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Xanthohumol AND Hops

Cristina Fernández-García, Lisa Rancan, Sergio D Paredes, César Montero, Mónica de la Fuente, Elena Vara, Jesús A F Tresguerres
BACKGROUND AND AIMS: Aging is associated with a deregulation of biological systems that lead to an increase in oxidative stress, inflammation, and apoptosis, among other effects. Xanthohumol is the main preylated chalcone present in hops (Humulus lupulus L.) whose antioxidant, anti-inflammatory and chemopreventive properties have been shown in recent years. In the present study, the possible protective effects of xanthohumol on liver alterations associated with aging were evaluated. METHODS: Male young and old senescence-accelerated prone mice (SAMP8), aged 2 and 10 months, respectively, were divided into four groups: non-treated young, non-treated old, old treated with 1 mg/kg/day xanthohumol, and old treated with 5 mg/kg/day xanthohumol...
March 13, 2018: European Journal of Nutrition
Jan Moritz Seliger, Livia Misuri, Edmund Maser, Jan Hintzpeter
Xanthohumol (XN), a prenylated chalcone unique to hops (Humulus lupulus) and two derived prenylflavanones, isoxanthohumol (IX) and 8-prenylnaringenin (8-PN) gained increasing attention as potential anti-diabetic and cancer preventive compounds. Two enzymes of the aldo-keto reductase (AKR) superfamily are notable pharmacological targets in cancer therapy (AKR1B10) and in the treatment of diabetic complications (AKR1B1). Our results show that XN, IX and 8-PN are potent uncompetitive, tight-binding inhibitors of human aldose reductase AKR1B1 (Ki  = 15...
December 2018: Journal of Enzyme Inhibition and Medicinal Chemistry
Kwang Sik Suh, Eun Mi Choi, Hyun-Sook Kim, So Young Park, Sang Ouk Chin, Sang Youl Rhee, Youngmi Kim Pak, Wonchae Choe, Joohun Ha, Suk Chon
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) is an environmental contaminant. Xanthohumol is a prenylated flavonoid found in hops (Humulus lupulus) and beer. The aim of the current study was to explore the role of xanthohumol in modulating the toxicity of TCDD in MC3T3-E1 osteoblastic cells. In cells treated with TCDD alone, intracellular Ca2+ concentrations, mitochondrial membrane potential disruption, reactive oxygen species production, cardiolipin peroxidation, nitric oxide release and cytochrome P450 1A1 expression were significantly increased...
March 8, 2018: Journal of Applied Toxicology: JAT
Zhihong Sun, Cheng Zhou, Feng Liu, Wenchao Zhang, Jing Chen, Yanlong Pan, Lianqing Ma, Qimin Liu, Yuping Du, Jinbo Yang, Qin Wang
Natural compounds derived from plants have been an important source of numerous clinically useful anticancer agents. Nevertheless, limited studies indicate that xanthohumol (XN), a major prenylated flavonoid in hop plants (Humulus lupulus), may possess anticarcinogenic properties. The purpose of the present study was to clarify the antitumorigenic effects and the underlying mechanism of XN on breast cancer in vivo and in vitro. A 4T1 breast tumor mouse model was used in the present study to investigate XN suppression of tumor growth as detected by tumorigenicity assays in vivo...
January 2018: Oncology Letters
Jae-Min Cho, Sun-Mi Yun, Young-Ho Choi, Jinyuk Heo, Nam-Jung Kim, Seok-Ho Kim, Eun-Hee Kim
Xanthohumol (XN), a prenylated chalcone isolated from the hop plant, has been reported to exhibit multiple biological functions including anti-inflammation. However, the pharmacological function of XN on colitis remains unknown. In this study, we investigated the anti-inflammatory effect of synthesized XN and molecular mechanism on dextran sulfate sodium (DSS)-induced experimental colitis. XN attenuated the colitis symptoms along with the prevention of colonic lesions after DSS challenge. XN inhibited the production of pro-inflammatory cytokines, oxidative stress and cyclooxygenase-2 expression in DSS-treated mice...
January 2, 2018: Oncotarget
Katerina Bogdanova, Magdalena Röderova, Milan Kolar, Katerina Langova, Martin Dusek, Petr Jost, Klara Kubelkova, Pavel Bostik, Jana Olsovska
Bacterial biofilms pose a serious medical problem due to their significant resistance to antimicrobials, and staphylococci are recognized as the most frequent cause of biofilm-associated infections. The hop plant (Humulus lupulus L.) contains substances that have been determined to act as anti-infective agents against bacteria, mainly in planktonic form. Therefore, we decided to investigate the antibiofilm properties of Humulus lupulus L.-derived compounds (humulone, lupulone and xanthohumol) against a selected group of Staphylococcus spp...
January 30, 2018: Research in Microbiology
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
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
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
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
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
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...
January 2018: Cancer Science
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
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
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
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
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
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
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
Tomasz Tronina, Paulina Strugała, Jarosław Popłoński, Aleksandra Włoch, Sandra Sordon, Agnieszka Bartmańska, Ewa Huszcza
The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol (2) and (Z)-6,4'-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)-major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2-3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4-9) were formed, of which four glycosides (6-9) have not been published so far...
July 21, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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