Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Open Chemistry

formerly Central European Journal of Chemistry

1 Issue per year


IMPACT FACTOR 2017: 1.425
5-year IMPACT FACTOR: 1.511

CiteScore 2017: 1.45

SCImago Journal Rank (SJR) 2017: 0.349
Source Normalized Impact per Paper (SNIP) 2017: 0.812

Open Access
Online
ISSN
2391-5420
See all formats and pricing
More options …
Volume 13, Issue 1

Issues

Volume 13 (2015)

Supercritical carbon dioxide hops extracts with antimicrobial properties

Edward Rój
  • Corresponding author
  • New Chemical Syntheses Institute, Al. Tysiąclecia Państwa Polskiego 13A, 24-110 Puławy, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vanja M. Tadić
  • Institute for Medicinal Plant Research “Dr Josif Pančić”, Tadeuša Košćuška 1, 11000 Belgrade, Serbia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Dušan Mišić
  • University of Belgrade, Faculty of Veterinary Medicine, Bulevar oslobodjenja 18, 11000 Belgrade, Serbia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Irena Žižović
  • University of Belgrade, Faculty of Technology and Metallurgy, Karnegijeva 4, 11000 Belgrade, Serbia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ivana Arsić / Agnieszka Dobrzyńska-Inger
  • New Chemical Syntheses Institute, Al. Tysiąclecia Państwa Polskiego 13A, 24-110 Puławy, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Dorota Kostrzewa
  • New Chemical Syntheses Institute, Al. Tysiąclecia Państwa Polskiego 13A, 24-110 Puławy, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2015-09-11 | DOI: https://doi.org/10.1515/chem-2015-0131

Abstract

Extracts obtained from hops (Humulus lupulus L., Cannabaceae) by supercritical fluid extraction (SFE), SFE followed by isomerization, as well as by conventional technique, were investigated for their chemical composition and antibacterial activity against selected foodborne pathogens and microorganisms capable to cause the food spoilage. The antibacterial activity of the extracts was compared with the antibacterial activity of xanthohumol, compound known for its broad pharmacological properties, isolated from the raw material remained after the SFE. Xanthohumol (XH, 96%) proved to posses the most prominent activity against all the tested strains, with the MIC values ranged between 2.5 and 20 μg mL-1. Supercritical hops extract and potassium isomerized supercritical hops extract showed strong antibacterial activity against the tested strains as well. Escherichia coli was not affected by the extracts, meaning that their oral admission would not cause the same problem as antibiotic application in intestinal flora. The chemical composition of the investigated hops extracts was analysed by GC-MS. Contents of α-acids, β-acids, iso-α-acids and xanthohumol in the samples were determined by HPLC.

Graphical Abstract

Keywords : supercritical hops extract; isomerized hops extract; supercritical CO2 extraction; xanthohumol; antibacterial activity

References

  • [1] Zanoli P., Zavatti M., Pharmacognostic and pharmacological profile of Humulus lupulus L., J. Ethnopharmacol., 2008, 116, 383-396. Web of ScienceGoogle Scholar

  • [2] Obara K., Mizutani M., Hitomi Y., Yajima H., Kondo K., Isohumulones, the bitter component of beer, improve hyperglycemia and decrease body fat in Japanase subjects with prediabetes, Clin. Nutr., 2009, 28, 278-284. CrossrefGoogle Scholar

  • [3] Negri G., Di Santi D., Tabach R., Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic, Rev. Bras. Farmacogn., 2010, 20, 850-859. Web of ScienceCrossrefGoogle Scholar

  • [4] Yamaguchi N., Satoh-Yamaguchi K., Ono M., In vitro evaluation of antibacterial, anticollagenase, and antioxidant activities of hop components (Humulus lupulus) addressing acne vulgaris, Phytomedicine, 2009, 16, 369-376. Web of ScienceCrossrefGoogle Scholar

  • [5] Srinivasan, V., Goldberg, D., Haas, G.J., Contributions to the antimicrobial spectrum of hop constituents, Econ. Bot., 2004. 58, S230-S238. Google Scholar

  • [6] Brown A.J., Clubb D., Antiseptic properties of hops, J. I. Brewing, 1913, 16, 261-295. CrossrefGoogle Scholar

  • [7] Larson A.E., Yu R.Y.R., Lee O.A., Price S, Haas G.J, Johnson E.A., Antimicrobial activity of hop extracts against Listeria monocytogenes in media and in food, Inter. J. Food Microb.,1996, 33, 195-207. Google Scholar

  • [8] Shen C., Sofos J.N., Antilisterial activity of hops beta acids in broth with or without other antimicrobials, J. Food Sci., 2008, 73, M438-M442. Web of ScienceGoogle Scholar

  • [9] Arimoto-Kobayashi S., Takata J., Nakandakari N., Fujioka R., Okamoto K., Konuma T., Inhibitory effects of heterocyclic Amine - induced DNA adduct formation in mouse liver and lung by beer, J. Agric. Food Chem., 2005, 53, 812-815. Google Scholar

  • [10] Gerhäuser C., Broad spectrum anti-infective potential of xanthohumol from hop (Humulus lupulus L.) in comparison with activities of other hop constituents and xanthohumol metabolites, Mol. Nutr. Food Res., 2005, 49, 827-831. Google Scholar

  • [11] Teuber M., Schmareck A.F., Membrane leakage in Bacillus subtilis 168 induced by the hop constituents lupulone, humulone, isohumulone and humulinic acid, Arch. Mikrobiol., 1973, 94, 159-171. Google Scholar

  • [12] Schmalreck A.F., Teuber M., Reininger W., Hartl A., Structural features determining antibiotic potencies of natural and synthetic hop bitter resins, their precursors and derivatives, Can. J. Microbiol., 1975, 21, 205-212. CrossrefGoogle Scholar

  • [13] Van Cleemput M., Cattoor K., De Bosscher K., Haegemang., De Keukeleire D., Heyerick A., Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds, J. Nat. Prod., 2009, 72, 1220-1230. Web of ScienceGoogle Scholar

  • [14] Teuber M., Low antibiotic potency of isohumulone, Appl. Microbiol., 1970, 19, 871. Google Scholar

  • [15] Yoshimaru T., Komatsu M., Tashiro E., Imoto M., Osada H., Miyoshi Y., et al., Xanthohumol suppresses oestrogen-signalling in breast cancer through the inhibition of BIG3-PHB2 interactions, Sci. Rep., 2014, 4, 7355, DOI: 10.1038/srep07355. Google Scholar

  • [16] Zhao F., Watanabe Y., Nozawa H., Daikonnya A., Kondo K., Kitanaka S., Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus), J. Nat. Prod., 2005, 68, 43-49. CrossrefGoogle Scholar

  • [17] Kostrzewa D., Dobrzyńska-Inger A., Rój E., Experimental data on xanthohumol solubility in supercritical carbon dioxide, Fluid Phase Equilib., 2013, 360, 445-450. Google Scholar

  • [18] Adams R.P., Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed., Allured Publishing Corporation, Carol Stream, IL, USA, 2007. Google Scholar

  • [19] Automated Mass Spectral Deconvolution and Identification System software (AMDIS ver. 2.1National Institute of Standards and Technology (NIST), Standard Reference Data Program, Gaithersburg, MD, USA, 2005. Google Scholar

  • [20] Clinical and Laboratory Standards Institute, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved standard-6th edition. M7-A6, Clinical and Laboratory Standards Institute, Wayne, PA, USA, 14, 2003. Google Scholar

  • [21] Taniguchi Y., Matsukura Y., Ozaki H., Nishimura K., Shindo K., Identification and quantification of the oxidation products derived from α-acids and β-acids during storage of hops ( Humulus lupulus L.), J Agric Food Chem., 2013, 61, 3121-3130. Web of ScienceGoogle Scholar

  • [22] James P., Tynan T., Murrough I. Mc., Byrne J., Preparation, purification and separation by high performance liquid chromatography of humulinic acids, dehydrohumulinic acids, and hulupones, J. Inst. Brew., 1990, 96, 137-141. Google Scholar

  • [23] Zhang X., Liang X., Xiao H., Xu Q., Direct characterization of bitter acids in a crude hop extract by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry, J. Am. Soc. Mass Spectrom., 2004, 15, 180-187. Google Scholar

  • [24] Ligor M., Stankevičius M., Wenda-Piesik A., Obelevičius K., Ragažinskienė O., Stanius Ž., et al., Comparative gas chromatographic–Mass spectrometric evaluation of hop (Humulus lupulus L.) essential oils and extracts obtained using different sample preparation methods, Food Anal. Method., 2014, 7, 1433-1442. Web of ScienceCrossrefGoogle Scholar

  • [25] Helmja K., Vaher M., Püssa T., Kamsol K., Orav A., Kaljurand M., Bioactive components of the hop strobilus: comparison of different extraction methods by capillary electrophoretic and chromatographic methods, J. Chromatogr. A, 2007, 1155, 222-229. Web of ScienceGoogle Scholar

  • [26] Mizobuchi S., Sato Y., A new flavanone with antifungal activity isolated from hops, Agric. Biol. Chem., 1985, 48, 2771-2775. Google Scholar

  • [27] Lu X., Liu J., Hou F., Liu Z., Cao X., Seo H., Gao B., Cholesterol induces pancreatic β cell apoptosis through oxidative stress pathway, Cell Stress Chaperon., 2011, 16, 539-548. Web of ScienceCrossrefGoogle Scholar

About the article

Received: 2015-02-23

Accepted: 2015-07-27

Published Online: 2015-09-11


Citation Information: Open Chemistry, Volume 13, Issue 1, ISSN (Online) 2391-5420, DOI: https://doi.org/10.1515/chem-2015-0131.

Export Citation

© 2015 Edward Rój et al.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Agnieszka Bartmańska, Ewa Wałecka-Zacharska, Tomasz Tronina, Jarosław Popłoński, Sandra Sordon, Ewa Brzezowska, Jacek Bania, and Ewa Huszcza
Molecules, 2018, Volume 23, Number 8, Page 2059
[2]
Lucas Mattos Duarte, Luiz Henrique Cantarino Adriano, and Marcone Augusto Leal de Oliveira
ELECTROPHORESIS, 2018
[3]
Yuki Hoshino, Masaki Ota, Yoshiyuki Sato, Richard Lee Smith, and Hiroshi Inomata
The Journal of Supercritical Fluids, 2018
[4]
Masaki Ota, Satoshi Sugahara, Yoshiyuki Sato, Richard Lee Smith, and Hiroshi Inomata
Fluid Phase Equilibria, 2017, Volume 434, Page 44
[5]
Thomasz Wasilewski, Dominik Czerwonka, and Urszula Piotrowska
Tenside Surfactants Detergents, 2016, Volume 53, Number 4, Page 368

Comments (0)

Please log in or register to comment.
Log in