Monoamine oxidase inhibitory activities of indolylalkaloid toxins from the venom of the colonial spider Parawixia bistriata: Functional characterization of PwTX-I

Toxicon

Volumn 54, Issue 6, 2009, Pages 717-724

  Saidemberg, Daniel M ^a   Ferreira, Marco A B ^b   Takahashi, Tatiane N ^a   Gomes, Paulo C ^a,c   Cesar Tognoli, Lilian M M ^a   da Silva Filho, Luiz C ^d   Tormena, Cláudio F ^e   da Silva, Gil V J ^b   Palma, Mario S ^a  

^a CEIS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c Ezequiel Dias Foundation   (Brazil)

^d SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^e UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Chiral chromatography; Indoylalkaloid; Monoamine oxidase; Parawixiatoxin; Spider venom

Indexed keywords

1 GUANIDINO 6 HYDROXY 3,5 DIHYDRO BETA CARBOLINE; 1,4 GUANIDINOBUTOXY 6 HYDROXY 1,2,3,4 TETRAHYDRO BETA CARBOLINE; 6 HYDROXYTRYPARGINE; ALKALOID DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; BETA CARBOLINE DERIVATIVE; SNAKE VENOM; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; COLONIAL SPECIES; CONTROLLED STUDY; DRUG IDENTIFICATION; ENANTIOMER; ENZYME INHIBITION; HONEYBEE; NONHUMAN; PARALYSIS; PICTET SPENGLER REACTION; PRIORITY JOURNAL; SPIDER; STEREOISOMERISM; STRUCTURE ANALYSIS; TOXICITY TESTING;

ANIMALS; INDOLE ALKALOIDS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; SPECTROMETRY, FLUORESCENCE; SPIDER VENOMS; SPIDERS; STEREOISOMERISM;

ANIMALIA; ARANEAE; HEXAPODA;

EID: 69049097009     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2009.05.027     Document Type: Article

References (31)

1. Atkinson P.W., Binnington K.C., and Roulston W.J. High monoamine oxidase activity in the tick Boophzlus Microplus, and inhibition by chlordimeform and related pesticides. Austral. J. Entomol. 13 (1974) 207-210
2. Bach A.W.C., Ian N.C., Johnson D.L., Abell C.W., Bembenek M.E., Kwan S.W., Seeburg A.H., and Shih J.C. cDNA cloning of human liver MAO-A and B: molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 4934-4938
3. Bhattacharya S.K. Anxiogenic activity of centrally administered scorpion (Mesobuthus tamulus) venom in rats. Toxicon 33 (1995) 1491-1499
4. Braestrup C., Nielsen M., and Olsen C.E. Urinary and brain beta-carboline-3-carboxylates as potent inhibitors of brain benzodiazepine receptors. Proc. Natl. Acad. Sci. U.S.A. 77 (1980) 2288-2292
5. Buckholtz N.S. Neurobiology of tetrahydro-β-carbolines. Life Sci. 27 (1980) 893-903
6. Catto M., Nicolotti O., Leonetti F., Carotti A., Favia A.D., Soto-Otero R., Mendez-Alvarez E., and Carotti A. Structural insights into monoamine oxidase inhibitory potency and selectivity of 7-substituted coumarins from ligand and target-based approaches. J. Med. Chem. 49 (2006) 4912-4925
7. Cesar L.M.M., Tormena C.F., Marques M.R., da Silva G.V.J., Mendes M.A., Rittner R., and Palma M.S. Structure determination of hydroxytrypargine: a new tetrahydro-β-carboline toxin from the venom of the spider Parawixia bistriata. Helv. Chim. Acta 88 (2005) 796-801
8. Cesar L.M.M., Mendes M.A., Tormena C.F., Marques M.R., De Souza B.M., Saidemberg D.M., Bittencourt J.C., and Palma M.S. Isolation and chemical characterization of PwTx-II: a novel alkaloid toxin from the venom of the spider Parawixia bistriata (Araneidae, Araneae). Toxicon 46 (2005) 786-796
9. Chou J., and Chou T.C. Dose-effect analysis with microcomputers (1987), Biosoft, Cambridge p. 93
10. Early S.L., and Michaelis E.K.J. Presence of proteins and glutamate as major constituents of the venom of the spider Araneus gemma. Toxicon 25 (1987) 433-442
11. Escoubas P., Diochot S., and Corzo G. Structure and pharmacology of spider venom neurotoxins. Biochimie 82 (2000) 893-907
12. Frew R., Hamilton M.G., and Lundy P.M. Identification of noradrenaline in venom from the funnel-web spider Hololena curta. Toxicon 32 (1994) 511-515
13. Herraiz T., and Chaparro C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants. J. Chromatogr. A 1120 (2006) 237-243
14. Hoover N.G., and Fortenberry J.D. Use of antivenin to treat priapism after a black widow spider bite. Pediatrics 114 (2004) 128-129
15. Huttunen P., and Myers R.D. Tetrahydro-β-carboline micro-injected into the hippocampus induces an anxiety-like state in the rat. Pharmacol. Biochem. Behav. 24 (1986) 1733-1738
16. Leonetti F., Capaldi C., Pisani L., Nicolotti O., Muncipinto G., Stefanachi A., Cellamare S., Caccia C., and Carotti A. Solid-phase synthesis and insights into structure-activity relationships of safinamide analogues as potent and selective inhibitors of type B monoamine oxidase. J. Med. Chem. 50 (2007) 4909-4916
17. Marques M.R., Mendes M.A., Tormena C.F., Souza B.M., Cesar-Tognoli L.M.M., Rittner R., and Palma M.S. Structure determination of a tetrahydro-β-carboline of arthropod origin: a novel alkaloid-toxin subclass from the web of the spider Nephila clavipes. Chem. Biodiv. 2 (2005) 525-535
18. McCormick J., Li Y., McCormick K., Duynstee H.I., Anke K., van Engen A.K., van der Marel G.A., Ganem B., van Boom J.H., and Meinwald J. Structure and total synthesis of HF-7, a neuroactive glyconucleoside disulfate from the funnel-web spider Hololena curta. J. Am. Chem. Soc. 121 (1999) 5661-5665
19. Nair N.P.V., Ahmed S.K., and Ying K. Biochemistry and pharmacology of reversible inhibitors of MAO-A agents: focus on moclobemide. J. Psychiatr. Neurosci. 18 (1993) 214-225
20. Nolen W.A., Hoencamp E., Bouvy P.F., and Haffmans P.M. Reversible monoamine oxidase-A inhibitors in resistant major depression. Clin. Neuropharmacol. 16 (1993) 69-76
21. Palma M.S., and Nakajima T. A natural combinatorial chemistry strategy in acylpolyamine toxins from nephilinae orb-web spiders. Toxin Rev. 24 (2005) 209-234
22. Quistad G.B., Lam W.W., and Casida J.E. Identification of bis(agmatine) oxalamine in venom from the primitive hunting spider, Plectreuris tristis (Simon). Toxicon 31 (1993) 920-924
23. Rebrin I., Geha R.M., Chen K., and Shih J.C. Effects of carboxyl-terminal truncations on the activity and solubility of human monoamine oxidase B. J. Biol. Chem. 276 (2001) 29499-29506
24. Rommelspacher H., Meier-Henco M., Smolka M., and Kloft C. The levels of norharman are high enough after smoking to affect monoamineoxidase B in platelets. Eur. J. Pharmacol. 441 (2002) 115-125
25. Schroeder F.C., Taggi A.E., Gronquist M., Malik R.U., Grant J.B., Eisner T., and Meinwald J. NMR-spectroscopic screening of spider venom reveals sulphated nucleosides as major components for the brown recluse spider and related species. PNAS 105 (2008) 14283-14287
26. Shimizu M., Ishikawa M., Komoda Y., and Nakajima T. Total synthesis of (-) Trypargine. Chem. Pharm. Bull. 30 (1982) 909-914
27. Ucar G., Tasb C., and Tümer A. Monoamine oxidase inhibitory activities of the scorpion Mesobuthus gibbosus (Buthidae) venom peptides. Toxicon 45 (2005) 43-52
28. Yamada M., and Yasuhara H. Clinical pharmacology of MAO inhibitors: safety and future. NeuroToxicology 25 (2004) 215-221
29. Yagodina O.V., Nikol'skaya E.B., Khovanskikh A.E., and Kormilitsyn B.N. Amine oxidases of microorganisms. J. Evol. Biochem. Physiol. 38 (2002) 251-258
30. Yu P.M., and Tipton T.F. Current neurochemical and pharmacological aspects of biogenic amines. Curr. Prog. Brain Res. 106 (1995) 85-90
31. Yildiz A., Biçeroglu S., Yakut N., Bilir C., Akdemir R., and Akilli A. Acute myocardial infarction in a young man caused by centipede Sting. Emerg. Med. J. 23 (2006) 30-33