Natural polyphenols based new therapeutic avenues for advanced biomedical applications

Drug Metabolism Reviews

Volumn 47, Issue 4, 2015, Pages 420-430

  Agrawal, Megha ^a  

^a University of Arkansas   (United States)

Author keywords

Antioxidant; Cancer; Epicatechin; Resveratrol; Stroke

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; FLAVANOL DERIVATIVE; POLYPHENOL; RESVERATROL; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; CATECHIN; STILBENE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; BLOOD BRAIN BARRIER; BRAIN ISCHEMIA; DRUG METABOLISM; DRUG SYNTHESIS; END STAGE RENAL DISEASE; FOOD ALLERGY; HUMAN; KIDNEY FAILURE; NEUROPROTECTION; NONHUMAN; REVIEW; STEREOCHEMISTRY; AGING; ANIMAL; BIOLOGICAL MODEL; DRUG EFFECTS; FOOD HYPERSENSITIVITY; NEOPLASMS; RENAL INSUFFICIENCY; STROKE;

AGING; ANIMALS; ANTI-INFECTIVE AGENTS; ANTIOXIDANTS; CATECHIN; FOOD HYPERSENSITIVITY; HUMANS; MODELS, BIOLOGICAL; NEOPLASMS; POLYPHENOLS; RENAL INSUFFICIENCY; STILBENES; STROKE;

EID: 84952637209     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.3109/03602532.2015.1102933     Document Type: Review

References (78)

1. Agrawal M, Biswas A. (2015). Molecular diagnostics of neurodegenerative disorders. Front Mol Biosci, Editorial article, 2(54). doi: 10.3389/fmolb.2015.00054
2. Agrawal M, Kumar V, Kashyap MP, et al. (2011). Ischemic insult induced apoptotic changes in PC12 cells: Protection by trans resveratrol. Eur J Pharmacol 666: 5-11
3. Agrawal M, Kumar V, Singh AK, et al. (2013). Trans-resveratrol protects ischemic PC12 cells by inhibiting the hypoxia associated transcription factors and increasing the levels of antioxidant defense enzymes. ACS Chem Neurosci 4: 285-294
4. Albani D, Polito L, Signorini A, Forloni G. (2010). Neuroprotective properties of resveratrol in different neurodegenerative disorders. Biofactors 36: 370-376
5. Athar M, Back JH, Tang X, et al. (2007). Resveratrol: A review of pre-clinical studies for human cancer prevention. Toxicol Appl Pharmacol 224: 274-283
6. Augustine N, Goel AK, Sivakumar KC, et al. (2014). Resveratrol-a potential inhibitor of biofilm formation in Vibrio cholerae. Phytomedicine 21: 286-289
7. Baur JA, Sinclair DA. (2006). Therapeutic potential of resveratrol: The in vivo evidence. Nat Rev Drug Discov 5: 493-506
8. Baxter RA. (2008). Anti-aging properties of resveratrol: Review and report of a potent new antioxidant skin care formulation. J Cosmet Dermatol 7: 2-7
9. Bishayee A. (2009). Cancer prevention and treatment with resveratrol: From rodent studies to clinical trials, cancer. Cancer Prev Res (Phila) 409 (May 2)
10. Bors W, Heller W, Michel C, Saran M. (1990). Flavonoids as antioxidants: Determination of radical Scavenging efficiencies. Methods Enzymol 186: 343-355
11. Botha JJ, Ferreira D, Roux DG. (1978). Condensed tannins: Direct synthesis, structure and absolute configuration of biflavonoids from black wattle bark (mimosa) extract. J Chem Soc Chem Commun. 16: 700-702
12. Brents LK, Medina-Bolivar F, Seely KA, et al. (2012). Natural prenylated resveratrol analogs arachidin-1 and-3 demonstrate improved glucuronidation profiles and have affinity for cannabinoid receptors. Xenobiotica 42: 139-156
13. Bringmann G, Gulder T, Gulder T, et al. (2011). Atroposelective total synthesis of axially chiral biaryl natural products. Chem Rev 111: 563-639
14. Burns TC, Verfaillie CM, Low WC. (2009). Stem cells for ischemic brain injury: A critical review. J Comp Neurol 515: 125-144
15. Chan PH. (2001). Reactive oxygen radicals in signaling and damage in the ischemic brain. J Cereb Blood Flow Metab 21: 2-14
16. Chander V, Chopra K. (2005). Role of nitric oxide in resveratrol-induced renal protective effects of ischemic preconditioning. J Vasc Surg 42: 1198-1205
17. Clark D, Tuor UI, Thompson R, et al. (2012). Protection against recurrent stroke with resveratrol: Endothelial protection. PLoS One 7: e47792
18. Deffieux D, Natangelo A, Malik G, et al. (2011). First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloyl-epi-punicacortein A. Chem Commun (Camb.) 47: 1628-1630
19. Dennell R. (1947). The occurrence and significance of phenolic hardening in the newly formed cuticle of Crustacea decapoda. Proc R S B 134: 485-503
20. Ding DF, You N, Wu XM, et al. (2010). Resveratrol attenuates renal hypertrophy in early-stage diabetes by activating AMPK. Am J Nephrol 31: 363-374
21. Wen PD, Nan LL, Gao DK, et al. (2008). Resveratrol attenuates ischemic brain damage in the delayed phase after stroke and induces messenger RNA and protein express for angiogenic factors. J Vasc Surg 48: 714
22. Feldman K, Ensel SM. (1994). Ellagitannin chemistry. Preparative and mechanistic studies of the biomimetic oxidative coupling of galloyl esters. J Amer Chem Soc 116: 3357-3366
23. Feldman KS, Lawlor MD, Sahasrabudhe K. (2000). Ellagitannin chemistry. Evolution of a three-component coupling strategy for the synthesis of the dimeric ellagitannin coriariin A and a dimeric gallotannin analogue. J Org Chem 65: 8011-8019
24. Feldman KS. (2004). Recent progress in ellagitannin chemistry, 4th Tannin Conference held at the Fall Meeting of the American Chemical Society, Phytochemistry; Philadelphia, 66:1984-2000
25. Fernández-Mar MI, Mateos R, García-Parrilla MC, et al. (2012). Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review. Food Chem 130: 797-813
26. Giovannelli L, Pitozzi V, Jacomelli M, et al. (2011). Protective effects of resveratrol against senescence-associated changes in cultured human fibroblasts. J Gerontol A Biol Sci Med Sci 66: 9-18
27. Giovannini L, Migliori M, Longoni BM, et al. (2001). Resveratrol, a polyphenol found in wine, reduces ischemia reperfusion injury in rat kidneys. J Cardiovasc Pharmacol 37: 262-270
28. Greer AK, Madadi NR, Bratton SM, et al. (2014). Novel resveratrol-based substrates for human hepatic, renal, and intestinal UDP-glucuronosyltransferases. Chem Res Toxicol 27: 536-545
29. Han YS, Bastianetto S, Dumont Y, Quirion R. (2006). Specific plasma membrane binding sites for polyphenols, including resveratrol, in the rat brain. J Pharmacol Exp Ther 318: 238-245
30. Harper CE, Patel BB, Wang J, et al. (2007). Resveratrol suppresses prostate cancer progression in transgenic mice. Carcinogenesis 28: 1946-1953
31. Hart JH, Hillis WE. (1974). Inhibition of wood-rotting fungi by stilbenes and other polyphenols in Eucalyptus sideroxylon. Phytopathology 64: 939-948
32. Hubbard BP, Gomes AP, Dai H, et al. (2013). Evidence for a common mechanism of SIRT1 regulation by allosteric activators. Science 339: 1216-1219
33. Itoh T, Chika J, Shirakami SS, et al. (1996). Synthesis of trideca-O-methyl-alpha-pedunculagin. Diastereo-favoritism studies on intramolecular ester-cyclization of axially chiral diphenic acids with carbohydrate core. J Org Chem 61: 3700-3705
34. Jang M, Cai L, Udeani GO, et al. (1997). Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275: 218-220
35. Jendekova L, Kojsova S, Andriantsitohaina R, Pechanova O. (2006). The time-dependent effect of provinolsTM on brain NO synthase activity in L-NAME-induced hypertension. Physiol Res 55: 31-37
36. Lee J, Ryu YKSY, et al. (2014). Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa. J Nat Prod 77: 168-172
37. Khanbabaee K, Grosser M. (2003). An efficient total synthesis of pedunculagin by using a twofold intramolecular double esterification strategy. Eur J Org Chem 11: 2128-2131
38. Khushwant S, Bhullar HP., Rupasinghe V. (2013). Polyphenols: Multipotent therapeutic agents in neurodegenerative diseases. Oxid Med Cell Longev 2013: 891748
39. Kimura Y, Okuda H. (2001). Resveratrol isolated from polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice. J Nutr 131: 1844-1849
40. Kitada M, Koya D. (2013). Renal protective effects of resveratrol. Oxid Med Cell Longev 2013: 568093
41. Kitada M, Zhang Z, Mima A, King GL. (2010). Molecular mechanisms of diabetic vascular complications. J Diabetes Investig 1: 77-89
42. Kovacsova M, Barta A, Parohova J, et al. (2010). Neuroprotective mechanisms of natural polyphenolic compounds. Act Nerv Super 52: 181-186
43. Kozikowski AP, Tückmantel W, Boettcher G, Romanczyk LJ. Jr. (2003). Studies in polyphenol chemistry and bioactivity. 4. (1) Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4β,8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest. J Org Chem 68: 1641-1658
44. Krasnow MN, Murphy TM. (2004). Polyphenol glucosylating activity in cell suspensions of grape (Vitis vinifera). J Agr Food Chem 52: 3467-3472
45. Krohn K, Ahmed I, John M, et al. (2010). Stereoselective synthesis of benzylated prodelphinidins and their diastereomers with use of the Mitsunobu reaction in the preparation of their gallocatechin precursors. Eur J Org Chem 2010: 2544-2554
46. Kundu JK, Surh YJ. (2008). Cancer chemopreventive and therapeutic potential of resveratrol: Mechanistic perspectives. Cancer Lett 269: 243-261
47. Leonard SS, Xia C, Jiang BH, et al. (2003). Resveratrol scavenges reactive oxygen species and effects radical-induced cellular responses. Biochem Biophys Res Commun 309: 1017-1026
48. Leonardo CC, Agrawal M, Singh N, et al. (2013). Oral administration of the flavanol (-)-epicatechin bolsters endogenous protection against focal ischemia through the Nrf2 cytoprotective pathway. Eur J Neurosci 38: 3659-3668
49. Lipshutz BH, Liu ZP, Kayser F. (1994). Cyanocuprate-mediated intramolecular biaryl couplings applied to an ellagitannin-synthesis of (+)-O-permethyltellimagrandin II. Tet Lett 35: 5567-5570
50. Malek SRA. (1961). Polyphenols and their quinone derivatives in the cuticle of the desert locust, Schistocerca gregaria (Forskål). Comp Biochem Physiol 2: 35-77
51. Nakai S. (2000). Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa. Water Res 34: 3026-3032
52. Nelson TD, Meyers AI. (1994). A rapid total synthesis of an ellagitannin. J Org Chem 59: 2577-2580
53. O'Connor DJ, Wong RWK, Rabie ABM. (2011). Resveratrol inhibits periodontal pathogens in vitro. Phytother Res 25: 1727-1731
54. Ohmori K, Shono T, Hatakoshi Y, et al. (2011). Integrated synthetic strategy for higher catechin oligomers. Angew Chem Int Ed Engl 50: 4862-4867
55. Okada Y, Nakamura YOY, et al. (2012). Dietary resveratrol prevents the development of food allergy in mice. PLoS One 7: e44338
56. Pandey KB, Rizvi SI. (2010). Protective effect of resveratrol on markers of oxidative stress in human erythrocytes subjected to in vitro oxidative insult. Phytother Res 1: 11-14
57. Park SJ, Ahmad F, Philp A, et al. (2012). Resveratrol ameliorates aging-related metabolic phenotypes by inhibiting cAMP phosphodiesterases. Cell 148: 421-433
58. Plumed-Ferrer C, Väkeväinen K, Komulainen H, et al. (2013). The antimicrobial effects of wood-associated polyphenols on food pathogens and spoilage organisms. Int J Food Microbiol. 164: 99-107
59. Popa V, Dumitru M, Volf I, Anghel N. (2008). Lignin and polyphenols as allelochemicals. Ind Crops Prod 27: 144-149
60. Pouysegu L, Deffieux D, Gaelle GM, et al. (2011). Synthesis of ellagitannin natural products. Nat Prod Rep 28: 853-874
61. Price NL, Gomes AP, Ling AJY, et al. (2012). SIRT1 is required for AMPK activation and the beneficial effects of resveratrol on mitochondrial function. Cell Metab 15: 675-690
62. Quideau S. (2011). Organic chemistry: Triumph for unnatural synthesis. Nature 474: 459-460
63. Quideau SP, Deffieux D, Douat-Casassus CL, Pouységu L. (2011). Plant polyphenols: Chemical properties, biological activities, and synthesis. Angew Chem Int Ed 50: 586-621
64. Riley PA. (1994). Free radicals in biology: Oxidative stress and the effects of ionizing radiation. Int J Radiat Biol 65: 27-33
65. Robb EL, Stuart JA. (2010). Trans-resveratrol as a neuroprotectant. Molecules 15: 1196-1212
66. 2 cells. Biopharm Drug Dispos 27: 181-189
67. Sakata Y, Zhuang H, Kwansa H, et al. (2010). Resveratrol protects against experimental stroke: Putative neuroprotective role of heme oxygenase 1. Exp Neurol 224: 325-329
68. Saleh MC, Connell BJ, Rajagopal D, et al. (2014). Co-administration of resveratrol and lipoic acid, or their synthetic combination, enhances neuroprotection in a rat model of ischemia/reperfusion. PLoS One 9: e87865
69. Singh N, Agrawal M, Dore S. (2013). Neuroprotective properties and mechanisms of resveratrol in in vitro and in vivo experimental cerebral stroke models. ACS Chem Neurosci, 4: 1151-1162
70. Smoliga JM, Baur JA, Hausenblas HA. (2011). Resveratrol and health-a comprehensive review of human clinical trials. Mol Nutr Food Res 55: 1129-1141
71. Snyder SA, Gollner A, Chiriac MI. (2011). Regioselective reactions for programmable resveratrol oligomer synthesis. Nature 474: 461-466
72. Steinberg GR, Kemp BE. (2009). AMPK in health and disease. Physiol Rev 89: 1025-1078
73. Tanner G, Francki KT, Abrahams S, et al. (2003). Proanthocyanidin biosynthesis in plants. J Biol Chem 278: 31647-31656
74. Tikoo K, Singh K, Kabra D, et al. (2008). Change in histone H3 phosphorylation, MAP kinase p38, SIR 2 and p53 expression by resveratrol in preventing streptozotocin induced type I diabetic nephropathy. Free Radical Res 42: 397-404
75. Tsai SK, Hung LM, Fu YT, et al. (2007). Resveratrol neuroprotective effects during focal cerebral ischemia injury via nitric oxide mechanism in rats. J Vasc Surg 46: 346-353
76. Wigglesworth VB. (1988). The source of lipids and polyphenols for the insect cuticle: The role of fat body, oenocytes and oenocytoids. Tissue Cell 20: 919-932
77. Zadak Z, Hyspler R, Ticha A, et al. (2009). Antioxidants and vitamins in clinical conditions. Physiol Res 58: 13-17
78. Zetterström CE, Hasselgren J, Salin O, et al. (2013). The resveratrol tetramer (-)-hopeaphenol inhibits type III secretion in the Gram-negative pathogens Yersinia pseudotuberculosis and Pseudomonas aeruginosa. PLoS One 8: 1-12