Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Inhibitory Effects of Quinoline Isolated from Ruta chalepensis and Its Structurally Related Derivatives against α-Amylase or α-Glucosidase

  • Park, Jun-Hwan (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 : 2014.09.01
  • Accepted : 2014.09.02
  • Published : 2015.03.31
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Abstract

This study was to isolate an active component of the chloroform fraction from the methanol extract of Ruta chalepensis leaves and to measure inhibitory effects against ${\alpha}$-glucosidase or ${\alpha}$-amylase. The inhibitory compound of R. chalepensis leaves was isolated using chromatographic methods and identified as quinoline. Quinoline and its structurally related derivatives were tested for their inhibitory activities by evaluating the $IC_{50}$ values against ${\alpha}$-amylase or ${\alpha}$-glucosidase and were compared with that of acarbose. Based on the $IC_{50}$ values, quinazoline exhibited the greatest inhibitory activity ($20.5{\mu}g/mL$), followed by acarbose ($66.5{\mu}g/mL$), and quinoline ($80.3{\mu}g/mL$) against ${\alpha}$-glucosidase. In case of ${\alpha}$-amylase, quinazoline had potent inhibitory activity, followed by quinoline ($179.5{\mu}g/mL$) and acarbose ($180.6{\mu}g/mL$). These results indicate that R. chalepensis extract, quinoline, and quinazoline could be useful for inhibiting ${\alpha}$-glucosidase or ${\alpha}$-amylase.

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References

  1. Al-mazraawi MS and Ateyyat M (2009) Insecticidal and repellent activities of medicinal plant extracts against the sweet potato whitefly Bemisia tabaci (Hom.: Aleyrodidae) and its parasitoid Eretmocerus mundus (Hym.: Aphelinidae). J Pestic Sci 82, 149-54. https://doi.org/10.1007/s10340-008-0233-x
  2. Alzoreky NS and Nakahara K (2003) Antibacterial activity of extracts from some edible plants commonly consumed in Asia. Int J Food Microbiol 80, 223-30. https://doi.org/10.1016/S0168-1605(02)00169-1
  3. American Diabetes Association (2005) Diagnosis and classification of diabetes mellitus. Diabetes Care 28, 37-42. https://doi.org/10.2337/diacare.28.suppl_1.S37
  4. Barrera-Necha LL, Bautista-Banos S, Flores-Moctezuma HE, and Estudillo AR (2008) Efficacy of essential oils on the conidial germination, growth of Colletotrichum gloeosporioides (Penz.) Penz. and Sacc and control of postharvest diseases in papaya (Carica papaya L.). Plant Pathol 7, 174-8. https://doi.org/10.3923/ppj.2008.174.178
  5. Borges de Melo E, Da Silveira Gomes A, and Carvalho I (2006) ${\alpha}$- and ${\beta}$- Glucosidase inhibitors: chemical structure and biological activity. Tetrahedron 62, 10277-302. https://doi.org/10.1016/j.tet.2006.08.055
  6. Cho JH, Lee CH, and Lee HS (2005) Antimicrobial activity of quinoline derivatives isolated from Ruta chalepensis toward human intestinal bacteria. J Microbiol Biotechnol 15, 646-51.
  7. Di Stasi LC, Oliveira GP, Carvalhaes MA, Queiroz-Junior M, Tien OS, Kahinami SH et al. (2002) Medicinal plants used in Brazilian tropical Atlantic forest. Fitoterapia 73, 69-91. https://doi.org/10.1016/S0367-326X(01)00362-8
  8. Frode TS and Medeiros YS (2008) Animal models to test drugs with potential antidiabetic activity. J Ethnopharmacol 115, 173-83. https://doi.org/10.1016/j.jep.2007.10.038
  9. Ghazanfar SA (1994) Handbook of Arabian Medicinal Plants. CRC Press (Boca Raton), 190.
  10. Holman RR and Turner RC (1991) Oral agents and insulin in the treatment of NIDDM. Text Book of Diabetes Blackwell Oxford 467-9.
  11. Iauk L, Mangano K, Rapisarda A, Ragusa S, Maiolino L, Musumeci R et al. (2004) Protection against murine endotoxemia by treatment with Ruta chalepensis L., a plant with anti-inflammatory properties. J Ethnopharmacol 90, 267-72. https://doi.org/10.1016/j.jep.2003.10.004
  12. 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.
  13. Kim SH, Hyun SH, and Choung SY (2006) Anti-diabetic effect of cinnamon extract on blood glucose in db/db mice. J Ethnopharmacol 104, 119-23. https://doi.org/10.1016/j.jep.2005.08.059
  14. Lee CH and Lee HS (2011) Relaxant effect of quinoline derivatives on histamine-induced contraction of the isolated guinea pig trachea. J Korean Soc Appl Biol Chem 54, 118-23.
  15. Lee HS (2002) Tyrosinase inhibitors of Pulsatilla cernua rootderived materials. J AgricFood Chem 50, 14003.
  16. 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
  17. Lee HS and Ahn YJ (1998) Growth-inhibiting effects of Cinnamomum cassia bark-devived materials on human intestinal bacteria. J Agric Food Chem 46, 8-12. https://doi.org/10.1021/jf970548y
  18. Lee HW, Yang JY, and Lee HS (2014) Quinoline-2-carboxylic acid isolated from Ephedra pachyclada and its structural derivatives show inhibitory effects against ${\alpha}$-glucosidase and ${\alpha}$-amylase. J Korean Soc Appl Biol Chem 57, 441-4. https://doi.org/10.1007/s13765-014-4156-3
  19. Nilubon JA, Megh RB, and Jun K (2006) ${\alpha}$-Glucosidase inhibitors from Devil tree (Alstonia scholaris). Food Chem 103, 1319-23.
  20. Rigat M, Bonet MA, Garcia S, Garnatje T, and Valles J (2007) Studies on pharmaceutical ethnobotany in the high river Ter valley (Pyrenees, Catalonia, Iberian Peninsula). J Ethnopharmacol 113, 267-77. https://doi.org/10.1016/j.jep.2007.06.004
  21. 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
  22. Ulubelen A and Guner H (1988) Isolation of dehydromoskachan C from Ruta chalepensis var. latifolia. J Nat Prod 51, 1012-3. https://doi.org/10.1021/np50059a040
  23. Ulubelen A and Terem B (1988) Alkaloids and coumarins from roots of Ruta chalepensis. Phytochemistry 27, 650-1. https://doi.org/10.1016/0031-9422(88)83169-8
  24. 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
  25. Yarnell E and Abascal K (2004) Botanical prevention and treatment of malaria: Part 1. Herbal mosquito repellents. Altern Complement Ther 10, 206-10. https://doi.org/10.1089/1076280041580332

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