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Comparative Study of Antimicrobial and Cytotoxic Effects of 1, 2-Octanediol and 1, 2-Octanediol Galactoside

1, 2-Octanediol과 1, 2-Octanediol Galactoside의 항균력 및 세포독성 비교연구

  • Kim, Jun-Sub (Department of Biotechnology, Korea National University of Transportation) ;
  • Jin, Hong-Jong (KPT Co., LTD) ;
  • Jung, Kyung-Hwan (Department of Biotechnology, Korea National University of Transportation)
  • 김준섭 (한국교통대학교 생명공학전공) ;
  • 진홍종 ((주)케이피티 연구소) ;
  • 정경환 (한국교통대학교 생명공학전공)
  • Received : 2021.04.27
  • Accepted : 2021.06.28
  • Published : 2021.06.30

Abstract

To develop a safer cosmetic preservative, we carried out a comparative study on characteristics of OD and OD-gal, where OD-gal was synthesized from OD using E. coli β-gal. OD-gal synthesis was confirmed by mass spectrometry analysis as sodium adduct ion (m/z=331.1731) and protonated ion (m/z=309.1926) of OD-gal. To compare the antimicrobial activities of OD and newly synthesized OD-gal, MIC values were investigated using E. coli, S. aureus, C. albicans, and A. niger. As a result, it was observed that there was no remarkable difference between MIC values of OD and OD-gal. In addition, to compare the cytotoxicity of OD-gal and OD, HaCaT cells were treated with OD or OD-gal, and then cell viability was quantified using EZ-Cytox assay. In the case of 1.5% OD, the cell viability was 64% at 24 h and 42% at 48 h compared to the control, and cell viability of 1.5% OD-gal-treated cells showed no significant change at 24 h and was 85% at 48 h. Consequently, the cytotoxicity of OD-gal-treated cells was reduced by more than 40% when compared with that of OD-treated cells. Thus, the newly synthesized OD-gal in this study is safer than the existing OD used as a cosmetic additive. In the future, OD-gal will be applicable as a substitute for OD as a less toxic preservative for the cosmetic industry.

안전성이 강화된 화장품용 방부제 소재를 개발하기 위하여, 대장균 β-gal을 이용하여 OD로부터 합성된 OD-gal의 성능을 기존의 OD와 비교하는 연구를 수행하였다. 먼저, mass spectrometry 분석을 통하여 OD-gal의 sodium adduct ion (m/z=331.1731)과 protonated ion (m/z=309.1926)으로 OD-gal 합성을 확인하였다. 새롭게 합성된 OD-gal과 OD의 항균력 비교를 위하여 E. coli, S. aureus, C. albicans, A. niger에 대한 MIC 값을 측정하였다. 그 결과, OD-gal과 OD의 MIC 값 사이에 그렇게 큰 차이를 관찰할 수 없었다. 또한, OD-gal과 OD의 세포독성을 비교하기 위하여, HaCaT 세포에 OD 또는 OD-gal을 처리한 후, 세포 생존율을 EZ-Cytox assay를 이용하여 정량 하였다. 1.5% OD의 경우에는 24 시간에서 세포생존율이 대조군과 비교하여 64%, 48 시간에서는 42%로 나타났고, 1.5% OD-gal을 처리한 세포의 세포생존율은 24 시간에서 유의적인 변화가 없었지만, 48 시간에서는 85%로 나타났다. 결국 OD-gal은 OD와 비교해서 약 40% 이상의 세포독성 감소효과가 있는 것으로 확인되었다. 이러한 결과로부터 OD에 한 분자의 galactose를 결합시킴으로 인하여 항균력은 어느 정도 유지하면서 피부 세포에 대한 독성이 감소된 OD-gal의 특성을 확인할 수 있었다. 앞으로 후속 연구를 진행하여 보다 안전한 화장품용 방부제 소재로서 OD-gal의 실용화 기반을 구축할 예정이다.

Keywords

Acknowledgement

본 연구는 2020년도 교육부의 재원으로 한국연구재단의 지원을 받아 수행된 지자체-대학 협력기반 지역혁신 사업의 결과입니다. 한국교통대학교 생명공학전공 안승혜, 이혜원, 신재혁, 오승준, 이재혁 학생이 본 연구에 도움을 주었습니다.

References

  1. W. Johnson Jr., W. F. Bergfeld, D. V. Belsito, R. A. Hill, C. D. Klaassen, D. Liebler, J. G. Marks Jr., R. C Shank, T. J. Slaga, P. W. Snyder, F. A. Andersen, "Safety assessment of 1, 2-glycols as used in cosmetics", International Journal of Toxicology, Vol.31(Supplement 2), pp. 147S-168S, (2012).
  2. E. Lee, S. An, S. -A. Cho, Y. Yun, J. Han, Y. K. Hwang, H. K. Kim, T. R. Lee, "The influence of alkane chain length on the skin irritation potential of 1, 2-alkanediols", International Journal of Cosmetic Science, Vol.33, Vol.5, pp. 421-425, (2011). https://doi.org/10.1111/j.1468-2494.2011.00646.x
  3. E. Q. Coelho, S. L. C. Wu, R. S. Nunes, V. M. S. Reis, "Contact urticaria following the use of a cosmetic containing caprylyl glycol: A case report", Contact Dermatitis, Vol.8, No.4, pp. 308-309, (2019).
  4. F. C. Kreeshan, J. D. L. Williams, "Allergic contact dermatitis to caprylyl glycol: A novel para-preservative allergen", Contact Dermatitis, Vol.83, No.5, pp. 418 -419, (2020). https://doi.org/10.1111/cod.13628
  5. H. -Y. Lee, H. -J. Jin, S. H. An, K. -H. Jung, "Confirmation of enzymatic synthesis of 1, 2-octanediol galactoside using mass spectrometry and NMR spectroscopy, Journal of the Korean Applied Science and Technology, Vol.38, No.3, pp. 824-831, (2021). https://doi.org/10.12925/JKOCS.2021.38.3.824
  6. S. E. Lee, T. M. Jo, H. -Y. Lee, J. Lee, K. -H. Jung, "β-Galactosidase-catalyzed synthesis of galactosyl chlorphenesin and its characterization", Applied Biochemistry and Biotechnology, Vol.171, No.6, pp. 1299-1312, (2013). https://doi.org/10.1007/s12010-013-0213-3
  7. S. E. Lee, H. -Y. Lee, K. -H. Jung, "Production of chlorphenesin galactoside by whole cells of β-galactosidasecontaining Escherichia coli", Journal of Microbiology and Biotechnology, Vol.23, No.6, pp. 826-832, (2013). https://doi.org/10.4014/jmb.1211.11009
  8. K. -H. Jung, H. -Y. Lee, "Escherichia coli β-galactosidase-catalyzed synthesis of 2-phenoxyethanol galactoside and its characterization", Bioprocess and Biosystems Engineering, Vol.38, No.2, pp. 365-372, (2015). https://doi.org/10.1007/s00449-014-1276-4
  9. H. -Y. Lee, K. -H. Jung, "Enzymatic synthesis of 2-phenoxyethanol galactoside by whole cells of β-galactosidasecontaining Escherichia coli", Journal of Microbiology and Biotechnology, Vol.24, No.9, pp. 1254-1259, (2014). https://doi.org/10.4014/jmb.1404.04004
  10. Y. -O. Kim, K. -H. Jung, "Enzymatic synthesis of 1, 2-hexandiol galactoside by whole cells of β-galactosidase-containing recombinant Escherichia coli", Journal of Life Science, Vol.26, No.5, pp. 608-613, (2016). https://doi.org/10.5352/JLS.2016.26.5.608
  11. Y. -O. Kim, H. -Y. Lee, K. -H. Jung, "NMR spectroscopy and mass spectrometry of 1, 2-hexanediol galactoside synthesized using Escherichia coli β-galactosidase", J. Korean Oil Chemists' Society", Vol.33, No.2, pp. 286-292, (2016). https://doi.org/10.12925/jkocs.2016.33.2.286
  12. H. -Y. Lee., K. -H. Jung, "NMR Spectroscopy and mass spectrometry of phenylethanol galactoside synthesized using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.37, No.5, pp. 1323-1329, (2020). https://doi.org/10.12925/JKOCS.2020.37.5.1323
  13. K. -H. Jung, "Optimal conditions for phenylethanol galactoside synthesis using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.38, No.1, pp. 99-106, (2021). https://doi.org/10.12925/JKOCS.2021.38.1.99
  14. J. -S. Kim, K. -H. Jung, "Cytotoxic effects of 1, 2-hexanediol and 1, 2-hexanediol galactoside on HaCaT cell", Journal of the Society of Cosmetic Scientists of Korea, Vol.44, No.3, pp. 343-347, (2018). https://doi.org/10.15230/SCSK.2018.44.3.343
  15. K. -H. Jung, "Enhanced enzyme activities of inclusion bodies of recombinant β-galactosidase via the addition of inducer analog after L-arabinose induction in the araBAD promoter system of Escherichia coli", Journal of Microbiology and Biotechnology, Vol.18, No.3, pp. 434-442, (2008).
  16. K. -H. Jung, "Purifications of phenoxyethanol galactoside and chlorphenesin galactoside using solvent extraction followed by gel chromatography", Journal of Oil and Applied Science, Vol.34, No.4, pp. 954-961, (2017). https://doi.org/10.12925/JKOCS.2017.34.4.954
  17. Y. -O. Kim, K. -H. Jung, "β-Galactosidase-catalyzed synthesis of 1,2-hexanediol galactoside and its purification using ethyl acetate extraction followed by silica gel chromatography", Journal of Korean Oil Chemists' Society, Vol.33 No.3, pp. 498-506, (2016). https://doi.org/10.12925/jkocs.2016.33.3.498
  18. I. K. Yoo, J. I. Kim, Y. K. Kang, "Conformational preferences and antimicrobial activities of alkanediols", Computational and Theoretical Chemistry, Vol.1064, pp. 15-24, (2015). https://doi.org/10.1016/j.comptc.2015.04.007
  19. R. Pillai, G. Schmaus, A. Pfeiffer, S. Lange, A. Trunet, "1, 2-Alkanediols for cosmetic preservation", Cosmetics and toiletries, Vol.123, No.10, pp. 53-64, (2008).
  20. W. -G. Cho, Y. -J. Cho, "Effects of various polyols on antiseptic system in emulsions", Journal of Korean Oil Chemists' Society, Vol.25, No.4, pp. 477-484, (2008).
  21. Y. -O. Kim, K. -H. Jung, "Water-holding capacity and antimicrobial activity of 1, 2-hexanediol galactoside synthesized by β-galactosidase", Journal of the Society of Cosmetic Scientists of Korea, Vol. 43, No. 4, pp. 373-379, (2017). https://doi.org/10.15230/SCSK.2017.43.4.373
  22. E. -Y. Choi, "Effect of phenoxyethanol and alkane diol mixture on the antimicrobial activity and antiseptic ability in cosmetics", Korean Journal of Aesthetics and Cosmetology, Vol.13, No.2, pp. 213-220, (2015).
  23. Z. Petric, J. Ruzic, I. Zuntar, "The controversies of parabens-an overview nowadays", Acta Pharmaceutica, Vol.71, No.1, pp. 17-32 (2021). https://doi.org/10.2478/acph-2021-0001
  24. S. Levy, A Dulichan, "Safety of a new preservative system containing 1,2-hexanediol and 1,2-octanediol for use in cosmetic products". Journal of the American Academy of Dermatology, Vol.58, pp. 55, (2008).
  25. J. Y. Suh, M. E. Yun, Y. S. Lee, S. H. Xuan, D. S. Park, S. N. Park, "Preservative efficacies according to the composition of 1, 3-butylene glycol and alkane diols in cosmetics", Journal of the Society of Cosmetic Scientists of Korea, Vol.44, No.4, pp. 363-373, (2018). https://doi.org/10.15230/scsk.2018.44.4.363
  26. J. I. Kim, Study on the challenge test and safety assessments of 1, 2-alkanediols in cosmetics, Doctoral dissertation, Hannam University, Daejeon, Korea, (2016).