Effect of umbelliferone (7-hydroxycoumarin, 7-HOC) on the enzymatic, edematogenic and necrotic activities of secretory phospholipase A2 (sPLA2) isolated from Crotalus durissus collilineatus venom

Toxicon

Volumn 53, Issue 4, 2009, Pages 417-426

  Toyama, D O ^a   Marangoni, S ^b   Diz Filho, E B S ^b   Oliveira, S C B ^b   Toyama, M H ^c  

^a Universitdade Presbiteriana Mackenzie   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Anti inflammatory; Anti venom; Circular dichroism; Secretory phospholipase A2 (sPLA2); Snake venom; Umbelliferone (7 HOC)

Indexed keywords

4 BROMOPHENACYL BROMIDE; BROMINE DERIVATIVE; CYPROHEPTADINE; DEXAMETHASONE; PHOSPHOLIPASE A2; SNAKE VENOM; UMBELLIFERONE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CIRCULAR DICHROISM; CONCENTRATION (PARAMETERS); ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME INHIBITION; ENZYME STRUCTURE; ENZYME SUBSTRATE; FLUORESCENCE; INFLAMMATION; MAST CELL DEGRANULATION; MOUSE; NECROSIS; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; SKIN EDEMA; SPECTROSCOPY; TWO DIMENSIONAL ELECTROPHORESIS;

ANIMALS; CELLS, CULTURED; CROTALID VENOMS; CROTALUS; EDEMA; MALE; MAST CELLS; MICE; PHOSPHOLIPASES A2, SECRETORY; RATS; RATS, WISTAR; SKIN; UMBELLIFERONES;

CROTALUS DURISSUS COLLILINEATUS;

EID: 60749114975     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2008.12.018     Document Type: Article

References (34)

1. Antunes-Neto J.M., Toyama M.H., Carneiro E.M., Boschero A.C., Pereira-da-Silva L., and Macedo D.V. Circulating leukocyte heat shock protein 70 (HSP70) and oxidative stress markers in rats after a bout of exhaustive exercise. Stress 9 (2006) 107-115
2. Barbosa P.S.F., Martins A.M.C., Alves R.S., Amora D.N., Martins R.D., Toyama M.H., Havt A., Nascimento N.R.F., Rocha V.L.C., Menezes D.B., Fonteles M.C., and Monteiro H.S.A. The role of indomethacin and tezosentan on renal effects induced by Bothrops moojeni Lys49 myotoxin I. Toxicon 47 (2006) 831-837
3. Camara P.R.S., Esquisatto L.C.M., Camargo E.A., Teresa M., Ribela M.T.C.P., Toyama M.H., Marangoni S., de Nucci G., and Antunes E. Inflammatory oedema induced by phospholipases A(2) isolated from Crotalus durissus sp in the rat dorsal skin: a role for mast cells and sensory C-fibers. Toxicon 41 (2003) 823-829
4. Chandra V., Jasti J., Kaur P., Betzel C., Srinivasan A., and Singh T.P. First structural evidence of a specific inhibition of phospholipase A2 by α-tocopherol (Vitamin E) and its implication in inflammation: crystal structure of the complex formed between phospholipase A2 and α-tocopherol at 1.8 Å resolution. J. Mol. Biol. 320 (2002) 215-222
5. Cirino G. Multiple controls in inflammation. Extracellular and intracellular phospholipase A2 inducible and constitutive cyclooxygenase, and inducible nitric oxide synthase. Biochem. Pharmacol. 55 (1998) 105-111
6. Di Carlo G., Mascolo N., Izzo A.A., and Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 65 (1999) 337-353
7. Fawzy A.A., Vishwanath B.S., and Franson R.C. Inhibition of human non-pancreatic phospholipases A2 by retinoids and flavonoids. Mechanism of action. Agents Actions 25 (1988) 394-400
8. Fuentes L., Hernández M., Nieto M.L., and Crespo M.S. Biological effects of group IIA secreted phospholipase A2. FEBS Lett. 531 (2002) 7-11
9. Fylaktakidou K.C., Hadjipavlou-Litina D.J., Litinas K.E., and Nicolaides D.N. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr. Pharm. Des. 10 (2004) 3813-3833
10. Gambero A., Landucci E.C., Toyama M.H., Marangoni S., Giglio J.R., Nader H.B., Dietrich C.P., de Nucci G., and Antunes E. Human neutrophil migration in vitro induced by secretory phospholipases A2: a role for cell surface glycosaminoglycans. Biochem. Pharmacol. 63 (2002) 65-72
11. Garcia R.F., Gazola V.A., Barrena H.C., Hartmann E.M., Berti J., Toyama M.H., Boschero A.C., Carneiro E.M., Manso F.C., and Bazotte R.B. Blood amino acids concentration during insulin induced hypoglycemia in rats: the role of alanine and glutamine in glucose recovery. Amino acids 33 (2006) 151-155
12. Gil B., Sanz M.J., Terencio M.C., Gunasegaran R., Payá M., and Alcaraz M.J. Morelloflavone, a novel biflavonoid inhibitor of human secretory phospholipase A2 with anti-inflammatory activity. Biochem. Pharmacol. 53 (1997) 733-740
13. Iglesias C.V., Aparicio R., Rodrigues-Simioni L., Camargo E.A., Antunes E., Marangoni S., Toyama D.O., Berian L.O.S., Monteiro H.S.A., and Toyama M.H. Effects of morin on snake venom phospholipase A(2) (PLA(2). Toxicon 46 (2005) 751-758
14. Kostova I., Monolov I., and Karaivonova M. Synthesis, physicochemical characterization, and cytotoxic screening of new zirconium complexes with coumarin derivatives. Arch. Pharm. (Weinheim) 334 (2001) 157-162
15. Landucci E.C., Toyama M., Marangoni S., Oliveira B., Cirino G., Antunes E., and de Nucci G. Effect of crotapotin and heparin on the rat paw oedema induced by different secretory phospholipases A2. Toxicon 38 (2000) 199-208
16. Lindahl M., and Tagesson C. Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. Inflammation 21 (1997) 347-356
17. Murray R.D. Coumarins. Nat. Prod. Rep. 6 (1989) 591-624
18. Ohno M., Chijiwa T., Oda-Ueda N., Ogawa T., and Hattori S. Molecular evolution of myotoxic phospholipase A2 from the snake venom. Toxicon 42 (2003) 841-854
19. Passero L.F., Tomokane T.Y., Corbett C.E., Laurenti M.D., and Toyama M.H. Comparative studies of the anti-leishmanial activity of three Crotalus durissus ssp. venoms. Parasitol. Res. 101 (2007) 1365-1371
20. Paya M., Goodwin P.A., De Las Heras B., and Hoult J.R. Superoxide scavenging activity in leukocytes and absence of cellular toxicity of a series of coumarins. Biochem. Pharmacol. 48 (1994) 445-451
21. Rigden D.J., Wen Hwa L., Marangoni S., Toyama M.H., and Polikarpov I. The structure of the D49 phospholipase A(2) piratoxin III from Bothrops pirajai reveals unprecedented structural displacement of the calcium-binding loop: possible relationship to cooperative substrate binding. Acta Crystallogr. D Biol. Crystallogr. 59 (2003) 255-262
22. Rotelli A.E., Guardia T., Juárez A.O., de la Rocha N.E., and Pelzer L.E. Comparative study of flavonoids in experimental models of inflammation. Pharmacol. Res. 48 (2003) 601-606
23. Takeda A.A., dos Santos J.I., Marcussi S., Silveira L.B., Soares A.M., and Fontes M.R. Crystallization and preliminary X-ray diffraction analysis of an acidic phospholipase A(2) complexed with p-bromophenacyl bromide and alpha-tocopherol inhibitors at 1.9- and 1.45-A resolution. Biochim. Biophys. Acta 1-2 (2004) 281-284
24. Toyama M.H., Carneiro E.M., Marangoni S., Barbosa R.L., Corso G., and Boschero A.C. Biochemical characterization of two crotamine isoforms isolated by a single step RP-HPLC from Crotalus durissus terrificus (South American rattlesnake) venom and their action on insulin secretion by pancreatic islets. Biochim. Biophys. Acta 1474 (2000) 56-60
25. Toyama M.H., Carneiro E.M., Marangoni S., Amaral M.E.C., Velloso L.A., and Boschero A.C. Isolation and characterization of a convulxin-like protein from Crotalus durissus collilineatus venom. J. Protein Chem. 20 (2001) 585-591
26. Toyama M.H., de Oliveira D.G., Beriam L.O., Novello J.C., Rodrigues-Simioni L., and Marangoni S. Structural, enzymatic and biological properties of new PLA(2) isoform from Crotalus durissus terrificus venom. Toxicon 41 (2003) 1033-1038
27. Toyama M.H., Toyama D.O., Joazeiro P.P., Carneiro E.M., Beriam L.O.S., Marangoni S., and Boschero A.C. Biological and structural characterization of a new PLA(2) from the Crotalus durissus collilineatus venom. Protein J. 24 (2005) 103-112
28. Turner O., Phoenix J., and Wray S. Developmental and gestational changes of phosphoethanolamine and taurine in rat brain, striated and smooth muscle. Exp. Physiol. 79 (1994) 681-689
29. Valentin E., and Lambeau G. Increasing molecular diversity of secreted phospholipase A2 and their receptor and binding protein. Biochim. Biphys. Acta 1488 (2000) 59-70
30. Vishwanath B.S., Fawzy A.A., and Franson R.C. Edema-inducing activity of phospholipase A2 purified from human synovial fluid and inhibition by aristolochic acid. Inflammation 12 (1988) 549-561
31. Wen-Hwa L., Toyama M.H., Soares A.M., Giglio J.R., Marangoni S., and Polikarpov I. Crystallization and preliminary X-ray diffraction studies of piratoxin III, a D-49 phospholipase A(2) from the venom of Bothrops pirajai. Acta Crystallogr. D Biol. Crystallogr. 55 (1999) 1229-1230
32. Wen-Hwa L., Giotto M.T.D., Marangoni S., Toyama M.H., Polikarpov I., and Garratt R.C. Structural basis for low catalytic activity in Lys49 phospholipases A2-A hypothesis: the crystal structure of piratoxin II complexed to fatty acid. Biochemistry 40 (2001) 28-36
33. Xu H., Ziegelin G., Schroder W., Frank J., Ayora S., Alonso J.C., Lanka E., and Saenger W. Flavones inhibit the hexameric replicative helicase RepA. Nucleic Acids Res. 29 24 (2001) 5058-5066
34. Zhao H., Tang L., Wang X., Zhou Y., and Lin Z. Structure of a snake venom phospholipase A2 modified by p-bromo phenacyl bromide. Toxicon 36 (1998) 875-886