Molecular docking and inhibition studies of α-amylase activity by labdane diterpenes from Alpinia nigra seeds

Medicinal Chemistry Research

Volumn 23, Issue 11, 2014, Pages 4836-4852

  Ghosh, Sudipta ^a   Rangan, Latha ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Alpinia nigra; Antidiabetic; Labdane diterpene; Molegro Virtual Docker; Non competitive inhibition; amylase

Indexed keywords

EID: 84939873999     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-014-1056-3     Document Type: Article

References (56)

1. Abe M, Ozawa Y, Uda Y, Yamada F, Morimitsu Y, Nakamura Y, Osawa T (2004) Antimicrobial activities of diterpene dialdehydes, constituents from Myoga (Zingiber mioga Roscoe), and their quantitative analysis. Biosci Biotechnol Biochem 68:1601-1604
2. Andrade-Cetto A, Becerra-Jiménez J, Cárdenas-Vázquez R (2008) Alfa-glucosidase-inhibiting activity of some Mexican plants used in the treatment of type 2 diabetes. J Ethnopharmacol 116: 27-32
3. Balba M, El-Hady NA, Taha N, Rezki N, El Ashry ESH (2011) Inhibition of α-glucosidase and α-amylase by diaryl derivatives of imidazole-thione and 1,2,4-triazole-thiol. Eur J Med Chem 46:2596-2601
4. Berendsen HJC, Van der Spoel D, Drunen RV (1995) GROMACS: a message passing parallel molecular dynamics implementation. Comput Phys Commun 91:43-56
5. Bernfeld P (1955) Amylases, α and β. Method Enzymol 1:149-154
6. Bolton E, Wang Y, Thiessen PA, Bryant SH (2008) PubChem: integrated platform of small molecules and biological activities. In: Annual reports in computational chemistry, vol 4, chap 12. American Chemical Society, Washington
7. Chiasson JL, Josse RG, Gomis R, Hanefeld M, Karasik A, Laakso M (2002) Acarbose for prevention of type 2 diabetes mellitus: the STOP-NIDDM randomised trial. Lancet 359:2072-2077
8. China Raju B, Tiwari AK, Kumar JA, Ali AZ, Agawane SB, Saidachary G, Madhusudana K (2010) α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorg Med Chem 18:358-365
9. Dai J, Mumper RJ (2010) Plant phenolics: extraction, analysis and their antioxidant and anticancer properties. Molecules 15:7313-7352
10. Elya B, Basah K, Mun'im A, Yuliastuti W, Bangun A, Septiana EK (2012) Screening of α-glucosidase inhibitory activity from some plants of Apocynaceae, Clusiaceae, Euphorbiaceae, and Rubiaceae. J Biomed Biotech. doi:10.1155/2012/281078
11. Elzaawely AA, Xuan TD, Tawata S (2007) Antioxidant activity and contents of essential oil and phenolic compounds in flowers and seeds of Alpiniazerumbet (Pers.) B.L. Burtt. & R.M. Sm Food Chem 104:1648-1653
12. Fujisawa T, Ikegami H, Inoue K, Kawabata Y, Ogihara T (2005) Effect of two α-glucosidase inhibitors, voglibose and acarbose, on postprandial hyperglycemia correlates with subjective abdominal symptoms. Metabolism 54:387-390
13. Gehlhaar DK, Verkhivker G, Rejto PA, Fogel DB, Fogel LJ, Freer ST (1995) Docking conformationally flexible small molecules into a protein binding site through evolutionary programming. In: Proceedings of the fourth international conference on evolutionary programming, pp 615-627
14. Gehlhaar DK, Bouzida D, Rejto PA (1998) Fully automated and rapid flexible docking of inhibitors covalently bound to serine proteases. In: Proceedings of the seventh international conference on evolutionary programming, pp 449-461
15. Ghadyale V, Takalikar S, Haldavnekar V, Arvindekar A (2012) Effective control of postprandial glucose level through inhibition of intestinal alpha glucosidase by Cymbopogon martinii (Roxb.). Evid-Based Complement Altern Med. doi:10.1155/2012/372909
16. Ghosh S, Rangan L (2013) Alpinia: the gold mine of future therapeutics. 3. Biotech 3:173-185
17. Ghosh S, Ahire M, Patil S, Jabgunde A, Dusane MB, Joshi BN, Pardesi K, Jachak S, Dhavale DD, Chopade BA (2012) Antidiabetic activity of Gnidia glauca and Dioscorea bulbifera: potent amylase and glucosidase inhibitors. Evid-Based Complement Altern Med. doi:10.1155/2012/929051
18. Ghosh S, Indukuri K, Bondalapati S, Saikia AK, Rangan L (2013a) Unveiling the mode of action of antibacterial labdane diterpenes from Alpinia nigra (Gaertn.) B. L Burtt seeds. Eur J Med Chem 66:101-105
19. Ghosh S, Padilla-González GF, Rangan L (2013b) Alpinia nigra seeds: a potential source of free radical scavenger and antibacterial agent. Indus Crops Prod 49:348-356
20. Hansawasdi C, Kawabata J, Kasai T (2000) Alpha-amylase inhibitors from roselle (Hibiscus sabdariffa Linn.) tea. Biosci Biotechnol Biochem 64:1041-1043
21. Haraguchi H, Kuwata Y, Inada K, Shingu K, Miyahara K, Nagao M, Yagi A (1996) Antifungal activity from Alpinia galanga and the competition for incorporation of unsaturated fatty acids in cell growth. Planta Med 62(4):308-313
22. Hess B, Kutzner C, Van der Spoel D, Lindahl E (2008) GROMACS 4: algorithms for highly efficient, load-balanced and scalable molecular simulation. J Chem Theory Comput 4:435-447
23. Hollander P (1992) Safety profile of acarbose, an alpha-glucosidsase inhibitor. Drugs 44:47-53
24. Huang GL, Liu MX, Mei XY, Wang Y (2005a) Synthesis, immunological activities, and scavenging ability toward superoxide anion of (1 → 3)-β-d-pentaglucoside and its epoxyalkyl derivatives. Bioorg Med Chem 13(12):3873-3877
25. Huang GL, Mei XY, Liu MX (2005b) Synthesis of (R)-2, 3-epoxypropyl(1 → 3)-β-D-pentaglucoside. Carbohydr Res 340(4): 603-608
26. Jain SK, Prakash V (1995) 22 genera and 178 species in India concentrated mainly in North eastern and the peninsular region (Zingiberaceae in India) phytogeography and endemism. Rheedea 5:154-169
27. Li C, Begum A, Numao S, Park KH, Withers SG, Brayer GD (2005) Acarbose rearrangement mechanism implied by the kinetic and structural analysis of human pancreatic α-amylase in complex with analogues and their elongated counterparts. Biochemistry 44:3347-3357
28. Li Y, Gao F, Gao F, Shan F, Bian J, Zhao C (2009) Study on the interaction between 3 flavonoid compounds and α-amylase by fluorescence spectroscopy and enzymatic kinetics. J Food Sci 74:C199-C203
29. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del Rev 23:3-25
30. Lo Piparo E, Scheib H, Frei N, Williamson G, Grigorov M, Chou CJ (2008) Flavonoids for controlling starch digestion: structural requirements for inhibiting human α-amylase. J Med Chem 51: 3555-3561
31. Malek SNA, Lee GS, Hong SL, Yaacob H, Wahab NA, Weber JF, Shah SAA (2011) Phytochemical and cytotoxic investigations of Curcuma manga rhizomes. Molecules 16:4539-4548
32. Matsui T, Ueda T, Oki T, Sugita K, Terahara N, Matsumoto K (2001) Alpha glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigment with potent inhibitory activity. J Agric Food Chem 49:1948-1951
33. Mcdougall GJ, Shpiro F, Doboson P, Smith P, Black A, Stewart D (2005) Different polyphenolic components of soft fruits inhibit a-amylase and α-glucosidase. J Agric Food Chem 53: 2760-2766
34. Murai A, Iwamura K, Takada M, Ogawa K, Usui T, Okumura J (2002) Control of postprandial hyperglycaemia by galactosyl-maltobionolactone and its novel anti-amylase effect in mice. Life Sci 71:1405-1415
35. Pogano G, Marena S, Corgiat-Mansin L, Cravero F, Giorda C, Bozza M, Rossi CM (1995) Comparison of miglitol and glibenclamide in diet-treated type 2 diabetic patients. Diabete Metab 21:162-167
36. Raj N, Nadeem S, Jain S, Raj C, Chouhan K, Nandi P (2011) Ameliorative effects of Alpinia calcarata in alloxan-induced diabetic rats. Dig J Nanomater Bios 6:991-997
37. Roy B, Swargiary A, Giri BR (2012) Alpinia Nigra (Family Zingiberaceae): an anthelmintic medicinal plant of north-east India. Adv Life Sci 2(3):39-51
38. Rydberg EH, Li C, Maurus R, Overall CM, Brayer GD, Withers SG (2002) Mechanistic analyses of catalysis in human pancreatic a-amylase: detailed kinetic and structural studies of mutants of three conserved carboxylic acids. Biochemistry 41: 4492-4502
39. Sales PM, Souza PM, Simeoni LA, Silveira D (2012) α-Amylase inhibitors: a review of raw material and isolated compounds from plant source. J Pharm PharmSci 15(1):141-183
40. Shobana S, Sreerama YN, Malleshi NG (2009) Composition and enzyme inhibitory properties of finger millet (Eleusine coracana L.) seed coat phenolics: mode of inhibition of α-glucosidase and pancreatic amylase. Food Chem 115:1268-1273
41. Singh SK, Rai PK, Jaiswal D, Watal G (2008) Evidence-based critical evaluation of glycemic potential of Cynodon dactylon . Evid- Based Complement Altern Med 5:415-420
42. Sirat HM, Masri D, Rahman AA (1994) The distribution of labdane diterpenes in the Zingiberaceae of Malaysia. Phytochemistry 36:699-701
43. Srividya AR, Dhanabal SP, Satishkumar MN, Parthkumar HB (2010) Antioxidant and antidiabetic activity of Alpinia galanga. IJPPR 3:6-12
44. Tarling CA, Woods K, Zhang R, Brastianos HC, Brayer GD, Andersen RJ, Withers SG (2008) The search for novel human pancreatic α-amylase inhibitors: high-throughput screening of terrestrial and marine natural product extracts. Chem Bio Chem 9:433-438
45. Thomsen R, Christensen M (2006) MolDock: a new technique for highaccuracy molecular docking. J Med Chem 49(11):3315-3321
46. Tushar, Basak S, Sarma GC, Rangan L (2010) Ethnomedical uses of Zingiberaceous plants of Northeast India. J Ethnopharmacol 132: 286-296
47. Ulrich B, Norman LA (1982) Molecular mechanics (ACS monograph 177). Am Chem Soc, Washington, DC
48. Upadhyay A, Chompoo J, Kishimoto W, Makise T, Tawata S (2011) HIV-1 integrase and neuraminidase inhibitors from Alpinia zerumbet. J Agric Food Chem 59:2857-2862
49. Van der Spoel D, Lindahl E, Hess B, Groenhof G, Mark AE, Berendsen HJ (2005) GROMACS: fast, flexible, and free. J Comput Chem 26:1701-1718
50. Wallace AC, Laskowski RA, Thornton JM (1995) LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng 8:127-134
51. Wang Y, Bolton E, Dracheva S, Karapetyan K, Shoemaker SA, Suzek TO, Wang J, Xiao J, Zhang J, Bryant SH (2010a) An overview of the PubChemBioAssay resource. Nucleic Acids Res 38:D255-D266
52. Wang Y, Yang Z, Wei X (2010b) Sugar compositions, α-glucosidase inhibitory and amylase inhibitory activities of polysaccharides from leaves and flowers of Camellia sinensis obtained by different extraction methods. Int J Biol Macromol 47: 534-539
53. Williams LK, Li C, Withers SG, Brayer GD (2012) Order and disorder: differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target. J Med Chem 55(22):10177-10186
54. Yang JM, Chen CC (2004) GEMDOCK: a generic evolutionary method for molecular docking. Proteins 5:288-304
55. Yasuhara T, Manse Y, Morimoto T, Qilong W, Matsuda H, Yoshikawa M, Muraoka O (2009) Acetoxybenzhydrols as highly active and stable analogues of 1′S-1′-acetoxychavicol, a potent antiallergic principal from Alpinia galanga. Bioorg Med Chem Lett 19:2944-2946
56. Zhang R, Li C, Williams LK, Rempel BP, Brayer GD, Withers SG (2009) Directed "in situ" inhibitor elongation as a strategy to structurally characterize the covalent glycosyl-enzyme intermediate of human pancreatic α-amylase. Biochemistry 48:10752-10764