the 3´-prenyl moiety from a 5´-prenyl aryl ether and an aldol condensation between 1-[(13) C]-2´,4´-bis(benzyloxymethyloxy)-6´-methoxy-3´-(3-methylbuten-2-yl)acetophenone and 1´-[(13) C]-4-(methoxymethyloxy)benzaldehyde...
October 6, 2017: Journal of Labelled Compounds & Radiopharmaceuticals
https://www.readbyqxmd.com/read/28960474/strong-antimicrobial-activity-of-xanthohumol-and-other-derivatives-from-hops-humulus-lupulus-l-on-gut-anaerobic-bacteria
#15
Pavel Cermak, Jana Olsovska, Alexandr Mikyska, Martin Dusek, Zuzana Kadleckova, Jiri Vanicek, Otakar Nyc, Karel Sigler, Vanda Bostikova, Pavel Bostik
Anaerobic bacteria, such as Bacteroides fragilis or Clostridium perfringens, are part of indigenous human flora. However, Clostridium difficile represents also an important causative agent of nosocomial infectious antibiotic-associated diarrhoea. Treatment of C. difficile infection is problematic, making it imperative to search for new compounds with antimicrobial properties. Hops (Humulus lupulus L.) contain substances with antibacterial properties. We tested antimicrobial activity of purified hop constituents humulone, lupulone and xanthohumol against anaerobic bacteria...
November 2017: APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica
https://www.readbyqxmd.com/read/28950154/protective-effect-of-xanthohumol-against-age-related-brain-damage
#16
Lisa Rancán, Sergio D Paredes, Irene García, Pedro Muñoz, Cruz García, Guzmán López de Hontanar, Mónica de la Fuente, Elena Vara, Jesús A F Tresguerres
It has been recently shown that xanthohumol, a flavonoid present in hops, possesses antioxidant, anti-inflammatory and chemopreventive properties. However, its role in the aging brain has not been addressed so far. Therefore, this study aimed to investigate the possible neuroprotective activity of xanthohumol against age-related inflammatory and apoptotic brain damage in male senescence-accelerated prone mice (SAMP8). Animals were divided into 4 groups: Untreated young mice, untreated old mice and old mice treated either with 1 mg kg-1 day-1 or 5 mg kg-1 day-1 xanthohumol...
November 2017: Journal of Nutritional Biochemistry
https://www.readbyqxmd.com/read/28940469/cytoprotective-effects-of-xanthohumol-against-methylglyoxal-induced-cytotoxicity-in-mc3t3-e1-osteoblastic-cells
#17
Kwang Sik Suh, Suk Chon, Eun Mi Choi
Methylglyoxal (MG) has been suggested to be a major source of intracellular reactive carbonyl compounds, and has been implicated in increasing the levels of advanced glycation end products in age-related diseases. Xanthohumol is a prenylated flavonoid found in hops (Humulus lupulus) and beer. In the present study, we investigated the effects of xanthohumol on MG-induced cytotoxicity in osteoblastic MC3T3-E1 cells. Xanthohumol attenuated MG-induced cytotoxicity, as evidenced by improved cell viability, and prevented MG-induced MG-protein adducts, inflammatory cytokines, reactive oxygen species and mitochondrial superoxide production...
September 20, 2017: Journal of Applied Toxicology: JAT
https://www.readbyqxmd.com/read/28858767/discovery-of-new-md2-targeted-anti-inflammatory-compounds-for-the-treatment-of-sepsis-and-acute-lung-injury
#18
Gaozhi Chen, Bing Xiao, Lingfeng Chen, Bin Bai, Yali Zhang, Zheng Xu, Lili Fu, Zhiguo Liu, Xiaokun Li, Yunjie Zhao, Guang Liang
Myeloid differentiation 2 (MD2) is essential to the recognition of lipopolysaccharide (LPS) and the subsequent mediation of toll-like receptor 4 (TLR4)-dependent acute inflammatory disorders including sepsis and acute lung injury. Inhibitors targeting MD2 may provide an alternative means to subdue acute inflammatory diseases. In the present study, 39 bisaryl-1,4-dien-3-one compounds with 5-carbon connection chains were designed and synthesized as MD2 inhibitors based on the analysis of the molecular docking of xanthohumol to MD2...
October 20, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28812892/designer-extracts-as-tools-to-balance-estrogenic-and-chemopreventive-activities-of-botanicals-for-women-s-health
#19
Birgit M Dietz, Shao-Nong Chen, René F Ramos Alvarenga, Huali Dong, Dejan Nikolić, Martin Biendl, Richard B van Breemen, Judy L Bolton, Guido F Pauli
Botanical dietary supplements contain multiple bioactive compounds that target numerous biological pathways. The lack of uniform standardization requirements is one reason that inconsistent clinical effects are reported frequently. The multifaceted biological interactions of active principles can be disentangled by a coupled pharmacological/phytochemical approach using specialized ("knock-out") extracts. This is demonstrated for hops, a botanical for menopausal symptom management. Employing targeted, adsorbent-free countercurrent separation, Humulus lupulus extracts were designed for pre- and postmenopausal women by containing various amounts of the phytoestrogen 8-prenylnaringenin (8-PN) and the chemopreventive constituent xanthohumol (XH)...
August 25, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28812343/xanthohumol-suppresses-mylip-idol-gene-expression-and-modulates-ldlr-abundance-and-activity-in-hepg2-cells
#20
Shih-Fen Chen, Pei-Yi Chen, Hao-Jen Hsu, Ming-Jiuan Wu, Jui-Hung Yen
Xanthohumol, a prenylated flavonoid found in hops (Humulus lupulus L.), exhibits multiple biological activities such as antiatherosclerosis and hypolipidemic activities. In this study, we aim to investigate the hypocholesterolemic effects and molecular mechanisms of xanthohumol in hepatic cells. We found that xanthohumol (10 and 20 μM) increased the amount of cell-surface low-density lipoprotein receptor (LDLR) from 100.0 ± 2.1% to 115.0 ± 1.3% and 135.2 ± 2.7%, and enhanced the LDL uptake activity from 100...
September 13, 2017: Journal of Agricultural and Food Chemistry
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