Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Isolation and Identification of Antimicrobial Compounds from Licorice Extracts

감초 추출물로부터 항균성 물질의 분리 및 동정

  • Lee, Jin-Man (Department of Food Science and Technology and Basic Science Institute, Hoseo University) ;
  • Lee, Yoon-Won (Department of Tourism Management, Joongbu University) ;
  • Hur, Sang-Sun (Department of Food Science and Biotechnology, Joongbu University)
  • 이진만 (호서대학교 식품생물공학과) ;
  • 이윤원 (중부대학교 관광경영학과) ;
  • 허상선 (중부대학교 식품생명과학과)
  • Received : 2016.05.12
  • Accepted : 2016.06.04
  • Published : 2016.06.30
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Abstract

Antimicrobial properties of Licorice(Glycyrrhizae radix L.) against food spoilage microorganism, Bacillus subtilis KCTC 1021 was investigated. Antibacterial activity of the essential oil was as equivalent as Potassium metabisulfite and myconazole. The licorice extracts was fractionated to hexane, chloroform, ethyl acetate, butanol and water fraction. Chloroform fraction showed the highest inhibitory effect on the Bacillus subtilis KCTC 1021. Chloroform fraction was further fractionated by silica gel column chromatography and thin layer chromatography(TLC). The antibacterial compound was isolated from their fractions and its chemical structures was identified as (R)-glabridin by ESI-MS, $^1H$-NMR and $^{13}C$-NMR.

식품부패미생물에 대한 감초추출물의 항균력을 확인하고 유효성분을 분리한 후 그 구조를 확인 하였다. 감초추출물은 대표적인 항균제인 메타중아황산칼륨과 myconazole과 비슷한 항균 활성을 나타내었다. 용매분획을 실시한 결과 chloroform fraction이 가장 항균활성이 높은 것으로 나타났다. 이에 chloroform분획을 silica gel column chromatography를 통해 분리하여 항균활성이 가장 큰 분획물인 KC를 분리하였다. 이 화합물은 ESI-MS 와 $^1H$-NMR, $^{13}C$-NMR 결과로부터 활성물질의 구조를 동정하였으며 그 결과 KC는 (R)-glabridin인 것으로 확인하였다.

Keywords

References

  1. N. T. Huang, C. T. Ho, and C. Y. Lee, Phenolic compounds in food and their effects on health(II): Antioxidants and cancer prevention, ACS Symp Series 507. American Chemical Society, Washington DC, 54-71 (1992).
  2. R. M. Alonso-Salces, E. Korta, A. Barranco, L. A. Burrueta, B. Gallo, and F. Vicente, Pressurized liquid extraction for the determination of polyphenols in apple, J. Chromatogr A, 933(9), 37-43 (2001). https://doi.org/10.1016/S0021-9673(01)01212-2
  3. N. C. Cook, and S. Samman, Flavonoidschemistry, metabolism, cardioprotective effects and dietary sources, J. Nutr. Biochem., 7(2), 66-76 (1996). https://doi.org/10.1016/0955-2863(95)00168-9
  4. C. Rice-Evans, N. Miller, and G. Paganga, Antioxidant properties of phenolic compounds, Trend Plant Sci. Technol., 2(4), 152-159 (1997). https://doi.org/10.1016/S1360-1385(97)01018-2
  5. M. I. Yoshimoto, S. Okuno, M. Yamaguchi, and O. Yamakawa, Antimutagenicity of deacylated anthocyanins in purple-fleshed sweetpotato, Biosci., Biotechnol. Biochem., 65(7), 1652-1655 (2001). https://doi.org/10.1271/bbb.65.1652
  6. C. Proestosa, I. S. Boziarisb, G-J. E. Nychasb, and M. Komaitis, Analysis of flavonoids and phenolic acids in Greek aromatic plants: Investigation of their antioxidant capacity and antimicrobial activity, Food Chem., 95(4), 664-671 (2006). https://doi.org/10.1016/j.foodchem.2005.01.049
  7. J. H. Jung, and S. H. Cho, Effect of steeping treatment in the natural antimicrobial agent solution on the quality control of processed tofu, Korean J. Food Preserv., 10(1), 41-46 (2003).
  8. L. R. Beuchat, and D. A. Dolden, Antimicrobials occurring naturally in foods. Food Technol., 43(1), 134-142 (1989).
  9. K. H. Lee, T. Ibuka, R. Y. Wu, and T. A. Geissman, Structure-antimicrobial activity relationships among the sesquiterpene lactones and related compounds, Phytochemistry., 16(8), 1177-1181 (1997).
  10. M. A. El-Shenawy, and E. H. Marth, Inhibition of inactivation of Listeria monocytogenes by sodium benzoate together with some organic acids, J. Food. Protect., 52(11), 768-832 (1989). https://doi.org/10.4315/0362-028X-52.11.768
  11. J. N Bizri, and I. A. Wahem, Citric acid and antimicrobials affect microbiological stability and quality of tomato juice, J. Food. Sci., 59(1), 130-135 (1994). https://doi.org/10.1111/j.1365-2621.1994.tb06916.x
  12. E. J Kim, and M. S. Anh, Antioxidative effect of ginger extracts. Korean J. Soc Food Sci., 9(1), 37-42 (1993).
  13. H. J. Kwak, Y. J. Kwon, P. H. Jeong, J. H. Kwon, and H. K. Kim, Physiological activity and antioxidative effect of methanol extract from onion(Allium cepa L.), J. korean Soc Food Nutr., 29(2), 349-355 (2000).
  14. P. H. Byun, W. J. Kim, and S. K. Yoon, Effect of extraction conditions on the functional properties of garlic extracts, Korean J. Food Sci Technol., 33(5), 507-513 (2001).
  15. S. G. Kim, Comparison of major active compounds in some crude drugs distributed in domestic markets, MS Thesis, Daegu University, Gyeongsan, (2011).
  16. E. J. Sohn, D. G. Kang, A. S. Lee, Y. M. Lee, M. H. Yin, K. B. Yeum, S. Y. Noh, and H. S. Lee, Antioxidant activities of Glycyrrhizin and its effect on renal expression of Na, K-ATPase in gentamicininduced acute renal failure rats, Korean J. Oriental Physiology & Pathology, 17(2), 542-548 (2003).
  17. S. Matsuia, H. Matsumotoc, Y. Sonodab, K. Andob, E. Aizu-Yokotab, T. Satoc, and T. Kasaharab, Glycyrrhizin and related compounds down-regulate production of inflammatory chemokines IL-8 and eotaxin 1 in a human lung fibroblast cell line, Int., Immunopharmacology, 4(13), 1633-1644 (2004). https://doi.org/10.1016/j.intimp.2004.07.023
  18. A. Wolkerstorfer, H. Kurz, N. Bachhofner, and O. H. J. Szolar, Glycyrrhizin inhibits influenza a virus uptake into the cell, Antiviral Res., 83(2), 171-178 (2009). https://doi.org/10.1016/j.antiviral.2009.04.012
  19. E. Y. Ahn, D. H. Shin, N. I. Baek, and J. A. Oh, Isolation and Identification of antimicrobial active substance from glycyrrhiza uralensis FISCH, Korean J. Food Sci Technol., 30(3), 680-687 (1998).
  20. M. S. Kim, D. C. Lee, J. E. Hong, K. S. Chang, H. Y. Cho, Y. K. Kwon, and H. Y. Kim, Antimicrobial effects of ethanol extracts from Korean and Indonesian plants Korean, J. Food Sci Technol., 32(4), 949-958 (2000).
  21. H. J. Kim, H. N. Jang, J. Y. Bae, J. H. Ha, and S. N. Park, Antimicrobial Activity, Quantification and Bactericidal Activities of Licorice Active Ingredients, Korean J. Microbiol Biotechnol., 42(4), 386-392 (2014). https://doi.org/10.4014/kjmb.1410.10002
  22. J. Y. Bae, H. N. Jang, J. H. Ha, J. H. Park, and S. N. Park, Antimicrobial activities of licorice extracts from various countries of origin according to extractioncondition, Korean J. Microbiol Biotechnol.,42(4), 361-366 (2014). https://doi.org/10.4014/kjmb.1408.08002
  23. M. H. Kim, S. U. Kim, Y. U. Kim, and J.H. Han, Absolute configurations of(${\pm}$)-glabridin enantiomers, Bull. KoreanChem Soc., 30(2), 415-418 (2009). https://doi.org/10.5012/bkcs.2009.30.2.415

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