Research Update:Hops and its findings.

  seminal trace...Hops Extract.CAS.NO.008016-25-9.Humulus lupulus L.10:1.Humulus lupulus extract,Extract of hops,Hop extract.Content.Sesquiterpene Humulene.CAS.RN.NO:6753-98-6.M.F.C15 H24.....

 


   Phytochemical info of Hops:

 Product Name:
 Synonym:
 Definition:Hops are majorly composed of
 Chemical information disclosed as following table:


  Research Update:Hops and its findings

  Extraction optimization study of flavonoids from Humulus lupulus.:Zhongguo Zhong Yao Za Zhi. 2006 May;31(10):809-11.Xiong HP, He GQ, Xuan GD, Ruan H.College of Biosystem Engineering and Food Science, Zhejiang University, Hangzhou 310029, China.

 OBJECTIVE: To optimize extracting parameters of flavonoids from Humulus lupulus. METHOD: Based on the single factors test on ethanol concentration, material and solvent ratio, extracting temperature and extracting time, orthogonal test was performed and the best combination was confirmed. Result: With the optimized technology, the maximal extracting amount of flavonoids from H. lupulus was 78 mg x g(-1). CONCLUSION: The optimal techniques obtained are 45% ethanol extracting at 60 degrees C with material and solvent ratio 1:25 for 90 min.

  Evidence that the beta-acids fraction of hops reduces central GABAergic neurotransmission.:J Ethnopharmacol. 2007 Jan 3;109(1):87-92. Epub 2006 Jul 11.Zanoli P, Zavatti M, Rivasi M, Brusiani F, Losi G, Puia G, Avallone R, Baraldi M.Department of Biomedical Sciences, Section of Pharmacology, National InterUniversity Consortium for the Study of Natural Active Principles (CINSPAN), University of Modena and Reggio Emilia, 41100 Modena, Italy. zanoli.paola@unimore.it

 Humulus lupulus (hops) is traditionally used as a tranquilizing herbal remedy. Here, we investigated the in vivo and in vitro effect of hop beta-acids on central nervous system function. Oral administration of beta-acids (5-10mg/kg) in rats produced an increased exploratory activity in the open field, a reduction in the pentobarbital hypnotic activity and a worsening of picrotoxin-induced seizures. When dosed at 10mg/kg, beta-acids increased, in the elevated plus maze, open arm entries reducing in parallel those in closed arms. In the forced swimming test, we observed a reduction in the immobility time that could suggest an antidepressant-like activity. Electrophysiological studies performed on cerebellar granule cells in culture showed that the beta-acids fraction decreased GABA-evoked current in a dose-dependent way. The effect was not inhibited by the benzodiazepine antagonist Ro 15-1788. Benzodiazepine receptors involvement was also excluded by [(3)H]-Ro 15-1788 binding assay. In conclusion, the behavioral effects of beta-acids fraction could be explained by a reduction in the GABAergic activity although we cannot rule out the involvement of other neurotransmitter systems.

  Sedating effects of Humulus lupulus L. extracts.:Phytomedicine. 2006 Sep;13(8):535-41. Epub 2006 Jul 24.Schiller H, Forster A, Vonhoff C, Hegger M, Biller A, Winterhoff H.

 It was the aim of the study to check ethanolic and CO2 extracts from Humulus lupulus for sedating activity. Both preparations reduced the spontaneous locomotor activity, increased the ketamine-induced sleeping time and reduced body temperature, confirming a central sedating effect. No indications of anxiolytic activity were found in the elevated plus maze test for any of the test preparations. This sedating activity could be attributed to three categories of constituents of lipophilic hops extracts. Though the alpha-bitter acids proved to the be most active constituents, the beta-bitter acids and the hop oil clearly contributed to the sedating activity of lipophilic Humulus extracts.

  In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.).:Pharm Res. 2006 May;23(5):864-72. Epub 2006 May 16.Nikolic D, Li Y, Chadwick LR, van Breemen RB.Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612-7231, USA.

 PURPOSE: The absorption potential and metabolism of 8-prenylnaringenin (8-PN) from hops (Humulus lupulus L.) were investigated. 8-PN is a potent estrogen with the potential to be used for the relief of menopausal symptoms in women. METHODS: Monolayers of the human intestinal epithelial cancer cell line Caco-2 and human hepatocytes were incubated with 8-PN to model its intestinal absorption and hepatic metabolism, respectively. RESULTS: The apparent permeability coefficients for 8-PN in the apical-to-basolateral and basolateral-to-apical directions of a Caco-2 monolayer were 5.2 +/- 0.7 x 10(-5) and 4.9 +/- 0.5 x 10(-5) cm/s, respectively, indicating good intestinal absorption via passive diffusion. Both glucuronide and sulfate conjugates of 8-PN were detected in the Caco-2 cell incubations. The 4'-O-glucuronide was the predominant Caco-2 cell metabolite, followed by 7-O-sulfate and 4'-O-sulfate. Both phase I and phase II metabolites of 8-PN were formed by human hepatocytes. The 7-O-glucuronide was the most abundant hepatocyte metabolite, and no sulfate conjugates were detected. Incubations with various cDNA-expressed UDP-glucuronosyltransferases indicated that the isozymes UGT1A1, UGT1A6, UGT1A8, and UGT1A9 were responsible for glucuronidation of 8-PN. CONCLUSIONS: Although orally administered 8-PN should be readily absorbed from the intestine, its bioavailability should be reduced significantly by intestinal and hepatic metabolism.

  In Vitro Studies of Intestinal Permeability and Hepatic and Intestinal Metabolism of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops (Humulus lupulus L.).:Pharm Res. 2006 May 16;Nikolic D, Li Y, Chadwick LR, van Breemen RB.Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois, 60612-7231, USA, breemen@uic.edu.

 PURPOSE: The absorption potential and metabolism of 8-prenylnaringenin (8-PN) from hops (Humulus lupulus L.) were investigated. 8-PN is a potent estrogen with the potential to be used for the relief of menopausal symptoms in women. METHODS: Monolayers of the human intestinal epithelial cancer cell line Caco-2 and human hepatocytes were incubated with 8-PN to model its intestinal absorption and hepatic metabolism, respectively. RESULTS: The apparent permeability coefficients for 8-PN in the apical-to-basolateral and basolateral-to-apical directions of a Caco-2 monolayer were 5.2 +/- 0.7 x 10(-5) and 4.9 +/- 0.5 x 10(-5) cm/s, respectively, indicating good intestinal absorption via passive diffusion. Both glucuronide and sulfate conjugates of 8-PN were detected in the Caco-2 cell incubations. The 4'-O-glucuronide was the predominant Caco-2 cell metabolite, followed by 7-O-sulfate and 4'-O-sulfate. Both phase I and phase II metabolites of 8-PN were formed by human hepatocytes. The 7-O-glucuronide was the most abundant hepatocyte metabolite, and no sulfate conjugates were detected. Incubations with various cDNA-expressed UDP-glucuronosyltransferases indicated that the isozymes UGT1A1, UGT1A6, UGT1A8, and UGT1A9 were responsible for glucuronidation of 8-PN. CONCLUSIONS: Although orally administered 8-PN should be readily absorbed from the intestine, its bioavailability should be reduced significantly by intestinal and hepatic metabolism.


  Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity.:J Agric Food Chem. 2006 Apr 19;54(8):2938-43.Monteiro R, Becker H, Azevedo I, Calhau C.Department of Biochemistry, Faculty of Medicine, University of Porto, 4200-319 Porto, Portugal. rosariom@med.up.pt

 The aim of this work was to study the effect of the prenylflavonoids xanthohumol, isoxanthohumol, and 8-prenylnaringenin on the activity and expression of the enzyme aromatase (estrogen synthase). The effect of different kinds of beer containing these prenylflavonoids was also tested. Aromatase activity was determined by measuring the release of tritiated water during the conversion of [(3)H]androstenedione to estrone. Aromatase expression was determined by RT-PCR. This assay was carried out in choriocarcinoma-derived JAR cells. The tested prenylflavonoids were able to inhibit estrogen formation, and their IC(50) values were determined, although no effect on aromatase expression was found. Lager beer, alcohol-free beer, stout beer, and xanthohumol-rich stout beer (200 microL/mL) significantly decreased aromatase activity. In conclusion, prenylflavonoids are able to modulate aromatase activity, decreasing estrogen synthesis, with relevance for the prevention and treatment of estrogen-dependent disorders such as breast cancer.

  The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties.:Phytomedicine. 2006 Jan;13(1-2):119-31. Epub 2005 Jul 1.Chadwick LR, Pauli GF, Farnsworth NR.UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. Ichadwick@kalsec.com

 As the population ages, there is an ever-increasing need for therapeutic agents that can be used safely and efficaciously to manage symptoms related to postmenopausal estrogen deficiency. Endogenous estrogens, e.g., 17beta-estradiol, of exogenous mammalian origin, e.g., horses, have long been used to manage such symptoms. There are more than 20 different classes of phytochemicals that have demonstrated affinity for human estrogen receptors in vitro. Some studies on exogenous estrogenic substances of botanical origin (phytoestrogens), such as standardized formulations of plant extracts with in vitro and in vivo estrogenic activity from soy (Glycine max Merill.) and red clover (Trifolium pratense L.), suggest clinical efficacy. Few clinical data for phytoestrogens other than isoflavonoids are available. In an exhaustive review of the literature through 2003, only two clinical trials were identified that were designed to evaluate the effect of hops (Humulus lupulus L.) on symptoms related to menopause. Folkloric, chemical, and biological literature relating primarily to the use of hops for their estrogenic activity, and two human clinical trials, are reviewed.

  Anti-inflammatory acylphloroglucinol derivatives from Hops (Humulus lupulus).:J Nat Prod. 2005 Oct;68(10):1545-8.Bohr G, Gerh?user C, Knauft J, Zapp J, Becker H.Fr. 8.2 Pharmakognosie und Analytische Phytochemie der Universit?t des Saarlandes, D-66041 Saarbr¨¹cken, Germany.

 The polyphenol-enriched fraction of an ethanolic hops extract (Humulus lupulus) was separated to provide four acylphloroglucinol-glucopyranosides (1-4). 1-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 1 has been isolated from hops before, whereas 1-(2-methylbutyryl)phloroglucinol-glucopyranoside 2, known as multifidol glucoside, and 1-(3-methylbutyryl)phloroglucinol-glucopyranoside 3 were found in hops for the first time. 5-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 4 was identified as a new natural product. The compounds were tested for inhibition of COX-1 activity. The aglycon 5, obtained by acid hydrolysis of 1, was equally effective as phloroglucinol, with an IC(50) of 3.8 microM. The inhibitory potential of the glucosides was 1>2>3 and decreased with increasing length of the acyl side chain. Compound 4 was about 2.5-fold less active than 1 (IC(50): 23.7 and 58.7 microM, respectively).


  The first occurrence in nature of two compounds from hops.:

 Two compounds, (p-methoxyphenyl) diphenylmethanol (1) and tribenzylamine (2), were isolated from Humulus lupulus. Their structures were established on the basis of spectral evidence (MS, IR, NMR, HMBC, HMQC, 1H-1H COSY experiments). Compounds 1 and 2 were found as natural products at the first time.

  Direct characterization of bitter acids in a crude hop extract by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.:

 The applicability of on-line coupling of reversed-phase high-performance liquid chromatography to atmospheric pressure ionization tandem mass spectrometry for the separation and characterization of hop acids mixture from the crude extract of Humulus lupulus was investigated. The solvent system consisting of acetonitrile-aqueous formic acid was used to give proper separation of the six main hop bitter acids within 30 min. Further structural information about the components was acquired by collision-induced dissociation (CID). On the basis of analyses of the fragmentation patterns of the major alpha- and beta-bitter acids respectively, identification of the minor ones was performed using selected reaction monitoring (SRM) with a group of qualitatively relevant selected precursor-product ion transitions for each bitter acid in a single high performance liquid chromatography (HPLC) run. Using this technique, six minor hop acids, including "adprelupulone" observed for the first time in natural resources, were detected along with the six major acids. This hyphenated techniques provides potency for rapid qualitative determination of analogs and homologs in mixtures.

  Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).:

 The ethyl acetate soluble fraction of hops (Humulus lupulus) showed potent inhibitory activity on the production of nitric oxide (NO) induced by a combination of LPS and IFN-gamma. Four known prenylflavonoids (1-4) and a new prenylflavonoid (5), hulupinic acid (6), lupulone (7), and its six new derivatives (8-13) were isolated from the active fraction. The structures were determined on the basis of physiochemical properties and spectroscopic analysis. Their inhibitory activities on the production of NO in macrophage RAW 264.7 cells were examined.

  Optimization of conditions for supercritical fluid extraction of flavonoids from hops (Humulus lupulus L.).:

 Waste hops are good sources of flavonoids. Extraction of flavonoids from waste hops (SC-CO(2) extracted hops) using supercritical fluids technology was investigated. Various temperatures, pressures and concentrations of ethanol (modifier) and the ratio (w/w) of solvent to material were tested in this study. The results of single factor and orthogonal experiments showed that at 50 degrees C, 25 MPa, the ratio of solvent to material (50%), ethanol concentration (80%) resulted in maximum extraction yield flavonoids (7.8 mg/g). HPLC-MS analysis of the extracts indicated that flavonoids obtained were xanthohumol, the principal prenylflavonoid in hops.

  Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography.:

 Proanthocyanidins extracted from hops (Humulus lupulus L. cv. Willamette) were subjected to Sephadex LH-20 column chromatography using a step gradient of methanol, water, and acetone. The resulting fractions were analyzed by acid catalysis, electrospray ionization and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS), and gel permeation chromatography (GPC). The proanthocyanidins contained catechin and epicatechin as monomers and as terminal and extension units. Epigallocatechin was found as extension units. The mean degree of polymerization (mDP) of the crude proanthocyanidins was 7.8, but heptamers were the largest oligomers visible in mass spectra of the whole. In the last-eluted fraction (mDP = 22.2), polymers as large as 20-mers were detected by MALDI-TOF-MS, demonstrating the effectiveness of prior separation in improving MS detection. GPC data correlated well with acid catalysis results, confirming the presence of large polymers that were not detected by MS.

  Determination of aneuploids in hop (Humulus lupulus L.) using flow cytometry.:

 In order to study the possibility that high-resolution flow cytometry can be used for determination of aneuploids, different genotypes of Humulus lupulus were analyzed. Triploid cultivars are bred by hybridization between diploid and tetraploid lines, and as the result of this process, some aneuploids are occasionally also formed. We analyzed eight triploid cultivars and seven putative aneuploids. Triploid cultivars Cerera, Cicero, Celeia, Cekin, Blisk, Mt. Hood, Huller Bit. and Willamette (3x = 30) were measured for nuclear DNA content using Trifolium repens as reference. No significant differences among peak positions of triploid cultivars (having an average CV value per peak of 1.94%) were found. Measurement of nuclear DNA content was also performed for seven lines: 175/75, 89/113, 89/154, 91/215, 175/17, 89/87 and 91/74 previously determined by chromosome counting to be aneuploids (CV per peak was 1.41%). A statistically lower DNA content was found for line 175/75 and higher values were measured for lines 89/154, 89/113 and 91/215. Repeated chromosome counting revealed that the number of chromosomes in line 175/75 was 29, while lines 89/154, 89/113 and 91/215 possessed 31 chromosomes. The other lines were identified as triploids. We conclude that flow cytometry can be efficiently used for determination of aneuploidy in Humulus lupulus.
 

  Sedating effects of Humulus lupulus L. extracts.:

 It was the aim of the study to check ethanolic and CO(2) extracts from Humulus lupulus for sedating activity. Both preparations reduced the spontaneous locomotor activity, increased the ketamine-induced sleeping time and reduced body temperature, confirming a central sedating effect. No indications of anxiolytic activity were found in the elevated plus maze test for any of the test preparations. This sedating activity could be attributed to three categories of constituents of lipophilic hops extracts. Though the alpha-bitter acids proved to the be most active constituents, the beta-bitter acids and the hop oil clearly contributed to the sedating activity of lipophilic Humulus extracts.


  Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity.:

 The aim of this work was to study the effect of the prenylflavonoids xanthohumol, isoxanthohumol, and 8-prenylnaringenin on the activity and expression of the enzyme aromatase (estrogen synthase). The effect of different kinds of beer containing these prenylflavonoids was also tested. Aromatase activity was determined by measuring the release of tritiated water during the conversion of [(3)H]androstenedione to estrone. Aromatase expression was determined by RT-PCR. This assay was carried out in choriocarcinoma-derived JAR cells. The tested prenylflavonoids were able to inhibit estrogen formation, and their IC(50) values were determined, although no effect on aromatase expression was found. Lager beer, alcohol-free beer, stout beer, and xanthohumol-rich stout beer (200 microL/mL) significantly decreased aromatase activity. In conclusion, prenylflavonoids are able to modulate aromatase activity, decreasing estrogen synthesis, with relevance for the prevention and treatment of estrogen-dependent disorders such as breast cancer.

  The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties.:

 As the population ages, there is an ever-increasing need for therapeutic agents that can be used safely and efficaciously to manage symptoms related to postmenopausal estrogen deficiency. Endogenous estrogens, e.g., 17beta-estradiol, of exogenous mammalian origin, e.g., horses, have long been used to manage such symptoms. There are more than 20 different classes of phytochemicals that have demonstrated affinity for human estrogen receptors in vitro. Some studies on exogenous estrogenic substances of botanical origin (phytoestrogens), such as standardized formulations of plant extracts with in vitro and in vivo estrogenic activity from soy (Glycine max Merill.) and red clover (Trifolium pratense L.), suggest clinical efficacy. Few clinical data for phytoestrogens other than isoflavonoids are available. In an exhaustive review of the literature through 2003, only two clinical trials were identified that were designed to evaluate the effect of hops (Humulus lupulus L.) on symptoms related to menopause. Folkloric, chemical, and biological literature relating primarily to the use of hops for their estrogenic activity, and two human clinical trials, are reviewed.

  Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).:

 Because the prevailing form of hormone replacement therapy is associated with the development of cancer in breast and endometrial tissues, alternatives are needed for the management of menopausal symptoms. Formulations of Trifolium pratense L. (red clover) are being used to alleviate menopause-associated hot flashes but have shown mixed results in clinical trials. The strobiles of Humulus lupulusL. (hops) have been reported to contain the prenylflavanone, 8-prenylnaringenin (8-PN), as the most estrogenic constituent, and this was confirmed using an estrogen receptor ligand screening assay utilizing ultrafiltration mass spectrometry. Extracts of hops and red clover and their individual constituents including 8-PN, 6-prenylnaringenin (6-PN), isoxanthohumol (IX), and xanthohumol (XN) from hops and daidzein, formononetin, biochanin A, and genistein from red clover were compared using a variety of in vitro estrogenic assays. The IC50 values for the estrogen receptor alpha and beta binding assays were 15 and 27 microg/mL, respectively, for hops and 18.0 and 2.0 microg/mL, respectively, for the red clover extract. Both of the extracts, genistein, and 8-PN activated the estrogen response element (ERE) in Ishikawa cells while the extracts, biochanin A, genistein, and 8-PN, significantly induced ERE-luciferase expression in MCF-7 cells. Hop and red clover extracts as well as 8-PN up-regulated progesterone receptor (PR) mRNA in the Ishikawa cell line. In the MCF-7 cell line, PR mRNA was significantly up-regulated by the extracts, biochanin A, genistein, 8-PN, and IX. The two extracts had EC50 values of 1.1 and 1.9 microg/mL, respectively, in the alkaline phosphatase induction assay. On the basis of these data, hops and red clover could be attractive for the development as herbal dietary supplements to alleviate menopause-associated symptoms.

  Estrogens and congeners from spent hops (Humulus lupulus).:

 Estrogenicity-directed fractionation of a methanol extract of the strobiles of Humulus lupulus that had been extracted previously with supercritical CO(2), known as "spent hops", led to the isolation and identification of 22 compounds including 12 prenylated chalcones (1-8, 10-13), five prenylflavanones (14-17), 4-hydroxybenzaldehyde (18), sitosterol-3-O-beta-glucopyranoside (19), humulinone (20), and cohumulinone (21). In addition, the prenylated chalcone xanthohumol C (9a) was obtained as a 6:1 mixture along with its 1' ',2' '-dihydro derivative (9b). Three new chalcones (4, 11, 12) and four previously unreported constituents of hops (5, 6, 9b, 13) are reported. The structures of the new compounds were determined through a combination of spectrometric techniques including 1D and 2D NMR, HRESIMS, and ESIMS-MS. Full 1H NMR spin system analyses were performed to characterize the higher-order glucopyranosyl, prenyl, and chalcone B-ring spectra of the isolates. The principle estrogen 8-prenylnaringenin (15) from hops is an artifact formed along with its positional isomer 6-prenylnaringenin (16) through the spontaneous isomerization of the pro-estrogenic chalcone DMX (7).
 

  The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine.:

 Hops, an essential beer ingredient, are a source of prenylflavonoids, including 8-prenylnaringenin (8-PN), one of the most potent phytoestrogens. Because 8-PN concentrations in beers are generally low, its health effects after moderate beer consumption were considered negligible. However, human intestinal microbiota may activate up to 4 mg/L isoxanthohumol (IX) in beer into 8-PN. Depending on interindividual differences in the intestinal transformation potential, this conversion could easily increase the 8-PN exposure 10-fold upon beer consumption. Here, we present a further investigation of the process both in vitro and in vivo. In vitro experiments with the dynamic SHIME model showed that hop prenylflavonoids pass unaltered through the stomach and small intestine and that activation of IX into 8-PN (up to 80% conversion) occurs only in the distal colon. In vitro incubations of 51 fecal samples from female volunteers with IX enabled us to separate the fecal microbiota into high (8 of 51), moderate (11 of 51) and slow (32 of 51) 8-PN producers, clearly illustrating an interindividual variability. Three women, selected from the respective groups, received a daily dose of 5.59 mg IX for 4 d. Intestinal IX activation and urinary 8-PN excretion were correlated (R(2) = 0.6417, P < 0.01). These data show that intestinal conversion of IX upon moderate beer consumption can lead to 8-PN exposure values that might fall within the range of human biological activity.


  In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.).:

 Purpose: The absorption potential and metabolism of 8-prenylnaringenin (8-PN) from hops (Humulus lupulus L.) were investigated. 8-PN is a potent estrogen with the potential to be used for the relief of menopausal symptoms in women. Methods: Monolayers of the human intestinal epithelial cancer cell line Caco-2 and human hepatocytes were incubated with 8-PN to model its intestinal absorption and hepatic metabolism, respectively. Results: The apparent permeability coefficients for 8-PN in the apical-to-basolateral and basolateral-to-apical directions of a Caco-2 monolayer were 5.2 +/- 0.7 x 10(-5) and 4.9 +/- 0.5 x 10(-5) cm/s, respectively, indicating good intestinal absorption via passive diffusion. Both glucuronide and sulfate conjugates of 8-PN were detected in the Caco-2 cell incubations. The 4'-O-glucuronide was the predominant Caco-2 cell metabolite, followed by 7-O-sulfate and 4'-O-sulfate. Both phase I and phase II metabolites of 8-PN were formed by human hepatocytes. The 7-O-glucuronide was the most abundant hepatocyte metabolite, and no sulfate conjugates were detected. Incubations with various cDNA-expressed UDP-glucuronosyltransferases indicated that the isozymes UGT1A1, UGT1A6, UGT1A8, and UGT1A9 were responsible for glucuronidation of 8-PN. Conclusions: Although orally administered 8-PN should be readily absorbed from the intestine, its bioavailability should be reduced significantly by intestinal and hepatic metabolism.

  Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines.:

 Chalcones xanthohumol (X) and desmethylxanthohumol (DMX), present in hops (Humulus lupulus L.), and the corresponding flavanones isoxanthohumol (IX, from X), 8-prenylnaringenin (8-PN, from DMX), and 6-prenylnaringenin (6-PN, from DMX), have been examined in vitro for their anti-proliferative activity on human prostate cancer cells PC-3 and DU145. X proved to be the most active compound in inhibiting the growth of the cell lines with IC(50) values of 12.3+/-1.1muM for DU145 and 13.2+/-1.1muM for PC-3. 6-PN was the second most active growth inhibitor, particularly in PC-3 cells (IC(50) of 18.4+/-1.2muM). 8-PN, a highly potent phytoestrogen, exhibited pronounced anti-proliferative effects on PC-3 and DU145 (IC(50) of 33.5+/-1.0 and 43.1+/-1.2muM, respectively), and IX gave comparable activities (IC(50) of 45.2+/-1.1muM for PC-3 and 47.4+/-1.1muM for DU145). DMX was the least active compound. It was evidenced for the first time that this family of prenylated flavonoids from hops effectively inhibits proliferation of prostate cancer cells in vitro.

  Broad spectrum anti-infective potential of xanthohumol from hop (Humulus lupulus L.) in comparison with activities of other hop constituents and xanthohumol metabolites.:

 This review summarizes the capacity of xanthohumol (XN) in comparison with additional hop constituents and metabolites to act as an antiinfective agent against microorganisms including bacteria, viruses, fungi and malarial protozoa. XN was shown to inhibit the Gram-positive bacteria Staphylococcus aureus and Streptococcus mutans. Antiviral activity was demonstrated against bovine viral diarrhea virus, cytomegalovirus, herpes simplex virus type 1 and 2 and human immunodeficiency virus 1. Inhibition of two Trichophyton spp. was indicative of antifungal activity. Finally, XN potently inhibited the replication of Plasmodium falciparum, the causative agent of malaria. This effect was linked to the inhibition of glutathione-mediated degradation and detoxification of haemin, a by-product of the parasitic digestion of haemoglobin. Overall, these activities further contribute to the broad spectrum of biological effects observed with XN.
 

  Influence of xanthohumol on the binding behavior of GABAA receptors and their lateral mobility at hippocampal neurons.:

 The influence of the xanthohumol from Humulus lupulus L. on the binding of muscimol-Alexa Fluor 532 (Mu-Alexa), a fluorescently labeled GABAA receptor agonist, was studied by fluorescence correlation spectroscopy. An incubation of hippocampal neurons with 75 nM of xanthohumol increased the specific Mu-Alexa binding by approximately 17%, which was selectively found in GABAA receptor Mu-Alexa complexes with hindered lateral mobility [D(bound2) = (0.11 +/- 0.03) microm2/s] as described with midazolam.

  Effects of beer and hop on ionotropic gamma-aminobutyric acid receptors.:

 Beer induced the response of the ionotropic gamma-aminobutyric acid receptors (GABA(A) receptors) expressed in Xenopus oocytes, indicating the presence of gamma-aminobutyric acid (GABA)-like activity. Furthermore, the pentane extract of the beer, hop (Humulus lupulus L.) oil, and myrcenol potentiated the GABA(A) receptor response elicited by GABA. The GABA(A) receptor responses were also potentiated by the addition of aliphatic esters, most of which are reported to be present in beer flavor. Aliphatic esters showed the tendency to decrease in the potentiation of the GABA(A) receptor response with an increase in their carbon chain length. When myrcenol was injected to mice prior to intraperitoneal administration of pentobarbital, the pentobarbital-induced sleeping time of mice increased additionally. Therefore, the beer contained not only GABA-like activity but also the modulator(s) of the GABA(A) receptor response.


  Anti-inflammatory acylphloroglucinol derivatives from Hops (Humulus lupulus).:

 The polyphenol-enriched fraction of an ethanolic hops extract (Humulus lupulus) was separated to provide four acylphloroglucinol-glucopyranosides (1-4). 1-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 1 has been isolated from hops before, whereas 1-(2-methylbutyryl)phloroglucinol-glucopyranoside 2, known as multifidol glucoside, and 1-(3-methylbutyryl)phloroglucinol-glucopyranoside 3 were found in hops for the first time. 5-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 4 was identified as a new natural product. The compounds were tested for inhibition of COX-1 activity. The aglycon 5, obtained by acid hydrolysis of 1, was equally effective as phloroglucinol, with an IC(50) of 3.8 microM. The inhibitory potential of the glucosides was 1>2>3 and decreased with increasing length of the acyl side chain. Compound 4 was about 2.5-fold less active than 1 (IC(50): 23.7 and 58.7 microM, respectively).

  Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin.:

 Hop, an essential ingredient in most beers, contains a number of prenylflavonoids, among which 8-prenylnaringenin (8-PN) would be the most potent phytoestrogen currently known. Although a number of health effects are attributed to these compounds, only a few reports are available about the bioavailability of prenylflavonoids and the transformation potency of the intestinal microbial community. To test these transformations, four fecal samples were incubated with xanthohumol, isoxanthohumol (IX), and 8-PN. Upon incubation with IX, present in strong ales up to 4 mg/L, 36% was converted into 8-PN in one fecal sample and the estrogenic properties of the sample drastically increased. In an experiment with 12 fecal cultures, this conversion was observed in one-third of the samples, indicating the importance of interindividual variability in the intestinal microbial community. Eubacterium limosum was identified to be capable of this conversion (O-demethylation) of IX into 8-PN, and after strain selection, a conversion efficiency of 90% was achieved. Finally, strain supplementation to a nonconverting fecal sample led to rapid and high 8-PN production at only 1% (v/v) addition. Up to now, the concentration of 8-PN in beer was considered too low to affect human health. However, these results show that the activity of the intestinal microbial community could more than 10-fold increase the exposure concentration. Because prenylflavonoids are present in many beers with IX being the major constituent, the results raise the question whether moderate beer consumption might contribute to increased in vivo levels of 8-PN and even influence human health.
 

  New insight in the neuropharmacological activity of Humulus lupulus L.:

 The purpose of the present study was to investigate the effects of Humulus lupulus CO2 extract and its fraction containing alpha-acids on the central nervous system of rats. Both tested substances were able to prolong pentobarbital sleeping time, without affecting the latency to the loss of the righting reflex. This effect was dose-dependent, starting from a minimal dose of 10 mg/kg. Neither the extract nor its alpha-acid fraction affected the locomotor activity in the open field test or exerted an anxiolytic effect in rats submitted to the elevated plus-maze test. Interestingly both compounds reduced the immobility time during the behavioral despair test when administered three times (24, 5 and 1 h) before the test. In conclusion this report shows that Humulus lupulus CO2 extract exerts: (a) a pentobarbital sleep-enhancing property without influencing the motor behavior of rats; (b) an antidepressant activity. The same effects were elicited by the administration of the Humulus lupulus fraction containing alpha-acids, which can be considered as the major responsible for the enhanced pentobarbital effect and for the antidepressant property.

  The antimycobacterial components of hops (Humulus lupulus) and their dereplication.:

 Bioassay-guided fractionation of a hexane extract of strobile hops (Humulus lupulus) was undertaken to isolate and characterize the antimycobacterial constituents using the fast-growing mycobacterial species Mycobacterium fortuitum. Activity was associated with a low polarity fraction and 1H NMR spectra indicated the presence of a fatty acid mixture with unsaturated components. GC-MS of the derivatives indicated the presence of palmitic, stearic and oleic acids with small quantities of lignoceric, arachidic, behenic and linoleic acids. These compounds were assessed against M. fortuitum and all saturated fatty acids were inactive at concentrations greater than 256 microg/ml, whereas the unsaturated fats oleic and linoleic acids displayed minimum inhibitory concentrations of between 4 and 16 microg/ml against the fast-growing species tested. The widespread occurrence of these components could render screening for antimycobacterials from natural sources highly problematic without adequate dereplication. We propose that GC-MS of derivatised components of lipophilic extracts be a first step before any antimycobacterial bioassay-guided study, as this technique is the method of choice for dereplication of fatty acids.

  Phytoestrogens in botanical dietary supplements: implications for cancer.:

 Phytoestrogens are plant constituents that possess either estrogenic or antiestrogenic activity. Although their activities are weak as compared with human endogenous estrogens, the consumption of phytoestrogens may have clinically significant consequences. A number of botanicals, or the compounds contained therein, have been identified as putative estrogenic agents, but consensus in the biomedical community has been hampered by conflicting data from various in vitro and in vivo models of estrogenic activity. Phytoestrogens may serve as chemopreventive agents while at the same time being capable of promoting growth in estrogen receptor positive cancer cell lines. Furthermore, they may exert their estrogenic influence through receptor-dependent and/or receptor-independent mechanisms. These findings have led to speculation that phytoestrogen intake might be ill advised for patients at an increased risk for hormone-dependent cancers, cancer patients, or cancer survivors. This article will attempt to sort out discrepancies between various experimental models and establish whether certain herbs possess estrogenic activity. The review will focus on 5 popular botanical dietary supplements: Trifolium pratense (red clover), Cimicifuga racemosa (black cohosh), Humulus lupulus (hops), Angelica sinensis (dong quai), and Glycyrrhiza glabra (licorice). It will address their mechanisms of action, clinical evidence bases, and implications for use in cancer.


  Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes.:

 The female flowers of hops are used throughout the world as a flavoring agent for beer. Recently, there has been increasing interest in the potential estrogenic properties of hop extracts. Among the possible estrogenic compounds in hops, 8-prenylnaringenin is perhaps most significant due to its high in vitro potency exceeding that of other known phytoestrogens. Since data regarding the pharmacokinetic properties of this compound are lacking, we investigated the in vitro metabolism of 8-prenylnaringenin by human liver microsomes. A total of 12 metabolites were identified, and biotransformation occurred on the prenyl group and the flavanone skeleton. The major site of oxidation was on the terminal methyl groups, and of the two possible isomers, the transisomer was more abundant. The double bond on the prenyl group was also oxidized to an epoxide that was opened by intramolecular reaction with the neighboring hydroxyl group. On the flavanone skeleton, the major site of oxidation was at 3'position on the B ring. Other metabolites included oxidation at carbon-3 as well as desaturation of the C ring to produce 8-prenylapigenin. An unusual hydroxy quinone product formed by ipso hydroxylation of the B ring of 8-prenylnaringenin was also detected. This product was probably an intermediate for the B ring cleavage product, 8-prenylchromone.
 

  Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore.:

 Prenylated 2'-hydroxychalcones and flavanones from the inflorescences of the female hop plant (Humulus lupulus) were shown to inhibit peroxynitrite-mediated oxidation of low-density lipoproteins (LDL) at low micromolar concentrations. LDL oxidation was induced by the peroxynitrite generator, 3-morpholinosydnonimine (SIN-1), and measured by the formation of conjugated dienes and thiobarbituric reactive substances. Human intake of prenylated chalcones and flavanones is mainly through beer, which contains up to 4 mg/L of these polyphenols. The two main oxidation products obtained by SIN-1 and peroxynitrite treatment of xanthohumol (XN), the principal prenylflavonoid of hops, were the aurone, auroxanthohumol (AUXN), and an endoperoxy derivative of XN, named endoperoxyxanthohumol (EPOX). In addition, the reaction produced smaller amounts of the nitro and nitroso derivatives of XN and EPOX. The formation of these nitrated products was enhanced in the presence of sodium bicarbonate (25 mM). SIN-1-induced formation of AUXN is considered to be a superoxide-mediated reaction, while the structure of EPOX points to a two electron oxidation reaction involving a Michael type addition with peroxynitrite as the nucleophile, followed by cyclization yielding a (1,2)-dioxepin-5-one ring structure. The flavanone isomer of XN, isoxanthohumol (IsoXN), unexpectedly showed a slight prooxidant effect instead of an inhibitory effect on LDL oxidation. Except for the formation of minor nitrated products, IsoXN remained largely unmodified upon treatment with SIN-1/peroxynitrite. Taken together, our results suggest that the alpha,beta-unsaturated keto functionality of chalcones is most reactive toward superoxide and peroxynitrite anions.

  Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.).:

 Important secondary metabolites, present in hops (Humulus lupulus L.), include alpha-acids and beta-acids, which are essential for the brewing of beer, as well as the prenylated chalcones, desmethylxanthohumol, and xanthohumol, which exhibit interesting bioactive properties. Their formation and accumulation in five selected hop varieties, Wye Challenger, Wye Target, Golding, Admiral, and Whitbread Golding Variety, were quantitatively monitored by high-performance liquid chromatography using UV detection. All target compounds were present from the onset of flowering, not only in female hop cones but also in male inflorescences, albeit in low concentrations. During development from female inflorescences to cones, levels of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol gradually increased, while each hop variety exhibited individual accumulation rates. Furthermore, these compounds were present in leaves of fully grown hops as well. The study demonstrated that key compounds for flavor and potential beneficial health effects associated with beer not only reside in the glandular lupulin structures but also are distributed over various parts of the hop plant.

  Inhibitors of nitric oxide production from hops (Humulus lupulus L.).:

 Nitric oxide (NO) plays an important role in many inflammatory responses and is also involved in carcinogenesis. In the present study, we investigated the inhibitory effect of extracts from Humulus lupulus L. on both the production of NO and the expression of inducible NO synthase (iNOS) in mouse macrophage RAW 264.7 cells. The production of NO was induced by a combination of lipopolysaccharide (LPS) and IFN-gamma, and determined by Griess assay. The expression of iNOS was detected by Western blotting. The LPS/IFN-gamma-induced production of NO and expression of iNOS were significantly inhibited by the ethyl acetate soluble fraction of Humulus lupulus L. Through bioactivity guided fractionation, humulene, five chalcones, 2,2-di-(3-methyl-2-butyleyl)-4,5-dihydoxy-cyclopent-4-en-1,3-dione, lupulone and three of its derivatives were isolated from the ethyl acetate soluble fraction. The chalcones, including xanthohumol, significantly inhibited the production of NO by suppressing the expression of iNOS.

  Systemic urticaria induced by hops:

 The authors report a patient who presented 4 times a systemic urticaria with arthralgias and fever treated by corticosteroids with efficacy. Wild hop (Humulus lupulus) was finally proved to be the causal factor. H.L. belongs to the cannabinaceas family. Hop dermatitis in hop workers population is the main widely described clinical manifestation. Rhinitis, conjunctivitis, asthma are rare as soon as contact urticaria. IgE-anti Hop induced allergies are described in the literature. However, in some cases of reactions to hop the mechanisms are uncertain: toxicity--possible role of lupuline--or immunoallergic processus with immunocomplexes (IC) (with increased IC in serum) and systemic urticaria such as in our observation.
 


  Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms.:

 Eight botanical preparations that are commonly used for the treatment of menopausal symptoms were tested for estrogenic activity. Methanol extracts of red clover (Trifolium pratense L.), chasteberry (Vitex agnus-castus L.), and hops (Humulus lupulus L.) showed significant competitive binding to estrogen receptors alpha (ER alpha) and beta (ER beta). With cultured Ishikawa (endometrial) cells, red clover and hops exhibited estrogenic activity as indicated by induction of alkaline phosphatase (AP) activity and up-regulation of progesterone receptor (PR) mRNA. Chasteberry also stimulated PR expression, but no induction of AP activity was observed. In S30 breast cancer cells, pS2 (presenelin-2), another estrogen-inducible gene, was up-regulated in the presence of red clover, hops, and chasteberry. Interestingly, extracts of Asian ginseng (Panax ginseng C.A. Meyer) and North American ginseng (Panax quinquefolius L.) induced pS2 mRNA expression in S30 cells, but no significant ER binding affinity, AP induction, or PR expression was noted in Ishikawa cells. Dong quai [Angelica sinensis (Oliv.) Diels] and licorice (Glycyrrhiza glabra L.) showed only weak ER binding and PR and pS2 mRNA induction. Black cohosh [Cimicifuga racemosa (L.) Nutt.] showed no activity in any of the above in vitro assays. Bioassay-guided isolation utilizing ER competitive binding as a monitor and screening using ultrafiltration LC-MS revealed that genistein was the most active component of red clover. Consistent with this observation, genistein was found to be the most effective of four red clover isoflavones tested in the above in vitro assays. Therefore, estrogenic components of plant extracts can be identified using assays for estrogenic activity along with screening and identification of the active components using ultrafiltration LC-MS. These data suggest a potential use for some dietary supplements, ingested by human beings, in the treatment of menopausal symptoms.

  The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids.:

 The female flowers of the hop plant have long been used as a preservative and a flavoring agent in beer, but they are now being included in some herbal preparations for women for "breast enhancement." This study investigated the relative estrogenic, androgenic and progestogenic activities of the known phytoestrogen, 8-prenylnaringenin, and structurally related hop flavonoids. 6-Prenylnaringenin, 6,8-diprenylnaringenin and 8-geranylnaringenin exhibited some estrogenicity, but their potency was less than 1% of that of 8-prenylnaringenin. 8-Prenylnaringenin alone competed strongly with 17ss-estradiol for binding to both the alpha- and ss-estrogen receptors. None of the compounds (xanthohumol, isoxanthohumol, 8-prenyl-naringenin, 6-prenylnaringenin, 3'-geranylchalconaringenin, 6-geranylnaringenin, 8-geranylnaringenin, 4'-O:-methyl-3'-prenylchalconaringenin and 6,8-diprenylnaringenin) nor polyphenolic hop extracts showed progestogenic or androgenic bioactivity. These results indicate that the endocrine properties of hops and hop products are due to the very high estrogenic activity of 8-prenylnaringenin and concern must be expressed about the unrestricted use of hops in herbal preparations for women.

  Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines.:

 Six flavonoids [xanthohumol (XN), 2',4',6',4-tetrahydroxy-3'-prenylchalcone (TP); 2',4',6',4-tetrahydroxy-3'-geranylchalcone (TG); dehydrocycloxanthohumol (DX); dehydrocycloxanthohumol hydrate (DH); and isoxanthohumol (IX)] from hops (Humulus lupulus) were tested for their antiproliferative activity in human breast cancer (MCF-7), colon cancer (HT-29) and ovarian cancer (A-2780) cells in vitro. XN, DX and IX caused a dose-dependent (0.1 to 100 microM) decrease in growth of all cancer cells. After a 2-day treatment, the concentrations at which the growth of MCF-7 cells was inhibited by 50% (IC50) were 13.3, 15.7 and 15.3 microM for XN, DX and IX, respectively. After a 4-day treatment, the IC50 for XN, DX and IX were 3.47, 6.87 and 4.69 microM, respectively. HT-29 cells were more resistant than MCF-7 cells to these flavonoids. In A-2780 cells, XN was highly antiproliferative with IC50 values of 0.52 and 5.2 microM after 2 and 4 days of exposure, respectively. At 100 microM, all the hop flavonoids were cytotoxic in the three cell lines. Growth inhibition of XN- and IX-treated MCF-7 cells was confirmed by cell counting. XN and IX inhibited DNA synthesis in MCF-7 cells. As antiproliferative agents, XN (chalcone) and IX (flavanone isomer of XN) may have potential chemopreventive activity against breast and ovarian cancer in humans.

  Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus.:

 A methanol extract of hops of Humulus lupulus (L.) showed inhibitory activity against rat liver diacylglycerol acyltransferase (DGAT). From DGAT inhibitory activity-guided fractionation, two chalcones were isolated. One was identified as xanthohumol and the other was found to be a new product designated xanthohumol B. The structure of xanthohumol B was shown to be 6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano ]- 3-(4-hydroxyphynyl)-2-propen-l-one by spectroscopic studies including various NMR measurements. Xanthohumol and xanthohumol B inhibited DGAT activity with IC50 values of 50.3 and 194 microM in rat liver microsomes, respectively. They showed preferential inhibition of triacylglycerol formation in intact Raji cells, indicating that they inhibit DGAT activity preferentially in living cells.

  Antimicrobial screening of essential oils and extracts of some Humulus lupulus L. cultivars.:

 The essential oils as well as solvent extracts of 11 hop cultivars, 1 hop variety and a wild type of hop were screened for their antimicrobial activities using the agar overlay technique. The oils were isolated from the cones of the various hop plants by hydrodistillation, the extracts were obtained by soaking the hop cones in chloroform. The oils and the extracts showed activity against the Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and the fungus (Trichophyton mentagrophytes var. interdigitale), but almost no activity against the Gram-negative bacterium (Escherichia coli) and the yeast (Candida albicans) used in the screening. The peak area percentages of the main volatile components and the contents of the bitter acids of the extracts were determined for all cultivars using chromatographic methods.
 


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  Scientific References:

  1.Research Update:Hops and its findings