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Lipase Inhibitory Mode of Dieckol Isolated from Eisenia bicyclis Ethanol Extract

Eisenia bicyclis 에탄올 추출물로부터 분리한 Dieckol의 Lipase 저해 Mode

  • Jung, Seul-A (Department of Food Science and Technology / Institute of Food Science, Pukyong National University) ;
  • Kim, Koth-Bong-Woo-Ri (Institute of Fisheries Sciences, Pukyong National University) ;
  • Kim, Dong-Hyun (Department of Food Science and Technology / Institute of Food Science, Pukyong National University) ;
  • Cho, Ji-Young (Department of marine biotechnology, Soonchunhyang University) ;
  • Kim, Tae-Wan (Department of Food Science and Biotechnology, Andong National University) ;
  • Ahn, Dong-Hyun (Department of Food Science and Technology / Institute of Food Science, Pukyong National University)
  • 정슬아 (부경대학교 식품공학과/식품연구소) ;
  • 김꽃봉우리 (부경대학교 수산과학 연구소) ;
  • 김동현 (부경대학교 식품공학과/식품연구소) ;
  • 조지영 (순천향대학교 해양생명공학과) ;
  • 김태완 (안동대학교 식품생명공학과) ;
  • 안동현 (부경대학교 식품공학과/식품연구소)
  • Received : 2012.10.11
  • Accepted : 2012.12.01
  • Published : 2013.03.28

Abstract

This study was performed to investigate the possible use of Eisenia bicyclis (EB) ethanol extract to inhibit activity against lipase. In tests, the lipase inhibitory activity of EB ethanol extract was noted as being 43, 27, and 24% at concentrations of 5, 2.5, and 1 mg/ml, respectively. Isolation was carried out by liquid and liquid extraction, silica-gel column chromatography, and HPLC. The results showed that the lipase inhibitory activity of the ethyl acetate (EA) fraction from EB ethanol extract exhibited the strongest lipase inhibitory activity with an $IC_{50}$ value of 1.31 mg/ml. The EA fraction was separated using silica-gel column chromatography and we obtained 22 sub-fractions. Amongst them, the EA1 fraction showed the highest lipase inhibitory activity with an $IC_{50}$ value of 0.54 mg/ml. Eight peaks were obtained from the EA1 fraction by HPLC. Fraction 5 also showed a strong lipase inhibitory activity with an $IC_{50}$ value of 0.37 mg/ml. The fraction 5 was identified as dieckol and the inhibition pattern analyzed from Lineweaver-Burk plots revealed a non-competitive inhibitor. These results suggest that EB has potential as a natural anti-obesity agent.

대황 ethyl acetate 분획은 $IC_{50}$ 값이 1.31 mg/ml으로 에탄올 추출물보다 높은 lipase 저해활성을 나타내었다. Silicagel column chromatography를 이용하여 ethyl acetate 분획으로부터 얻은 sub-fraction 중 EA1 fraction이 $IC_{50}$ 값 0.54 mg/ml로 가장 높은 저해활성을 보였으며 더 나아가 HPLC를 이용하여 8개의 sub-fraction으로 분리하였다. HPLC fraction 중 fraction 5가 $IC_{50}$ 값 0.37 mg/ml로 높은 lipase 저해활성을 보였다. 이 fraction 5는 분자량 741.1로 $C_{36}H_{22}O_{18}$ 화합물인 phlorotannin derivative dieckol로 확인되었으며 lipase에 대해 비경쟁적 저해타입을 나타내었다. 이상의 결과로, 대황 에탄올 추출물로부터 분리한 dieckol의 lipase 저해 활성 및 저해 타입 확인을 통해 식품 산업에 항비만 소재로서 응용할 수 있을 것으로 사료되어진다.

Keywords

References

  1. Ahn, M. J., K. D. Yoon, S. Y. Min, J. S. Lee, J. H. Kim, T. G.Kim, S. H. Kim, N. K. Kim, H. Huh, and J. W. Kim. 2004. Inhibition of HIV-1 reverse transcriptase and protease by phlorotannins from the brown alga Ecklonia cava. Biol. Pharm. Bull. 27: 544-547. https://doi.org/10.1248/bpb.27.544
  2. Barwell, C. J., G. Blunden, and P. D. Manandhar. 1989. Isolation and characterization of brown algal polyphenols as inhibitors of α-amylase, lipase and trypsin. J. Appl. Phycol. 1: 319-323. https://doi.org/10.1007/BF00003468
  3. Birari, R. B. and K. K. Bhutani. 2007. Pancreactic lipase inhibitors from natural sources: unexplored potential. Drug Discov. Today 12: 879-889. https://doi.org/10.1016/j.drudis.2007.07.024
  4. Bitou, N., M. Ninomiya, T. Tsujita, and H. Okuda. 1999. Screening of inhibitors from marine algae. Lipids 34: 441-445. https://doi.org/10.1007/s11745-999-0383-7
  5. Bray, G. A. and B. M. Popkin. 1998. Dietary fat intake dose affect obesity. Am. J. Clin. Nutr. 68: 1157-1173.
  6. Cahyana, A. H., Y. Shuto, and Y. Kinoshita. 1992. Pyropheophytin a as an antioxidative substance from the marine alga, Arame (Eisenia bicyclis). Biosci. Biotech. Bioch. 56: 1533- 1535. https://doi.org/10.1271/bbb.56.1533
  7. Chu, M. A. and B. H. Choe. 2010. Obesity and metabolic syndrome among children and adolescents in Korea. J. Korean Med. Assoc. 53: 142-152. https://doi.org/10.5124/jkma.2010.53.2.142
  8. Cleland, W. W. 1967. Enzyme Kinetics. Annu. Rev. Biochem. 36: 77-112. https://doi.org/10.1146/annurev.bi.36.070167.000453
  9. Deavile, E. R., R. J. Green, I. Muller-Harvey, I. Willoughby, and R. A. Frazier. 2007. Hydrolyzable tannin structures influence relative globular and random coil protein binding strengths. J. Agr. Food Chem. 55: 4554-4561. https://doi.org/10.1021/jf063770o
  10. Drent, M. L., I. Larsson, T. William-Olsson, F. Quaade, F. Czubayko, K. Von Bergmann, W. Strobel, L. Sjotro, and E. A. Van der Veen. 1995. Orlistat (RO 18-0647), a lipase inhibitor, in the treatment of human obesity: a multiple dose study. Int. J. Obesity. 19: 221-226.
  11. Eom, S. H., M. S. Lee, E. W. Lee, Y. M. Kim, and T. H. Kim. 2012. Pancreatic lipase inhibitory activity of phlorotannins isolated from Eisenia bicyclis. Phytother. Res. DOI: 10.1002/ptr. 4696.
  12. Gibbons, G. F. and D. Wiggins. 1995. Intracellular triacylglycerol lipase: Its role in the assembly of hepatic very low density lipoprotein (VLDL). Adv. Enzyme Regul. 35: 179-198. https://doi.org/10.1016/0065-2571(94)00006-O
  13. Hadvay, P., H. Lengsfeld, and H. Wolter. 1988. Inhibition of pancreatic lipase in vitro by covalent inhibitor tetrahydrolipstatin. Biochem. J. 256: 357-361.
  14. Joo, D. S., J. K. Lee, Y. S. Choi, S.Y. Cho, Y. K. Je, and J. W. Choi. 2003. Effect of sea tangle oligosaccharide drink on serum and hepatic lipids in rats fed a hyperlipidemic diet. J. Korean Soc. Food Sci. Nutr. 32: 1364-1369. https://doi.org/10.3746/jkfn.2003.32.8.1364
  15. Kang, K., Y. Park, H. J. Hwang, S. H. Kim, J. G. Lee, and H. C. Shin. 2003. Antioxidative properties of brown algae polyphenolics and their perspectives as chemopreventive agents against vascular risk factors. Arch. Pharm. Res. 26: 286-293. https://doi.org/10.1007/BF02976957
  16. Kang, M. C., Y. J. Lee, R. K. Ko, H. B. Kim, S. H. Hong, and G. O. Kim. 2008. Melanin inhibitory effect and anti-inflammatory effects of Dietyota coriacea extracts derived from adjacent sea of the Jeju island. Korean J. Biotechnol. Bioeng. 23: 311-316.
  17. Kang, S. M., S. J. Heo, K. N. Kim, S. H. Lee, H. M. Yang, A. D. Kim, and Y. J. Jeon. 2012. Molecular docking studies of a phlorotannin, dieckol isolated from Ecklonia cava with tyrosinase inhibitory activity. Bioorgan. Med. Chem. 20: 311-316. https://doi.org/10.1016/j.bmc.2011.10.078
  18. Kim, D. H., E. H. Lee, J. C. Hwang, J. H. Jeung, D. H. Kim, J. Y. Cheong, S. W. Cho, and Y. B. Kim. 2002. A case of acute cholestatic hepatitis associated with orlistat. Korean J. Hepatol. 8: 317-320.
  19. Kim, J. A., J. M. Lee, D. B. Shin, and N. H. Lee. 2004. The antioxidant activity and tyrosinase inhibitory of phlorotannin in Ecklonia cava. Food Sci. Biotechnol. 13: 476-480.
  20. Kim, J. H., H. J. Kim, C. Y. Kim, H. Y. Jung, Y. O. Kim, J. Y. Ju, and C. S. Shin. 2007. Development of lipase inhibitors from various derivatives of monascus pigment produced by Monascus fermentation. Food Chem. 101: 357-364. https://doi.org/10.1016/j.foodchem.2005.11.055
  21. Kim, K. B. W. R., J. Y. Jung, J. Y. Cho, and D. H. Ahn. 2012. Lipase inhibitory activity of ethyl acetate fraction from Ecklonia cava extracts. Biotechnol. Bioprocess Eng. 17: 739-745. https://doi.org/10.1007/s12257-011-0671-9
  22. Kim, K. Y., K. A. Nama, H. Kurihara, and S. M. Kim. 2008. Potent $\alpha$-glucosidase inhibitors purified from the red alga Grateloupia elliptica. Phytochemistry 69: 2820-2825. https://doi.org/10.1016/j.phytochem.2008.09.007
  23. Kim, S. A., J. Kim, M. K. Woo, C. S. Kwak, and M. S. Lee. 2005. Antimutagenic and cytotoxic effects of ethanol extracts from five kinds of seaweeds. J. Korean Soc. Food Sci. Nutr. 34: 451-459.
  24. Kim, Y. M., C. K. Han, S. J. Bang, and J. H. Park. 2006. Effect of laminaran from Eisenia bicyclis on serum lipids in rats fed high choelsterol diet. J. Korean Soc. Food Sci. Nutr. 36: 841-846.
  25. Kobayashi, A., T. Osaka, Y. Namba, S. Inoue, T. H. Lee, and S. Kimura. 1998. Capsaicin activates heat loss and heat production simultaneously and independently in rats. Am. J. Physiol. 275: 92-98.
  26. Kong, C. S., Y. R. Um, J. I. Lee, Y. A. Kim, J. S. Lee, and Y. W. Seo. 2008. Inhibition effects of extracts and its solvent fractions isolated from Limonium tetragonum on growth of human cancer cells. Korean J. Biotechnol. Bioeng. 23: 177-182.
  27. Lee, H. O., D. S. Kim, J. R. Do, and Y. S. Ko. 1999. Angiotensin- I converting enzyme inhibitory activity of algae. J. Korean Fish Soc. 32: 427-431.
  28. Lee, S. H., Y. Li, F. Karadeniz, M. M. Kim, and S. K. Kim. 2009. $\alpha$-Glucosidase and α-amylase inhibitory activities of phloroglucinal derivatives from edible marine brown alge, Ecklonia cava. J. Sci. Food Agric. 89: 1552-1558. https://doi.org/10.1002/jsfa.3623
  29. Mattes, R. D. and L. Bormann. 2000. Effects of hydroxycitric acid on appetitive variables. Physiol. Behav. 71: 87-94. https://doi.org/10.1016/S0031-9384(00)00321-8
  30. Moon, H. E., M. N. Islam, B. R. Ahn, S. S. Chowdhury, H. S. Sohn, H. A. Jung, and J. S. Choi. 2011. Protein tyrosine phosphatase 1B and α-glucosidase inhibitory phlorotannins from edible brown algae, Ecklonia stolonifera and Eisenia bicyclis.Biosci. Biotech. Bioch. 75: 1472-1480. https://doi.org/10.1271/bbb.110137
  31. Nakamura, T., K. Nagayama, K. Uchida, and R. Tanaka. 1996. Antioxidant activity of phlorotannins isolated from the brown alge Eisenia bicylis. Fisheries Sci. 62: 923-926.
  32. Pi-Sunyer, F. X. 1991. Health implications of obesity. Am. J. Clin. Nutr. 5: 15955-16035.
  33. Prpkins, B. M. and C. M. Doak. 1998. The obesity prevalence is a worldwide phenomenon. Nutr. Rev. 56: 104-114.
  34. Sugiura, Y., K. Matsuda, Y. Yamada, M. Nishikawa, K. Shioya, H. Katsuzaki, K. lmai, and H. Amano. 2006. Isolation of a new anti-allergic phlorotannin, phlorofucofuroeckol-B, from and edible brown alge, Eisenia arborea. Biosci. Biotech. Biochem. 70: 2807-2811. https://doi.org/10.1271/bbb.60417
  35. Westerterp-Plantenga, M. S., A. Smeets, and M. P. G. Lejeune. 2005. Sensory and gastrointestinal satiety effects of capsaicin on food intake. Int. J. Obesity. 29: 682-688. https://doi.org/10.1038/sj.ijo.0802862
  36. Witvrouw, M. and E. De Clercq. 1997. Sulfated polysaccharides extracted from sea algae as potential antiviral drugs. Gen. Pharmacol. 29: 497-511. https://doi.org/10.1016/S0306-3623(96)00563-0

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