DOI QR코드

DOI QR Code

2-Hydroxyquinoline and Its Structural Analogs Show Antidiabetic Effects against α-Amylase and α-Glucosidase

  • Lee, Hwa-Won (Department of Bioenvironmental Chemistry and Institute of Agricultural Science & Technology, College of Agriculture & Life Science, Chonbuk National University) ;
  • Lee, Hoi-Seon (Department of Bioenvironmental Chemistry and Institute of Agricultural Science & Technology, College of Agriculture & Life Science, Chonbuk National University)
  • Received : 2014.05.29
  • Accepted : 2014.06.24
  • Published : 2015.03.31

Abstract

This study investigated the inhibitory activities of 2-hydroxyquinoline and its analogs against ${\alpha}$-glucosidase and ${\alpha}$-amylase. Based on the $IC_{50}$ values of 2-hydroxyquinoline analogs tested against ${\alpha}$-glucosidase and ${\alpha}$-amylase, 2-hydroxyquinoline had potent inhibitory activity (64.4 and $130.5{\mu}g/mL$, respectively), while 2-methyl-8-hydroxyquinoline showed weakly inhibitory activity (90.7 and $215.4{\mu}g/mL$, respectively). 2-Methylquinoline demonstrated no activity against ${\alpha}$-glucosidase and ${\alpha}$-amylase. In conclusion, 2-hydroxyquinoline analogs, with the existence of a methyl group and hydroxyl on quinoline, can be useful as a new diabetes treatment.

Keywords

References

  1. Bhandari MR, Nilubon JA, Gao H, and Kawabata J (2008) ${\alpha}$-Glucosidase and ${\alpha}$-amylase inhibitory activities of Nepalese medicinal herb Pakhanbhed (Bergenia ciliate, Haw.). Food Chem 106, 247-52. https://doi.org/10.1016/j.foodchem.2007.05.077
  2. Choi HJ, Jeong YK, Kang DO, and Joo WH (2008) Inhibitory effects of four solvent fractions of Alnus firma on ${\alpha}$-amylase and ${\alpha}$-glucosidase. J Life Sci 18, 1005-10. https://doi.org/10.5352/JLS.2008.18.7.1005
  3. Hu W, Jung MJ, Heo SI, and Wang MH (2008) Antioxidant and antidiabetic activities of aralia elata seeds. J Appl Biol Chem 51, 111-6. https://doi.org/10.3839/jabc.2008.020
  4. Jeong EY, Cho KS, and Lee HS (2012) ${\alpha}$-Amylase and ${\alpha}$-glucosidase inhibitors isolated from Triticum aestivum L. sprouts. J Korean Soc Appl Biol Chem 55, 47-51.
  5. Lee HS (2002) Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J Agric Food Chem 50, 1400-03. https://doi.org/10.1021/jf011230f
  6. Lee HS (2005) Cuminaldehyde: aldose reductase and ${\alpha}$-glucosidase inhibitor derived from Cuminum cyminum L. seeds. J Agric Food Chem 53, 2446-50. https://doi.org/10.1021/jf048451g
  7. Lee HS and Ahn YJ (1998) Growth-inhibiting effects of cinnamomum cassia bark-derived materials on human intestinal bacteria. J Agric Food Chem 46, 8-12. https://doi.org/10.1021/jf970548y
  8. Lee SH, Lee JK, and Kim IH (2012a) Trends and perspectives in the development of antidiabetic drugs for Type 2 diabetes mellitus. Korean J Microbiol Biotechnol 3, 180-5.
  9. Lee YJ, Lee YJ, Yoon JJ, Lee SM, Kim HY, Shin SH et al. (2012b) Antidiabetic and anti-inflammatory effects of water extract of Ligustrum japonicum Leaves in db/db mouse. Kor J Herbology 27, 107-14.
  10. Matsuda H, Li Y, Murakami T, Matsumura N, Yamahara J, and Yoshikawa M (1998) Antidiabetic principles of natural medicines. III. Structure-related inhibitory activity and action mode of oleanolic acid glycosides on hypoglycemic activity. Europe pubmed central 46, 1399-403.
  11. Miura T, Nishiyama Y, Ichimaru M, Moriyasu M, and Kato A (1996) Hypoglycemic activity and structure-activity relationship of iridoidal glycosides. Europe pubmed central 19, 160-1.
  12. Shinde J, Taldone T, Barietta M, Kunaparaju N, Hu B, and Kumar S (2008) ${\alpha}$-Glucosidase inhibitory activity of Syzygium cumini (Linn.) skeels seed kernel in vitro and in goto-kakizake (GK) rats. Carbohydr Res 343, 1278-81. https://doi.org/10.1016/j.carres.2008.03.003
  13. Toshiro M, Tetsuya U, Tomoyuki O, Koichi S, Norihiko T, and Kiyoshi M (2001) Alpha-glucosidase inhibitory action of natural acylated anthocyanins. 1. survey of natural pigments with potent inhibitory activity. J Agric Food Chem 49, 1948-51. https://doi.org/10.1021/jf001251u
  14. Wang H, Du YJ, and Song HC (2010) ${\alpha}$-Glucosidase and ${\alpha}$-amylase inhibitory activities of guava leaves. Food Chem 123, 6-13. https://doi.org/10.1016/j.foodchem.2010.03.088
  15. Yang JY, Jeong EY, Kim DK, and Lee HS (2011) Antioxidative and ${\alpha}$-glucosidase inhibitory effects in Triticum aestivum sprouts treated to chilling temperature. J Korean Soc Appl Biol Chem 54, 644-8.
  16. Yang YC, Lee SG, Lee HK, Kim MK, Lee SH, and Lee HS (2002) A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae. J Agric Food Chem 50, 3765-7. https://doi.org/10.1021/jf011708f

Cited by

  1. Miniaturized and Automated Synthesis of Biomolecules—Overview and Perspectives vol.31, pp.26, 2015, https://doi.org/10.1002/adma.201806656
  2. Sulfonamides and Sulphonyl Ester of Quinolines as Non-Acidic, Non- Steroidal, Anti-inflammatory Agents vol.17, pp.None, 2015, https://doi.org/10.2174/1570180817999201005201308