Screening and identification of salicin compound from Desmodium gangeticum and its in vivo anticancer activity and docking studies with cyclooxygenase (COX) proteins from mus musculus

Journal of Proteomics and Bioinformatics

Volumn 6, Issue 5, 2013, Pages 109-124

  Srivastava, Preeti ^a   Singh, Vinay K ^a   Singh, Brahma Deo ^a   Srivastava, Gaurava ^b   Misra, Bhuwan B ^a   Tripathi, Vyasji ^a  

^a BANARAS HINDU UNIVERSITY   (India)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

Anti cancer; Cyclooxygenase; Desmodium gangeticum; Docking; Functional motif; Molecular modeling; Salicin

Indexed keywords

CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; FLUOROURACIL; HEMOGLOBIN; PROSTAGLANDIN SYNTHASE; SALICIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DESMODIUM GANGETICUM; DRUG BINDING; DRUG DESIGN; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; ERYTHROCYTE COUNT; FEMALE; HEMOGLOBIN BLOOD LEVEL; IN VIVO STUDY; LYMPHOCYTE COUNT; MEDICINAL PLANT; MOLECULAR DOCKING; MONOCYTE; MOUSE; NEUTROPHIL COUNT; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT LEAF; STRUCTURE ANALYSIS; TUMOR VOLUME;

DESMODIUM GANGETICUM; MUS; MUS MUSCULUS;

EID: 84878740612     PISSN: None     EISSN: 0974276X     Source Type: Journal    
DOI: 10.4172/jpb.1000269     Document Type: Article

References (85)

1. Samuelsson G (2004) Drugs of Natural Origin: a Textbook of Pharmacognosy, 5th Swedish Pharma Press, Stockholm, Sweden.
2. Balick MJ, Cox PA (1997) Plants, People, and Culture: the Science of Ethnobotany. Scientific American Library, New York, NY, USA.
3. Balick MJ, Cox PA (2001) Pharmacognosy in the 21st century. J Pharm Pharmacol 53: 135-148.
4. Newman DJ, Cragg GM, Snader KM (2000) The influence of natural products upon drug discovery. Nat Prod Rep 17: 215-234.
5. Butler MS (2004) The role of natural product chemistry in drug discovery. J Nat Prod 67: 2141-2153.
6. Ley SV, Baxendale IR (2002) New tools and concepts for modern organic synthesis. Nat Rev Drug Discov 1: 573-586.
7. Geysen HM, Schoenen F, Wagner D, Wagner R (2003) Combinatorial compound libraries for drug discovery: an ongoing challenge. Nat Rev Drug Discov 2: 222-230.
8. Lombardino JG, Lowe JA 3rd (2004) The role of the medicinal chemist in drug discovery--then and now. Nat Rev Drug Discov 3: 853-862.
9. Newman DJ, Cragg GM, Snader KM (2000) The influence of natural products upon drug discovery. Nat Prod Rep 17: 215-234.
10. Bray F, Møller B (2006) Predicting the future burden of cancer. Nat Rev Cancer 6: 63-74.
11. Anand P, Kunnumakkara AB, Sundaram C, Harikumar KB, Tharakan ST, et al. (2008) Cancer is a preventable disease that requires major lifestyle changes. Pharm Res 25: 2097-2116.
12. Federsel HJ (2003) Logistics of process R&D: transforming laboratory methods to manufacturing scale. Nat Rev Drug Discov 2: 654-664.
13. Piggott AM, Karuso P (2004) Quality, not quantity: the role of natural products and chemical proteomics in modern drug discovery. Comb Chem High Throughput Screen 7: 607-630.
14. Tan DS (2004) Current progress in natural product-like libraries for discovery screening. Comb Chem High Throughput Screen 7: 631-643.
15. Koehn FE, Carter GT (2005) The evolving role of natural products in drug discovery. Nat Rev Drug Discov 4: 206-220.
16. FitzGerald GA, Patrono C (2001) The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med 345: 433-442.
17. Méric JB, Rottey S, Olaussen K, Soria JC, Khayat D, et al. (2006) Cyclooxygenase-2 as a target for anticancer drug development. Crit Rev Oncol Hematol 59: 51-64.
18. Liu CH, Chang SH, Narko K, Trifan OC, Wu MT, et al. (2001) Overexpression of cyclooxygenase-2 is sufficient to induce tumorigenesis in transgenic mice. J Biol Chem 276: 18563-18569.
19. Subbaramaiah K, Dannenberg AJ (2003) Cyclooxygenase 2: a molecular target for cancer prevention and treatment. Trends Pharmacol Sci 24: 96-102.
20. Brown JR, DuBois RN (2005) COX-2: a molecular target for colorectal cancer prevention. J Clin Oncol 23: 2840-2855.
21. Dempke W, Rie C, Grothey A, Schmoll HJ (2001) Cyclooxygenase-2: a novel target for cancer chemotherapy? J Cancer Res Clin Oncol 127: 411-417.
22. Sorokin A (2004) Cyclooxygenase-2: potential role in regulation of drug efflux and multidrug resistance phenotype. Curr Pharm Des 10: 647-657.
23. Fantappiè O, Masini E, Sardi I, Raimondi L, Bani D, et al. (2002) The MDR phenotype is associated with the expression of COX-2 and iNOS in a human hepatocellular carcinoma cell line. Hepatology 35: 843-852.
24. DuBois RN, Radhika A, Reddy BS, Entingh AJ (1996) Increased cyclooxygenase-2 levels in carcinogen-induced rat colonic tumors. Gastroenterology 110: 1259-1262.
25. Shiff SJ, Rigas B (1999) The role of cyclooxygenase inhibition in the antineoplastic effects of nonsteroidal antiinflammatory drugs (NSAIDs). J Exp Med 190: 445-450.
26. Hao X, Bishop AE, Wallace M, Wang H, Willcocks TC, et al. (1999) Early expression of cyclo-oxygenase-2 during sporadic colorectal carcinogenesis. J Pathol 187: 295-301.
27. Thun MJ, Henley SJ, Patrono C (2002) Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues. J Natl Cancer Inst 94: 252-266.
28. Pommery N, Taverne T, Telliez A, Goossens L, Charlier C, et al. (2004) New COX-2/5-LOX inhibitors: apoptosis-inducing agents potentially useful in prostate cancer chemotherapy. J Med Chem 47: 6195-6206.
29. Peek RM Jr (2004) Prevention of colorectal cancer through the use of COX-2 selective inhibitors. Cancer Chemother Pharmacol 54: S50-S56.
30. Lu X, Xie W, Reed D, Bradshaw WS, Simmons DL (1995) Nonsteroidal antiinflammatory drugs cause apoptosis and induce cyclooxygenases in chicken embryo fibroblasts. Proc Natl Acad Sci U S A 92: 7961-7965.
31. Higuchi T, Iwama T, Yoshinaga K, Toyooka M, Taketo MM, et al. (2003) A randomized, double-blind, placebo-controlled trial of the effects of rofecoxib, a selective cyclooxygenase-2 inhibitor, on rectal polyps in familial adenomatous polyposis patients. Clin Cancer Res 9: 4756-4760.
32. Chopra RN, Nayar SL, Chopra IC (1956) Glossary of Indian Medicinal Plants, CSIR, New Delhi, India.
33. Bakshi DNG, Sensarma P, Pal DC (2001) A lexicon of medicinal plants in India. Naya Prakash, Calcutta. 2: 52-53.
34. Trout K (2004) Trout's notes on the Genus Desmodium: Trout note #2. Myriatre Production.
35. Jabbar S, Khan MT, Choudhuri MS (2001) The effects of aqueous extracts of Desmodium gangeticum DC. (Leguminosae) on the central nervous system. Pharmazie 56: 506-508.
36. Rathi A, Rao ChV, Ravishankar B, De S, Mehrotra S (2004) Anti-inflammatory and anti-nociceptive activity of the water decoction Desmodium gangeticum. J Ethnopharmacol 95: 259-263.
37. Mishra PK, Singh N, Ahmad G, Dube A, Maurya R (2005) Glycolipids and other constituents from Desmodium gangeticum with antileishmanial and immunomodulatory activities. Bioorg Med Chem Lett 15: 4543-4546.
38. Iwu MM, Jackson JE, Tally JD, Klayman DL (1992) Evaluation of plant extracts for antileishmanial activity using a mechanism-based radiorespirometric microtechnique (RAM). Planta Med 58: 436-441.
39. Dharmani P, Mishra PK, Maurya R, Chauhan VS, Palit G (2005) Desmodium gangeticum: a potent anti-ulcer agent. Indian J Exp Biol 43: 517-521.
40. Govindarajan R, Vijayakumar M, Rao ChV, Shirwaikar A, Kumar S, et al. (2007) Antiinflammatory and antioxidant activities of Desmodium gangeticum fractions in carrageenan-induced inflamed rats. Phytother Res 21: 975-979.
41. Jain V, Prasad V, Pandey RS (2006) Wound healing activity of Desmodium gangeticum in different wound models. J Plant Sci 1: 247-53.
42. Purushotaman KK, Kishore VM, Narayanaswamy V, Conolly JD (1971) The Structure and stereochemistry of gangetin, a new pterocarpan from Desmodium gangeticum (Leguminosae). J Chem Soc 13: 2420-2422.
43. Govindarajan R, Rastogi S, Vijayakumar M, Shirwaikar A, Rawat AK, et al. (2003) Studies on the antioxidant activities of Desmodium gangeticum. Biol Pharm Bull 26: 1424-1427.
44. Behari M, Varshney A (1986) Sterols from Desmodium species. Indian Drugs 23: 434-435.
45. Ghosal S, Bhattacharya SK (1972) Desmodium alkaloids. II. Chemical and pharmacological evaluation of D. gangeticum. Planta Med 22: 434-440.
46. Pilotto A, Franceschi M, Longoa MG, Scarcelli C, Orsitto G, et al. (2004) Helicobacter pylori infection and the prevention of peptic ulcer with proton pump inhibitors in elderly subjects taking low-dose aspirin. Dig Liver Dis 36: 666-670.
47. Hawkey CJ (2004) Non-steroidal anti-inflammatory drugs: who should receive prophylaxis? Aliment Pharmacol Ther 20 Suppl 2: 59-64.
48. Bigler J, Whitton J, Lampe JW, Fosdick L, Bostick RM, et al. (2001) CYP2C9 and UGT1A6 genotypes modulate the protective effect of aspirin on colon adenoma risk. Cancer Res 61: 3566-3569.
49. Macarthur M, Sharp L, Hold GL, Little J, El-Omar EM (2005) The role of cytokine gene polymorphisms in colorectal cancer and their interaction with aspirin use in the northeast of Scotland. Cancer Epidemiol Biomarkers Prev 14: 1613-1618.
50. (2009) WHO monographs on selected medicinal plants.
51. Nayeem A, Sitkoff D, Krystek S Jr (2006) A comparative study of available software for high-accuracy homology modeling: from sequence alignments to structural models. Protein Sci 15: 808-824.
52. Köckenberger W, De Panfilis C, Santoro D, Dahiya P, Rawsthorne S (2004) High resolution NMR microscopy of plants and fungi. J Microsc 214: 182-189.
53. Guignard L, Ozawa K, Pursglove SE, Otting G, Dixon NE (2002) NMR analysis of in vitro-synthesized proteins without purification: a high-throughput approach. FEBS Lett 524: 159-162.
54. Du Q, Jerz G, Ha Y, Li L, Xu Y, et al. (2005) Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography. J Chromatogr A 1074: 43-46.
55. Wishart DS, Knox C, Guo AC, Eisner R, Young N, et al. (2009) HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res 37: D603-D610.
56. Felsenstein J (1985) Confidence limits on phylogenies: An approach using the bootstrap. Evolution 39: 783-791.
57. Efron B (1982) The jackknife, the bootstrap, and other resampling plans. Society of Industrial and Applied Mathematics CBMS-NSF Monographs 38.
58. Arber N (2008) Cyclooxygenase-2 inhibitors in colorectal cancer prevention: point. Cancer Epidemiol Biomarkers Prev 17: 1852-1857.
59. Marnett LJ, Rowlinson SW, Goodwin DC, Kalgutkar AS, Lanzo CA (1999) Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J Biol Chem 274: 22903-22906.
60. Smith WL, Garavito RM, DeWitt DL (1996) Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and-2. J Biol Chem 271: 33157-33160.
61. Kulmacz RJ (1998) Cellular regulation of prostaglandin H synthase catalysis. FEBS Lett 430: 154-157.
62. Herschman HR (1996) Prostaglandin synthase 2. Biochim Biophys Acta 1299: 125-140.
63. Picot D, Loll PJ, Garavito RM (1994) The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature 367: 243-249.
64. Luong C, Miller A, Barnett J, Chow J, Ramesha C, et al. (1996) Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 3: 927-933.
65. Bakhle YS (2001) COX-2 and cancer: a new approach to an old problem. Br J Pharmacol 134: 1137-1150.
66. Dannhardt G, Kiefer W (2001) Cyclooxygenase inhibitors--current status and future prospects. Eur J Med Chem 36: 109-126.
67. Loll PJ, Garavito RM, Carrell CJ, Carrell HL (1996) 2-bromoacetoxybenzoic acid, a brominated aspirin analog. Acta Crystallogr C 52: 375-377.
68. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, et al. (1996) Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 384: 644-648.
69. Ermondi G, Caron G, Lawrence R, Longo D (2004) Docking studies on NSAID/COX-2 isozyme complexes using contact statistics analysis. J Comput Aided Mol Des 18: 683-696.
70. Singh P, Bhardwaj A (2010) Mono-, di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation. J Med Chem 53: 3707-3717.
71. Taylor RD, Jewsbury PJ, Essex JW (2002) A review of protein-small molecule docking methods. J Comput Aided Mol Des 16: 151-166.
72. Schulz-Gasch T, Stahl M (2003) Binding site characteristics in structure-based virtual screening: evaluation of current docking tools. J Mol Model 9: 47-57.
73. Wang R, Lu Y, Wang S (2003) Comparative evaluation of 11 scoring functions for molecular docking. J Med Chem 46: 2287-2303.
74. Ferrara P, Gohlke H, Price DJ, Klebe G, Brooks CL 3rd (2004) Assessing scoring functions for protein-ligand interactions. J Med Chem 47: 3032-3047.
75. Vane JR, Flower RJ, Botting RM (1990) History of aspirin and its mechanism of action. Stroke 21: IV12-23.
76. Akao T, Yoshino T, Kobashi K, Hattori M (2002) Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury. Planta Med 68: 714-718.
77. Ashwin KA, Bairy KL, Vidyasagar S, Verma M, Prashanth CK, et al. (2007) Aspirin resistance. Indian J Physiol Pharmacol 51: 109-117.
78. Kurogi Y, Güner OF (2001) Pharmacophore modeling and three-dimensional database searching for drug design using catalyst. Curr Med Chem 8: 1035-1055.
79. Oshiro CM, Kuntz ID, Dixon JS (1995) Flexible ligand docking using a genetic algorithm. J Comput Aided Mol Des 9: 113-130.
80. Willard L, Ranjan A, Zhang H, Monzavi H, Boyko RF, et al. (2003) VADAR: a web server for quantitative evaluation of protein structure quality. Nucleic Acids Res 31: 3316-3319.
81. Kiefer JR, Pawlitz JL, Moreland KT, Stegeman RA, Hood WF, et al. (2000) Structural insights into the stereochemistry of the cyclooxygenase reaction. Nature 405: 97-101.
82. Hillarp A, Palmqvist B, Lethagen S, Villoutreix BO, Mattiasson I (2003) Mutations within the cyclooxygenase-1 gene in aspirin non-responders with recurrence of stroke. Thromb Res 112: 275-283.
83. OBERLING C, GUERIN M (1954) The role of viruses in the production of cancer. Adv Cancer Res 2: 353-423.
84. Prasad SB, Giri A (1994) Antitumor effect of cisplatin against murine ascites Dalton's lymphoma. Indian J Exp Biol 32: 155-162.
85. Sur P, Bag SP, Sur B, Khanam JA (1997) Chloroaceto hydroxamic acid as antitumor agent against Ehrlich ascites carcinoma in mice. Neoplasma 44: 197-201.