• Journal of the Society of Cosmetic Scientists of Korea
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• v.41 no.2
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• pp.127-134
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• 2015

We investigated the growth-inhibitory activities of cosmetics and their preservatives against pathogens and resident skin bacteria. Of the tested cosmetics, preservatives such as parabens, 1,2-hexanediol, phenoxyethanol-contained toner, emulsion, cream and baby cream exhibited potent antibacterial effects against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Parabens, 1,2-hexanediol and phenoxyethanol inhibited the growth of pathogens, as well as skin-resident bacteria such as Staphilococcus epidermidis, Shigella flexneri, Enterobacter aerogenes and so on. The application of a basic cream containing phenoxyethanol to human skin was shown to disturb the skin microbiota: at the phylum level, Proteobacteria increased and at species level, 4P004125_s increased and Propionibacterium humerusii decreased. Based on these findings, parabens, 1,2-hexanediol and phenoxyethanol have antimicrobial activity and cosmetics containing phenoxyethanol may disturb skin microbiota.

• Journal of the Korean Applied Science and Technology
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• v.38 no.3
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• pp.629-637
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• 2021

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.

• Journal of Life Science
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• v.26 no.5
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• pp.608-613
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• 2016

Recently, it has been reported that some preservatives used in cosmetics lead to skin problems. Among the many cosmetic ingredients, 1, 2-hexanediol (HD) is used as both a preservative and humectant. In order to develop safer ingredients, we studied the synthesis of 1, 2-hexanediol galactoside (HD-G) by a transgalactosylation reaction using β-galactosidase (β-gal)-containing recombinant Escherichia coli cells. The transgalactosylation reaction was carried out under high-lactose conditions for 24 hr. After 12 hr had elapsed, a new spot was identified by thin-layer chromatography (TLC) analysis, and we presumptively designated this new spot as HD-G. Then, we carried out the purification of the presumptive HD-G spot from the reaction mixture by using silica gel chromatography, and its mass was measured by electrospray ionization-mass spectrometry. The purified new spot on the chromatograph was identified a sodium adduct ion ([M+Na]⁺, m/z = 303.1423) of HD-G. In addition, when purified HD-G was hydrolyzed using commercially available E. coli β-gal, it was observed that a galactose molecule was released from HD-G. That is, it was demonstrated that HD-G is a galactoside derivative of HD. Finally, we confirmed that HD-G was enzymatically synthesized by E. coli β -gal as a new molecular entity. In the future, we plan to determine the minimum inhibitory concentrations of HD-G against different bacterial species. The cytotoxicity of HD-G against human skin cells will also be examined. It is expected hopefully that the galactosylation of HD would improve the functionality of HD-G.

• Journal of the Korean Applied Science and Technology
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• v.33 no.2
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• pp.286-292
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• 2016

1, 2-Hexanediol galactoside (HD-gal) has been synthesized from 1, 2-hexanediol (HD), a cosmetic preservative, using recombinant Escherichia coli ${\beta}$-galactosidase (${\beta}$-gal) at the high lactose concentration (300 g/l). To confirm the molecular structure of synthesized HD-gal, NMR ($^1H$- and $^{13}C$-) spectroscopy and mass spectrometry of HD-gal were conducted. $^1H$ NMR spectrum of HD-gal showed multiple peaks corresponding to the galactocyl group, which is an evidence of galactocylation on HD. Downfield proton peaks at ${\delta}_H$ 4.44 ppm and multiple peaks from ${\delta}_H$3.96~3.58 ppm were indicative of galactocylation on HD. Up field proton peaks at ${\delta}_H$ 1.60~1.35 ppm and 0.92 ppm showed the presence of $CH_2$ and $CH_3$ protons of HD. $^{13}C$ NMR spectrum revealed the presence of 21 carbons suggestive of ${\alpha}$- and ${\beta}$-anomers of HD-gal. Among 12 carbon peaks from each anomers, the 3 peaks at dC 68.6, 60.9 and 13.2 ppm were assigned to be overlapped showing only 21 peaks out of total 24 peaks. The mass value (protonated HD-gal, m/z = 281.1601) from mass spectrometry analysis of HD-gal, and $^1H$ and $^{13}C$ NMR spectral data were in well agreement with the expecting structure of HD-gal. For further study, the minimum inhibitory concentrations (MICs) of HD-gal against bacteria will be investigated, and, in addition, cytotoxicity to human skin cells of HD-gal will be examined. It is expected that it will eventually be able to develop a new cosmetic preservative, which have low cytotoxicity against human skin cell and maintains antimicrobial effect.

• Proceedings of the Korean Society of Crop Science Conference
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• 2022.10a
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• pp.263-263
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• 2022

물봉선속(Impatiens L.)은 일년생 또는 다년생 초본으로 우리나라에 5-7종이 분포한다. 물봉선의 화장품용 항산화제 및 천연 방부제로서의 유용성이 밝혀졌으며, 최근 항염, 항산화 등 생리활성에 대한 연구가 국내 자생하는 물봉선 및 노랑물봉선을 대상으로 수행된 바 있으나 이하 분류군에 대한 연구는 미비한 실정이다. 본 연구에서는 국내 자생하는 물봉선속 분류군들의 항산화활성과 생리 활성물질의 함량을 분석하고 지역 간 분류군별 차이를 확인하고자 하였다. 따라서 국내 자생하는 물봉선속 분류군들의 항산화활성을 검정하기 위하여 DPPH, ABTS, TPC, TFC 4가지 방법을 이용하여 분석하였다. 국내 자생하는 물봉선속 5분류군 가야물봉선(Impatiens atrosanguinea (Nakai) B.U.Oh & Y.P.Hong), 노랑물봉선(Impatiens noli-tangere L), 물봉선(Impatiens textorii Miq), 미색물봉선(Impatiens noli-tangere var. pallescens Nakai), 처진물봉선(Impatiens furcillata Hemsl)이 12개 지역에서 수집되었으며, 잎 추출물(70% 에탄올)에 대해 분석되었다. 물봉선속 분류군들의 잎 추출물의 DPPH 라디칼 소거 활성 검정 결과 가야물봉선(4.91 ± 3.00 mgAAE/g)이 가장 높았고 처진물봉선(1.77 ± 0.55 mgAAE/g)이 가장 낮았으며, ABTS의 경우 가야물봉선(3.14 ± 1.35 mgAAE/g)로 가장 높았고 미색물봉선(1.87 ± 0.16 mgAAE/g)이 가장 낮았다. TPC의 경우 미색물봉선(5.48 ± 1.05 ugGAE)이 가장 높았고 노랑물봉선(2.78 ± 1.98 ugGAE)이 가장 낮았으며, TFC의 경우 물봉선(0.70 ± 0.20 ugGAE/g)이 가장 높았고 노랑물봉선(0.45 ± 0.08 ugGAE/g)이 가장 낮게 나타났다. 수집지역별로는 각각 DPPH와 ABTS의 경우 노랑물봉선, TPC의 경우 가야물봉선, 노랑물봉선, 물봉선, TFC의 경우 처진물봉선이 지역별 차이를 보였다. 이번 연구 결과를 토대로 국내 자생하는 물봉선속 분류군 별 항산화활성과 생리활성물질 차이를 확인할 수 있었고 추후 유용 소재로써의 이용과 우수 개체선발에 도움이 될 것으로 사료 된다.

• Journal of the Korean Applied Science and Technology
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• v.38 no.3
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• pp.824-831
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• 2021

1, 2-Octanediol galactoside (OD-gal) has been synthesized from 1, 2-octanediol (OD), as a safer cosmetic preservative, using recombinant Escherichia coli β-galactosidase (β-gal). To confirm the molecular structure of synthesized OD-gal, mass spectrometry and NMR (¹H- and ¹³C-) spectroscopy of OD-gal were carried out. In the reaction mixture, a sodium adduct ion of OD-gal (m/z=331.1732) was identified using mass spectrometry analysis. In addition, ¹H NMR spectrum of OD-gal showed multiple peaks corresponding to the galactosyl group, which is evidence of galactosylation on OD. Downfield proton peaks at δ_H 4.39 ppm and multiple peaks from δ_H 3.98~3.55 ppm were indicative of galactosylation on OD. Up field proton peaks at δ_H 1.52~1.26 ppm and 0.89 ppm showed the presence of CH₂ and CH₃ protons of OD. ¹³C NMR spectrum revealed the presence of 24 carbons suggestive of α- and β-anomers of OD-gal. Among 14 carbon peaks from each anomer, the 4 peaks at δ_C 31.4, 29.0, 22.3, and 13.7 ppm were assigned to be overlapped showing only 24 peaks out of a total of 28 peaks. The mass value from mass spectrometry analysis of OD-gal, and ¹H and ¹³C NMR spectral data were in good agreement with the expecting structure of OD-gal. Finally, we identified a galactose molecule from the hydrolysate of OD-gal using β-gal. We are expecting that through future study it will eventually be able to develop a safe cosmetic preservative.

• Journal of Life Science
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• v.25 no.10
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• pp.1164-1168
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• 2015

Previous research showed that chlorphenesin galactoside (CPN-Gal), a preservative in cosmetics, was safer than CPN against human skin cells [9]. To establish a stable and long-term process for CPN-Gal production, we investigated the repeated-batch process. In this process, β-gal-producing recombinant Escherichia coli cells were immobilized in calcium alginate beads, and CPN was converted to CPN-Gal by the transgalactosylation reaction. The process was conducted in a 300 ml flask, which contained E. coli cell-immobilized alginate beads, 33.8 mM of CPN, and 400 g/l of lactose. The pH and temperature were 7.0 and 40℃, respectively. During the repeated-batch operation, four consecutive batch operations were conducted successfully until 192 hr. The conversion yield of CPN to CPN-Gal was 64% during 192 hr, which was higher than the values in previous reports [3, 13]. Thereafter, however, the conversion yield gradually decreased until the operation was finished at 336 hr. Western blotting of immobilized E. coli cells revealed that β-gal gradually decreased after 192 hr. In addition, alginate beads were cracked when the operation was finished. It is probable that, including this loss of E. coli cells by cracks, deactivation, and product inhibition of E. coli β-gal might lead to a gradual decrease in the production of CPN-Gal after 192 hr. However, as the purification of β-gal is not necessary with β-gal-producing recombinant E. coli cells, β-gal-producing E. coli cells might be a practical and cost-effective approach for enzymatically synthesizing CPN-Gal. It is expected that this process will be extended to long-term production process of CPN-Gal for commercialization.

• Journal of the Korean Applied Science and Technology
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• v.36 no.2
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• pp.572-580
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• 2019

Recently, it has been reported that benzyl alcohol (BzOH) as an additive in cosmetics, food, and medicine lead to toxicity and allergy problem. Then, to circumvent this hurdle, we carried out the synthesis of benzyl alcohol galactoside (BzO-gal). Previously, it was confirmed that BzO-gal was synthesized by transgalactosylation reaction using Escherichia coli (E. coli) ${\beta}$-galactosidase (${\beta}-gal$). Meanwhile, in this study, two peaks of BzO-gal as sodium adduct ion (m/z=293.1004) and protonated ion (m/z=271.1180) were detected in the reaction mixture by liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS). In addition, the amount of ${\beta}-gal$ and BzOH concentration, temperature, pH, and lactose concentration, respectively, were optimized (${\beta}-gal$, 0.75 U/mL; BzOH, 185 mM; temperature, $40^{\circ}C$, pH, 7.5; lactose, 350 g/l). Under these optimal conditions, 185 mM BzOH was converted into about 131 mM BzO-gal, in which the conversion yield was about 72%. In the future, BzO-gal will be applicable as a substitute for BzOH as a less toxic preservative for the cosmetic, pharmaceutical, and food industries, and we are planning to investigate the characteristics of BzO-gal as a preservative.