Top

Journal of Materials Science

Published in:

19-11-2018 | Materials for life sciences

Characterization and antimicrobial activity of a 2-O-methyl-β-cyclodextrin inclusion complex containing hexahydro-β-acids

Authors: Na Lu, Haining Xu, Yumei Liu

Published in: Journal of Materials Science | Issue 5/2019

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

An inclusion complex of hexahydro-β-acids (HBA) and 2-O-methyl-β-cyclodextrin (M-β-CD) was prepared using the grinding method to improve the water solubility of HBA. Complex formation was assessed using ultraviolet and visible light (UV–Vis) spectroscopy, Fourier transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), nuclear magnetic resonance (¹HNMR), and scanning electron microscopy (SEM). Results showed that the HBA molecule resided within the M-β-CD cavity. The water solubility test indicated that the effect of the M-β-CD encapsulation extended beyond increasing the solubility of HBA. Furthermore, the antibacterial activity of the HBA/M-β-CD inclusion complex, pure HBA, and M-β-CD against different food-related microorganisms was determined by an agar diffusion assay. Particularly, the HBA/M-β-CD inclusion complex exhibited better antibacterial activity against Listeria monocytogenes. These results suggest that incorporation of the HBA/M-β-CD inclusion complex in food might effectively inhibit L. monocytogenes growth.

previous article In vitro evaluation of the biocompatibility and bioactivity of plasma electrolyte oxidized titania/calcium phosphate nanocoatings on Ti

next article Si, N-codoped carbon dots: preparation and application in iron overload diagnosis

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Guo Y, Huang E, Yang X, Zhang L, Yousef AE, Zhong J (2016) Isolation and characterization of a Bacillus atrophaeus strain and its potential use in food preservation. Food Control 60:511–518CrossRef

Srikanth CV, Cherayil BJ (2007) Intestinal innate immunity and the pathogenesis of salmonella enteritis. Immunol Res 37(1):61–78CrossRef

Powell DA, Jacob CJ, Chapman BJ (2011) Enhancing food safety culture to reduce rates of foodborne illness. Food Control 22(6):817–822CrossRef

Gandhi M, Chikindas ML (2007) Listeria: a foodborne pathogen that knows how to survive. Int J Food Microbiol 113(1):1–15CrossRef

Mclauchlin J (1996) The relationship between Listeria and listeriosis. Food Control 7(4–5):187–193CrossRef

White DG, Zhao S, Simjee S, Wagner DD, Mcdermott PF (2002) Antimicrobial resistance of foodborne pathogens. Microbes Infect 4(4):405–412CrossRef

Shen X, Sun X, Xie Q, Liu H, Zhao Y, Pan Y, Hwang CA, Wu VCH (2014) Antimicrobial effect of blueberry (Vaccinium corymbosum L.) extracts against the growth of Listeria monocytogenes and salmonella enteritidis. Food Control 35(1):159–165CrossRef

Gutiérrez-Larraínzar M, Rúa J, Caro I, Castro CD, Arriaga DD, García-Armesto MR, Valle PD (2012) Evaluation of antimicrobial and antioxidant activities of natural phenolic compounds against foodborne pathogens and spoilage bacteria. Food Control 26(2):555–563CrossRef

Wu CH, Qiu X, Bushway A, Harper L (2008) Antibacterial effects of American cranberry (Vaccinium macrocarpon) concentrate on foodborne pathogens. LWT Food Sci Technol 41(10):1834–1841CrossRef

10.

Tajkarimi MM, Ibrahim SA, Cliver DO (2010) Antimicrobial herb and spice compounds in food. Food Control 21(9):1199–1218CrossRef

11.

Lee KM, Jung JS, Song DK, Kraeuter M, Kim YH (1993) Effects of Humulus lupulus extract on the central nervous system in mice. Planta Med 59(7):A691CrossRef

12.

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(11):5100–5105CrossRef

13.

Natarajan P, Katta S, Andrei I, Babu RAV, Leonida M, Haas GJ (2008) Positive antibacterial co-action between hop (Humulus lupulus) constituents and selected antibiotics. Phytomedicine 15(3):194–201CrossRef

14.

Chin YC, Chang NC, Anderson HH (1949) Factors influencing the antibiotic activity of lupulon. J Clin Investig 28(5 Pt 1):909–915CrossRef

15.

Briggs DE, Boulton C, Brookes PA, Stevens R (2004) Brewing: science and practice. CRC Press, Boca RatonCrossRef

16.

de Almeida NE, do Nascimento ESP, Cardoso DR (2012) On the reaction of lupulones, hops β-acids, with 1-hydroxyethyl radical. J Agric Food Chem 60(42):10649–10656CrossRef

17.

Rückle L, Senn T (2006) Hop acids can efficiently replace antibiotics in ethanol production. Int Sugar J 108(1287):139–147

18.

Yajima H, Ikeshima E, Shiraki M, Kanaya T, Fujiwara D, Odai H, Tsuboyamakasaoka N, Ezaki O, Oikawa S, Kondo K (2004) Isohumulones, bitter acids derived from hops, activate both peroxisome proliferator-activated receptor alpha and gamma and reduce insulin resistance. J Biol Chem 279(32):33456–33462CrossRef

19.

Gouin S (2004) Microencapsulation: industrial appraisal of existing technologies and trends. Trends Food Sci Technol 15(7–8):330–347CrossRef

20.

Sanguansri P, Augustin MA (2006) Nanoscale materials development: a food industry perspective. Trends Food Sci Technol 17(10):547–556CrossRef

21.

Abarca RL, Rodríguez FJ, Guarda A, Galotto MJ, Bruna JE (2016) Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component. Food Chem 196:968–975CrossRef

22.

Marques HMC (2010) A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour Fragr J 25(5):313–326CrossRef

23.

Song LX, Bai L, Xu XM, He J, Pan SZ (2009) Inclusion complexation, encapsulation interaction and inclusion number in cyclodextrin chemistry. Coord Chem Rev 253(9–10):1276–1284CrossRef

24.

Carrier RL, Miller LA, Ahmed I (2007) The utility of cyclodextrins for enhancing oral bioavailability. J Controll Release 123(2):78–99CrossRef

25.

Brewster ME, Loftsson T (2007) Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59(7):645–666CrossRef

26.

Tomren MA, Másson M, Loftsson T, Tønnesen HH (2007) Studies on curcumin and curcuminoids XXXI. Symmetric and asymmetric curcuminoids: stability, activity and complexation with cyclodextrin. Int J Pharm 338(1–2):27–34CrossRef

27.

Blanchemain N, Karrout Y, Tabary N, Neut C, Bria M, Siepmann J, Hildebrand HF, Martel B (2011) Methyl-β-cyclodextrin modified vascular prosthesis: influence of the modification level on the drug delivery properties in different media. Acta Biomater 7(1):304–314CrossRef

28.

Liu Y, Tang J, Liu K, Chen D (2008) Study on synthesis technology of hexahydro-beta acids, a novel antibacterial agent. Sci Technol Food Ind 29(11):225–229

29.

Hill LE, Gomes C, Taylor TM (2013) Characterization of beta-cyclodextrin inclusion complexes containing essential oils (trans-cinnamaldehyde, eugenol, cinnamon bark, and clove bud extracts) for antimicrobial delivery applications. LWT Food Sci Technol 51(1):86–93CrossRef

30.

Zhang D, Zhang J, Jiang K, Li K, Cong Y, Pu S, Jin Y, Lin J (2016) Preparation, characterisation and antitumour activity of β-, γ- and HP-β-cyclodextrin inclusion complexes of oxaliplatin. Spectrochim Acta Part A Mol Biomol Spectrosc 152:501–508CrossRef

31.

Gómez-Estaca J, Lacey ALD, López-Caballero ME, Gómez-Guillén MC, Montero P (2010) Biodegradable gelatin–chitosan films incorporated with essential oils as antimicrobial agents for fish preservation. Food Microbiol 27(7):889–896CrossRef

32.

Atwood JL, Lehn JM (1996) Comprehensive supramolecular chemistry, vol 34(3). Pergamon, New York, pp 199–206

33.

Gao YA, Li ZH, Du JM, Prof BXH, Dr GZL, Hou WG, Shen D, Zheng LQ, Zhang GY (2005) Preparation and characterization of inclusion complexes of β-cyclodextrin with ionic liquid. Chemistry 11(20):5875–5880CrossRef

34.

Yuan C, Jin Z, Xu X (2012) Inclusion complex of astaxanthin with hydroxypropyl-β-cyclodextrin: UV, FTIR, ¹H NMR and molecular modeling studies. Carbohydr Polym 89(2):492–496CrossRef

35.

Michalska P, Wojnicz A, Ruiz-Nuño A, Abril S, Buendia I, León R (2017) Inclusion complex of ITH12674 with 2-hydroxypropyl-β-cyclodextrin: preparation, physical characterization and pharmacological effect. Carbohydr Polym 157:94–104CrossRef

36.

Szente L, Szejtli J (2004) Cyclodextrins as food ingredients. Trends Food Sci Technol 15(3–4):137–142CrossRef

Title: Characterization and antimicrobial activity of a 2-O-methyl-β-cyclodextrin inclusion complex containing hexahydro-β-acids
Authors: Na Lu
Haining Xu
Yumei Liu
Publication date: 19-11-2018
Publisher: Springer US
Published in: Journal of Materials Science / Issue 5/2019
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI: https://doi.org/10.1007/s10853-018-3148-9

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 5/2019

Effect of the preparation method on the morphology and proton conductivity of membranes based on sulfonated ABA triblock copolymers

Design and efficient fabrication of micro-sized clusters of hydroxyapatite nanorods for dental resin composites

Observation of the transformation of silica phytoliths into SiC and SiO2 particles in biomass-derived carbons by using SEM/EDS, Raman spectroscopy, and XRD

Atomistic modeling of interfacial segregation and structural transitions in ternary alloys

3D microstructure of magnesium potassium phosphate ceramics from X-ray tomography: new insights into the reaction mechanisms

Manufacture of glass and mirrors from lunar regolith simulant

Premium Partners