한국산학기술학회논문지 (Journal of the Korea Academia-Industrial cooperation Society)

  • 제9권6호
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  • Pages.1787-1794
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  • 2008
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  • 1975-4701(pISSN)
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  • 2288-4688(eISSN)
한국산학기술학회 (The Korea Academia-Industrial cooperation Society)
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Coenzyme Q10 유도체들의 항산화 및 세포독성 효과

Antioxidant and Cytotoxic Effects of Coenzyme Q10 Derivatives

  • 최원식 (순천향대학교 자연과학대학 생명공학과) ;
  • 남석우 (순천향대학교 자연과학대학 생명공학과) ;
  • 안은경 (순천향대학교 자연과학대학 생명공학과) ;
  • 어진용 (순천향대학교 자연과학대학 생명공학과) ;
  • 임상호 (남양유업(주) 중앙연구소)
  • 발행 : 2008.12.31
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초록

Coenzyme $Q_{10}$과 그 유도체 coenzyme $Q_n$ 6종을 합성하고, 이들 유도체에 대하여 상피세포(LLC-PK1 cell)를 이용한 항산화 효과와 NIH/3T3 세포를 이용한 세포독성 실험을 실시하였다. 그 결과, 합성한 coenzyme $Q_n$ 유도체들이 coenzyme $Q_{10}$에 비해 우수한 항산화 효과를 나타내었으며, 그 중 coenzyme $Q_3$-C가 모든 농도에서 $107.7{\sim}135.9%$로 가장 우수한 효과를 나타내었다. 또한, 모든 coenzyme $Q_n$ 유도체들이 Coenzyme $Q_{10}$과 유사한 세포독성을 나타내었다. Coenzyme $Q_n$의 n수에 따른 항산화 효과 및 세포독성 실험에서 isoprene unit의 수가 적은 유도체들에서 우수한 효과를 나타내었다.

Coenzyme $Q_{10}$ and six derivatives of coenzyme $Q_n$ were synthesized and tested for their antioxidative effects occurred in proximal tubular epithelial cell (LLC-PK1 cell) and cytotoxicities using in NIH/3T3 cell. As the result, synthetic coenzyme $Q_n$ derivatives showed a potent antioxidative effect compared to coenzyme $Q_{10}$. Among these synthetic compounds, coenzyme $Q_3$-C at ranged 0.04 to 0.4 mmol showed the $107.7{\sim}135.9%$ of cell viability in LLC-PK1 cell. In the test of NIH/3T3, all synthesized coenzyme $Q_n$ derivatives showed the similar effect compared with coenzyme $Q_{10}$. A correlation between isoprene unit number of coenzyme $Q_n$ derivatives and its biological effects, we suggest reduction of isoprene unit number of $Q_n$ derivatives may be related to the increase of antioxidants effects and the reduction of cytotoxicities.

키워드

참고문헌

  1. Crans, F. L.; Hatefi, Y.; Lester, R. L.; Widmer, C. "Isolation of a quinone from beef heart mitochondria", Biochem. Biophys. Acta, 25, pp. 220-221, 1957. https://doi.org/10.1016/0006-3002(57)90457-2
  2. Catherine, F. C. "New advances in coenzyme Q biosynthesis", Protoplasma, 213, pp. 134-147, 2000. https://doi.org/10.1007/BF01282151
  3. Wolf, D. E.; Hoffman, C. H.; Trenner, N. R. ; Arison, B. H.; Shunk, C. H.; Linn, B. O.; McPherson, J. F.; Folkers, K. "Structure studies on the coenzyme Q group", J. Am. Chem. Soc, 80, pp. 4752-4758, 1958. https://doi.org/10.1021/ja01550a096
  4. Meganathan, A. "Biosynthesis of the isoprenoid quinones, menaquinone (vitamin K2) and ubiquinone(coenzyme Q)", In Escherichia coli and Salmonella. Am. Soc. Micro, pp. 642-656, 1996.
  5. Szarkowska, L. "The restoration of DPNH oxidase activity by coenzyme Q(ubiquinone)", Arch. Biochem. Biophys, 113(3), pp. 519-525, 1966. https://doi.org/10.1016/0003-9861(66)90228-1
  6. Kaikkonen, J.; Nyyssonen, K.; Tuomainen, T. P. "Det erminants of plasma Coenzyme Q10 in humans", FEBS. Lett, 443(2), pp. 163-165, 1999. https://doi.org/10.1016/S0014-5793(98)01712-8
  7. Britta, S.; Robert, K. P. "Microbial ubiquinones; multiple roles in respiration gene regulation and oxidative stress management", SGM, 145, pp. 1817-1830, 1999 https://doi.org/10.1099/13500872-145-8-1817
  8. Ernster, L.; Dallner, G. "Biochemical, physiological and medical aspects of ubiquinone function", Biochem. Biophys. Acta, 1271, pp. 195-204, 1995. https://doi.org/10.1016/0925-4439(95)00028-3
  9. Crane, F. L.; Navas, P. "The diversity of coenzyme Q function", Molec. Aspects Med, 18, pp. 81-86, 1997.
  10. James, A. M.; Smith, R. A.; Murphy, M P. "Antioxidant and prooxidant properties of mitochondrial coenzyme Q", Arch. Biochem. Biophys, 423, pp. 47-56, 2004. https://doi.org/10.1016/j.abb.2003.12.025
  11. Turunen, M.; Olsson, J.; Dallner, G. "Metabolism and function of coenzyme Q", Biochim. Biophys. Acta, 1660, pp. 171-199, 2004. https://doi.org/10.1016/j.bbamem.2003.11.012
  12. Hundal, T.; Forsmark, P.; Ernster, L.; Andersson, B. "Antioxidant activity of reduced plastoquinone in thylacoid membranes during strong illumination", EBE C. Short Report, 7, pp. 6-8, 1992.
  13. Hoppe, U.; Bergemann, J.; Diembeck, W.; Ennen, J.; Gohla, S.; Jarris, I.; Jacob, J.; Jielholz, J.; Mei, W.; Pollet, D.; Schachtschabel, D.; Sauermann, G.; Schreiner, V.; Stab, F.; Steckel, F. "Coenzyme Q10, cutaneous antioxidant and energizer", Biofactors, 9(2-4), pp. 371-378, 1999. https://doi.org/10.1002/biof.5520090238
  14. Podda, M.; Traber, M. G.; Weber, C.; Liang jun, Y.; Paker, L. "UV-irradiation depletes antioxidants and causes oxidative damage in a model of human skin", Free Rad. Biol. And Med, 24, pp. 55-65, 1998. https://doi.org/10.1016/S0891-5849(97)00142-1
  15. Frederick M. R.; Ruth, A. S.; John B. W.; "Effects of coenzyme Q10 treatment on antioxidant pathway in normal and streptozotocin induced diabetic rats", J. Biochem. Mol. Toxicol, 15, pp. 41-46, 2001. https://doi.org/10.1002/1099-0461(2001)15:1<41::AID-JBT5>3.0.CO;2-Z
  16. Wright, H.; Laureta, P.; Richard, R. W.; James M. M.; "Uptake, recycling, and antioxidant actions of ${\alpha}-Lipoic$ acid in endothelial cells", Free Rad. Biol. Med, 33, pp. 83-93.
  17. 최원식, 어진용, 남석우, 김재훈, 이영행. "Coenzyme Qn 유도체들의 합성", 대한화학회지, 제 51권 6호, pp. 585-590, 2007. https://doi.org/10.5012/jkcs.2007.51.6.585
  18. Yokozawa T, Cho E. J.; Hara Y.; Kitani K. "Antioxidative activity of green tea treated with radical inhibitor 2,2'-azobis(2-amidinopropane)dihydrochloride", J. Agirc. Food Chem., 48, pp. 5068-5073, 2000. https://doi.org/10.1021/jf000253b
  19. T. Mosmann. "Rapid colorimetric assay for cellular growth and survival : application to proliferation and cytotoxic assay:, J. Immunol. Meth, 65, pp. 55-63, 1983. https://doi.org/10.1016/0022-1759(83)90303-4
  20. Gordon, P. R.; Mansur, C. P.; Gilichrest, B. A. "Regulation of human melanocyte growth, dendricity, and melanization by keratinocyte derived factor", J. Invest. Dermatol. 92, pp. 565, 1998.