Download PDF
Planta Med 2020; 86(15): 1089-1096
DOI: 10.1055/a-1158-1699
Biological and Pharmacological Activity
Original Papers

Composition and Antibacterial Effect of Mint Flavorings in Candies and Food Supplements[#]

Karmen Kapp
1   Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, Finland
,
Anne Orav
2   Institute of Chemistry, Tallinn University of Technology, Estonia
,
Mati Roasto
3   Chair of Food Hygiene and Veterinary Public Health, Estonian University of Life Sciences, Estonia
,
Ain Raal
4   Institute of Pharmacy, Faculty of Medicine, University of Tartu, Estonia
,
Tõnu Püssa
3   Chair of Food Hygiene and Veterinary Public Health, Estonian University of Life Sciences, Estonia
,
Heikki Vuorela
1   Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, Finland
,
Päivi Tammela
1   Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, Finland
,
Pia Vuorela   †
1   Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, Finland
› Author AffiliationsSupported by: Pia Vuorela Academy of Finland/grant no. 272266
Supported by: Päivi Tammela Academy of Finland/grant no. 277001
Supported by: Karmen Kapp FinPharma Doctoral Programme
› Further Information
    Permissions and Reprints

Abstract

Mint flavorings are widely used in confections, beverages, and dairy products. For the first time, mint flavoring composition of mint candies and food supplements (n = 45), originating from 16 countries, as well as their antibacterial properties, was analyzed. The flavorings were isolated by Marcussonʼs type micro-apparatus and analyzed by GC-MS. The total content of the mint flavoring hydrodistilled extracts was in the range of 0.01 – 0.9%. The most abundant compounds identified in the extracts were limonene, 1,8-cineole, menthone, menthofuran, isomenthone, menthol and its isomers, menthyl acetate. The antimicrobial activity of 13 reference substances and 10 selected mint flavoring hydrodistilled extracts was tested on Escherichia coli and Staphylococcus aureus by broth dilution method. Linalool acetate and (−)-carvone, as most active against both bacteria, had the lowest MIC90 values. (+)-Menthyl acetate, (−)-menthyl acetate, and limonene showed no antimicrobial activity. Three of the tested extracts had antimicrobial activity against E. coli and 8 extracts against S. aureus. Their summary antimicrobial activity was not always in concordance with the activities of respective reference substances.

Key words

Mentha - Lamiaceae - GC-MS - terpenoids - Escherichia coli - Staphylococcus aureus

# In Honour of Em. o. Univ. Prof. Mag. pharm. Dr. Wolfgang Kubelka on the occasion of his 85th birthday and in recognition of his outstanding contribution to natural product research.


† Deceased 1.10.2017.


Supporting Information

    Relative total content (%; w/w) and percentage composition (%) of mint flavoring hydrodistilled extracts, as well as retention indices of compounds, are available in Supporting information (Table 1S, sugar candies, pastilles, and food supplements; Table 2S, chocolates).

    Inhibition zones (mm) of reference substances and mint flavoring hydrodistilled extracts (10%; v/v in n-hexane) determined during preliminary susceptibility testing by agar diffusion method are available in Supporting information, Table 3S.

  • Supporting Information


Publication History

Received: 15 January 2020

Accepted: 07 April 2020

Article published online:
04 May 2020

© 2020. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Cohen SM, Eisenbrand G, Fukushima S, Gooderham NJ, Guengerich FP, Hecht SS, Rietjens IMCM, Bastaki M, Davidsen JM, Harman CL, McGowen MM, Taylor SV. FEMA GRAS assessment of natural flavor complexes: Mint, buchu, dill and caraway derived flavoring ingredients. Food Chem Toxicol 2020; 135: 110870
    CrossrefPubMedGoogle Scholar
  • 2 Hayes JR, Stavanja MS, Lawrence BM. Mint. The Genus Mentha. Medical and aromatic Plants – Industrial Profiles. London, New York: CRC Press, Taylor & Francis Group; 2006: 422-483
    Google Scholar
  • 3 Kanatt SR, Chander R, Sharma A. Chitosan and mint mixture: a new preservative for meat and meat products. Food Chem 2008; 107: 845-852
    CrossrefPubMedGoogle Scholar
  • 4 Najeeb AP, Mandal PK, Pal UK. Efficacy of leaves (drumstick, mint and curry leaves) powder as natural preservatives in restructured chicken block. Int J Food Sc Tech 2015; 52: 3129-3133
    CrossrefPubMedGoogle Scholar
  • 5 Shahdadi F, Mirzaie H, Kashaninejad M, Khomeiri M, Ziaiifar AM, Akbarian A. Effects of various essential oils on chemical and sensory characteristics and activity of probiotic bacteria in drinking yoghurt. Agric Communic 2015; 3: 16-21
    PubMedGoogle Scholar
  • 6 Verma A, Ansari R, Broadway AA. Preparation of herbal ice cream by using aloe vera with mint flavor. J Pharmacogn Phytochem 2018; 7: 391-394
    PubMedGoogle Scholar
  • 7 Ibrahim OAE, Mohamed AG, Bahgaat WK. Natural peppermint-flavored cheese. Acta Sci Pol Technol Aliment 2019; 18: 75-85
    PubMedGoogle Scholar
  • 8 Arctander S. Perfume and Flavor Chemicals (Aroma Chemicals). 2nd edition. Montclair, New Jersey: Allured Publishing Co; 1969
    Google Scholar
  • 9 Tucker AO. Mint. The Genus Mentha. Medical and aromatic Plants – Industrial Profiles. London, New York: CRC Press, Taylor & Francis Group; 2006: 519-522
    Google Scholar
  • 10 Eccles R. Menthol and related cooling compounds. J Pharm Pharmacol 1994; 46: 618-630
    CrossrefPubMedGoogle Scholar
  • 11 Salles C. Odour-taste Interactions in Flavor Perception. In: Etievant P, Voileey A. eds. Flavor in Food. Woodhead Publishing Series in Food Science, Technology and Nutrition. Sawston, Cambridge: Woodhead Publishing; 2006: 345-363
    Google Scholar
  • 12 Parker JK. Introduction to Aroma Compounds in Food. In: Parker JK, Elmore JS, Metheven L. eds. Flavor Development, Analysis and Perception in Food Beverages Woodhead Publishing Series in Food Science, Technology and Nutrition. Sawston, Cambridge: Woodhead Publishing; 2015: 3-30
    Google Scholar
  • 13 İşcan G, Kįrįmer N, Kürkcüoğlu M, Başer KHC, Demįrcį F. Antimicrobial screening of Mentha piperita essential oils. J Agric Food Chem 2002; 50: 3943-3946
    CrossrefPubMedGoogle Scholar
  • 14 Mkaddem M, Bouajila J, Monia E, Lebrihi A, Mathieu F, Romdhane M. Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils. J Food Sci 2009; 74: M358-M363
    CrossrefPubMedGoogle Scholar
  • 15 Hussain AI, Anwar F, Nigam SP, Ashraf M, Gilani AH. Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species. J Sci Food Agric 2010; 90: 1827-1836
    CrossrefPubMedGoogle Scholar
  • 16 Reddy DN, Al-Rajab AJ, Sharma M, Mary Moses M, Reddy GR, Albratty M. Chemical constituents, in vitro antibacterial and antifungal activity of Mentha × piperita L. (peppermint) essential oils. J King Saud Univ Sci 2019; 31: 528-533
    CrossrefPubMedGoogle Scholar
  • 17 Moro IJ, Gondo GDGA, Pierri EG, Pietro RCLR, Soares CP, de Sousa DP, dos Santos AG. Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives. Braz J Pharm 2017; 53: e00076
    PubMedGoogle Scholar
  • 18 Orav A, Kann J. Determination of peppermint and orange aroma compounds in food and beverages. Proc Estonian Acad Sci Chem 2001; 50: 217-225
    CrossrefPubMedGoogle Scholar
  • 19 Mimica-Dukić N, Božin B, Soković M, Mihajlović B, Matavulj M. Antimicrobial and antioxidant activities of three Mentha species essential oils. Planta Med 2003; 69: 413-419
    Article in Thieme ConnectPubMedGoogle Scholar
  • 20 Orav A, Kapp K, Raal A. Chemosystematic markers for the essential oils of Mentha spp. leaves cultivated or growing naturally in Estonia. Proc Estonian Acad Sci Chem 2012; 62: 175-186
    CrossrefPubMedGoogle Scholar
  • 21 Kapp K, Hakala E, Orav A, Pohjala L, Vuorela P, Püssa T, Vuorela H, Raal A. Commercial peppermint (Mentha × piperita L.) teas: antichlamydial effect and polyphenolic composition. Food Res Int 2013; 53: 758-766
    CrossrefPubMedGoogle Scholar
  • 22 de Sousa Barros A, de Morais SM, Ferreira PATF, Viera ÍGP, Craveiro AA, dos Santos Fontenelle RO, de Menezes JESA, da Silva FWF, de Sousa HA. Chemical composition and functional properties of essential oils from Mentha species. Ind Crops Prod 2015; 76: 557-564
    CrossrefPubMedGoogle Scholar
  • 23 Shabani B, Rezaei R, Charehgani H, Salehi A. Study on antibacterial effect of essential oils of six plant species against Pseudomonas syringae pv. syringae Van Hall 1902 and Pseudomonas fluorescens Migula 1894. J Plant Physiol 2019; 101: 671-675
    PubMedGoogle Scholar
  • 24 Beckett S. Preparation of chocolate with limonene to reduce fat content. US Patent 6200625, 2001
    PubMedGoogle Scholar
  • 25 Do T, Vieira J, Hargreaves J, Wolf B, Mitchell J. Impact of limonene on the physical properties of reduced fat chocolate. J Am Oil Chem Soc 2008; 85: 911-920
    CrossrefPubMedGoogle Scholar
  • 26 Ray J, MacNaughtan W, Chong P, Vieira J, Wolf B. The effect of limonene on the crystallization of cocoa butter. J Am Oil Chem Soc 2012; 89: 437-445
    CrossrefPubMedGoogle Scholar
  • 27 Rigolle A, Goderis B, Van Den Abeele K, Foubert I. Isothermal crystallization behavior of cocoa butter at 17 and 20 °C with and without limonene. J Agric Food Chem 2016; 64: 3405-3416
    CrossrefPubMedGoogle Scholar
  • 28 Stapley AGF, Tewkesbury H, Fryer PJ. The effects of shear and temperature history on the crystallization of chocolate. J Am Oil Chem Soc 1999; 76: 677-685
    CrossrefPubMedGoogle Scholar
  • 29 Beckett ST. Science of Chocolate. 2nd edition. Cambridge: The Royal Society of Chemistry; 2008
    CrossrefGoogle Scholar
  • 30 van Malssen K, van Langevelde A, Peschar R, Schenk H. Phase behavior and extended phase scheme of static cocoa butter investigated with real-time X-ray powder diffraction. J Am Oil Chem Soc 1999; 76: 669-676
    CrossrefPubMedGoogle Scholar
  • 31 Menthyl acetate. Available at (Accessed January 13, 2020): https://pubchem.ncbi.nlm.nih.gov/compound/Menthyl-acetate
    PubMedGoogle Scholar
  • 32 Limonene. Available at (Accessed January 13, 2020): https://pubchem.ncbi.nlm.nih.gov/compound/Limonene
    PubMedGoogle Scholar
  • 33 Prasanthi D, Lakschmi PK. Terpenes: Effect of lipophilicity in enhancing transdermal delivery of alfuzosin hydrochloride. J Adv Pharm Tech Res 2012; 3: 216-223
    CrossrefPubMedGoogle Scholar
  • 34 Serota DG. 28-Day oral Toxicity Study in Rats: Compound B100. Unpublished report. Vienna, VA, USA: Hazelton Laboratories America Inc.;
    Google Scholar
  • 35 Thorup I, Würtzen G, Carstensen J, Olsen P. Short term toxicity study in rats dosed with peppermint oil. Toxicol Lett 1983; 19: 211-215
    CrossrefPubMedGoogle Scholar
  • 36 Kapperud G, Gustavsen S, Hellesnes I, Hansen AH, Lassen J, Hirn J, Jahkola M, Montenegro MA, Helmuth R. Outbreak of Salmonella typhimurium infection traced to contaminated chocolate and caused by strain lacking the 60-megadalton virulence plasmid. J Clin Microbiol 1990; 28: 2597-2601
    CrossrefPubMedGoogle Scholar
  • 37 Pearson LJ, Marth EH. Behavior of Listeria monocytogenes in the presence of cocoa, carrageenan, and sugar in a milk medium incubated with and without agitation. J Food Prot 1990; 53: 30-37
    CrossrefPubMedGoogle Scholar
  • 38 Baylis CL, MacPhee S, Robinson AJ, Griffiths R, Lilley K, Betts RP. Survival of Escherichia coli O157:H7, O111:H- and O26:H11 in artificially contaminated chocolate and confectionary products. Int J Food Microbiol 2004; 96: 35-48
    CrossrefPubMedGoogle Scholar
  • 39 Karagözlü N, Ergönül B, Özcan D. Determination of antimicrobial effect of mint and basil essential oils on survival of E. coli O157:H7 and S. typhimurium in fresh-cut lettuce and purslane. Food Control 2011; 22: 1851-1855
    CrossrefPubMedGoogle Scholar
  • 40 Evrendilek GA, Balasubramaniam VM. Inactivation of Listeria monocytogenes and Listeria innocua in yogurt drink applying combination of high pressure processing and mint essential oils. Food Control 2011; 22: 1435-1441
    CrossrefPubMedGoogle Scholar
  • 41 Bicchi C, Dʼamato A, Nano GM, Frattini C. Improved method for the analysis of small amounts of essential oils by microdistillation followed by capillary gas chromatography. J Chrom A 1983; 279: 409-416
    CrossrefPubMedGoogle Scholar
  • 42 Pikkemaat MG, Oostra-van Dijk S, Schouten J, Rapallini M, van Egmond HJ. A new microbial screening method for the detection of antimicrobial residues in slaughter animals: The Nouws antibiotic test (NAT-screening). Food Control 2008; 19: 781-789
    CrossrefPubMedGoogle Scholar
  • 43 Raudsepp P, Anton D, Roasto M, Meremäe K, Pedastsaar P, Mäesaar M, Raal A, Laikoja K, Püssa T. The antioxidative and antimicrobial properties of the blue honeysuckle (Lonicera caerulea L.), Siberian rhubarb (Rheum rhaponticum L.) and some other plants, compared to ascorbic acid and sodium nitrite. Food Control 2013; 31: 129-135
    CrossrefPubMedGoogle Scholar