DOI QR코드

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Synthesis, Antioxidant and Molecular Docking Studies of (-)-Catechin Derivatives

  • Kumar, Deepak (Department of Chemistry, Changwon National University) ;
  • Kumar, Raj (Division of Applied Life Science (BK21 Plus), Systems and Synthetic Agrobiotech Center, Plant Molecular Biology and Biotechnology Research Center, Research Institute of Natural Science, Gyeongsang National University) ;
  • Ramajayam, R. (Pharmacy Department, DIT University) ;
  • Lee, Keun Woo (Division of Applied Life Science (BK21 Plus), Systems and Synthetic Agrobiotech Center, Plant Molecular Biology and Biotechnology Research Center, Research Institute of Natural Science, Gyeongsang National University) ;
  • Shin, Dong-Soo (Department of Chemistry, Changwon National University)
  • 투고 : 2021.01.12
  • 심사 : 2021.01.14
  • 발행 : 2021.04.20

초록

12 kinds of (-)-catechin derivatives were designed and synthesized. The catechin derivatives were evaluated their antioxidant activities using DPPH method. Most of them showed good antioxidant activity, particularly compounds 1d, 1e and 1j exhibited more activity than butylated hydroxytoluene (BHT). Molecular docking studies for compounds 1d, 1e and 1j with STAT1 showed not only sufficent characteristics binding cavity but also agreement with the observed biological activity. Acording to docking results, the compounds showed greater than hydrogen bonding, hydrophobic interactions, electrostatic interactions, and Van der Waals interactions as compared to the reference compound. They formed hydrogen bonds with important residues such as Lys566, His568, Leu570, and Phe644. The compounds showed a novel hydrogen bonding interaction with Arg649, which was not reported previously. Our results might suggest the compounds could serve as a novel anti-oxidant agent.

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참고문헌

  1. Azam, F. Therapeutic Potential of Free Radical Scavengers in Neurological Disorders in Handbook of Free Radicals: Formation, Types and Effects; Chapter 2; Kozyrev, D., Slutsky, V., Eds.; Nova Science Pub. Inc.: Hauppauge, NY, USA, 2010; pp. 57.
  2. Slusarczyk, S.; Hajnos, M.; Skalicka-Wozniak, K.; Matkowski, A. Food Chem. 2009, 113, 134. https://doi.org/10.1016/j.foodchem.2008.07.037
  3. Dakubo, G. D. Mitochondrial Genetics and Cance; Springer-Verlag Berlin Heidelberg: Berlin, Germany, 2010; doi: 10.1007/978-3-642-11416-8.
  4. Torreggiani, A.; Tamba, M. Trends Heterocycl. Chem. 2005, 10, 115.
  5. Karali, N.; Guzel, O.; Ozsoy, N.; Ozbey, S.; Salman, A. Eur. J. Med. Chem. 2010, 45, 1068. https://doi.org/10.1016/j.ejmech.2009.12.001
  6. Patil, V. P.; Markad, V. L.; Kodam, K. M.; Waghmode, S. B. Bioorg. Med. Chem. Lett. 2013, 23, 6259. https://doi.org/10.1016/j.bmcl.2013.09.088
  7. Nair, U. J.; Floyd, R. A.; Nair, J.; Bussachini, V.; Friesen, M.; Bartsch, H. Chem. Biol. Interact. 1987, 63, 157. https://doi.org/10.1016/0009-2797(87)90095-0
  8. Stich, H. F.; Anders, F. Mutat. Res. 1989, 214, 47. https://doi.org/10.1016/0027-5107(89)90197-8
  9. Halliwell, B. Ann. Rheum. Dis. 1995, 54, 505. https://doi.org/10.1136/ard.54.6.505
  10. Fearson, I. M.; Faux, F. P. J. Mol. & Cellular Cardiology, 2009, 47, 372. https://doi.org/10.1016/j.yjmcc.2009.05.013
  11. Singh, R. P.; Sharad, S.; Kapur, S. J. Indian. Acad. Clin. Med. 2004, 5, 218.
  12. Uttara, B.; Singh, A. V.; Zamboni, P.; Mahajan, R. T. Curr. Neuropharmacol. 2009, 7, 65. https://doi.org/10.2174/157015909787602823
  13. Hamid, A. A.; Aiyelaagbe, O. O.; Usman, L. A.; Ameen, O. M.; Lawal, A. African J. Pure Appl. Chem. 2010, 4, 142.
  14. Bendich, A. J. Dairy Sci. 1993, 76, 2789. https://doi.org/10.3168/jds.s0022-0302(93)77617-1
  15. Banon, S.; Diaz, P.; Rodriguez, M.; Garrido, M. D.; Price, A. Meat Sci. 2007, 77, 626. https://doi.org/10.1016/j.meatsci.2007.05.015
  16. Bera, D.; Lahiri, D.; Nag, A. J. Food Eng. 2006, 74, 542. https://doi.org/10.1016/j.jfoodeng.2005.03.042
  17. Nordberg J.; Arner, E. S. Free Radic. Biol. Med. 2001, 31, 1287. https://doi.org/10.1016/S0891-5849(01)00724-9
  18. Rice, M. E. Trends Neurosci. 2000, 23, 209. https://doi.org/10.1016/S0166-2236(99)01543-X
  19. McCay, P. B. Ann. Rev. Nutr. 1985, 5, 323. https://doi.org/10.1146/annurev.nu.05.070185.001543
  20. Fiedor, J.; Burda, K. Nutrients 2014, 6, 466. https://doi.org/10.3390/nu6020466
  21. Agati, G.; Azzarello, E.; Pollastri, S.; Tattini, M. Plant Sci. 2012, 196, 67. https://doi.org/10.1016/j.plantsci.2012.07.014
  22. Scalbert, A.; Manach, C.; Morand, C.; Remesy, C. Critical Rev. Food Sci. Nutrition, 2005, 45, 287. https://doi.org/10.1080/1040869059096
  23. Paradiso, V. M.; Summo, C.; Trani, A.; Caponio, F. J. Cereal Sci. 2008, 47, 322. https://doi.org/10.1016/j.jcs.2007.04.009
  24. Weber J. M.; Ruzindana-Umunyana A.; Imbeault, L.; Sicar, S. Antivial Res. 2003, 58, 167. https://doi.org/10.1016/S0166-3542(02)00212-7
  25. Isaacs, C. E.; Xu, W.; Merz, G.; Hiller, S; Rohan, L.; Wen, G. Y. Antimicrob. Agents & Chemotherapy 2011, 55, 5546. https://doi.org/10.1128/AAC.05531-11
  26. Ho, H. Y.; Cheng, M. L.; Weng, S. F.; Leu, Y. L.; Chiu, D. T. J. Agric. Food Chem. 2009, 57, 6140. https://doi.org/10.1021/jf901128u
  27. Park, M.; Yamada, H.; Matsushita, K.; Kaji, S.; Goto, T.; Okada, Y. Kazuhiro, K.; Toshiro, K. J. Nutr. 2011, 141, 1862. https://doi.org/10.3945/jn.110.137547
  28. Cabrera, C.; Artacho, R.; Gimenez, R. J. Am. Coll. Nutr. 2006, 25, 79. https://doi.org/10.1080/07315724.2006.10719518
  29. Kumar, D.; Poomima, M.; Kushwaha, R. N.; Won, T.-J.; Ahn, C.; Kumar, C.; Jang, K.; Shin, D-S. J. Korean Soc. Appl. Biol. Chem. 2015, 58, 581. https://doi.org/10.1007/s13765-015-0079-x
  30. Finotti, E.; Bersani, E.; Friedman, M. J. Agric. Food Chem. 2011, 9, 864. https://doi.org/10.1021/jf101717t
  31. Toda, M.; Okubo, S.; Ikigai, H.; Suzuki, T.; Suzuki, Y.; Shimamura, T. Microbiol. Immunol. 1992, 36, 999. https://doi.org/10.1111/j.1348-0421.1992.tb02103.x
  32. Muneaki, T.; Kuniyasu O, Japanese Dental Science Rev. 2012, 48, 126. https://doi.org/10.1016/j.jdsr.2012.02.004
  33. Han, Y. Biol. Pharm. Bull. 2007, 30, 1693. https://doi.org/10.1248/bpb.30.1693
  34. Sitheeque, M. A.; Panagoda, G. J.; Yau, J.; Amarakoon, A. M.; Udagama, U. R.; Samaranayake, L. P. Chemotherapy 2009, 55, 189. https://doi.org/10.1159/000216836
  35. Kumar, D.; Harshavardhan, S. J.; Chirumarry, S.; Poornachandra, Y.; Jang, K.; Kumar, C. G.; Yoon, Y. J.; Zhao, B. X.; Miao, J. Y.; Shin, D.-S. Bull. Korean Chem. Soc. 2015, 36, 564. https://doi.org/10.1002/bkcs.10108
  36. Hoshiyama, Y.; Kawaguchi, T.; Miura, Y.; Mizou, T.; Tokui, N.; Yatsuya, H.; Sakata, K.; Kondo, T.; Kikuchi, S.: Toyoshima, H.; Hayakawa, N.; Tamakoshi, A.; Takesumi Yoshimura, T. J. Epidemiol. 2005, 15, S109. https://doi.org/10.2188/jea.15.S109
  37. Smith, A.; Giunta, B.; Bickford, P. C.; Fountain, M.; Tan, J.; Shytle, R. D. Int. J. Pharm. 2010, 389, 207. https://doi.org/10.1016/j.ijpharm.2010.01.012
  38. Berletch, J. B.; Liu, C.; Love, W. K.; Andrews, L. G.; Katiyar, S. K.; Tollefsbol, T. O. J. Cell. Biochem. 2008, 103, 509. https://doi.org/10.1002/jcb.21417
  39. Zhou, L.; Elias, R. J. Food Chem. 2013, 138, 1503. https://doi.org/10.1016/j.foodchem.2012.09.132
  40. Moon, J. H.; Terao, J. J. Agric. Food Chem. 1998, 46, 5062. https://doi.org/10.1021/jf9805799
  41. Bors, W.; Heller, W.; Michel, C.; Saran, M. Methods Enzymol. 1990, 186, 343. https://doi.org/10.1016/0076-6879(90)86128-I
  42. Kumar, R.; Son, M.; Bavi, R.; Lee, Y.; Park, C.; Arulalapperumal, V.; Cao G. P.; Kim, H. H.; Suh, J. K.; Kim, Y. S.; Kwon, Y. J.; Lee, K. W. Acta Pharmacol Sinica 2015, 36, 998. https://doi.org/10.1038/aps.2015.17
  43. Menegazzi, M.; Mariotto, S.; Dal-Bosco, M.; Darra, E.; Vaiana, N.; Shoji, K.; Safwat, A. A.; Marechal, J. D.; Perahia, D.; Suzuki, H.; Romeo, S. FEBS J. 2014, 281, 724. https://doi.org/10.1111/febs.12618
  44. Wang, J.; Tang, H.; Hou, B.; Zhang, P.; Wang, Q.; Zhang, B.-L.; Huang, Y.-W.; Wang, Y.; Xiang, Z.-M.; Zi, C.-T.; Xuan-Jun, Wang, X.-J.; Seng, J. RSC Adv. 2017, 7, 54136. https://doi.org/10.1039/C7RA11496F
  45. Menegazzi, M.; Tedeschi, E.; Dussin, D.; De Prati, A. C.; Cavalieri, E.; Mariotto, S.; Suzuki, H. FASEB J. 2001, 15, 1309. https://doi.org/10.1096/fj.00-0519fje
  46. Tedeschi, E.; Menegazzi, M.; Yao, Y.; Suzuki, H.; Forstermann, U.; Kleinert, H. Mol. Pharmacol. 2004, 65, 111. https://doi.org/10.1124/mol.65.1.111
  47. Mao, X.; Ren, Z.; Parker, G. N.; Sondermann, H.; Pastorello, M. A.; Wang, W.; McMurray, J. S.; Demeler, B.; Darnel Jr., J. E.; Chen, X. Mol. Cell 2005, 17, 761. https://doi.org/10.1016/j.molcel.2005.02.021