A strong protective action of Guttiferone-A, a naturally occurring prenylated benzophenone, against iron-induced neuronal cell damage

Journal of Pharmacological Sciences

Volumn 116, Issue 1, 2011, Pages 36-46

  Núñez Figueredo, Yanier ^a   García Pupo, Laura ^a   Cuesta Rubio, Osmany ^b   Delgado Hernández, René ^a   Naal, Zeki ^c,d   Curti, Carlos ^c   Pardo Andreu, Gilberto L ^b  

^a CENTRO DE INVESTIGACIÓN Y DESARROLLO DE MEDICAMENTOS CIDEM   (Cuba)

^b INSTITUTO DE FARMACIA Y ALIMENTOS   (Cuba)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

^d UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Antioxidant; Guttiferone A; Iron; Iron chelation; Neuroprotection

Indexed keywords

BENZOPHENONE DERIVATIVE; FERRIC ION; FERROUS ASCORBATE; FERROUS ION; GUTTIFERONE A; IRON COMPLEX; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; AUTOOXIDATION; BRAIN HOMOGENATE; BRAIN NERVE CELL; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DRUG SCREENING; DRUG STRUCTURE; ELECTROCHEMICAL ANALYSIS; EMBRYO; IC 50; IRON CHELATION; IRON OVERLOAD; LIPID PEROXIDATION; NERVE CELL CULTURE; NERVE CELL LESION; NEUROPROTECTION; NONHUMAN; OXIDATIVE STRESS; OXYGEN CONSUMPTION; PHEOCHROMOCYTOMA CELL; RAT;

EID: 79956220044     PISSN: 13478613     EISSN: 13478648     Source Type: Journal    
DOI: 10.1254/jphs.10273FP     Document Type: Article

References (50)

1. Youdim MB, Fridkin M, Zheng H. Bifunctional drug derivatives of MAO-B inhibitor rasagiline and iron chelator VK-28 as a more effective approach to treatment of brain ageing and ageing neurodegenerative diseases. Mech Ageing Dev. 2005;126:317-326. (Pubitemid 40038353)
2. Bolognin S, Messori L, Zatta P. Metal ion physiopathology in neurodegenerative disorders. Neuromolecular Med. 2009;11:223-238.
3. Berg D. In vivo detection of iron and neuromelanin by transcranial sonography - a new approach for early detection of substantia nigra damage. J Neural Transm. 2006;113:775-780.
4. Castellani RJ, Moreira PI, Liu G, Dobson J, Perry G, Smith MA, et al. Iron: the Redox-active center of oxidative stress in Alzheimer disease. Neurochem Res. 2007;32:1640-1645. (Pubitemid 47428860)
5. Double KL, Gerlach M, Youdim MB, Riederer P. Impaired iron homeostasis in Parkinson's disease. J Neural Transm. 2000;60:37-58. (Pubitemid 32037184)
6. Halliwell B. Oxidative stress and neurodegeneration: where are we now. J Neurochem. 2006;97:1634-1658. (Pubitemid 43873658)
7. Meissner W, Hill MP, Tison F, Gross CE, Bezard E. Neuroprotective strategies for Parkinson's disease: conceptual limits of animal models and clinical trials. Trends Pharmacol Sci. 2004;25:249-253. (Pubitemid 38553826)
8. Jiang H, Luan Z, Wang J, Xie J. Neuroprotective effects of iron chelator Desferal on dopaminergic neurons in the substantia nigra of rats with iron-overload. Neurochem Int. 2006;49:605-609. (Pubitemid 44528090)
9. Carbonell T, Rama R. Iron, oxidative stress and early neurological deterioration in ischemic stroke. Curr Med Chem. 2007;14:857-874. (Pubitemid 46863616)
10. Zheng H, Weiner LM, Bar-Am O, Epsztejn S, Cabantchik ZI, Warshawsky A, et al. Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer's, Parkinson's, and other neurodegenerative diseases. Bioorg Med Chem. 2005;13:773-783. (Pubitemid 40093620)
11. Kupershmidt L, Weinreb O, Amit T, Mandel S, Carri MT, Youdim MB. Neuroprotective and neuritogenic activities of novel multimodal iron-chelating drugs in motor-neuron-like NSC-34 cells and transgenic mouse model of amyotrophic lateral sclerosis. FASEB J. 2009;23:3766-3779.
12. Hanson LR, Roeytenberg A, Martinez PM, Coppes VG, Sweet DC, Rao RJ, et al. Intranasal deferoxamine provides increased brain exposure and significant protection in rat ischemic stroke. J Pharmacol Exp Ther. 2009;330:679-686.
13. Youdim MB, Stephenson G, Ben Shachar D. Ironing iron out in Parkinson's disease and other neurodegenerative diseases with iron chelators: a lesson from 6-hydroxydopamine and iron chelators, desferal and VK-28. Ann N Y Acad Sci. 2004;12:306-325. (Pubitemid 38453534)
14. Zheng H, Blat D, Fridkin M. Novel neuroprotective neurotrophic NAP analogs targeting metal toxicity and oxidative stress: potential candidates for the control of neurodegenerative diseases. J Neural Transm Suppl. 2006;71:163-172. (Pubitemid 351412118)
15. Guo Q, Zhao B, Li M, Shen S, Xin W. Studies on protective mechanisms of four components of green tea polyphenols against lipid peroxidation in synaptosomes. Biochim Biophys Acta. 1996;1304:210-222. (Pubitemid 26426992)
16. Ono K, Yoshiike Y, Takashima A, Hasegawa K, Naiki H, Yamada M. Potent anti-amyloidogenic and fibrildestabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer's disease. J Neurochem. 2003;87:172-181. (Pubitemid 37210651)
17. Levites Y, Amit T, Mandel S, Youdim MBH. Neuroprotection and neurorescue against Aβ toxicity and PKC dependent release of nonamyloidogenic soluble precursor protein by green tea polyphenol (-)-epigallocatechin-3-gallate. FASEB J. 2003;17:952-954.
18. Gustafson KR, Blunt JW, Munro MHG, Fuller RW, McKee TC, Cardellina JH, et al. The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea. Tetrahedron. 1992;48:10093-10102.
19. Williams RB, Hoch J, Glass TE, Evans R, Miller JS, Wisse JH, et al. A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Suriname Rainforest. Planta Med. 2003;69:864-866. (Pubitemid 37346579)
20. Ngouela S, Lenta BN, Noungoue DT, Ngoupayo J, Boyom FF, Tsamo E, et al. Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f. Phytochemistry. 2006;67:302-306. (Pubitemid 43061357)
21. Pereira IO, Marques MJ, Pavan ALR, Codonho BS, Barbieri CL, Beijo LA, et al. Leishmanicidal activity of benzophenone sand extracts from Garcinia brasiliensis Mart. Fruits. Phytomedicine. 2010;17:339-345.
22. Cuesta-Rubio O, Padrón A, Velez Castro H, Pizza C, Rastrelli L. Aristophenones A and B. A new tautomeric pair of polyisoprenylated benzophenones from Garcinia Aristata. J Nat Prod. 2001;64:973-975.
23. Whittemore ER, Loo DT, Watt JA, Cotman CW. A detailed analysis of hydrogen peroxide-induced cell death in primary neuronal culture. Neuroscience. 1995;67:921-932.
24. Hermes-Lima M, Castilho RF, Meinicke AR, Vercesi AE. Characteristics of Fe(II) ATP complex-induced damage to the rat liver mitochondria. Mol Cell Biochem. 1995;145:53-60.
25. Genet S, Kale RK, Baquer NZ. Alterations in antioxidant enzymes and oxidative damage in experimental diabetic rat tissues: effect of vanadate and fenugreek (Trigonellafoenum graecum). Mol Cell Biochem. 2002;236:7-12. (Pubitemid 34851222)
26. Buege JA, Aust SD. Microsomal lipid peroxidation. Methods Enzymol. 1978;52:302-310.
27. Aruoma OI. Deoxyribose assay for detecting hydroxyl radicals. Methods Enzymol. 1994;23:57-66.
28. Pariente F, Lorenzo E, Abruna HD. Electrocatalysis of NADH oxidation with electropolymerized films of 3,4-dihydroxybenzaldehyde. Anal Chem. 1994;66:4337-4344. (Pubitemid 124006384)
29. Qu W, Fan L, Kim YC, Ishikawa S, Iguchi-Ariga SM, Pu XP, et al. Kaempferol derivatives prevent oxidative stress-induced cell death in a DJ-1-dependent manner. J Pharmacol Sci. 2009;110:191-200.
30. Nishida H, Kushida M, Nakajima Y, Ogawa Y, Tatewaki N, Sato S, et al. Amyloid-β-induced cytotoxicity of PC-12 cell was attenuated by Shengmai-san through redox regulation and outgrowth induction. J Pharmacol Sci. 2007;104:73-81.
31. Ito Y, Shimazawa M, Akao Y, Nakajima Y, Seki N, Nozawa Y, et al. Lig-8, a bioactive lignophenol derivative from bamboo lignin, protects against neuronal damage in vitro and in vivo. J Pharmacol Sci. 2006;102:196-204. (Pubitemid 44690977)
32. Miura H, Takano K, Kitao Y, Hibino S, Choshi T, Murakami R, et al. A carbazole derivative protects cells against endoplasmic reticulum (ER) stress and glutathione depletion. J Pharmacol Sci. 2008;108:164-171.
33. Cho SO, Ban JY, Kim JY, Jeong HY, Lee IS, Song KS, et al. Aralia cordata protects against amyloid β protein (25-35)-induced neurotoxicity in cultured neurons and has antidementia activities in mice. J Pharmacol Sci. 2009;111:22-32.
34. Cheng HY, Hsieh MT, Wu CR, Tsai FH, Lu TC, Hsieh CC, et al. Schizandrin protects primary cultures of rat cortical cells from glutamate-induced excitotoxicity. J Pharmacol Sci. 2008;107:21-31.
35. Hiroi M, Ogihara T, Hirano K, Hasegawa M, Morinobu T, Tamai H, et al. Regulation of apoptosis by glutathione redox state in PC12 cells exposed simultaneously to iron and ascorbic acid. Free Radic Biol Med. 2005;38:1057-1072. (Pubitemid 40386552)
36. Pardo-Andreu G, Sánchez-Baldoquín C, Ávila- González R, Delgado R, Naal Z, Curti C. Fe(III) improves antioxidant and cytoprotecting activities of mangiferin. Eur J Pharmacol. 2006;547:31-36. (Pubitemid 44389751)
37. Pardo-Andreu GL, Sánchez-Baldoquín C, Avila-González R, Yamamoto ET, Revilla A, Uyemura SA, et al. Interaction of Vimang (Mangifera indica L. extract) with Fe(III) improves its antioxidant and cytoprotecting activity. Pharmacol Res. 2006;54:389-395. (Pubitemid 44550179)
38. Pardo-Andreu GL, Cavalheiro RA, Dorta DJ, Naal Z, Delgado R, Vercesi AE, et al. Fe(III) shifts the mitochondria permeability transition-eliciting capacity of mangiferin to protection of organelle. J Pharmacol Exp Ther. 2007;320:646-653. (Pubitemid 46147944)
39. Welch KD, Davies TZ, Aust SD. Iron autoxidation and free radical generation: effects of buffer, ligands and chelators. Arch Biochem Biophys. 2002;397:360-369. (Pubitemid 34852304)
40. Andreu GP, Delgado R, Velho JA, Curti C, Vercesi AE. Iron complexing activity of mangiferin, a naturally occurring glucosylxanthone, inhibits mitochondrial lipid peroxidation induced by Fe2+-citrate. Eur J Pharmacol. 2005;513:47-55. (Pubitemid 40692245)
41. 2+-citrate-induced lipoperoxidation in isolated rat liver mitochondria. Pharmacol Res. 2005;51:427-435.
42. Pardo-Andreu GL, Delgado R, Núñez-Sellés AJ, Vercesi AE. Dual mechanism of mangiferin protection against iron-induced damage to 2-deoxyribose and ascorbate oxidation Pharmacol Res. 2006;53:253-260.
43. Pardo-Andreu GL, Delgado R, Núñez-Sellés AJ, Vercesi AE. Mangifera indica L. extract (Vimang) inhibits 2-deoxyribose damage induced by Fe (III) plus ascorbate. Phytother Res. 2006;20:120-124. (Pubitemid 43266836)
44. Halliwell B, Gutteridge JMC. Antioxidant defenses. In: Halliwell B, Gutteridge JMC, editors. Free radical in biology and medicine, 3rd ed. Oxford: Oxford University Press; 1999. p. 105-245.
45. Halliwell B. Drug antioxidant effects. A basis for drug selection? Drugs. 1991;42:569-605.
46. Martins FT, Assis DM, Dos Santos MH, Camps I, Veloso MP, Juliano MA, et al. Natural polyprenylated benzophenones inhibiting cysteine and serine proteases. Eur J Med Chem. 2009;44:1230-1239.
47. Yamaguchi F, Saito M, Ariga T, Yoshimura Y, Nakazawa H. Free radical scavenging activity and antiulcer activity of Garcinol from Garcinia indica fruit rind. J Agric Food Chem. 2000;48:2320-2325. (Pubitemid 30431234)
48. Lia C-H, Ho C-T, Lin J-K. Effects of garcinol on free radical generation and NO production in embryonic rat cortical neurons and astrocytes. Biochem Biophys Res Comm. 2005;329:1306-1314. (Pubitemid 40568712)
49. Millan M, Sobrino T, Castellanos M, Nombela F, Arenillas JF, Riva E, et al. Increased body iron stores are associated with poor outcome after thrombolytic treatment in acute stroke. Stroke. 2007;38:90-95. (Pubitemid 46035612)
50. Erdemoglu AK, Ozbakir S. Serum ferritin levels and early prognosis of stroke. Eur J Neurol. 2002;9:633-637. (Pubitemid 36961290)