Skip to main content
Log in

Hydrophilic and lipophilic characteristics of non-fatty acid moieties: significant factors affecting antibacterial activity of lauric acid esters

  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

A Correction to this article was published on 12 June 2018

This article has been updated

Abstract

It has been proposed that the hydrophilic and/or lipophilic characteristics of fatty acid derivatives affect their antibacterial activities according to their ability to incorporate into the bacterial cell membrane. To verify this hypothesis, six kinds of lauric acid derivatives esterified with different non-fatty acid moieties were selected to confirm whether antibacterial activity from their precursor (i.e., lauric acid) is retained or lost. Three compounds, monolaurin, sucrose laurate, and erythorbyl laurate, exerted bacteriostatic and bactericidal effects against Gram-positive bacteria, while the others showed no inhibitory activity. Interestingly, the calculated log P (octanol–water partition coefficient) values of monolaurin, sucrose laurate, and erythorbyl laurate were − 4.122, − 0.686, and 3.670, respectively, relatively lower than those of the other compounds without antibacterial activity. Moreover, the hydrophilic-lipophilic balance values of the three compounds with antibacterial activity were higher than those of the other compounds, corresponding to the log P result.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Change history

  • 12 June 2018

    In the original version of these 14 articles the reference list was unfortunately not represented according to the journal’s new bibliographical style, which should have been implemented from January 2018.

References

  1. Altieri C, Bevilacqua A, Cardillo D, Sinigaglia M. Effectiveness of fatty acids and their monoglycerides against gram‐negative pathogens. Int J Food Sci Tech. 44: 359–366 (2009)

    Article  CAS  Google Scholar 

  2. Arouri A, Mouritsen OG. Membrane-perturbing effect of fatty acids and lysolipids. Prog Lipid Res. 52: 130–140 (2013)

    Article  CAS  PubMed  Google Scholar 

  3. Bechert T, Steinrücke P, Guggenbichler J-P. A new method for screening anti-infective biomaterials. Nat Med. 6: 1053–1056 (2000)

    Article  CAS  PubMed  Google Scholar 

  4. Dayrit FM. The Properties of Lauric Acid and Their Significance in Coconut Oil. J Am Oil Chem Soc. 92: 1–15 (2015)

    Article  CAS  Google Scholar 

  5. Desbois AP, Smith VJ. Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential. Appl Microbiol Biotechnol. 85: 1629–1642 (2010)

    Article  CAS  PubMed  Google Scholar 

  6. Friberg S, Larsson K, Sjoblom J. Food emulsions. 4th edn. CRC Press, Boca Raton, FL (2003)

    Book  Google Scholar 

  7. Guo X, Rong Z, Ying X. Calculation of hydrophile–lipophile balance for polyethoxylated surfactants by group contribution method. J Colloid Interface Sci. 298: 441–450 (2006)

    Article  CAS  PubMed  Google Scholar 

  8. Hopkins AL, Keserü GM, Leeson PD, Rees DC, Reynolds CH. The role of ligand efficiency metrics in drug discovery. Nat Rev Drug Discov. 13: 105 (2014)

    Article  CAS  PubMed  Google Scholar 

  9. Hyldgaard M, Sutherland DS, Sundh M, Mygind T, Meyer RL. Antimicrobial Mechanism of Monocaprylate. Appl Environ Microbiol. 78: 2957–2965 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Kabara J, Vrable R, Jie MLK. Antimicrobial lipids: natural and synthetic fatty acids and monoglycerides. Lipids. 12: 753–759 (1977)

    Article  CAS  PubMed  Google Scholar 

  11. Kabara JJ, Swieczkowski DM, Conley AJ, Truant JP. Fatty acids and derivatives as antimicrobial agents. Antimicrob Agents Chemother. 2: 23–28 (1972)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Karmee SK. Lipase catalyzed synthesis of ester-based surfactants from biomass derivatives. Biofuels, Bioprod Biorefin. 2: 144–154 (2008)

    Article  CAS  Google Scholar 

  13. Lieberman S, Enig MG, Preuss HG. A review of monolaurin and lauric acid: natural virucidal and bactericidal agents. Alternative and Complementary Therapies. 12: 310–314 (2006)

    Article  Google Scholar 

  14. Luther M, Parry J, Moore J, Meng J, Zhang Y, Cheng Z, Yu LL. Inhibitory effect of Chardonnay and black raspberry seed extracts on lipid oxidation in fish oil and their radical scavenging and antimicrobial properties. Food Chem. 104: 1065–1073 (2007)

    Article  CAS  Google Scholar 

  15. Magalhães L, Nitschke M. Antimicrobial activity of rhamnolipids against Listeria monocytogenes and their synergistic interaction with nisin. Food Control. 29: 138–142 (2013)

    Article  CAS  Google Scholar 

  16. Meylan WM, Howard PH. Atom/fragment contribution method for estimating octanol–water partition coefficients. J Pharm Sci. 84: 83–92 (1995)

    Article  CAS  PubMed  Google Scholar 

  17. Nakatsuji T, Kao MC, Fang J-Y, Zouboulis CC, Zhang L, Gallo RL, Huang C-M. Antimicrobial property of lauric acid against Propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris. J Invest Dermatol. 129: 2480–2488 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Nobmann P, Bourke P, Dunne J, Henehan G. In vitro antimicrobial activity and mechanism of action of novel carbohydrate fatty acid derivatives against Staphylococcus aureus and MRSA. J Appl Microbiol. 108: 2152–2161 (2010)

    CAS  PubMed  Google Scholar 

  19. Park K-M, Jo S-K, Yu H, Park J-Y, Choi SJ, Lee CJ, Chang P-S. Erythorbyl laurate as a potential food additive with multi-functionalities: Antibacterial activity and mode of action. Food Control. 86: 138–145 (2018)

    Article  CAS  Google Scholar 

  20. Park K-M, Lee MJ, Jo S-K, Choi SJ, Lee J, Chang P-S. Erythorbyl laurate as a potential food additive with multi-functionalities: Interfacial characteristics and antioxidant activity. Food Chem. 215: 101–107 (2017)

    Article  CAS  PubMed  Google Scholar 

  21. Park K-M, Sung H, Lee J, Chang P-S. Lipase-catalysed synthesis of erythorbyl laurate in acetonitrile. Food Chem. 129: 59–63 (2011)

    Article  CAS  Google Scholar 

  22. Pridmore A, Burch D, Lees P. Determination of minimum inhibitory and minimum bactericidal concentrations of tiamulin against field isolates of Actinobacillus pleuropneumoniae. Vet Microbiol. 151: 409–412 (2011)

    Article  CAS  PubMed  Google Scholar 

  23. Royer M, Nollet M, Catté M, Collinet M, Pierlot C. Towards a new universal way to describe the required hydrophilic lipophilic balance of oils using the phase inversion temperature of C10E4/n-octane/water emulsions. Colloids Surf Physicochem Eng Aspects. 536: 165–171 (2018)

    Article  CAS  Google Scholar 

  24. Sabljic A, Guesten H, Hermens J, Opperhuizen A. Modeling octanol/water partition coefficients by molecular topology: chlorinated benzenes and biphenyls. Environ Sci Technol. 27: 1394–1402 (1993)

    Article  CAS  Google Scholar 

  25. Watanabe Y, Ishido E, Fang X, Adachi S, Matsuno R. Oxidation kinetics of linoleic acid in the presence of saturated acyl l-ascorbate. J Am Oil Chem Soc. 82: 389–392 (2005)

    Article  CAS  Google Scholar 

  26. Wiegand I, Hilpert K, Hancock RE. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc. 3: 163–175 (2008)

    Article  CAS  PubMed  Google Scholar 

  27. Yan Y, Bornscheuer UT, Schmid RD. Lipase-catalyzed synthesis of vitamin C fatty acid esters. Biotechnol Lett. 21: 1051–1054 (1999)

    Article  CAS  Google Scholar 

  28. Yi B, Kim M-J, Lee J. Effects of emulsifier charges on the oxidative stability in oil-in-water emulsions under riboflavin photosensitization. Food Sci Biotechnol. 25: 1003–1009 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Zhao L, Zhang H, Hao T, Li S. In vitro antibacterial activities and mechanism of sugar fatty acid esters against five food-related bacteria. Food Chem. 187: 370–377 (2015)

    Article  CAS  PubMed  Google Scholar 

  30. Zheng CJ, Yoo JS, Lee TG, Cho HY, Kim YH, Kim WG. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Lett. 579: 5157–5162 (2005)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT, & Future Planning (NRF-2017R1A2B4009230) and the Ministry of Education (NRF-R1A6A3A01012396).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Pahn-Shick Chang.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 231 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Park, KM., Lee, S.J., Yu, H. et al. Hydrophilic and lipophilic characteristics of non-fatty acid moieties: significant factors affecting antibacterial activity of lauric acid esters. Food Sci Biotechnol 27, 401–409 (2018). https://doi.org/10.1007/s10068-018-0353-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-018-0353-x

Keywords

Navigation