아이소리퀴리티게닌을 담지한 2-하이드록시프로필-베타사이클로덱스트린의 물리화학적 특성 및 항균활성 연구

김해수; 임나리; 박수남; Hae Soo Kim; Na Ri Im; Soo Nam Park

Applied Chemistry for Engineering, Vol.26, No.6, 719-724, December, 2015

DOI10.14478/ace.2015.1107 Export Citation

아이소리퀴리티게닌을 담지한 2-하이드록시프로필-베타사이클로덱스트린의 물리화학적 특성 및 항균활성 연구

Enhanced Antimicrobial Activities and Physicochemical Characteristics of Isoliquiritigenin Encapsulated in Hydroxypropyl-β-Cyclodextrin

김해수, 임나리, 박수남 ^†

서울과학기술대학교, 화장품종합기술연구소 정밀화학과 나노바이오화장품연구실

Hae Soo Kim, Na Ri Im, and Soo Nam Park^†

Department of Fine Chemistry, Seoul National University of Science and Technology, Cosmetic R&D Center, 232 Gongneung-ro, Nowon-gu, Seoul 01811, Korea

E-mail:

초록

아이소리퀴리티게닌은 감초의 구성 성분으로서 항산화, 항균 활성과 같은 다양한 약리학적 활성을 가지고 있는 소수성 물질이다. 본 연구에서는 소수성 약물의 용해도를 증진시키기 위해서 아이소리퀴리티게닌/2-하이드록시프로필-베타사이클로덱스트린 복합체를 freeze-drying 방식으로 제조하였고, 상평형 연구, DSC, SEM, 1H NMR을 통하여 그 특성을 확인하였다. 항균 활성은 Staphylococcus aureus (S. aureus)와 Escherichia coli (E. coli)에 대해 broth dilution assay 측정법으로 최소성장억제농도(minimum inhibitory concentration, MIC)를 확인하였다. 상평형 연구를 통해 아이소리퀴리티게닌/2-하이드록시프로필-베타사이클로덱스트린 복합체는 1 : 1 몰비율로 형성되는 것을 확인하였다. S. aureus와 E.coli에 대한 MIC는 아이소리퀴리티게닌/2-하이드록시프로필-베타사이클로덱스트린 복합체의 경우 각각 1.25 및 2.5mg/mL이었으며, free한 아이소리퀴리티게닌은 각각 5, 5 mg/mL로 아이소리퀴리티게닌/2-하이드록시프로필-베타사이클로덱스트린 복합체가 더 높은 항균 활성을 나타내었다. 이는 아이소리퀴리티게닌/사이클로덱스트린 복합체가 식품 및 화장품 산업에서 합성 방부제를 대체하고 천연 방부제로서 응용 가능성이 있음을 시사한다.

Isoliquiritigenin (ILG) is a hydrophobic component in licorice and has a variety of pharmaceutical and biological activities. In this study, we prepared an isoliquiritigenin-hydroxypropyl-β-cyclodextrin (ILG/HP-β-CD) complex by freeze-drying method to enhance its water solubility. The complex was characterized by phase solubility studies, DSC, SEM, and 1H NMR. Antimicrobial activities against Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli) were evaluated by broth dilution method. The results showed that the stoichiometry of ILG/HP-β-CD complex was 1 : 1. The antimicrobial activity of ILG/HP-β-CD complex was higher than that of using free ILG against S. aureus and E. coli. Therefore, we suggest that ILG/HP-β-CD complex may be used as a natural antiseptic and could potentially replace synthetic preservatives in cosmetic and food industries.

Keywords:isoliquiritigenin;hydroxypropyl-β-cyclodextrin;complexation;characterization;antimicrobial activity

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[2] Haraguchi H, Ishikawa H, Mizutani K, Tamura Y, Kinoshita T, Bioorg. Med. Chem., 6, 339 (1998)

[3] Kim JY, Park SJ, Yun KJ, Cho YW, Park HJ, Lee KT, Eur. J. Pharmacol., 584, 175 (2008)

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[6] Loftsson T, Brewster ME, J. Pharm. Sci., 85, 1017 (1996)

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[9] Danciu C, Soica C, Oltean M, Avram S, Borcan F, Csanyi E, Ambrus R, Zupko I, Muntean D, Dehelean CA, Craina M, Popovici RA, Int. J. Mol. Sci., 15, 1962 (2014)

[10] Liang H, Yuan Q, Vriesekoop F, Lv F, Food Chem., 135, 1020 (2012)

[11] Kamimura JA, Santos EH, Hill LE, Gomes CL, LWT-Food. Sci. Technol., 57, 701 (2014)

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[13] Brandt AL, Castillo A, Harris KB, Keeton JT, Hardin MD, Taylor TM, J. Food. Sci., 75, 557 (2010)

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