Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

Revista Brasileira de Farmacognosia

Volumn 20, Issue 6, 2010, Pages 850-859

  Negri, Giuseppina ^a   di Santi, Daniel ^a   Tabach, Ricardo ^a  

^a FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Flavonoid glycosides; HPLC DAD MS MS; Humulus lupulus; Oxidized hop bitter acids

Indexed keywords

ADHUMULONE; ADLUPULONE; ANXIOLYTIC AGENT; COHULUPONE; COHUMULINONE; COHUMULONE; COLUPULON; HULUPINIC ACID; HUMULINONE; HUMULON; HUMULUS LUPULUS EXTRACT; KAEMPFEROL 7 O RUTINOSIDE; LUPULON; PHENOL DERIVATIVE; PROCYANIDIN B1; RUTOSIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; MALE; NONHUMAN; PHASE SEPARATION; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TRANQUILIZING ACTIVITY; ULTRAVIOLET RADIATION;

EID: 79551637783     PISSN: 0102695X     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0102-695X2010005000051     Document Type: Article

References (58)

1. Aoshima H, Takeda K, Okita Y, Hossain SJ, Koda H, Kiso Y 2006. Effects of beer and hop on ionotropic gammaaminobutyric acid receptors. J Agric Food Chem 54: 514-2519.
2. Arraez-Roman D, Cortacero-Ramirez S, Segura-Carretero A, Contreras JAML, Fernandez-Gutierrez A 2006. Characterization of the methanolic extract of hops using capillary electrophoresis-electrospray ionization-mass spectrometry. Electrophoresis 27: 197-2207.
3. Awad R, Levac D, Cybulska P, Merali Z, Trudeau VL, Arnason JT 2007. Effects of traditionally used anxiolytic botanicals on enzymes of the gamma-aminobutyric acid (GABA) system. Can J Physiol Pharmacol 85: 933-942.
4. Berwanger S, Zapp J, Becker H 2005. 13C-Labelling of xanthohumol in hops cones (Humulus lupulus L.). Planta Med 71: 530-534.
5. Bohr G, Klimo K, Zapp, J, Becker H, Gerhauser C 2008. Cancer chemopreventive potential of humulones and isohumulones (Hops α- and iso-α-acids): induction of NAD(P)H: quinine reductase as a novel mechanism. Nat Prod Comm 3: 1971-1976.
6. Callemien D, Collin S 2008. Use of RP-HPLC-ESI(-)-MS/MS to differentiate various proanthocyanidin isomers in lager beer extracts. J Am Soc Brew Chem 66: 109-115.
7. Carlini EA, Burgos V 1979. ''Screening'' farmacológico de ansiolíticos: metodologia laboratorial e comparação entre o diazepam e o clorobenzapam. Rev Assoc Bras Psiquiatr 1: 25-31.
8. Chacur C, Raymond R, Hipolide DC, Giugliano EB, Leite JR, Nobrega JN 1999. Immediate increase in benzodiazepine binding in rat brain after a single brief experience in the plus maze: a paradoxical effect. Neurosci Lett 269: 29-32.
9. Chadwick LR 2006. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine 13: 119-131.
10. Chen WJ, Lin JK 2004. Mechanisms of cancer chemoprevention by hop bitter acids (beer aroma) through induction of apoptosis mediated by faz and caspase cascades. J Agric Food Chem 52: 55-64.
11. Ciochina R, Grossman RB 2006. Polycyclic polyprenylated acylphloroglucinols. Chem Rev 106: 3963-3986.
12. Colombo R, Yariwake JH, Queiroz EF, Ndjoko K, Hostettmann K 2006. On-line identification of further flavone C- and O-glycosides from sugarcane (Soccharum officinarum L., Gramineae) by HPLC-UV-MS. Phytochem Anal 17: 337-343.
13. Cowan PE 1977. Neophobia and neofilia: new-object and newplace reactions of the three ratus species. J Comp Physiol Psychol 91: 63-71.
14. De Keukeleire J, Janssens I, Heyerick A, Ghekiere G, Cambie J, Roldan-Ruiz I, Van Bockstaele E, De Keukeleire D 2007. Relevance of organic farming and effect of climatological conditions on the formation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol in hop (Humulus lupulus L.). J Agric Food Chem 55: 61-66.
15. De Keukeleire J, Ooms G, Heyerick A, Roldan-Ruiz I, Van Bockstaele E, De Keukeleire D 2003. Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.). J Agric Food Chem 51: 4436-4441.
16. De Keukeleire D 2000. Fundamentals of beer and hop chemistry. Quim Nova 23: 108-112.
17. Diller RA, Riepl HM, Rose O, Frias C, Henze G, Prokop A 2007. Ability of prenylflavanones present in hops to induce apoptosis in a human Burkitt lymphoma cell line. Planta Med 73: 755-761.
18. Ennaceur A, Michalikova S, Van Rensburg R, Chazot PL 2008. Are benzodiazepines really anxiolytic? Evidence from a 3D maze spatial navigation task. Behav Brain Res 188: 136-153.
19. Foster BC, Kearns N, Arnason, JT, Saleem A, Ogrodowczyk C, Desjardins S 2009. Comparative study of hop-containing products on human cytochrome P450-mediated metabolism. J Agric Food Chem 57: 5100-5105.
20. Garcia-Villalba R, Cortacero-Ramirez S, Segura-Carretero A, Contreras JAML, Fernandez-Gutierrez A 2006. Analysis of hop acids and their oxidized derivatives and iso-alphaacids in beer by capillary electrophoresis-electrospray ionization mass spectrometry. J Agric Food Chem 54: 5400-5409.
21. Gerhauser C 2005. Beer constituents as potential cancer chemopreventive agents. Eur J Cancer 41: 1941-1954.
22. Hall AJ, Babish JG, Darland GK, Carroll BJ, Konda VR, Lerman RH, Bland JS, Tripp ML 2008. Safety, efficacy and anti-inflammatory activity of rho iso-alpha-acids from hops. Phytochemistry 69: 1534-1547.
23. Handley SL, Mithani S 1984. Effects of alpha adrenoceptor agonists in a maze exploration model of fear motivated behavior. N-S Arch Pharmacol 327: 1-5.
24. Haseleu G, Intelmann D, Hofmann T 2009a. Identification and RP-HPLC-ESI-MS/MS quantitation of bitter-tasting beta-acid transformation products in beer. J Agric Food Chem 57: 7480-7489.
25. Haseleu G, Intelmann D, Hofmann T 2009b. Structure determination and sensory evaluation of novel bitter compounds formed from beta-acids of hop (Humulus lupulus L.) upon wort boiling. Food Chem 116: 71-81.
26. Heinrich M, Barnes J, Gibbons S, Williamson EM 2004. Fundamentals of pharmacognosy and phytotherapy. Churchill Livingstone: Elsevier science limited.
27. Hellstrom J, Sinkkonen J, Karonen M, Mattila P 2007. Isolation and structure elucidation of procyanidin oligomers from saskatoon berries (Amelanchier alnifolia). J Agric Food Chem 55: 157-164.
28. Helmja K, Vaher M, Puessa T, Kamsol K, Orav A, Kaijurand M. 2007. Bioactive components of the hop strobilus: Comparison of different extraction methods by capillary electrophoretic and chromatographic methods. J Chromatogr A 1155: 222-229.
29. Herrera-Ruiz M, Roman-Ramos R, Zamilpa A, Tortoriello J, Jimenez-Ferrer JE 2008. Flavonoids from Tilia americana with anxiolytic activity in plus-maze test. J Ethnopharmacol 118: 312-317.
30. Howard GA, Slater CA 1958. The chemistry of hop constituents. The structure of humulinone. J Chem Soc 12: 1460-1462.
31. Hughes P 2006. Differences in the UV-spectra of the Hop-derived cis- and trans-iso-alpha-acids. J Am Soc Brew Chem 64: 47-51.
32. Intelmann D, Haseleu G, Hofmann T 2009. LC-MS/MS Quantitation of hop-derived bitter compounds in beer using the ECHO technique. J Agric Food Chem 57: 1172-1182.
33. Jaskula B, Goiris K, Van Opstaele F, De Rouck G, Aerts G, De Cooman L 2009. Hopping technology in relation to alphaacids isomerization yield, final utilization, and stability of beer bitterness. J Am Soc Brew Chem 67: 44-57.
34. Kac J, Vovk T 2007. Sensitive electrochemical detection method for alpha-acids, beta-acids and xanthohumol in hops (Humulus lupulus L.). J Chromatogr B 850: 531-537.
35. Khatib A, Kim HK, Wilson EG., Verpoorte R 2006. High performance liquid chromatographic method for isoalpha-acids. J Liq Chromatogr R T 29: 293-302.
36. Lee JC, Kundu JK, Hwang DM, Na HK, Surh YJ 2007. Humulone inhibits phorbol ester-induced COX-2 expression in mouse skin by blocking activation of NF-kappa B and AP-1: I kappa B kinase and c-Jun-N-terminal kinase as respective potential upstream targets. Carcinogenesis 28: 1491-1498.
37. Li HJ, Deinzer ML 2006. Structural identification and distribution of proanthocyanidins in 13 different hops. J Agric Food Chem 54: 4048-4056.
38. Lupinacci E, Meijerink J, Vincken, JP, Gabriele B, Gruppen H, Witkamp RF 2009. Xanthohumol from Hop (Humulus lupulus L.) is an efficient inhibitor of monocyte chemoattractant protein-1 and tumor necrosis factoralpha release in LPS-stimulated RAW 264.7 Mouse macrophages and U937 human monocytes. J Agric Food Chem 57: 7274-7281.
39. Magalhães PJ, Dostalek P, Cruz JM, Guido LF, Barros AA 2008. The Impact of a xanthohumol-enriched hop product on the behavior of xanthohumol and isoxanthohumol in pale and dark beers: a pilot scale approach. J Inst Brew 114: 246-256.
40. Meissner O, Haberlein H 2006. Influence of xanthohumol on the binding behavior of GABA (A) receptors and their lateral mobility at hippocampal neurons. Planta Med 72: 656-658.
41. Mendes V, Monteiro R, Pestana D, Teixeira D, Calhau C, Azevedo I 2008. Xanthohumol influences preadipocyte differentiation: implication of anti proliferative and apoptotic effects. J Agric Food Chem 56: 11631-11637.
42. Mendes FR, Mattei R, Carlini EA 2002. Activity of Hypericum brasiliense and Hypericum cordatum on the central nervous system in rodents. Fitoterapia 73: 462-471.
43. Morris HV, Dawson GR, Reynolds DS, Atack JR, Stephens DN 2006. Both alpha 2 and alpha 3 GABA(A) receptor subtypes mediate the anxiolytic properties of benzodiazepine site ligands in the conditioned emotional response paradigm. Eur J Neurosci 23: 2495-2504.
44. Nikolic D, Li Y, Chadwick LR, Pauli GF, Van Breemen RB 2005. Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.) by human liver microsomes. J Mass Spectrom 40: 289-299.
45. Schiller H, Forster A, Vonhoff C, Hegger M, Biller A, Winterhoff H 2006. Sedating effects of Humulus lupulus L. extracts. Phytomedicine 13: 535-541.
46. Schwekendiek A, Spring O, Heyerick A, Pickel B, Pitsch NT, Peschke F, de Keukeleire D, Weber G 2007. Constitutive expression of a grapevine stilbene synthase gene in transgenic hop (Humulus lupulus L.) yields resveratrol and its derivatives in substantial quantities. J Agric Food Chem 55: 7002-7009.
47. Segawa S, Yasui K, Takata Y, Kurihara T, Kaneda H, Watari J 2006. Flavonoid glycosides extracted from hop (Humulus lupulus L.) as inhibitors of chemical mediator release from human basophilic KU812 cells. Biosci Biotech Bioch 70: 2990-2997.
48. Stahl E 1969. Thin layer chromatography. A laboratory handbook. Berlin: Springer Verlag.
49. Stevens JF, Page JE 2004. Molecules of interest xanthohumol and related prenylflavonoids from hops and beer: to your good health. Phytochemistry 65: 1317-1330.
50. Van Cleemput M, Cattoor K, De Bosscher K, Haegeman G, De Keukeleire D, Heyerick A 2009. Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds. J Nat Prod 72: 1220-1230.
51. Verzele M, De Keukeleire D 1991. Chemistry and analysis of hop and beer bitter acids. Amsterdam: Elsevier.
52. Vogel S, Heilmann J 2008. Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus. J Nat Prod 71: 1237-1241.
53. Wagner H, Bladt S 1996. Plant drug analysis. A thin layer chromatography atlas. Berlin: Springer.
54. Xu YK, Yang SP, Liao SG, Zhang H, Lin LP, Ding J, Yue JM 2006. Alkaloids from Gelsemium elegans. J Nat Prod 69: 1347-1350.
55. Zanoli P, Zavatti M 2008. Pharmacognostic and pharmacological profile of Humulus lupulus L. J Ethnopharmacol 116: 383-396.
56. Zanoli P, Zavatti M, Rivasi M, Brusiani F, Losi G, Puia G, Avallone R, Baraldi M 2007. Evidence that the beta-acids fraction of hops reduces central GABAergic neurotransmission. J Ethnopharmacol 109: 87-92.
57. Zanoli P, Rivasi M, Zavatti M, Brusiani F, Baraldi M 2005. New insight in the neuropharmacological activity of Humulus lupulus L. J Ethnopharmacol 102: 102-106.
58. Zhao F, Watanabe Y, Nozawa H, Daikonnya A, Kondo K, Kitanaka S 2005. Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). J Nat Prod 68: 43-49.