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Xanthohumol AND Hops

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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/29138867/effect-of-xanthohumol-on-th1-th2-balance-in-a-breast-cancer-mouse-model
#4
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
#5
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
#6
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/29048380/hop-phytochemicals-and-their-potential-role-in-metabolic-syndrome-prevention-and-therapy
#7
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
#8
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
#9
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
#10
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
#11
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/28812892/designer-extracts-as-tools-to-balance-estrogenic-and-chemopreventive-activities-of-botanicals-for-women-s-health
#12
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
#13
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
https://www.readbyqxmd.com/read/28754033/the-influence-of-glycosylation-of-natural-and-synthetic-prenylated-flavonoids-on-binding-to-human-serum-albumin-and-inhibition-of-cyclooxygenases-cox-1-and-cox-2
#14
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
https://www.readbyqxmd.com/read/28750311/synthesis-and-antiangiogenic-activity-study-of-new-hop-chalcone-xanthohumol-analogues
#15
Elisa Nuti, Barbara Bassani, Caterina Camodeca, Lea Rosalia, AnnaRita Cantelmo, Cristina Gallo, Denisa Baci, Antonino Bruno, Elisabetta Orlandini, Susanna Nencetti, Douglas M Noonan, Adriana Albini, Armando Rossello
Angiogenesis induction is a hallmark of cancer. Antiangiogenic properties of Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of a series of XN derivatives, where different substituents on the B-ring of the chalcone scaffold were inserted. The new XN derivatives inhibited human umbilical-vein endothelial cell (HUVEC) proliferation, adhesion, migration, invasion and their ability to form capillary-like structures in vitro at 10 μM concentration...
September 29, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28674253/effect-of-valerian-hop-mixture-on-sleep-related-behaviors-in-drosophila-melanogaster
#16
Hyeon-Son Choi, Bong Soo Ko, Hae Dun Kim, Ki-Bae Hong, Hyung Joo Suh
The aim of this study was to investigate the sleep-promoting effect of a Valerian/Hops mixture in fruit flies. The HPLC analysis showed that Valerenic acid (1260.53 µg/g of extract) and Xanthohumol (Cascade: 827.49 µg/g, Hallertau: 763.60 µg/g, Saaz: 186.93 µg/g) were contained in Valerian and Hop, respectively. The sleep patterns of fruit flies on the Valerian/Hops were examined in both baseline and caffeine-treated conditions. Total activities of flies significantly decreased in 20 mg/mL Valerian (74%), 10 mg/mL Cascade (25%), and 5 mg/mL Hallertau (11%) during nighttime or daytime compared with the control...
2017: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/28665345/in-vitro-effect-of-8-prenylnaringenin-and-naringenin-on-fibroblasts-and-glioblastoma-cells-cellular-accumulation-and-cytotoxicity
#17
Monika Stompor, Łukasz Uram, Rafał Podgórski
Gliomas are one of the most aggressive and treatment-resistant types of human brain cancer. Identification and evaluation of anticancer properties of compounds found in plants, such as naringenin (N) and 8-prenylnaringenin (8PN), are among the most promising applications in glioma therapy. The prenyl group seems to be crucial to the anticancer activity of flavones, since it may lead to enhanced cell membrane targeting and thus increased intracellular activity. It should be noted that 8PN content in hop cones is 10 to 100 times lower compared to other flavonoids, such as xanthohumol...
June 30, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28627872/xanthohumol-blocks-proliferation-and-migration-of-vascular-smooth-muscle-cells-in-vitro-and-reduces-neointima-formation-in-vivo
#18
Rongxia Liu, Elke H Heiss, Daniel Schachner, Baohong Jiang, Wanhui Liu, Johannes M Breuss, Verena M Dirsch, Atanas G Atanasov
Xanthohumol (1) is a principal prenylated chalcone found in hops. The aim of this study was to examine its influence on platelet-derived growth factor (PDGF)-BB-triggered vascular smooth muscle cell (VSMC) proliferation and migration in vitro and on experimentally induced neointima formation in vivo. Quantification of resazurin conversion indicated that 1 can inhibit PDGF-BB-induced VSMC proliferation concentration-dependently (IC50 = 3.49 μM). Furthermore, in a wound-healing assay 1 potently suppresses PDGF-BB-induced VSMC migration at 15 μM...
July 28, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28501703/xanthohumol-a-hop-derived-prenylated-flavonoid-promotes-macrophage-reverse-cholesterol-transport
#19
Hiroshi Hirata, Harumi Uto-Kondo, Masatsune Ogura, Makoto Ayaori, Kazusa Shiotani, Ami Ota, Youichi Tsuchiya, Katsunori Ikewaki
Xanthohumol, a prominent prenyl flavonoid from the hop plant (Humulus lupulus L.), is suggested to be antiatherogenic since it reportedly increases high-density lipoprotein (HDL) cholesterol levels. It is not clear whether xanthohumol promotes reverse cholesterol transport (RCT), the most important antiatherogenic property of HDL; therefore, we investigated the effects of xanthohumol on macrophage-to-feces RCT using a hamster model as a CETP-expressing species. In vivo RCT experiments showed that xanthohumol significantly increased fecal appearance of the tracer derived from intraperitoneally injected [(3)H]-cholesterol-labeled macrophages...
April 22, 2017: Journal of Nutritional Biochemistry
https://www.readbyqxmd.com/read/28413193/effect-of-dietary-purified-xanthohumol-from-hop-humulus-lupulus-l-pomace-on-adipose-tissue-mass-fasting-blood-glucose-level-and-lipid-metabolism-in-kk-ay-mice
#20
Koki Takahashi, Kyoichi Osada
We previously showed that xanthohumol-rich hop extract (XRHE, ~18% xanthohumol) exerts anti-obesity effects in rats fed a high-fat diet through regulation of fatty acid metabolism. In this study, we examined the effects of dietary purified xanthohumol from XRHE (PX, ~91.9% xanthohumol) in KK-Ay mice in order to understand the anti-obesity effects of xanthohumol alone because XRHE contains 82% unknown compounds. Dietary consumption of PX significantly inhibited an increase in the visceral fat weight of mice compared to those fed control diet without PX...
May 1, 2017: Journal of Oleo Science
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