Natural products of dietary origin as lead compounds in virtual screening and drug design

Current Pharmaceutical Biotechnology

Volumn 13, Issue 1, 2012, Pages 117-124

  Geldenhuys, Werner J ^a   Bishayee, Anupam ^a,b   Darvesh, Altaf S ^a   Carroll, Richard T ^a  

^a NORTHEAST OHIO MEDICAL UNIVERSITY   (United States)

^b American University of Health Sciences   (United States)

Author keywords

Caffeine; Chemoprevention; Curcumin; Genistein; Istradefylline; Resveratrol

Indexed keywords

ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN INHIBITOR; CAFFEINE; CURCUMIN; G PROTEIN COUPLED RECEPTOR; GENISTEIN; HISTONE DEACETYLASE; ISTRADEFYLLINE; LEAD; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PICEATANNOL; PROTEIN KINASE C; RESVERATROL; STILBENE;

DRUG DESIGN; DRUG SCREENING; HUMAN; LIPID PEROXIDATION; NONHUMAN; PARKINSON DISEASE; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; BIOLOGICAL AGENTS; CAFFEINE; CURCUMIN; DIET; DRUG DESIGN; GENISTEIN; HUMANS; STILBENES;

EID: 84855824565     PISSN: 13892010     EISSN: 18734316     Source Type: Journal    
DOI: 10.2174/138920112798868548     Document Type: Review

References (79)

1. Strohl, W. R. The role of natural products in a modern drug discovery program. Drug Discov. Today, 2000, 5(2), 39-41.
2. Patrono, C.; Rocca, B. Aspirin, 110 years later. J. Thromb. Haemost., 2009, 7 Suppl 1, 258-261.
3. Tobert, J. A. Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors. Nat. Rev. Drug Discov., 2003, 2(7), 517-526.
4. Kingston, D. G.; Newman, D. J. Taxoids: cancer-fighting compounds from nature. Curr. Opin. Drug Discov. Dev., 2007, 10(2), 130-144.
5. Strobel, G. A. Rainforest endophytes and bioactive products. Crit. Rev. Biotechnol., 2002, 22(4), 315-333.
6. Strobel, G.; Daisy, B. Bioprospecting for microbial endophytes and their natural products. Microbiol. Mol. Biol. Rev., 2003, 67(4), 491-502.
7. Gyllenhaal, C.; McChesney, J. D. Intellectual property rights, naturally derived bioactive compounds, and resource conservation. Meeting report. J. Nat. Prod., 1996, 59(3), 334-337.
8. Harvey, A. L. Natural products in drug discovery. Drug Discov. Today, 2008, 13(19-20), 894-901.
9. Hawkins, P. C.; Skillman, A. G.; Warren, G. L.; Ellingson, B. A.; Stahl, M. T. Conformer generation with OMEGA: algorithm and validation using high quality structures from the protein databank and Cambridge structural database. J. Chem. Inf. Model., 2010.
10. Hawkins, P. C.; Skillman, A. G.; Nicholls, A. Comparison of shape-matching and docking as virtual screening tools. J. Med. Chem., 2007, 50(1), 74-82.
11. Altieri, A.; Kombarov, R.; Kochubey, V.; Titarenko, Z.; Genis, D.; Kirpichenok, M. Natural Products Inform Library Design. Genetic Engineering News, 2010, 30(2), 18.
12. Franke, L.; Schwarz, O.; Muller-Kuhrt, L.; Hoernig, C.; Fischer, L.; George, S.; Tanrikulu, Y.; Schneider, P.; Werz, O.; Steinhilber, D.; Schneider, G. Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening. J. Med. Chem., 2007, 50(11), 2640-2646.
13. Pace-Asciak, C. R.; Hahn, S.; Diamandis, E. P.; Soleas, G.; Goldberg, D. M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin. Chim. Acta, 1995, 235(2), 207-219.
14. Burns, J.; Yokota, T.; Ashihara, H.; Lean, M. E.; Crozier, A. Plant foods and herbal sources of resveratrol. J. Agric. Food Chem., 2002, 50(11), 3337-3340.
15. Lyons, M. M.; Yu, C.; Toma, R. B.; Cho, S. Y.; Reiboldt, W.; Lee, J.; van Breemen, R. B. Resveratrol in raw and baked blueberries and bilberries. J. Agric. Food Chem., 2003, 51(20), 5867-5870.
16. Kundu, J. K.; Surh, Y. J. Cancer chemopreventive and therapeutic potential of resveratrol: mechanistic perspectives. Cancer Lett., 2008, 269(2), 243-261.
17. Bishayee, A. Cancer prevention and treatment with resveratrol: from rodent studies to clinical trials. Cancer Prev. Res. (Phila Pa), 2009, 2(5), 409-418.
18. Handler, N.; Brunhofer, G.; Studenik, C.; Leisser, K.; Jaeger, W.; Parth, S.; Erker, T. 'Bridged' stilbene derivatives as selective cyclooxygenase-1 inhibitors. Bioorg. Med. Chem., 2007, 15(18), 6109-6118.
19. Murias, M.; Handler, N.; Erker, T.; Pleban, K.; Ecker, G.; Saiko, P.; Szekeres, T.; Jager, W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem., 2004, 12(21), 5571-5578.
20. Surh, Y. J.; Chun, K. S.; Cha, H. H.; Han, S. S.; Keum, Y. S.; Park, K. K.; Lee, S. S. Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: downregulation of COX-2 and iNOS through suppression of NF-kappa B activation. Mutat. Res., 2001, 480-481, 243-268.
21. Ruweler, M.; Gulden, M.; Maser, E.; Murias, M.; Seibert, H. Cytotoxic, cytoprotective and antioxidant activities of resveratrol and analogues in C6 astroglioma cells in vitro. Chem. Biol. Interact., 2009, 182(2-3), 128-135.
22. Park, J. H.; Min, H. Y.; Kim, S. S.; Lee, J. Y.; Lee, S. K.; Lee, Y. S. Styrylquinazolines: a new class of inhibitors on prostaglandin E2 production in lipopolysaccharide-activated macrophage cells. Arch. Pharm. (Weinheim), 2004, 337(1), 20-24.
23. Cai, Y. J.; Fang, J. G.; Ma, L. P.; Yang, L.; Liu, Z. L. Inhibition of free radical-induced peroxidation of rat liver microsomes by resveratrol and its analogues. Biochim. Biophys. Acta, 2003, 1637(1), 31-38.
24. Tadolini, B.; Juliano, C.; Piu, L.; Franconi, F.; Cabrini, L. Resveratrol inhibition of lipid peroxidation. Free Radic. Res., 2000, 33(1), 105-114.
25. Murias, M.; Jager, W.; Handler, N.; Erker, T.; Horvath, Z.; Szekeres, T.; Nohl, H.; Gille, L. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem. Pharmacol., 2005, 69(6), 903-912.
26. Rimando, A. M.; Nagmani, R.; Feller, D. R.; Yokoyama, W. Pterostilbene, a new agonist for the peroxisome proliferatoractivated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J. Agric. Food Chem., 2005, 53(9), 3403-3407.
27. Mizuno, C. S.; Ma, G.; Khan, S.; Patny, A.; Avery, M. A.; Rimando, A. M. Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARalpha. Bioorg. Med. Chem., 2008, 16(7), 3800-3808.
28. Patil, B. S.; Jayaprakasha, G. K.; Chidambara Murthy, K. N.; Vikram, A. Bioactive compounds: historical perspectives, opportunities, and challenges. J. Agric. Food. Chem., 2009, 57(18), 8142-8160.
29. Anand, P.; Thomas, S. G.; Kunnumakkara, A. B.; Sundaram, C.; Harikumar, K. B.; Sung, B.; Tharakan, S. T.; Misra, K.; Priyadarsini, I. K.; Rajasekharan, K. N.; Aggarwal, B. B. Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochem. Pharmacol., 2008, 76(11), 1590-1611.
30. Jayaprakasha, G. K.; Jena, B. S.; Negi, P. S.; Sakariah, K. K. Evaluation of antioxidant activities and antimutagenicity of turmeric oil: a byproduct from curcumin production. Z. Naturforsch C., 2002, 57(9-10), 828-835.
31. Negi, P. S.; Jayaprakasha, G. K.; Jagan Mohan Rao, L.; Sakariah, K. K. Antibacterial activity of turmeric oil: a byproduct from curcumin manufacture. J. Agric. Food Chem., 1999, 47(10), 4297-4300.
32. Sharma, O. P. Antioxidant activity of curcumin and related compounds. Biochem. Pharmacol., 1976, 25(15), 1811-1812.
33. Ak, T.; Gulcin, I. Antioxidant and radical scavenging properties of curcumin. Chem. Biol. Interact., 2008, 174(1), 27-37.
34. Bisht, K.; Wagner, K. H.; Bulmer, A. C. Curcumin, resveratrol and flavonoids as anti-inflammatory, cyto-and DNA-protective dietary compounds. Toxicology, 2009.
35. Jurenka, J. S. Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: a review of preclinical and clinical research. Altern. Med. Rev., 2009, 14(2), 141-153.
36. Nandal, S.; Dhir, A.; Kuhad, A.; Sharma, S.; Chopra, K. Curcumin potentiates the anti-inflammatory activity of cyclooxygenase inhibitors in the cotton pellet granuloma pouch model. Methods Find. Exp. Clin. Pharmacol., 2009, 31(2), 89-93.
37. Chen, D.; Nie, M.; Fan, M. W.; Bian, Z. Anti-inflammatory activity of curcumin in macrophages stimulated by lipopolysaccharides from Porphyromonas gingivalis. Pharmacology, 2008, 82(4), 264-269.
38. Murakami, Y.; Ishii, H.; Takada, N.; Tanaka, S.; Machino, M.; Ito, S.; Fujisawa, S. Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor. Anticancer Res., 2008, 28(2A), 699-707.
39. Ortiz-Ortiz, M. A.; Moran, J. M.; Ruiz-Mesa, L. M.; Niso-Santano, M.; Bravo-SanPedro, J. M.; Gomez-Sanchez, R.; Gonzalez-Polo, R. A.; Fuentes, J. M. Curcumin exposure induces expression of the Parkinson's disease-associated leucine-rich repeat kinase 2 (LRRK2) in rat mesencephalic cells. Neurosci. Lett., 2009, 468(2), 120-124.
40. Bar-Sela, G.; Epelbaum, R.; Schaffer, M. Curcumin as an anticancer agent: review of the gap between basic and clinical applications. Curr. Med. Chem., 2010, 17(3), 190-197.
41. Anonymous Curcumin, piperine could play role in preventing breast cancer. Cancer Biol. Ther., 2009, 8(24), i-i.
42. Glienke, W.; Maute, L.; Wicht, J.; Bergmann, L. Curcumin inhibits constitutive STAT3 phosphorylation in human pancreatic cancer cell lines and downregulation of survivin/BIRC5 gene expression. Cancer Invest., 2010, 28(2), 166-171.
43. Majumdar, A. P.; Banerjee, S.; Nautiyal, J.; Patel, B. B.; Patel, V.; Du, J.; Yu, Y.; Elliott, A. A.; Levi, E.; Sarkar, F. H. Curcumin synergizes with resveratrol to inhibit colon cancer. Nutr. Cancer, 2009, 61(4), 544-553.
44. Teiten, M. H.; Gaascht, F.; Eifes, S.; Dicato, M.; Diederich, M. Chemopreventive potential of curcumin in prostate cancer. Genes Nutr., 2009.
45. Ravindran, J.; Prasad, S.; Aggarwal, B. B. Curcumin and cancer cells: how many ways can curry kill tumor cells selectively? AAPS J., 2009, 11(3), 495-510.
46. Kurien, B. T.; Scofield, R. H. Curry spice curcumin and prostate cancer. Mol. Nutr. Food Res., 2009, 53(7), 939-940.
47. Singh, N.; Misra, K. Computational screening of molecular targets in Plasmodium for novel non resistant anti-malarial drugs. Bioinformation, 2009, 3(6), 255-262.
48. Irwin, J. J.; Shoichet, B. K. ZINC--a free database of commercially available compounds for virtual screening. J. Chem. Inf. Model., 2005, 45(1), 177-182.
49. Padhye, S.; Yang, H.; Jamadar, A.; Cui, Q. C.; Chavan, D.; Dominiak, K.; McKinney, J.; Banerjee, S.; Dou, Q. P.; Sarkar, F. H. New difluoro Knoevenagel condensates of curcumin, their Schiff bases and copper complexes as proteasome inhibitors and apoptosis inducers in cancer cells. Pharm. Res., 2009, 26(8), 1874-1880.
50. Bora-Tatar, G.; Dayangac-Erden, D.; Demir, A. S.; Dalkara, S.; Yelekci, K.; Erdem-Yurter, H. Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies. Bioorg. Med. Chem., 2009, 17(14), 5219-5228.
51. Sun, M. K.; Hongpaisan, J.; Alkon, D. L. Postischemic PKC activation rescues retrograde and anterograde long-term memory. Proc. Natl. Acad. Sci. U S A., 2009, 106(34), 14676-14680.
52. Nelson, T. J.; Alkon, D. L. Neuroprotective versus tumorigenic protein kinase C activators. Trends Biochem. Sci., 2009, 34(3), 136-145.
53. Palaniyandi, S. S.; Sun, L.; Ferreira, J. C.; Mochly-Rosen, D. Protein kinase C in heart failure: a therapeutic target? Cardiovasc. Res., 2009, 82(2), 229-239.
54. Sun, M. K.; Alkon, D. L. Pharmacology of protein kinase C activators: Cognition-enhancing and antidementic therapeutics. Pharmacol. Ther., 2010.
55. Alkon, D. L.; Sun, M. K.; Nelson, T. J. PKC signaling deficits: a mechanistic hypothesis for the origins of Alzheimer's disease. Trends Pharmacol. Sci., 2007, 28(2), 51-60.
56. Reddy, S.; Aggarwal, B. B. Curcumin is a non-competitive and selective inhibitor of phosphorylase kinase. FEBS Lett., 1994, 341(1), 19-22.
57. Lin, J. K.; Chen, Y. C.; Huang, Y. T.; Lin-Shiau, S. Y. Suppression of protein kinase C and nuclear oncogene expression as possible molecular mechanisms of cancer chemoprevention by apigenin and curcumin. J. Cell. Biochem. Suppl., 1997, 28-29, 39-48.
58. Majhi, A.; Rahman, G. M.; Panchal, S.; Das, J. Binding of curcumin and its long chain derivatives to the activator binding domain of novel protein kinase C. Bioorg. Med. Chem., 2010, 18(4), 1591-1598.
59. Aggarwal, B. B.; Kumar, A.; Bharti, A. C. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res., 2003, 23(1A), 363-398.
60. Fuchs, J. R.; Pandit, B.; Bhasin, D.; Etter, J. P.; Regan, N.; Abdelhamid, D.; Li, C.; Lin, J.; Li, P. K. Structure-activity relationship studies of curcumin analogues. Bioorg. Med. Chem. Lett., 2009, 19(7), 2065-2069.
61. Magkos, F.; Kavouras, S. A. Caffeine use in sports, pharmacokinetics in man, and cellular mechanisms of action. Crit. Rev. Food Sci. Nutr., 2005, 45(7-8), 535-562.
62. Ribeiro, J. A.; Sebastiao, A. M. Caffeine and adenosine. J. Alzheimers Dis., 2010, 20, 3-15.
63. Ross, G. W.; Abbott, R. D.; Petrovitch, H.; Morens, D. M.; Grandinetti, A.; Tung, K. H.; Tanner, C. M.; Masaki, K. H.; Blanchette, P. L.; Curb, J. D.; Popper, J. S.; White, L. R. Association of coffee and caffeine intake with the risk of Parkinson disease. JAMA., 2000, 283(20), 2674-2679.
64. Ross, G. W.; Petrovitch, H. Current evidence for neuroprotective effects of nicotine and caffeine against Parkinson's disease. Drugs Aging, 2001, 18(11), 797-806.
65. Chen, J. F.; Xu, K.; Petzer, J. P.; Staal, R.; Xu, Y. H.; Beilstein, M.; Sonsalla, P. K.; Castagnoli, K.; Castagnoli, N., Jr.; Schwarzschild, M. A. Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease. J. Neurosci., 2001, 21(10), RC143.
66. Kalda, A.; Yu, L.; Oztas, E.; Chen, J. F. Novel neuroprotection by caffeine and adenosine A(2A) receptor antagonists in animal models of Parkinson's disease. J. Neurol. Sci., 2006, 248(1-2), 9-15.
67. Petzer, J. P.; Castagnoli, N., Jr.; Schwarzschild, M. A.; Chen, J. F.; Van der Schyf, C. J. Dual-target-directed drugs that block monoamine oxidase B and adenosine A(2A) receptors for Parkinson's disease. Neurotherapeutics, 2009, 6(1), 141-151.
68. Schwarzschild, M. A.; Xu, K.; Oztas, E.; Petzer, J. P.; Castagnoli, K.; Castagnoli, N., Jr.; Chen, J. F. Neuroprotection by caffeine and more specific A2A receptor antagonists in animal models of Parkinson's disease. Neurology, 2003, 61(11 Suppl 6), S55-61.
69. Bibbiani, F.; Oh, J. D.; Petzer, J. P.; Castagnoli, N., Jr.; Chen, J. F.; Schwarzschild, M. A.; Chase, T. N. A2A antagonist prevents dopamine agonist-induced motor complications in animal models of Parkinson's disease. Exp. Neurol., 2003, 184(1), 285-294.
70. Petzer, J. P.; Steyn, S.; Castagnoli, K. P.; Chen, J. F.; Schwarzschild, M. A.; Van der Schyf, C. J.; Castagnoli, N. Inhibition of monoamine oxidase B by selective adenosine A2A receptor antagonists. Bioorg. Med. Chem., 2003, 11(7), 1299-1310.
71. Youdim, M. B.; Riederer, P. F. Monoamine oxidase A and B inhibitors in Parkinson's disease. Handb. Clin. Neurol., 2007, 84, 93-120.
72. Youdim, M. B.; Edmondson, D.; Tipton, K. F. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci., 2006, 7(4), 295-309.
73. Youdim, M. B.; Bakhle, Y. S. Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness. Br. J. Pharmacol., 2006, 147 Suppl 1, S287-296.
74. Pretorius, J.; Malan, S. F.; Castagnoli, N., Jr.; Bergh, J. J.; Petzer, J. P. Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E, E)-8-(4-phenylbutadien-1-yl)caffeine analogues. Bioorg. Med. Chem., 2008, 16(18), 8676-8684.
75. Lethaby, A. E.; Brown, J.; Marjoribanks, J.; Kronenberg, F.; Roberts, H.; Eden, J. Phytoestrogens for vasomotor menopausal symptoms. Cochrane Database Syst. Rev., 2007, (4), CD001395.
76. Yu, H. L.; Li, L.; Zhang, X. H.; Xiang, L.; Zhang, J.; Feng, J. F.; Xiao, R. Neuroprotective effects of genistein and folic acid on apoptosis of rat cultured cortical neurons induced by beta-amyloid 31-35. Br. J. Nutr., 2009, 102(5), 655-662.
77. Schreihofer, D. A.; Redmond, L. Soy phytoestrogens are neuroprotective against stroke-like injury in vitro. Neuroscience, 2009, 158(2), 602-609.
78. Bhuva, H. A.; Kini, S. G. Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors. J. Mol. Graph. Model., 2010.
79. Dancik, V.; Seiler, K. P.; Young, D. W.; Schreiber, S. L.; Clemons, P. A. Distinct biological network properties between the targets of natural products and disease genes. J. Am. Chem. Soc., 2010, 132(27), 9259-9261.