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Secondary metabolites, antioxidant and anti-proteinase activities of methanolic extracts from cones of hop (Humulus lupulus L.) cultivars

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Abstract

Contents of polyphenols, flavonoids, bitter acids, α-bitter acids, xanthohumol, desmethylxanthohumol, essential oils, antioxidant activities, and inhibitory activities against trypsin, thrombin, urokinase, and papain were analysed in methanolic extracts prepared from the hope cones. Significant differences between extracts from eight hop cultivars in all measured parameters were found. Two cultivars—Agnus and Vital—could be designated as the very special, all possessing high content of bitter acids, α-acids, essential oils, xanthohumol, and desmethylxanthohumol. The other two cultivars—Bohemie and Sládek—had interesting inhibitory activities against analysed proteinases. Differences between cultivars were also in content of total polyphenols, total flavonoids, as well as in antioxidant activity. All analysed hop cultivars developed originally for brewing contained also secondary metabolites with valuable biological activities related to health conditions associated with antioxidant status and some pathophysiological agents of proteinase character.

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References

  • Analytica EBC, European Brewery Convention (1998) Fachverlag Hans Carl: Nűrmberg, Germany, 5th edn 1998, Section 7

  • Benelli R, Venè R, Ciarlo M, Carlone S, Barbieri O, Ferrari N (2012) The AKT/NF-κB inhibitor xanthohumol is a potent anti-lymphocytic leukemia drug overcoming chemoresistance and cell infiltration. Biochem Pharmacol 83:1634–1642. doi:10.1016/j.bcp.2012.03.006

    Article  CAS  Google Scholar 

  • Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. LWT Food Sci Technol 28:25–30. doi:10.1016/S0023-6438(95)80008-5

    Article  CAS  Google Scholar 

  • Chadwick LR, Pauli GF, Farnsworth NR (2006) The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine 13:119–131. doi:10.1016/j.phymed.2004.07.006

    Article  CAS  Google Scholar 

  • 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 47:1145–1698. doi:10.1021/jf034263z

    Google Scholar 

  • Delmulle L, Bellahcène A, Dhooge W, Comhaire F, Roelens F, Huvaere K, Heyerick A, Castronovo V, De Keukeleire D (2006) Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine 13:732–734. doi:10.1016/j.phymed.2006.01.001

    Article  CAS  Google Scholar 

  • Feng Y, Ni L, Wang Q (2013) Administration of cathepsin B inhibitor CA-074Me reduces inflammation and apoptosis in polymyositis. J Dermatol Sci 72:158–167. doi:10.1016/j.jdermsci.2013.06.014

    Article  CAS  Google Scholar 

  • Ferri M, Gianotti A, Tassoni A (2013) Optimisation of assay conditions for the determination of antioxidant capacity and polyphenols in cereal food components. J Food Compos Anal 30:94–101. doi:10.1016/j.jfca.2013.02.004

    Article  CAS  Google Scholar 

  • Jayaprakasha GK, Singh RP, Sakariah KK (2001) Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro. Food Chem 73:285–290. doi:10.1016/S0308-8146(00)00298-3

    Article  CAS  Google Scholar 

  • Jelínek L, Šneberger M, Karabín M, Dostálek P (2010) Comparison of Czech hop cultivars based on their contents of secondary metabolites. Czech J Food Sci 28:309–316

    Google Scholar 

  • Kähkönen MP, Hopia AI, Vuorela HJ, Rauha JP, Pihlaja K, Kujala TS, Heinonen M (1999) Antioxidant activity of plant extracts containing phenolic compounds. J Agric Food Chem 47:3954–3962. doi:10.1021/jf990146l

    Article  Google Scholar 

  • Karabín M, Hudcová T, Jelínek L, Dostálek P (2016) Biologically active compounds from hops and prospects for their use. Compr Rev Food Sci Food Saf 15:542–567. doi:10.1111/1541-4337.12201

    Article  Google Scholar 

  • Kovačevič M, Kač M (2001) Solid-phase microextraction of hop volatiles: potential use for determination and verification of hop varieties. J Chromatogr A 918:159–167. doi:10.1016/S0021-9673(01)00719-1

    Article  Google Scholar 

  • Kowalczyk D, Świeca M, Cichocka J, Gawlik-Dziki U (2013) The phenolic content and antioxidant activity of the aqueous and hydroalcoholic extracts of hops and their pellets. J Inst Brew 119:103–110. doi:10.1002/jib.73

    CAS  Google Scholar 

  • Krofta K, Mikyška A, Hašková D (2008) Antioxidant characteristics of hops and hop products. J Inst Brew 114:160–166. doi:10.1002/j.2050-0416.2008.tb00321.x

    Article  CAS  Google Scholar 

  • Lee Y-M, Hsieh K-H, Lu W-J, Chou H-C, Chou D-S, Lien L-M, Sheu J-R, Lin K-H (2012) Xanthohumol, a prenylated flavonoid from hops (Humulus lupulus), prevents platelet activation in human platelets. Evid-Based Complementary Altern Med (Article ID 852362):10. doi: 10.1155/2012/852362

  • Maliar T, Jedinák A, Kadrabová J, Šturdík E (2004) Structural aspects of flavonoids as trypsin inhibitors. Eur J Med Chem 39:241–248. doi:10.1016/j.ejmech.2003.12.003

    Article  CAS  Google Scholar 

  • Maliar T, Drobná J, Kraic J, Maliarová M, Jurovatá J (2011) Proteinase inhibition and antioxidant activity of selected forage crops. Biologia 66:96–103. doi:10.2478/s11756-010-0149-9

    Article  CAS  Google Scholar 

  • Martorell L, Rodriguez C, Calvayrac O, Gentile M, Badimon L (2008) Thrombin and protease-activated receptors (PARs) in atherothrombosis. Thromb Haemost 99:305–315. doi:10.1160/TH07-08-0481

    CAS  Google Scholar 

  • Nesvadba V, Krofta K (2009) Variability in the contents of important compounds for pharmaceutical and brewing industries within hop gene pool. Agriculture 55:10–16

    CAS  Google Scholar 

  • Nesvadba V, Krofta K, Polončíková Z (2011) Hop (Humulus lupulus L.) breeding aimed at high content of desmethylxanthohumol (DMX). Agriculture 57:105–109. doi:10.2478/v10207-011-0011-2

    CAS  Google Scholar 

  • Nesvadba V, Polončíková Z, Henychová A (2012) Hop breeding in the Czech Republic. Kvasný Průmysl 58:36–39

    Article  Google Scholar 

  • Pšenáková I, Hetešová L, Nemeček P, Faragó J, Kraic J (2010) Genotype and seasonal variation n antioxidant activity of hop extracts. Agriculture 56:106–113

    Google Scholar 

  • Rakotoarison D, Greissier B, Trotin F, Brunet C, Dine T, Luycky M, Vasseur J, Cazin M, Cazin JC, Pinkas M (1997) Antioxidant activities of polyphenolic extracts from flowers, in vitro callus and cell suspension cultures of Crataegus monogyna. Pharmazia 1:60–64

    Google Scholar 

  • Silbernagl S, Lang F (2009) Color atlas of pathophysiology, 2nd edn. Georg Thieme, Stuttgart

    Google Scholar 

  • Slinkard K, Singleton VL (1977) Total phenol analysis: automation and comparison with manual methods. Am J Enol Vitic 28:49–55

    CAS  Google Scholar 

  • Steenackers B, De Cooman L, De Vos D (2015) Chemical transformations of characteristic hop secondary metabolites in relation to beer properties and the brewing process: a review. Food Chem 172:742–756. doi:10.1016/j.foodchem.2014.09.139

    Article  CAS  Google Scholar 

  • Stevens JF, Ivancic M, Hsu VL, Deinzer ML (1997) Prenylflavonoids from Humulus lupulus. Phytochemistry 44:1575–1585. doi:10.1016/S0031-9422(96)00744-3

    Article  CAS  Google Scholar 

  • Stevens JF, Taylor AW, Deinzer ML (1999) Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A 832:97–107. doi:10.1016/S0021-9673(98)01001-2

    Article  CAS  Google Scholar 

  • Stratil P, Klejdus B, Kubáň V (2007) Determination of phenolic compounds and their antioxidant activity in fruits and cereals. Talanta 71:1741–1751. doi:10.1016/j.talanta.2006.08.012

    Article  CAS  Google Scholar 

  • Tabata N, Ito M, Tomoda H, Omura S (1997) Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus. Phytochemistry 46:683–687. doi:10.1016/S0031-9422(97)00157-X

    Article  CAS  Google Scholar 

  • Tapiero H, Tew KD, Ba GN, Mathé G (2002) Polyphenols: do they play a role in the prevention of human pathologies? Biomed Pharmacother 56:200–207. doi:10.1016/S0753-3322(02)00178-6

    Article  CAS  Google Scholar 

  • Ulisse S, Baldini E, Sorrenti S, D’Armiento M (2009) The urokinase plasminogen activator system: a target for anti-cancer therapy. Curr Cancer Drug Targets 9:32–71. doi:10.2174/156800909787314002

    Article  CAS  Google Scholar 

  • Ürgeová E, Polívka Ľ (2009) Secondary metabolites with antibacterial effects from leaves of different cultivars during vegetal period. Nova Biotechnologica 9:327–332

    Google Scholar 

  • 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. doi:10.1021/np800740m

    Article  Google Scholar 

  • Volf I, Ignat I, Neamtu M, Popa VI (2014) Thermal stability, antioxidant activity, and photo-oxidation of natural polyphenols. Chem Pap 68:121–129. doi:10.2478/s11696-013-0417-6

    Article  CAS  Google Scholar 

  • Zanoli P, Zavatti M (2008) Pharmacognostic and pharmacological profile of Humulus lupulus L. J Ethnopharmacol 116:383–396. doi:10.1016/j.jep.2008.01.011

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Acknowledgements

This work was supported by the Grant No. VEGA 1/0635/13 “Hop as an important source of phytomedically active substances” supported by the Scientific Grant Agency of the Slovak Academy of Sciences and Ministry of Education, Science, Research and Sport of the Slovak Republic.

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Correspondence to Ján Kraic.

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Maliar, T., Nemeček, P., Ürgeová, E. et al. Secondary metabolites, antioxidant and anti-proteinase activities of methanolic extracts from cones of hop (Humulus lupulus L.) cultivars. Chem. Pap. 71, 41–48 (2017). https://doi.org/10.1007/s11696-016-0034-2

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