Xanthohumol and related prenylflavonoids from hops and beer: To your good health!

Phytochemistry

Volumn 65, Issue 10, 2004, Pages 1317-1330

  Stevens, Jan F ^a   Page, Jonathan E ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

8 Prenylnaringenin; Antioxidant; Beer; Breast enhancement; Cancer chemoprevention; Flavonoids; Hops; Humulus lupulus; Phytoestrogen; Prenylflavonoids; Xanthohumol

Indexed keywords

8 PRENYLNARINGENIN; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CHALCONE SYNTHASE; DIMETHYLALLYLTRANSFERASE; FLAVONOID; HUMULON; HUMULUS LUPULUS EXTRACT; ISOXANTHOHUMOL; METHYLTRANSFERASE; NORXANTHOHUMOL; PHYTOESTROGEN; POLYKETIDE; TRANSFERASE; UNCLASSIFIED DRUG; XANTHOHUMOL;

ANTIOXIDANT ACTIVITY; BEER; BIOTECHNOLOGICAL PRODUCTION; BREAST AUGMENTATION; BREEDING; BREWING; CANCER; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHEMOPROPHYLAXIS; DIETARY INTAKE; DRUG ACTIVITY; DRUG MANUFACTURE; DRUG SYNTHESIS; ESTROGEN ACTIVITY; HEALTH CARE; HOT FLUSH; HUMAN; HUMULUS LUPULUS; IC 50; INFLORESCENCE; MENOPAUSAL SYNDROME; MENOPAUSE; METABOLIC ACTIVATION; METHYLATION; NONHUMAN; OSTEOPOROSIS; PRENYLATION; REVIEW;

HUMULUS; HUMULUS LUPULUS;

EID: 3042559902     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.04.025     Document Type: Article

References (72)

1. Arimoto-Kobayashi S., Sugiyama C., Harada N., Takeuchi M., Takemura M., Hayatsu H. Inhibitory effects of beer and other alcoholic beverages on mutagenesis and DNA adduct formation induced by several carcinogens. J. Agric. Food Chem. 47:1999;221-230
2. Biendl M., Eggers R., Czerwonatis N., Mitter W. Studies on the production of a xanthohumol-enriched hops product. Cerveza y Malta. 38:2001;25-29
3. Bovy A., de Vos R., Kemper M., Schijlen E., Almenar Pertejo M., Muir S., Collins G., Robinson S., Verhoeyen M., Hughes S., et al. High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. Plant Cell. 14:2002;2509-2526
4. Collakova E., DellaPenna D. Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis. Plant Physiol. 127:2001;1113-1124
5. Colliver S., Bovy A., Collins G., Muir S., Robinson S., de Vos C.H.R., Verhoeyen M.E. Improving the nutritional content of tomatoes through reprogramming their flavonoid biosynthetic pathway. Phytochem. Rev. 1:2002;113-123
6. Dixon R.A., Ferreira D. Genistein. Phytochemistry. 60:2002;205-211
7. Etteldorf N., Etteldorf N., Becker H. New chalcones from Hop, Humulus lupulus L. Z. Naturforsch. C. 54:1999;610-612
8. Fellermeier M., Zenk M.H. Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett. 427:1998;283-285
9. Forkmann G., Martens S. Metabolic engineering and applications of flavonoids. Curr. Opin. Biotechnol. 12:2001;155-160
10. Gerhauser C., Alt A., Heiss E., Gamal-Eldeen A., Klimo K., Knauft J., Neumann I., Scherf H.R., Frank N., Bartsch H., Becker H. Cancer chemopreventive activity of xanthohumol, a natural product derived from hop. Mol. Cancer Ther. 1:2002;959-969
11. Gester S., Metz P., Zierau O., Vollmer G. An efficient synthesis of the potent phytoestrogens 8-prenyl naringenin and 6-(1, 1-dimethylallyl)naringenin by europium(III)-catalysed claisen rearrangement. Tetrahedron. 57:2001;1015-1018
12. 2H-NMR study on the building blocks of humulone. Eur. J. Biochem. 263:1999;447-454
13. Haensel R., Schulz J. Desmethylxanthohumol: isolierung aus Hopfen und Cyclisierung zu Flavanonen. (Weinheim, Ger.). Arch. Pharm. 321:1988;37-40
14. Halliwell B., Gutteridge J.M.C. Free Radicals in Biology and Medicine. third ed. 1999;Oxford University Press, Oxford
15. Henderson M.C., Miranda C.L., Stevens J.F., Deinzer M.L., Buhler D.R. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica. 30:2000;235-251
16. Henikoff S., Comai L. Single-nucleotide mutations for plant functional genomics. Annu. Rev. Plant Physiol. Plant Mol. Biol. 54:2003;375-401
17. Herath W., Ferreira D., Khan S.I., Khan I.A. Identification and biological activity of microbial metabolites of xanthohumol (Tokyo). Chem. Pharm. Bull. 51:2003;1237-1240
18. Herath W.H., Ferreira D., Khan I.A. Microbial transformation of xanthohumol. Phytochemistry. 62:2003;673-677
19. Hertog M.G., Feskens E.J., Hollman P.C., Katan M.B., Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet. 342:1993;1007-1011
20. Horlemann C., Schwekendiek A., Hohnle M., Weber G. Regeneration and Agrobacterium-mediated transformation of hop (Humulus lupulus L.). Plant Cell Rep. 22:2003;210-217
21. Huebner H., Riedl W. Zur Konstitution des Xanthohumols. Chem. Ber. 93:1960;312-317
22. Ibrahim R.K., Bruneau A., Bantignies B. Plant O-methyltransferases: molecular analysis, common signature and classification. Plant Mol. Biol. 36:1998;1-10
23. Jez J.M., Bowman M.E., Dixon R.A., Noel J.P. Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase. Nat. Struct. Biol. 7:2000;786-791
24. Jones G., Campbell C.A.M., Barry J., Pye B.J., Maniar S.P., Mudd A. Repellent and oviposition-deterring effects of hop beta-acids on the two-spotted spider mite, Tetranychus urticae. Pesticide Sci. 47:1996;165-169
25. Joshi C.P., Chiang V.L. Conserved sequence motifs in plant S-adenosyl-L-methionine-dependent methyltransferases. Plant Mol. Biol. 37:1998;663-674
26. Matousek J., Novak P., Briza J., Patzak J., Niedermeierova H. Cloning and characterisation of chs-specific DNA and cDNA sequences from hop (Humulus lupulus L.). Plant Sci. (Amsterdam, Neth.). 162:2002;1007-1018
27. Matousek J., Novak P., Patzak J., Briza J., Krofta K. Analysis of true chalcone synthase from Humulus lupulus L. and biotechnology aspects of medicinal hops. Rostlinna Vyroba. 48:2002;7-14
28. ′ -O-methyltransferase, an enzyme specifically involved in the biosynthesis of an inducer of Rhizobium meliloti nodulation genes Plant J. 4:1993;971-981
29. McCaskill D., Croteau R. Strategies for bioengineering the development and metabolism of glandular tissues in plants. Nat. Biotechnol. 17:1999;31-36
30. Milligan S., Kalita J., Pocock V., Heyerick A., De Cooman L., Rong H., De Keukeleire D. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction Bristol, UK. 123:2002;235-242
31. Milligan S.R., Kalita J.C., Heyerick A., Rong H., De Cooman L., De Keukeleire D. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J. Clin. Endocrinol. Metab. 84:1999;2249-2252
32. Milligan S.R., Kalita J.C., Pocock V., Van De Kauter V., Stevens J.F., Deinzer M.L., Rong H., De Keukeleire D. The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. J. Clin. Endocrinol. Metab. 85:2000;4912-4915
33. Miranda C.L., Aponso G.L., Stevens J.F., Deinzer M.L., Buhler D.R. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Lett. 149:2000;21-29
34. Miranda C.L., Stevens J.F., Helmrich A., Henderson M.C., Rodriguez R.J., Yang Y.H., Deinzer M.L., Barnes D.W., Buhler D.R. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem. Toxicol. 37:1999;271-285
35. Miranda C.L., Stevens J.F., Ivanov V., McCall M., Frei B., Deinzer M.L., Buhler D.R. Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro. J. Agric. Food Chem. 48:2000;3876-3884
36. Miranda C.L., Yang Y.H., Henderson M.C., Stevens J.F., Santana-Rios G., Deinzer M.L., Buhler D.R. Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2. Drug Metab. Dispos. 28:2000;1297-1302
37. Mizobuchi S., Sato Y. A new flavanone with antifungal activity isolated from hops. Agric. Biol. Chem. 48:1984;2771-2775
38. Muir S.R., Collins G.J., Robinson S., Hughes S., Bovy A., Ric De Vos C.H., van Tunen A.J., Verhoeyen M.E. Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols. Nat. Biotechnol. 19:2001;470-474
39. Neve R.A. Hops. 1991;Chapman & Hall, London
40. Nikolic D., Li Y., Chadwick L.R., Grubjesic S., Schwab P., Metz P., van Breemen R.B. Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes. Drug Metab. Dispos. 32:2004;272-279
41. Nookandeh A., Frank N., Steiner F., Ellinger R., Schneider B., Gerhauser C., Becker H. Xanthohumol metabolites in faeces of rats. Phytochemistry. 65:2004;561-570
42. Okada Y., Ito K. Cloning and analysis of valerophenone synthase gene expressed specifically in lupulin gland of hop (Humulus lupulus L.). Biosci. Biotechnol. Biochem. 65:2001;150-155
43. Orth W.A., Riedl W. Konstitution und Synthese des Tetrahydroxanthohumols. Liebigs Ann. Chem. 663:1963;74-82
44. Pepper M.S., Hazel S.J., Humpel M., Schleuning W.D. 8-Prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo. J. Cell Physiol. 199:2004;98-107
45. Powell G., Hardie J., Pickett J.A. Laboratory evaluation of antifeedant compounds for inhibiting settling by cereal aphids. Entomol. Exp. Appl. 84:1997;189-193
46. Power F.B., Tutin F., Rogerson H. The constituents of hops. J. Chem. Soc. 103:1913;1267-1292
47. Rodriguez R.J., Miranda C.L., Stevens J.F., Deinzer M.L., Buhler D.R. Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes. Food Chem., Toxicol. 39:2001;437-445
48. Sägesser M., Deinzer M. HPLC-ion spray-tandem mass spectrometry of flavonol glycosides in hops. J. Am. Soc. Brew. Chem. 54:1996;129-134
49. Schaefer O., Humpel M., Fritzemeier K.H., Bohlmann R., Schleuning W.D. 8-Prenyl naringenin is a potent ERalpha selective phytoestrogen present in hops and beer. J. Steroid Biochem. Mol. Biol. 84:2003;359-360
50. Small E. The relationships of hop cultivars and wild variants of Humulus lupulus. Can. J. Bot. 58:1980;676-686
51. Stevens J.F., Ivancic M., Hsu V., Deinzer M.L. Prenylflavonoids from Humulus lupulus. Phytochemistry. 44:1997;1575-1585
52. ′ -hydroxychalcones as a novel antioxidant pharmacophore Chem. Res. Toxicol. 16:2003;1277-1286
53. Stevens J.F., Taylor A.W., Clawson J.E., Deinzer M.L. Fate of xanthohumol and related prenylflavonoids from hops to beer. J. Agric. Food Chem. 47:1999;2421-2428
54. Stevens J.F., Taylor A.W., Deinzer M.L. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J. Chromatogr., A. 832:1999;97-107
55. ′ -O-methylxanthohumol Phytochemistry. 53:2000;759-775
56. Sun S., Watanabe S., Saito T. Chalcones from Humulus lupulus. Phytochemistry. 28:1989;1776-1777
57. Tabata N., Ito M., Tomoda H., Omura S. Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus. Phytochemistry. 46:1997;683-687
58. Tekel J., De Keukeleire D., Rong H., Daeseleire E., Van Petegem C. Determination of the hop-derived 8-prenylnaringenin, in beer by gas chromatography/mass spectrometry. J. Agric. Food Chem. 47:1999;5059-5063
59. Tobe H., Muraki Y., Kitamura K., Komiyama O., Sato Y., Sugioka T., Maruyama H.B., Matsuda E., Nagai M. Bone resorption inhibitors from hop extract. Biosci. Biotechnol. Biochem. 61:1997;158-159
60. USDA, 2003. US Department of Agriculture, Economic Research Service. Statistics Reports at http://www.ers.usda.gov/data/foodconsumption/datasystem. asp
61. Vandewalle M. On the synthesis of xanthohumol and isoxanthohumol. Bull. Soc. Chim. Belg. 70:1961;163-167
62. Verzele M., Stockx J., Fontijn F., Anteunis M. Xanthohumol, a new natural chalcone. Bull. Soc. Chim. Belg. 66:1957;452-475
63. Vinson J.A., Mandarano M., Hirst M., Trevithick J.R., Bose P. Phenol antioxidant quantity and quality in foods: beers and the effect of two types of beer on an animal model of atherosclerosis. J. Agric. Food Chem. 51:2003;5528-5533
64. Winkel-Shirley B. Biosynthesis of flavonoids and effects of stress. Curr. Opin. Plant Biol. 5:2002;218-223
65. Yazaki K., Kunihisa M., Fujisaki T., Sato F. Geranyl diphosphate:4- hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a key enzyme in shikonin biosynthesis. J. Biol. Chem. 277:2002;6240-6246
66. Yilmazer, M., 2001. Xanthohumol, a flavonoid from hops (Humulus lupulus): in vitro and in vivo metabolism, antioxidant properties of metabolites, and risk assessment in humans. Ph.D. Thesis, Oregon State University
67. Yilmazer M., Stevens J.F., Buhler D.R. In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes. FEBS Lett. 491:2001;252-256
68. Yilmazer M., Stevens J.F., Deinzer M.L., Buhler D.R. In vitro biotransformation of xanthohumol, a flavonoid from hops (Humulus lupulus), by rat liver microsomes. Drug Metab. Dispos. 29:2001;223-231
69. Zenisek A., Bednar J. Contribution to the identification of the estrogen activity of hops. Am. Perfum. Arom. 75:1960;61-62
70. Zhao F., Nozawa H., Daikonnya A., Kondo K., Kitanaka S. Inhibitors of nitric oxide production from hops (Humulus lupulus L.). Biol. Pharm. Bull. 26:2003;61-65
71. Zubieta C., He X.Z., Dixon R.A., Noel J.P. Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases. Nat. Struct. Biol. 8:2001;271-279
72. Zuurbier K.W.M., Fung S.-Y., Scheffer J.C.C., Verpoorte R. In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in Humulus lupulus. Phytochemistry. 49:1998;2315-2322