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α-Glucosidase Inhibition Kinetics and Molecular Docking Studies with the Bioactive Constituents from Canna indica L. Rhizome Extract
Corresponding Author(s) : Hariprasad Puttaswamy
Asian Journal of Chemistry,
Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020
Abstract
The present study investigated the phytochemical constituents from Canna indica rhizome acetone extract, which was earlier reported to possess α-glucosidase inhibiting potential. Different fractions were collected from column chromatography of the acetone extract and the in vitro enzyme inhibition and the kinetic study was performed with the active fraction. The active fraction exhibited competitive inhibition of α-glucosidase. HRLC-MS/MS technique was used to identify the lead compounds from the active fraction. The major compounds were psoromic acid, usnic acid and rosmarinic acid. Molecular docking study of the compounds with the crystal structure of α-glucosidase was performed using ParDOCK. Psoromic acid and usnic acid exhibited strong binding affinity with the active site nucleophiles Asp349 and Asp212, respectively. Usnic acid also stabilized the catalytic residue Glu274. Rosmarinic acid formed multiple hydrogen bonds with the catalytic residue Glu274 and also bonded to non-catalytic residues Gln276, Arg312 and Glu408. The study illustrated informative data on the phytochemical constituents from Canna indica rhizome as α-glucosidase inhibitor and as potential candidates for the development of antidiabetic drugs.
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- D. Soumya and B. Srilatha, J. Diabetes Metab., 02, (2011); https://doi.org/10.4172/2155-6156.1000167
- G. Arumugam, P. Manjula and N. Paari, J. Acute Dis., 2, 196 (2013);https://doi.org/10.1016/S2221-6189(13)60126-2
- A. Salsali and M. Nathan, Am. J. Therap., 13, 349 (2006);https://doi.org/10.1097/00045391-200607000-00012
- M. Murea, L. Ma and B. I. Freedman, Rev. Diabet. Stud., 9, 6 (2012);https://doi.org/10.1900/RDS.2012.9.6
- R.R. Koski, J. Pharmacy Pract., 17, 39 (2004);https://doi.org/10.1177/0897190003261307
- B. Lorenzati, C. Zucco, S. Miglietta, F. Lamberti and G. Bruno, Pharmaceuticals, 3, 3005 (2010);https://doi.org/10.3390/ph3093005
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- M.U. Rao, M. Sreenivasulu, B. Chengaiah, K.J. Reddy and C.M. Chetty,
- Int. J. PharmTech Res., 2, 1883 (2010).
- K.A. Wadkar, C.S. Magdum, S.S. Patil and N.S. Naikwade, J. Herbal Med., 2, 45 (2008).
- R. A. DeFronzo, Ann. Intern. Med., 131, 281 (1999);https://doi.org/10.7326/0003-4819-131-4-199908170-00008
- H.E. Lebovitz, Endocrinol. Metabol. Clin. North Am., 26, 539 (1997);https://doi.org/10.1016/S0889-8529(05)70266-8
- W. Benalla, S. Bellahcen and M. Bnouham, Curr. Diab. Rev., 6, 247 (2010);https://doi.org/10.2174/157339910791658826
- D. Western and M. Wright, Natural Connections: Perspectives in Community Based Conservation, Island Press (2013).
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- T. Matsui, I. Ogunwande, K. Abesundara and K. Matsumoto, Mini-Rev. Med. Chem., 6, 349 (2006);https://doi.org/10.2174/138955706776073484
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- T. Mishra, A.K. Goyal, S.K. Middha and A. Sen, Indian J. Nat. Prod. Resour., 2, 315 (2011).
- H.C. Ong and J.S. Siemonsma, in Plant Resources of South-East Asia; Plants Yielding Non-Seed Carbohydrates, Backhuys Publishers: Leiden, Chap. 9, pp. 63-66 (1996).
- K. Piyachomkwan, S. Chotineeranat, C. Kijkhunasatian, R. Tonwitowat, S. Prammanee, C. G. Oates and K. Sriroth, Ind. Crops Prod., 16, 11 (2002);https://doi.org/10.1016/S0926-6690(02)00003-1
- A. Duke and E.S. Ayensu, Medicinal Plants of China, Reference Publ., Inc. Algonac. Michigan: USA (1985).
- T. Odugbemi, O. Akinsulire, I. Aibinu and P. Fabeku, African J. Trad. Compl. Altern. Med., 4, (2008);https://doi.org/10.4314/ajtcam.v4i2.31207
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- K. Yamamoto, H. Miyake, M. Kusunoki and S. Osaki, FEBS J., 277, 4205 (2010);https://doi.org/10.1111/j.1742-4658.2010.07810.x
- A. Gupta, P. Sharma and B. Jayaram, Protein Pept. Lett., 14, 632 (2007);https://doi.org/10.2174/092986607781483831
- Z. Yin, W. Zhang, F. Feng, Y. Zhang and W. Kang, Food Sci. Human Wellness, 3, 136 (2014);https://doi.org/10.1016/j.fshw.2014.11.003
- Y.Q. Li, F.C. Zhou, F. Gao, J. S. Bian and F. Shan, J. Agric. Food Chem., 57, 11463 (2009);https://doi.org/10.1021/jf903083h
- P. Jiang, J. Xiong, F. Wang, M.H. Grace, M.A. Lila and R. Xu, J. Chem., 8516964 (2017);https://doi.org/10.1155/2017/8516964
- R. Subramanian, M. Z. Asmawi and A. Sadikun, Acta Biochim. Pol., 55, 391 (2008).
- B. C. Behera, N. Mahadik and M. Morey, Pharm. Biol., 50, 968 (2012);https://doi.org/10.3109/13880209.2012.654396
- C. Deraeve, Z. Guo, R.S. Bon, W. Blankenfeldt, R. DiLucrezia, A. Wolf, S. Menninger, E.A. Stigter, S. Wetzel, A. Choidas, K. Alexandrov, H. Waldmann, R.S. Goody and Y.-W. Wu, J. Am. Chem. Soc., 134, 7384 (2012);https://doi.org/10.1021/ja211305j
- M. Petersen, Phytochemistry, 62, 121 (2003);https://doi.org/10.1016/S0031-9422(02)00513-7
References
D. Soumya and B. Srilatha, J. Diabetes Metab., 02, (2011); https://doi.org/10.4172/2155-6156.1000167
G. Arumugam, P. Manjula and N. Paari, J. Acute Dis., 2, 196 (2013);https://doi.org/10.1016/S2221-6189(13)60126-2
A. Salsali and M. Nathan, Am. J. Therap., 13, 349 (2006);https://doi.org/10.1097/00045391-200607000-00012
M. Murea, L. Ma and B. I. Freedman, Rev. Diabet. Stud., 9, 6 (2012);https://doi.org/10.1900/RDS.2012.9.6
R.R. Koski, J. Pharmacy Pract., 17, 39 (2004);https://doi.org/10.1177/0897190003261307
B. Lorenzati, C. Zucco, S. Miglietta, F. Lamberti and G. Bruno, Pharmaceuticals, 3, 3005 (2010);https://doi.org/10.3390/ph3093005
L. Dey, A.S. Attele and C.-S. Yuan, Altern. Med. Rev., 7, 45 (2002).
M.U. Rao, M. Sreenivasulu, B. Chengaiah, K.J. Reddy and C.M. Chetty,
Int. J. PharmTech Res., 2, 1883 (2010).
K.A. Wadkar, C.S. Magdum, S.S. Patil and N.S. Naikwade, J. Herbal Med., 2, 45 (2008).
R. A. DeFronzo, Ann. Intern. Med., 131, 281 (1999);https://doi.org/10.7326/0003-4819-131-4-199908170-00008
H.E. Lebovitz, Endocrinol. Metabol. Clin. North Am., 26, 539 (1997);https://doi.org/10.1016/S0889-8529(05)70266-8
W. Benalla, S. Bellahcen and M. Bnouham, Curr. Diab. Rev., 6, 247 (2010);https://doi.org/10.2174/157339910791658826
D. Western and M. Wright, Natural Connections: Perspectives in Community Based Conservation, Island Press (2013).
H. Matsuda, T. Morikawa and M. Yoshikawa, Pure Appl. Chem., 74, 1301 (2002);https://doi.org/10.1351/pac200274071301
T. Matsui, I. Ogunwande, K. Abesundara and K. Matsumoto, Mini-Rev. Med. Chem., 6, 349 (2006);https://doi.org/10.2174/138955706776073484
S.A. Nirmal, S.M. Shelke, P.B. Gagare, P.R. Jadhav and P.M. Dethe, Nat. Prod. Res., 21, 1042 (2007);https://doi.org/10.1080/14786410701526016
L.C. van Jaarsveld, W.-M. Kriel and A. Minnaar, Plant Dis., 90, 113 (2006);https://doi.org/10.1094/PD-90-0113C
T. Mishra, A.K. Goyal, S.K. Middha and A. Sen, Indian J. Nat. Prod. Resour., 2, 315 (2011).
H.C. Ong and J.S. Siemonsma, in Plant Resources of South-East Asia; Plants Yielding Non-Seed Carbohydrates, Backhuys Publishers: Leiden, Chap. 9, pp. 63-66 (1996).
K. Piyachomkwan, S. Chotineeranat, C. Kijkhunasatian, R. Tonwitowat, S. Prammanee, C. G. Oates and K. Sriroth, Ind. Crops Prod., 16, 11 (2002);https://doi.org/10.1016/S0926-6690(02)00003-1
A. Duke and E.S. Ayensu, Medicinal Plants of China, Reference Publ., Inc. Algonac. Michigan: USA (1985).
T. Odugbemi, O. Akinsulire, I. Aibinu and P. Fabeku, African J. Trad. Compl. Altern. Med., 4, (2008);https://doi.org/10.4314/ajtcam.v4i2.31207
S. Ayusman, P. Duraivadivel, H.G. Gowtham, S. Sharma and P. Hariprasad, Food Biosci., 35, 100544 (2020);https://doi.org/10.1016/j.fbio.2020.100544
C. Proença, M. Freitas, D. Ribeiro, E.F.T. Oliveira, J.L.C. Sousa, S.M. Tomé, M.J. Ramos, A.M.S. Silva, P.A. Fernandes and E. Fernandes, J. Enzyme Inhib. Med. Chem., 32, 1216 (2017);https://doi.org/10.1080/14756366.2017.1368503
K. Yamamoto, H. Miyake, M. Kusunoki and S. Osaki, FEBS J., 277, 4205 (2010);https://doi.org/10.1111/j.1742-4658.2010.07810.x
A. Gupta, P. Sharma and B. Jayaram, Protein Pept. Lett., 14, 632 (2007);https://doi.org/10.2174/092986607781483831
Z. Yin, W. Zhang, F. Feng, Y. Zhang and W. Kang, Food Sci. Human Wellness, 3, 136 (2014);https://doi.org/10.1016/j.fshw.2014.11.003
Y.Q. Li, F.C. Zhou, F. Gao, J. S. Bian and F. Shan, J. Agric. Food Chem., 57, 11463 (2009);https://doi.org/10.1021/jf903083h
P. Jiang, J. Xiong, F. Wang, M.H. Grace, M.A. Lila and R. Xu, J. Chem., 8516964 (2017);https://doi.org/10.1155/2017/8516964
R. Subramanian, M. Z. Asmawi and A. Sadikun, Acta Biochim. Pol., 55, 391 (2008).
B. C. Behera, N. Mahadik and M. Morey, Pharm. Biol., 50, 968 (2012);https://doi.org/10.3109/13880209.2012.654396
C. Deraeve, Z. Guo, R.S. Bon, W. Blankenfeldt, R. DiLucrezia, A. Wolf, S. Menninger, E.A. Stigter, S. Wetzel, A. Choidas, K. Alexandrov, H. Waldmann, R.S. Goody and Y.-W. Wu, J. Am. Chem. Soc., 134, 7384 (2012);https://doi.org/10.1021/ja211305j
M. Petersen, Phytochemistry, 62, 121 (2003);https://doi.org/10.1016/S0031-9422(02)00513-7