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

Phytomedicine - Tập 13 Số 1-2 - Trang 119-131 - 2006
Lucas R. Chadwick1, Guido F. Pauli1, Norman R. Farnsworth1
1UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA

Tóm tắt

Từ khóa


Tài liệu tham khảo

1946

Anonymous, 1999. The Plant Names Project. International Plant Names Index, Published on the Internet, http://www.ipni.org, Accessed October 2003.

2002

Anonymous, 2003. Beilstein Database (Beilstein-Institut zur Förderung der Chemischen Wissenschaften); Accessed November 2003

Bae, 1996, Screening on the cytotoxicity of medicinal plants against L1210 and HL60 cancer cells, Korean J. Pharmacog., 27, 173

Baker, 1928, Synthetical experiments in the isoflavone group. III. Synthesis of genistein, J. Chem. Soc., 131, 3115, 10.1039/JR9280003115

Bednar, 1961, Identification of the estrogenic activity of hops, Brauwissenschaft, 14, 4

Behre, 1999, The history of beer additives in Europe – a review, Veget. Hist. Archeobot., 8, 35, 10.1007/BF02042841

Bickoff, 1961, Estrogen-like substances in plants, 93

2000

Bolton, 1998, Role of quinoids in estrogen carcinogenesis, Chem. Res. Toxicol., 11, 1113, 10.1021/tx9801007

Bouchardy, 1953, A pharmacological study of the action of lupulin and orange flowers on fish, Pharm. Acta Helv., 28, 183

Bradbury, 1951, The chemistry of subterranean clover. Part I. Isolation of formononetin and genistein, J. Chem. Soc., 3447, 10.1039/jr9510003447

Brown, 2001, Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones, Lab. Invest., 81, 735, 10.1038/labinvest.3780282

Burgess, 1964

Chadwick, 2004, Estrogens and congeners from spent hops (Humulus lupulus L.), J. Nat. Prod., 67, 2024, 10.1021/np049783i

Chury, 1961, Experimental contribution to the chromatographic separation of sexually active substances in plant extracts, Sb. Vys. Sk. Zemedel Brne Rada B, 9, 411

Coldham, 2001, Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement, Food Chem. Toxicol., 39, 1211, 10.1016/S0278-6915(01)00081-3

Culbreth, 1927

De Keukeleire, D., Milligan, S.R., Kalita, J.C., Pocock, V., De Cooman, L., Heyerick, A., Rong, H., Roelens, F., 2001. Prenylated flavonoids are key agents in relation to health-beneficial properties of beer. Proceedings of the 28th International Congress of the European Brewery Convention, Budapest, Hungary.

Donsback, 1977

Eri, 2000, Direct thermal desorption-gas chromatography and gas chromatography- mass spectrometry profiling of hop (Humulus lupulus L.) essential oils in support of varietal characterization, J. Agric. Food Chem., 48, 1140, 10.1021/jf9911850

Ettinger, 2003, Effect of the Women's Health Initiative on women's decisions to discontinue postmenopausal hormone therapy, Obstet. Gynecol., 102, 1225, 10.1016/j.obstetgynecol.2003.08.007

Farnsworth, N.R. (Ed.), 2003. NAPRALERT®: A Database of World Literature of Natural Products. Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago.

Fenselau, 1973, Is oestrogenic activity present in hops?, Food Cosmet. Toxicol., 11, 597, 10.1016/S0015-6264(73)80330-X

Fluckiger, 1879

Gathercoal, 1936

Gerhard, 1996, Vigilance-decreasing effects of 2 plant-derived sedatives, Schweiz. Rundsch. Med. Prax., 85, 473

Gerhäuser, 2001, Antioxidant and radical-scavenging potential of phenolic constituents of beer, Proc. Am. Assoc. Cancer Res., 42, 19

Gerhäuser, 2001, Xanthohumol from hop (Humulus lupulus) as a novel potential cancer chemopreventive agent, Proc. Am. Assoc. Cancer Res., 42, 18

Gerhäuser, 2002, Cancer chemopreventive activity of Xanthohumol, a natural product derived from hop, Mol. Cancer Ther., 1, 959

Goetz, 1990, Traitment des bouffees de chaleur par insuffisance ovarienne par l’extrait de houblon (Humulus lupulus), Rev. Phytother. Prat., 13

Grange, 1990, Detection of antituberculous activity in plant extracts, J. Appl. Bacteriol., 68, 587, 10.1111/j.1365-2672.1990.tb05224.x

Greenish, 1909

Greuter, W., Mcneill, J., Barrie, F.R., Burdet, H.-M., Demoulin, V., Filgueiras, T.S., Nicolson, D.H., Silva, P.C., Skog, J.E., Trehane, P., Turland, N.J., Hawksworth, D.L., 2000. Regnum Vegetabile, vol. 138. International Code of Botanical Nomenclature (St. Louis Code) Adopted by the Sixteenth International Botanical Congress St. Louis, MO, July–August 1999. Koeltz Scientific Books, Königstein.

Grodstein, 1997, Postmenopausal hormone therapy and mortality, N. Engl. J. Med., 336, 1769, 10.1056/NEJM199706193362501

Grumbach, 1955, The pharmacological determination of lupulin, Bull. Soc. Pharm. (Bordeaux), 94, 196

Hahn, 1989, Compliance considerations with estrogen replacement: withdrawal bleeding and other factors, Am. J. Obstet. Gynecol., 161, 1854, 10.1016/S0002-9378(89)80006-7

Hampton, 2002, Comparative chemical attributes of native North American hop, Humulus lupulus var. lupuloides E. Small, Phytochemistry, 61, 855, 10.1016/S0031-9422(02)00376-X

Hänsel, 1980, Narcotic action of 2-methyl-3-butene-2-ol contained in the hops essential oil, Z. Naturforsch. Ser. C, 35C, 1096, 10.1515/znc-1980-11-1240

Hänsel, 1988, Desmethylxanthohumol: Isolierung aus Hopfen und Cyclisierung zu Flavanonen, Arch. Pharm. Weinheim., 321, 37, 10.1002/ardp.19883210112

Harris, 1990, Are women using postmenopausal estrogens? A community survey, Am. J. Public Health, 80, 1266, 10.2105/AJPH.80.10.1266

Henderson, 1997, The epidemiology of estrogen replacement therapy and Alzheimer's disease, Neurology, 48, S27, 10.1212/WNL.48.5_Suppl_7.27S

Hensyl, 1990

Holinka, 1986, Effects of steroid hormones and antisteroids on alkaline phosphatase activity in human endometrial cancer cells (Ishikawa line), Cancer Res,, 46, 2771

Honma, 1998, Induction of differentiation of myelogenous leukemia cells by humulone, a bitter acid in the hop, Leukemia Res., 22, 605, 10.1016/S0145-2126(98)00046-0

Inoue, 1996, Identification of a novel isoform of estrogen receptor, a potential inhibitor of estrogen action, in vascular smooth muscle cells, Biochem. Biophys. Res. Commun., 219, 766, 10.1006/bbrc.1996.0308

Jackson, 1968

Kitaoka, 1998, Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure–activity relationship, Planta Med., 64, 511, 10.1055/s-2006-957504

Koch, 1953, Östrogene harmone in Hopfen und Bier, Muench. Med. Wochenschr., 95, 845

Kuiper, 1996, Cloning of a novel estrogen receptor expressed in rat prostate and ovary, Proc. Natl. Acad. Sci. (USA), 93, 5925, 10.1073/pnas.93.12.5925

Langezaal, 1992, Antimicrobial screening of essential oils and extracts of some Humulus lupulus L. cultivars, Pharm. Weekbl. Sci., 14, 353, 10.1007/BF01970171

Lecce, 2001, Presence of estrogen receptor beta in the human endometrium through the cycle: expression in glandular, stromal, and vascular cells, J. Clin. Endocrinol. Metab., 86, 1379, 10.1210/jc.86.3.1379

Lee, 1993, Effects of Humulus lupulus extract on the central nervous system in mice, Planta Med., 59, A691, 10.1055/s-2006-959980

Liegeois, 2000, Measuring antioxidant eficiency of wort, malt, and hops against the 2,2′-azobis(2-amidinopropane) dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid, J. Agric. Food Chem., 48, 1129, 10.1021/jf9911242

Liu, 2001, Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms, J. Agric. Food Chem., 49, 2472, 10.1021/jf0014157

Lorenzetti, 1991, Myrcene mimics the peripheral analgesic activity of lemongrass tea, J. Ethnopharmacol., 34, 43, 10.1016/0378-8741(91)90187-I

Maisch, 1892

Masaki, 1995, Active-oxygen scavenging activity of plant extracts, Biol. Pharm. Bull., 18, 162, 10.1248/bpb.18.162

Matos, 2001, Antibacterial Activity of Humulus lupulus against Helicobacter pylori, Gut, 49, A5

Meyer, J., 1960. Hops. In: The Herbalist. Clarence Meyer, self published.

Milligan, 1999, Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer, J. Clin. Endocrinol. Metab., 84, 2249, 10.1210/jc.84.6.2249

Milligan, 2000, The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids, J. Clin. Endocrinol. Metab., 85, 4912, 10.1210/jc.85.12.4912

Milligan, 2002, Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin, Reproduction, 123, 235, 10.1530/rep.0.1230235

Millspaugh, 1974

Miranda, 1999, Antiproliferative and cytotoxic effects of prenylated flavonoids from hops in human cancer cell lines, Food Chem. Toxicol., 37, 271, 10.1016/S0278-6915(99)00019-8

Miranda, 2000, Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1×1C7 cells, Cancer Lett., 149, 21, 10.1016/S0304-3835(99)00328-6

Miranda, 2000, Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo-4,5-fluoroquinoline, mediated by cDNA-expressed human CYP1A2, Drug. Metab. Dispos., 28, 1297

Mizobuchi, 1994, A new flavanone with antifungal activity isolated from hops, Agric. Biol. Chem., 48, 2771, 10.1271/bbb1961.48.2771

Mosselman, 1996, ER beta: identification and characterization of a novel human estrogen receptor, FEBS Lett., 392, 49, 10.1016/0014-5793(96)00782-X

Muller-Limmroth, 1977, Experimental studies of the effects of Seda–Kneipp on the sleep of sleep disturbed subjects; implications for the treatment of different sleep disturbances, Med. Klin., 72, 1119

Munch, 1933, Quantitative applications of the modified Türk test, J. Am. Pharm. Assoc., 22, 1078, 10.1002/jps.3080221103

Nastainczyk, W., 1972. Untersuchung über die östrogene Wirkung des Hopfens und des Bieres. Ph.D. Dissertation, Universität Saarbrücken, Germany

Neve, 1991

Nikolic, 2004, Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops, by human liver microsomes, Drug. Metab. Dispos., 32, 272, 10.1124/dmd.32.2.272

Nishida, 1985, Establishment of a new human endometrial adenocarcinoma cell line, Ishikawa cells, containing estrogen and progesterone receptors, Acta Obstet. Gynacol. Japan, 37, 1103

Nookandeh, 2004, Xanthohumol metabolites in faeces of rats, Phytochemistry, 65, 561, 10.1016/j.phytochem.2003.11.016

Ohsugi, 1997, Antibacterial activity of traditional medicines and an active constituent lupulone from Humulus lupulus against Helicobacter pylori, J. Trad. Med., 14, 186

Oyaizu, 1994, Antioxidative activity of extracts from hop (Humulus lupulus L.), Yukagaku, 42, 1003

Parker, H.H., 1991. The Hop Industry. P.S. King, London (1934) as cited in Neve.

Pettersson, 2001, Role of estrogen receptor beta in estrogen action, Annu. Rev. Physiol., 63, 165, 10.1146/annurev.physiol.63.1.165

Pink, 1996, A novel 80kDa human estrogen receptor containing a duplication of exons 6 and 7, Nucleic Acids Res., 24, 962, 10.1093/nar/24.5.962

Polo-Kantola, 1998, When does ERT improve sleep quality?, Am. J. Obstet. Gynecol., 178, 1002, 10.1016/S0002-9378(98)70539-3

Polo-Kantola, 2001, Aetiology and treatment of sleep disturbances during perimenopause and postmenopause, CNS Drugs, 15, 445, 10.2165/00023210-200115060-00003

Prokopenko, 1986, Pharmacological and chemical properties of hops Humulus lupulus, Farm. Zh. (Kiev.), 1, 28

Rabin, 1999, Why menopausal women do not want to take hormone replacement therapy, Menopause, 6, 61, 10.1097/00042192-199906010-00012

Racz, 1980, Trichomonazide und anthelmintische Wirkung in der rumanischen Volksmedizin verwendeten Pflanzen, Planta Med., 39, 257

Rao, 1990, Effect of myrcene on nociception in mice, J. Pharm. Pharmacol., 42, 877, 10.1111/j.2042-7158.1990.tb07046.x

Rong, 2001, 8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells, Eur. J. Cell Biol., 80, 580, 10.1078/0171-9335-00190

Rossouw, 2002, Risks and benefits of estrogen plus progestin in healthy postmenopausal women: principal results from the Women's Health Initiative randomized controlled trial, JAMA, 288, 321, 10.1001/jama.288.3.321

Rusiecki, 1938, Hypnotic properties of hops, Chim. Ind., 38, 319

Schaefer, 2003, 8-Prenylnaringenin is a potent ERalpha selective phytoestrogen present in hops and beer, J. Steroid Biochem. Mol. Biol., 84, 359, 10.1016/S0960-0760(03)00050-5

Schleif, 1907

Schmitz, 1998, Comparative study for assessing quality of life of patients with exogenous sleep disorders (temporary sleep onset and sleep interruption disorders) treated with a hops-valarian preparation and a benzodiazepine drug, Wien. Med. Wochenschr., 148, 291

Schulz, 2001

Seefelder, 2000, Genetic diversity and phylogenetic relationships among accessions of hop, Humulus lupulus, as determined by amplified fragment length polymorphism fingerprinting compared with pedigree data, Plant Breed., 119, 257, 10.1046/j.1439-0523.2000.00500.x

Shipp, 1994, The effect of colupulone (a hops b-acid) on hepatic cytochrome p-450 enzymatic activity in the rat, Food Chem. Toxicol., 32, 1007, 10.1016/0278-6915(94)90140-6

Shughrue, 2001, Distribution of estrogen receptor beta immunoreactivity in the rat central nervous system, J. Comp. Neurol., 436, 64, 10.1002/cne.1054

Sikorski, 1938, The sedative action of various constituents of hops, Bull. Intern. Acad. Polon. Sci. Classe Med., 1936, 73

Simpson, 1992, Factors affecting antibacterial activity of hop compounds and their derivatives, J. Appl. Bacteriol., 72, 327, 10.1111/j.1365-2672.1992.tb01843.x

Small, 1978, A numerical and nomenclatural analysis of morpho-geographic taxa of Humulus, Syst. Bot., 3, 37, 10.2307/2418532

Small, 1980, The relationships of hop cultivars and wild variants of Humulus lupulus, Can. J. Bot., 58, 676, 10.1139/b80-086

Staven-Groenberg, 1928, Action upon frogs of substances derived from hops, Arch. Exptl. Path. Pharm. 1927, 123, 272

Steidle, 1932, The pharmacology of hops, Arch. Exptl. Path. Pharm. 1931, 161, 154, 10.1007/BF01868901

Stevens, 1997, Prenylflavonoids from Humulus lupulus, Phytochemistry, 44, 1575, 10.1016/S0031-9422(96)00744-3

Stevens, 1998, Chemistry and biology of hop flavonoids, J. Am. Soc. Brew. Chem., 56, 136

Stevens, 1999, Fate of xanthohumol and related prenylflavonoids from hops to beer, J. Agric. Food Chem., 47, 2421, 10.1021/jf990101k

Stevens, 1999, Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry, J. Chromatogr. A, 832, 97, 10.1016/S0021-9673(98)01001-2

Stevens, 2000, Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4 ′-O-methylxanthohumol, Phytochemistry, 53, 759, 10.1016/S0031-9422(00)00005-4

Stevens, 2002, Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species, J. Agric. Food Chem., 50, 3435, 10.1021/jf0116202

Strenkovskaya, A.G., 1968. Estrogenic hops extract for cosmetics. Russian Patent 19680530 (Chem. Abstr. 69, 80115d)

Sun, 2003, Morning/evening menopausal formula relieves menopausal symptoms: a pilot study, J. Altern. Complement Med., 9, 403, 10.1089/107555303765551624

Tabata, 1997, Xanthohumols: diacylglycerol acyltransferase inhibitors from Humulus lupulus, Phytochemistry, 46, 683, 10.1016/S0031-9422(97)00157-X

Tabata, 1998, Hexahydrocolupulone and its antitumor cell proliferation activity in vitro, Biochem. Pharmacol., 55, 505, 10.1016/S0006-2952(97)00469-3

Tagashira, 1995, Antioxidative activity of hop bitter acids and their analogues, Biosci. Biotechnol. Biochem., 59, 740, 10.1271/bbb.59.740

Tagashira, 1997, Inhibition by hop bract polyphenols of cellular adherence and water-insoluble glucan synthesis of Mutans Streptococci, Biosci. Biotechnol. Biochem., 61, 332, 10.1271/bbb.61.332

Tobe, 1997, Apoptosis to HL-60 by humulone, Biosci. Biotechnol. Biochem., 61, 1027, 10.1271/bbb.61.1027

Tobe, 1997, Bone resorption inhibitors from hop extract, Biosci. Biotechnol. Biochem., 61, 158, 10.1271/bbb.61.158

Tomlan, 1992

Vanhoenacker, 2002, Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.), Nat. Prod. Lett., 16, 57, 10.1080/1057563029001/4863

Verzele, 1957, Xanthohumol, a new natural chalcone, Bull. Soc. Chim. Belg., 66, 452, 10.1002/bscb.19570660137

Verzele, 1991

Vonderheid-Guth, 2000, Pharmacodynamic effects of valerian and hops extract combination (Ze 91019) on the quantitative-topographical EEG in healthy volunteers, Eur. J. Med. Res., 5, 139

Washburn, 1927

Wilcox, 1912

Wohlfart, 1982, Nachweis sedativ-hypnotischer Wirkstoffe im Hopfen, 3, Planta Med., 45, 224, 10.1055/s-2007-971377

Yamada, 1998, Color scanning electron microscopy of peltate glandular trichomes of fresh developing hops (Humulus lupulus L.), J. Electron Microsc., 47, 539, 10.1093/oxfordjournals.jmicro.a023626

Yamamoto, 2000, Suppression of cyclooxygenase-2 gene transcription by humulon of beer hop extract studied with reference to glucocorticoid, FEBS Lett., 465, 103, 10.1016/S0014-5793(99)01727-5

Yasukawa, 1995, Humulon, a bitter in the hop, inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin, Oncology, 52, 156, 10.1159/000227448

Yilmazer, 2001, In vitro biotransformation of xanthohumol, a flavonoid from hops (Humulus lupulus), by rat liver microsomes, Drug Metab. Dispos., 29, 223

Yilmazer, 2001, In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes, FEBS Lett., 491, 252, 10.1016/S0014-5793(01)02210-4

Young, 1977, Estradiol and its biosynthesis in Phaseolus vulgaris L, Nature (London), 267, 429, 10.1038/267429a0

Youngken, 1950

Zagari, 1992

Zenisek, 1960, Contribution to the identification of the estrogen activity of hops, Am. Perf. Arom., 75, 61

Zhang, 2001, Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases, Chem. Res. Toxicol., 14, 1654, 10.1021/tx010158c

Zierau, 2002, Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin, Planta Med., 68, 449, 10.1055/s-2002-32089

Zuurbier, 1998, 4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates, Phytochemistry, 49, 1945, 10.1016/S0031-9422(98)00346-X