PLA2 mediated arachidonate free radicals: PLA2 inhibition and neutralization of free radicals by anti-oxidants - A new role as anti-inflammatory molecule

Current Topics in Medicinal Chemistry

Volumn 7, Issue 8, 2007, Pages 765-777

  Nanda, B L ^a   Nataraju, A ^a   Rajesh, R ^a   Rangappa, K S ^a   Shekar, M A ^b   Vishwanath, B S ^a  

^a UNIVERSITY OF MYSORE   (India)

^b Government Medical College   (India)

Author keywords

Lipid peroxidation; LOX pathway; Phytochemicals; Proinflammatory eicosanoids; Prostaglandin; Terpenes

Indexed keywords

4 HYDROXYNONENAL; ACROLEIN; ALKALOID DERIVATIVE; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; ARACHIDONIC ACID; BETA CAROTENE; CATECHIN; DITERPENE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; FREE RADICAL; ICOSANOID; ISOENZYME; ISOPRENOID; KAEMPFEROL; LIPID PEROXIDE; MYRICETIN; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; POLYPHENOL DERIVATIVE; PROSTAGLANDIN SYNTHASE; QUERCETIN; REACTIVE OXYGEN METABOLITE; TAXIFOLIN; TERPENE DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR; UNINDEXED DRUG; GROUP II SECRETORY PHOSPHOLIPASE A2; PHOSPHOLIPASE A; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARACHIDONIC ACID METABOLISM; CELL DAMAGE; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; INFLAMMATION; LIPID PEROXIDATION; NONHUMAN; PROTEIN FUNCTION; REVIEW; STRUCTURE ACTIVITY RELATION; CHEMISTRY; DRUG ANTAGONISM; METABOLISM;

ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; ARACHIDONIC ACID; FREE RADICALS; HUMANS; PHOSPHOLIPASES A;

EID: 34247892430     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802607780487623     Document Type: Review

References (122)

1. 2 in eicosanoid generation. Am. J. Respir. Crit. Care Med. 2000, 161 (2 Pt 2), S32-S35.
2. Nugteren, D. H.; Beerthuis, R. K.; van Dorp, D. A. Recl. Trav. Chim. Pays-Bas Belg. 1966, 85, 405-419.
3. 1α. J. Biol. Chem. 1967, 242, 5336-5343.
4. Porter, N. A.; Funk, M. O. Letter: Peroxy radical cyclization as a model for prostaglandin biosynthesis. J. Org. Chem. 1975, 40 3614-3615.
5. Kastuki, H.; Okuda, S.; Arachidonic, acid as a neurotoxic and neurotrophic substance. Prog. Neurobiol. 1995, 46, 607-636.
6. 2 enzymes: Classification and characterization. Biochim. Biophys. Acta 2000, 1488, 1-19.
7. 2 regulation of arachidonic acid mobilization. FEBS Lett. 2002 531, 2-6.
8. 2 enzymes. Foreword. Biol Pharm Bull. 2004, 27, 1157.
9. 2. Biol. Pharm. Bull. 2004, 27, 1174-1178.
10. 2 from snake venom to human secreted forms. J. Mol. Evol. 1990, 31, 228-238.
11. 2. 1994, 269, 13057-13060.
12. 2 activation. J. Leukocyte Biol. 1999, 65, 330-336.
13. 2s. Adv. Immunol. 2001, 77 163-194.
14. Valentin, E.; Lambeau,G. Increasing molecular diversity of secreted phosphilipases (2) and their receptors and binding proteins. Biochim. Biophys. Acta 2000, 1488, 9-70.
15. 2. Biol. Pharm. Bull. 2004, 7, 1168-1173.
16. 2. Biol. Pharm. Bull. 2004, 27, 1158-1164.
17. 2. J. Biol. Chem. 1997, 272 16069-16072.
18. 2. FEBS Lett. 2002, 531, 7-11.
19. 2 isoforms in the checkpoint control of acute inflammation. FASEB J. 2004, 18, 489-498.
20. 2. J Biol. Chem. 1989, 264, 5768-5775.
21. 2 present in rheumatoid arthritic synovial fluid. J. Biol. Chem. 1989, 264, 5335-5338.
22. 2--a mediator between proximal and distal effectors of inflammation. Immunol Today, 1991 12, 143-146.
23. 2 in rat cultured astrocytes. Two distinct pathways of the gene expression. J. Biol. Chem. 1991, 266, 9956-9960.
24. 2. J. Immunol. 2000, 165, 4024-4031.
25. Pfeilschifter, J.; Schalkwijk, C.; Briner, V. A., van den Bosch, H. Cytokine stimulated secretion of group II phospholipase A2 by rat mesangial cells. Its contribution to arachidonic acid release and prostaglandin synthesis by cultured rat glomerular cells. J. Clin. Invest. 1993, 92, 2516-2523.
26. 2. Annu. Rev. Pharmacol. Toxicol. 1999, 39, 175-189.
27. 2 induces an inflammatory response in rabbit joints. J. Immunol. 1991, 146, 3904-3910.
28. 2 by retinoids and flavonoids. Mechanism of action. Agents Actions 1988, 25, 394-400.
29. 2 - induced pleural inflammation in rats. Int. J. Tissue React. 1989, 11, 129-136.
30. 2 in development. Curr. Pharmaceut. Des. 2001, 7, 181-198.
31. 2 group IIA. Curr. Med. Chem. 2005, 12, 3011-3026.
32. Halliwell, B.; Gutteridge, J.M.C. Free radicals in Biology and Medicine, 2nd edn., Clarendon Press, Oxford. 1989.
33. Fridovich, I. The biology of oxygen radicals. Science 1978 201, 875-880.
34. Fessel, J.P.; Porter, N.A.; Moore, K.P.; Sheller, J.R.; Roberts, L.J2nd. Discovery of lipid peroxidation products formed in vivo with a substituted tetrahydrofuran ring(isofurans) that are favored by increased oxygen tension. Proc. Natl. Acad. Sci. USA 2002 99, 16713-16718.
35. 2, an oxidation product of arachidonic acid. Biochim. Biophys. Acta 1997, 1344, 1-5.
36. Mexmain, S.; Gualde, N.; Aldigier, J.C.; Motta, C.; Chable-Rabinovitch, H.; Rigaud, M. Specific binding of HETE to lymphocytes. Effects on the fluidity of plasmatic membranes. Prostaglandins Leukotrienes Med. 1984, 13, 93-97.
37. Hochgraf, E.; Mokady, S.; Cogan, U. Dietary oxidized linoleic acid modifies lipid composition of rat liver microsomes and increases their fluidity. J. Nutr. 1997, 127, 681-686.
38. Imai, K.; Aimoto, T.; Shima, T,; Nakashima, T.; Sato, M.; Kimura, R. Alteration in membrane fluidity of rat liver microsomes and of liposomes by protoporphyrin and its anti-lipidperoxidative effect. Biol. Pharm. Bull. 2000, 23, 415-419.
39. Kuhn, H.; Pliquett, F.; Wunderlich, S.; Schewe, T.; Krause, W. Reticulocyte lipoxygenase changes the passive electrical properties of bovine heart submitochondrial particles. Biochem. Biophys. Acta. 1983, 735, 283-290.
40. Rapoport, S. M.; Schewe, T. The maturational breakdown of mitochondria in reticulocytes. Biochim. Biophys. Acta. 1986, 864 471-495.
41. Keller, J.N.; Mattson, M.P. Roles of lipid peroxidation in modulation of cellular signaling pathways,cell dysfunction, and death in the nervous system. Rev. Neurosci. 1998, 9, 105-116.
42. Uchida, K.; Shiraishi, M.; Naito, Y.; Torii, Y.; Nakamura Osawa, T. Activation of stress signaling pathways by the end product of lipid peroxidation. 4-Hydroxy-2 nonenal is a potential inducer of intracellular peroxide production. J. Biol. Chem. 1999, 274, 2234-2242.
43. Suzuki, Y. J.; Forman, H. J.; Sevanian, A. Oxidants as stimulators of signal transduction. Free Radic. Biol. Med. 1997, 22 269-285.
44. Beauchamp, C.; Fridovich, I. A mechanism for the production of ethylene from methional. The generation of the hydroxyl radical by xanthine oxidase. J. Biol. Chem. 1970, 245, 4641-4646.
45. Brown, J. P. A review of the genetic effects of naturally occurring flavonoids, anthoquinones and related compounds. Mutat. Res. 1980, 75, 243-277.
46. H2-type cytokine production by activated human basophils. J. Allergy Clin. Immunol. 2003, 111, 1299-1306.
47. Kim, H.P.; Son, K.H.; Chang, H.W.; Kang, S.S. Anti-inflammatory plant flavonoids and cellular action mechanism. J. Pharmacol. Sci. 2004, 96, 229-245.
48. 2 and inflammatory response in mice. Life Sci. 1994, 54, 333-338.
49. Ferrandiz, M. L.; Alcaraz, M. J. Antiinflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents Actions 1991, 32, 283-288.
50. Middleton, E.; Kandaswamy, C. Effects of flavonoids on immune and inflammatory cell functions. Biochem. Pharmacol. 1992, 43, 1167-1179.
51. Tzeng, S. H.; Ko, W. C.; Ko, F. N.; Teng, C. M. Inhibition of platelet aggregation by some flavonoids. Thromb. Res. 1991, 64 91-100.
52. Frankel, E. Nutritional benefits of flavonoids. International conference on food factors: Chemistry and cancer prevention. Hamamatsu, Japan. Abstracts. 1995, C6.
53. Hanasaki, Y.; Ogawa, S.; Fukui. S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Rad. Biol. Med. 1994, 16, 845-850.
54. Ursini, F.; Maiorino, M.; Morazzoni.; Roveri, A.; Pifferi, G. A novel antioxidant flavonoid (IdB 1031) affecting molecular mechanisms of cellular activation. Free Rad. Biol. Med. 1994, 16, 547-553.
55. Korkina, L.G.; Afanas'ev, I. B.In Antioxidants in disease Mechanisms and Therapy; Sies, H., Ed.; Academic Press: San Diego. 1997, 151-163.
56. 2+ ions: Implications for their antioxidant properties. Biochem. J. 1998, 330 1173-1178.
57. Cotelle, N.; Bernie, J. L.; Catteau, J. P.; Pommery, J.; Wallet, J. C.; Gaydou, E. M. Antioxidant properties of hydroxy- flavones. Free Radic. Biol. Med. 1996, 20, 35-4.
58. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical- scavenging efficiencs. Methods Enzymol. 1990, 186, 343-355.
59. Rice-Evans, C. A.; Miller, N. J.; Bolwell, P. G.; Bramley, P. M.; Pridham, J. B. The relative antioxidant activities of plant derived polyphenolic, flavonoids. Free Radic. 1995, 22, 375-383.
60. Nakayama, T.; Yamada, M.; Osawa, T.; Kawakishi, S. Suppresion of active oxygen- induced cytotoxicity by flavonoids. Biochem. Pharmacol. 1993, 45, 265-267.
61. 2. Free Radic. Biol. Med. 1991, 11, 1-8.
62. g) quenching. J. Photochem. Photobiol. B: Biol. 1993, 19, 205-215.
63. Rapta, P.; Misik, V.; Stasko, A.; Vrabel, I. Redox intermediates of flavonoids and caffeic acid esters from propolis: An EPR spectroscopy and cyclic voltammetry study. Free Radic. Biol. Med. 1995 18, 901-908.
64. Saija, A.; Scalese, M.; Lanza, M.; Marzullo, D.; Bonina, F.; Castelli, F. Flavonoids as antioxidant agents: Importance of their interaction with biomembranes. Free Radic. Biol. Med. 1995, 19, 481-486.
65. Manach, C.; Morand, C.; Texier, O.; Favier, M. L.; Agullo, G.; Demigne, C.; Regerat, F.; Remesy, C. Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin. J. Nutr. 1995, 125 1911-1922.
66. Velikova, V.; Edreva, A.; Loreto, F. Endogenous isoprene protects Phragmites australis leaves against singlet oxygen. Physiol. Plant. 2004, 122, 219-225.
67. Havaux, M. Carotenoids as membrane stabilizers in chloroplasts. Trends Plant Sci. 1998, 3, 147-151.
68. Munne'-Bosch, S.; Alegre, L. The function of tocopherols and tocotrienols in plants. Crit. Rev. Plant Sci. 2002, 21 31-57.
69. Munne'-Bosch, S.; Alegre, L. Drought-induced changes in the redox state of a- tocopherol, ascorbate, and the diterpene carnosic acid in chloroplasts of Labiatae species differing in carnosic acid contents. Plant Physiol. 2003, 131, 1816-1825.
70. Rackova, I.; Stefek, M.; Majekova, M. Structural aspects of antioxidant activity of substituted pyridoindoles. Redox Pep. 2002, 7 4), 207-214.
71. Rackova, L.; Majekova, M.; Kost'alova, D.; Stefek, M. Antiradical and Antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorg. Med. Chem. 2004, 12(17), 4709-4715.
72. 2 and other leukocyte functions. J. Nat. Prod. 2001, 64, 612-615.
73. Minale, L.; Riccio, R.; Sodano, G. Avarol, a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge Dysidea avara. Tetrahedron Lett. 1974, 38, 3401.
74. de Guzman, F.S.; Copp, B.R.; Mayne, C.L.; Concepcion, G.P.; Mangalindan, G.C.; Barrows, L.R.; Ireland, C.M. Bolinaquinone: A novel cytotoxic sesquiterpene hydroxyquinone from a Philippine Dysidea sponge. J. Org. Chem. 1998, 63, 8041.
75. 2 inhibitor from the sponge Dysidea sp. Tetrahedron Lett. 2000, 41 3257.
76. Mayol, L.; Piccialli, V.; Sica, D. Gracilin A, an unique norditerpene metabolite from the marine sponge spongionella gracilis. Tetrahedron Lett. 1985, 26, 1357.
77. 2 inhibitors from marine organisms. J. Nat. Prod. 1992, 55(12), 1701-1717.
78. Karuso, P.; Taylor, W.C. The constituents of marine sponges. II. The isolation from Aplysilla rosea(Dendroceratida) of (5R°, 7S°, 8R°, 9S°, 10R°, 13S°, 14S°, 15S**)-15,17-Epoxy-17-Hydroxy-16-Oxosponian-7-Y1 Butyrate (Aplyroseol-1) and related diterpenes (Aplyroseol-2 to Aplyroseol-6). Aust. J Chem. 1986, 39(10), 1629-1641.
79. de silva, E.D.; Scheuer, P.J. Manoalidate, an antibiotic sesterpenoid from the marine sponge Luffariella variavilis(Polejaeff). Tetrahedron Lett. 1980, 21, 1611.
80. Cimino, S.G.; de Stefano, S.; Minale, L. Scalaradial, a third sesterterpene with the tetracarbocyclic skeleton of scalarin, from the sponge Cacospongia mollior. Experientia 1974, 30, 846.
81. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Pronzato, R.; Zavodnik, N. Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa. J. Nat. Prod. 1995, 58(11), 1776-1780.
82. 2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides. J. Nat. Prod. 1998, 61(7), 931-935.
83. 2 inhibitors from the new Caledonian marine sponge Petrosaspongia nigra. J. Nat. Prod. 1998, 61 171-575.
84. De Marino, S.; Iorizzi, M.; Zollo, F.; Debitus, C.; Menou, J.L.; Ospina, L.F.; Alcaraz, M.J.; M. Paya, M. New pyridinium alkaloids from a marine sponge of the genus Spongia with a human phospholipase A(2) inhibitor profile. J. Nat. Prod. 2000, 63, 322-326.
85. Schmidt, E.W.; Faulkner, D.J. Palauolol, a new anti-inflammatory sesterterpene from the sponge Fascaplysinopsis sp. from Palau. Tetrahedron Letts. 1996, 37, 3951-3954.
86. Kernan, M.R.; Faulkner, D.J.; Parkanyi, L.; Clardy, J.; de Carvalho, M.S.; Jacobs, R.S. Luffolide, a novel anti-inflammatory terpene from the sponge Luffariella sp. Experientia 1989, 45(4), 388-390.
87. 2 with anti-inflammatory activity. J. Pharmacol. Exp. Ther. 1997, 282, 123.
88. Keyzers, R.A.; Davies-Coleman, M.T. Anti-inflammatory metabolites from marine sponges. Chem. Soc. Rev. 2005 34 355.
89. 2 and α-Tocopherol at 1.8 A Resolution. J. Mol. Biol. 2002 320, 215-222.
90. Tsujii, S.; Rinehart, K.L.; Gunasekara, S.P.; Kashman, Y.; Cross, S.S.; Lui, M.S.; Pomponi, S.A.; Diaz, M.C. Topsentin, Bromotopsentin and dihydrodeoxybromotopsentin: Antiviral and antitumor bis(indoyl) imidazoles from Caribbean dee-sea sponges of the family Halichondriidae. Structural and synthetic studies. J. Org. Chem. 1988, 53, 5446-5453.
91. Bartik, K.; Braekman, J. C.; Daloze, D.; Stoller, C.; Huysecom, J.; Vandevyer, G.; Ottinger, R. Topsentins, new toxic bis-indole alkaloids from the marine sponge Topsentiagenitrix. Can. J. Chem. 1987 65, 2118-2121.
92. 2 inhibitors. Prog. Surg. 1997, 24 146.
93. Wylie, B.L.; Grace, K.; Jacobs, R.S. Bis-indole alkaloid marine natural products as novel anti-inflammatory agents. FASEB J. 1995, 9, A955.
94. 2 from vipera russelli venom with aristolochic acid: A Circular dichroism study. Toxicon 1987, 25(9), 39-46.
95. 2 inhibition for the synthesis of prostaglandins by the plant alkaloid aristolochic acid from a 1.7 A crystal structure. Biochemistry 2002, 41, 10914-9
96. 2 and a plant alkaloid ajmaline at 2.0A resolution. To be published.
97. 2 in complex with atropine at 1.23A resolution. To be published.
98. 2 saponins from an antiinflammatory extract of Zanha africana root bark. J. Nat. Prod. 1997, 60(11), 1158-1160.
99. 2 by quercetin. Inflammation 1993, 17, 573-582.
100. 2 by naturally occurring biflavonoid, ochnaflavone. Biochem. Biophys. Res. Commun. 1994 205 843-849.
101. Lee, T. P.; Matteliano, M.L.; Middleton, E.; JR. Effect of quercetin on human polymorphonuclear leukocyte lysosomal enzyme release and phospholipids metabolism. Life Sci. 1982, 31, 2765-2774.
102. Heras, B.; Hoult, J.R.S. Non-cytotoxic inhibition of macrophage eicosanoid eiosynthesis and effects on leukocyte functions and reactive oxygen species of two novel anti-inflammatory plant diterpenoids. Planta Med. 1994, 60, 501-506.
103. Welton, A.F.; Tobias, L.D.; Fiedler-Nagy, C.; Anderson,W.; Hope, W.; Meyer, K.; Coffey, J.W. Effect of flavonoids on arachidonic acid metabolism. In: Cody V, Middleton E, Harborne JB, editors. Plant flavonoids in biology and medicine. New York: Alan R. Liss. 1986, 231-242.
104. 2 enzyme by bilirubin: A new role as endogenous anti-inflammatory molecule. Mol. Cell Biochem. 2005, 1-7.
105. 2 with anti-inflammatory activity. Life Sci. 2006, (in press).
106. 2 activity in human neutrophils. J. Immunol. 1993, 151 4918-4925.
107. 2 for activation of the assembled NADPH oxidase in human neutrophils. Biochem. J. 1994, 297, 217-223.
108. 2 -mediated arachidonic acid release in cultured intestinal epithelial cells (INT 407). Scand. J. Gastroenterol. 1991, 26, 237-247.
109. Rice-Evans, C.A.; Nicholas, J. M.; George Paganga. Structure-Antioxidant activity relationship of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20, 7, 933-956.
110. Guohua, C.; Emin, S.; Ronald, L. Prior. Antioxidant and prooxidant behavior of flavonoids: Structure-Activity relationships. Free Radic. Biol. Med. 1997, 22, 5, 749-760.
111. Pier-Giorgio, P. Flavonoids as Antioxidants. J. Nat. Prod. 2000, 63, 1035-1042.
112. Sanz, M.J.; Ferrandiz, M.L.; Cejudo, M.; Terencio, M.C.; Gil, B.; Bustos, G.; Ubeda, A.; Gunasegaran, R.M.J. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica 1994, 24(7), 689-699.
113. Kang, S.S.; Lee, J.Y.; Choi, Y.K.; Song, S.S.; Kim, J.S.; Jeon, S. J.; Han, Y.N.; Son, K.H.; Han, B.H. Neuroprotective effects of naturally occurring biflavonoids. Bioorg. Med. Chem. Lett. 2005, 15, 3588-3591.
114. 2. Inflammation 1997, 21, 3, 1997.
115. 2 on TNF-α, iNOS, and COX-2 expression inactivated macrophages. Shock 1999, 12, 473-478.
116. 2 with anti-inflammatory activity. Biochem. Pharmacol. 1997, 53, 733-740.
117. 2- inhibitory activity. Biol. Pharm. Bull. 2003, 26, 299-302.
118. Yamaguchi, T.; Horio, F.; Hashizume, T.; Tanaka, M.; Ikada, S.; Kakinuma, A.; Nakajima, H. Bilirubin is oxidized in rats treated with endotoxin and acts as a physiological antioxidant synergistically with ascorbic acid in vivo. Biochem. Biophys. Res. Commun. 1995, 5, 214(1), 11-9.
119. Yamaguchi, T.; Terakado, M.; Horio, F.; Aoki, K.; Tanaka, M.; Nakajima, H. Role of bilirubin as an antioxidant in an ischemia-reperfusion of rat liver and induction of herne oxygenase. Biochem. Biophys. Res. Commun. 1996, 223(1), 129-135.
120. Kozaki, N.; Shimizu, S.; Chijiiwa, K.; Yamaguchi, K.; Kuroki, S.; Shimoharada, K.; Yamaguchi, T.; Nakajima, H.; Tanaka, M. Bilirubin as an anti-oxidant for surgical stress: A preliminary report of bilirubin oxidative metabolites. HPB Surg. 1999, 11(4), 241-248.
121. Mindori, H.; Lester, P. Antioxidant Activity of Retinoids. Methods Enzymol. 1990, 190, 273-280.
122. Packer, L.; Witt, R.H.; Tritschler, H.J. alpha-Lipoic acid as a biological antioxidant. Free Radic. Biol. Med. 1995, 19 2), 227-250.