락톤형 소포로리피드의 물리화학적 특성 및 항균효과

조수아; 엄경태; 진병석; Soo A Cho; Gyeong Tae Eom; Byung Suk Jin

Applied Chemistry for Engineering, Vol.30, No.3, 303-307, June, 2019

DOI10.14478/ace.2019.1023 Export Citation

락톤형 소포로리피드의 물리화학적 특성 및 항균효과

Physico-chemical Properties and Antibacterial Activities of Lactonic Sophorolipid

조수아, 엄경태¹, 진병석 ^†

동덕여자대학교 화학⋅화장품학부
¹한국화학연구원 바이오화학연구센터

Soo A Cho, Gyeong Tae Eom¹, and Byung Suk Jin^†

Division of chemistry and cosmetics, Dongduk Women’s University, Seoul 02748, Korea
¹Korea Research Center for Industrial Chemical Biotechnology, KRICT, Ulsan 44429, Korea

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초록

소포로리피드(sophorolipid)는 Candida bombicola에 의해 생산되는 당지질 구조의 생물 계면활성제로, 일반적으로 산성형과 락톤형의 혼합으로 존재한다. 본 연구에서는 소포로리피드 생산균주의 유전자조절과 대사공학적 방법을 통해 락톤형이 96% 이상으로 존재하는 소포로리피드의 물리화학적 특성, 항균 특성, 세포독성 등을 살펴보았다. 락톤형 소포로리피드를 물에 1 wt%에서 0.001 wt% 농도로 희석시키면 pH가 3.2~4.6 범위의 약산성을 나타내었다. 산-염기 적정곡선으로부터 락톤형 소포로리피드의 pKa 값은 대략 4.3으로 측정되었다. 임계 마이셀 농도(CMC)는 10-2 wt%로, 이때 수용액의 표면장력은 36 mN/m까지 감소하였다. 락톤형 소포로리피드의 항균 활성을 살펴본 결과, Propionibacterium acnes에 대하여 1 × 10-3 g/mL, Corynebacterium xerosis에 대하여 5 × 10-3 g/mL의 최소저지농도(MIC) 값을 보였다. MTT assay 실험 결과로부터 락톤형 소포로리피드의 세포독성이 트리클로산보다 10배 더 낮은 것으로 나타났다.

Sophorolipid is a biological surfactant of the glycolipid structure produced by Candida bombicola, which generally exists as a mixture of acidic and lactonic forms. In this study, we investigated physico-chemical properties, antibacterial activities, and cytotoxicity of the sophorolipid containing more than 96% of the lactonic form, produced by the gene regulation of production strains and application of a metabolic engineering technique. The lactonic sophorolipid showed a weak acidity in the range of pH 3.2~4.6 when diluted in water at the concentrations from 1 to 0.001 wt%. The pKa value of the lactonic sophorolipid was estimated to be around 4.3 from the acid-base titration curve. The critical micelle concentration (CMC) of the lactonic sophorolipid was 10-2 wt%, at which the surface tension of aqueous solution was reduced to 36 mN/m. The lactonic sophorolipid showed the minimum inhibitory concentrations (MIC) of 1 × 10-3 and 5 × 10-3 g/mL against Propionibacterium acnes and Corynebacterium xerosis, respectively. The MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide] assay showed that cytotoxicity of the lactonic sophorolipid was ten times lower than that of triclosan.

Keywords:Lactonic sophorolipid;Physico-chemical properties;P. acne;C. xerosis;Cytotoxicity

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[1] Gorin PAJ, Spencer JFT, Tulloch AP, Torulopsis magnoliae. Can. J. Chem., 39, 846 (1961)

[2] Van Bogaert INA, Zhang JX, Soetaert W, Process Biochem., 46(4), 821 (2011)

[3] Hirata Y, Ryu M, Oda Y, Igarashi K, Nagatsuka A, Furuta T, Sugiura M, J. Biosci. Bioeng., 108(2), 142 (2009)

[4] Gudina EJ, Rangarajan V, Sen R, Rodrigues LR, Trends Pharmacol. Sci., 34, 667 (2013)

[5] de Oliveira MR, Magri A, Baldo C, Camilios-Neto D, Minucelli T, Celligoi MAPC, Int. J. Adv. Biotechnol. Res., 6(2), 161 (2015)

[6] Develter D, Renkin M, Jacobs I, Eur. Patent 01445302 (2006).

[7] Marchal R, Lemal J, Sulzer C, Davila AM, US Patent 5,900,366 (1999).

[8] Furuta T, Igarashi K, Hirata Y, World Patent 03/002700 (2003).

[9] Sohn HY, Kim YS, Kim EJ, Kwon YS, Son KH, Korean J. Microbiol. Biotechnol., 34, 265 (2006)

[10] Ha MH, Cho SH, Propionibacterium acnes, Asian J. Beauty Cosmetol., 2(3), 69-75 (2004).

[11] Choi SM, Kim MJ, Choi YH, Ahn HJ, Yun YP, Propionibacterium acnes, Arch. Pharm. Res., 42(1), 89-94 (1998).

[12] Mikamia E, Goto T, Ohno T, Matsumoto H, Nishid M, J. Pharm. Biomed. Anal., 28(2), 261 (2002)

[13] Zhang JP, Chen QX, Song KK, Xie JJ, Food Chem., 95, 579 (2006)

[14] Carey DE, McNamara PJ, Front. Microbiol., 5, 1 (2015)

[15] Kim NH, Mun SJ, Kim AH, Min JH, Ahn JH, Ha WH, Kim BI, J. Korean Acad. Oral Health, 35(1), 10 (2011)

[16] Aiell AE, Larson EL, Levy SB, Clin. Infect. Dis., 45, 137 (2007)

[17] Elshikh M, Moya-Ramirez I, Moens H, Roelants S, Soetaert W, Marchant R, Banat IM, J. Appl. Microbiol., 123(5), 1111 (2017)

[18] Hu Y, Ju LK, J. Biotechnol., 87, 263 (2001)

[19] Kim HS, Kim YB, Lee BS, Kim EK, J. Microbiol. Biotechnol., 15(1), 55 (2005)

[20] Cho WG, Park HS, Ahn BJ, J. Soc. Cosmet. Sci. Korea, 34(4), 317 (2008)

[21] Farhadieh B, J. Pharm. Sci., 62(10), 1685 (1973)