Isolation and chemical characterization of PwTx-II: A novel alkaloid toxin from the venom of the spider Parawixia bistriata (Araneidae, Araneae)

Toxicon

Volumn 46, Issue 7, 2005, Pages 786-796

  Cesar, Lilian M M ^a   Mendes, Maria A ^a   Tormena, Claudio F ^b   Marques, Maurício R ^a   De Souza, Bibiana M ^a   Saidemberg, Daniel Menezes ^a   Bittencourt, Jackson C ^b   Palma, Mario S ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Alkaloid; Natural compound; Natural product; Neurotoxicity; Spectroscopy; Spider toxin; Spider venom; Structure determination

Indexed keywords

1 (4 GUANIDINO)BUTOXY 6 HYDROXY 1,2,3,4 TETRAHYDRO BETA CARBOLINE; BETA CARBOLINE; NEUROTOXIN; SPIDER VENOM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; PARAWIXIA BISTRIATA; PRIORITY JOURNAL; RAT; SPECTROSCOPY; SPIDER; ULTRAVIOLET RADIATION;

ANIMALS; CARBOLINES; DOSE-RESPONSE RELATIONSHIP, DRUG; LETHAL DOSE 50; MALE; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; SEIZURES; SPIDER VENOMS; SPIDERS; TOXINS, BIOLOGICAL;

ANIMALIA; APIS MELLIFERA; ARANEAE; ARANEIDAE; HEXAPODA; RATTUS NORVEGICUS;

EID: 27444438167     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2005.08.005     Document Type: Article

References (31)

1. R.A. Abramovitch, and I.D. Spencer The carbolines Adv. Heterocycl. Chem. 3 1964 79 88
2. T. Akizawa, K. Yamazaki, T. Yasuhara, T. Nakajima, M. Roseghini, and G.F. Spasmer Trypargine, a new tetrahydro-β-carboline of animal origin: isolation and chemical chracterization from the skin of the African rhacophorid frog, Kassina senegalensis Biomed. Res. 3 1982 232 234
3. S.A. Barker, R.E.W. Harrison, J.G.B. Brown, and S.T. Christian Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro- β-carboline as in vivo constituents of rat brain and adrenal gland Biochem Pharmacol. 30 1981 9 15
4. S. Braun, H.O. Kalinowski, and S. Berger 100 and More Basic NMR Experiments: a Practical Course Course 1996 VCH New York p. 413
5. C. Carmona, R. Ghanem, M. Balón, M.A. Muñoz, and P. Guardado Chemical and photochemical oxidation of tetrahydrobetacarboline J. Photochem. Photobiol. A Chem. 135 2000 171 177
6. L.M.M. Cesar, C.F. Tormena, M.R. Marques, G.V.J. Silva, M.A. Mendes, R. Rittner, and M.S. Palma 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
7. J. Chou, and T.C. Chou Dose-effect analysis with microcomputers 1987 Biosoft Cambridge p.93
8. A.C.K. Fontana, M.A. Cairrão, A.J. Colusso, W.F. Santos, and J. Coutinho-Netto Activity of the Parawixia bistriata crude venom in a new bioassay in termites Toxicon 38 2000 133 138
9. K. Hostettmann, M. Hostettmann, S. Rodriguez, and J. Wolfender LC-hyphenated techiques in the search for new bioactive plant constituents K. Nakanishi R. Cooper J.K. Snyder The Biology-Chemistry Interface 1999 120 (Printed in the United States of America)
10. J.V. Johnson, R.A. Yost, O. Beck, and K.F. Faull M.A. Collins Aldehyde Adducts in Alcoholism 1985 Alan R. Liss New York 161
11. N. Kawai, and T. Nakajima Neurotoxins from spider venoms A.L. Harvey Natural and Synthetic Neurotoxins 1993 Acad. Press London 319 345
12. H.W. Levi Spiders of orb-weaver genus Parawixia in America (Araneae:araneidae) Bull. Mus. Comp. Zool. 153 1992 1 46
13. M.F. Manzoli-Palma, N. Gobbi, and M.S. Palma Insects as models to assay spider and scorpion venom toxicity J. Venom. Anim. Toxins Incl. Tropical Diseases 9 2003 174 185
14. M.R. Marques, M.A. Mendes, C.F. Tormena, B.M. Souza, L.M.M. César, R. Rittner, and M.S. Palma Structure Determination of a Tetrahydro-β- Carboline of Arthropod Origin: a Novel Alkaloid Toxin Subclass from the Web of Spider Nephila Clavipes. Chem. Biodiv. 2 2005 525 534
15. M.R. Marques, M.A. Mendes, C.F. Tormena, B.M. Souza, S.P. Ribeiro, R. Rittner, and M.S. Palma Structure determination of an organometallic 1-(diazenaryl) ethanol: a novel toxin subclass from the web of the spider Nephila clavipes Chem. Biodiv. 830 2004 838
16. J. McCormick, K. McCormick, H.I. Duysntee, A.K. van Egen, G.A. van der Marel, B. Ganem, and J.H. van Boon Structure and total synthesis of HF-7, a neuroactive glyconucleside dissulfate from funnel-web spider Hololena curta J. Am. Chem. Soc. 121 1999 5661 5665
17. N.A.S. 1996. National Academy of Sciences. Guide for the Care and Use of Laboratory Animals; Institute of Laboratory Animal Resources; Commission on Life Sciences; National Research Council, National Academy Press; Washington,D.C.(available on line at: http://www.nap.edu/readingroom/books/ labrats/).
18. K. Nakanishi, R. Goodnow, K. Konno, M. Niwa, R. Bukownik, T.A. Kallimpoulus, P. Usherwood, A.T. Eldefrawi, and M.E. Eldefrawi Philanthotoxin-433 (PhTX-433), a non-competitive glutamate receptor inhibitor Pure Appl. Chem. 62 1990 1223 1230
19. OECD, 2001. Guidance document on acute oral toxicity testing. OECD Environment, Health and Safety Monograph Series on Testing and Assessment, 4 (available on-line at http://www.oecd.org/esh/).
20. M.S. Palma, T. Fujita, Y. Itagaki, H. Naoki, and T. Nakajima Mass spectrometric structure determination of spider toxins arginine containing from the venoms of Brazilian Garden spider Nephilengys cruentata Nat. Toxins. 5 1997 47 57
21. M.S. Palma, and T. Nakajima Natural combinatorial chemistry strategy in acylppolyamines toxins from Nephilinae Orb-Web spiders Toxin. Rev. 24 2005 209 234
22. G.B. Quistad, W.W. Lam, and J.E. Casida Identification of bis(agmatine) oxalamide in venom from the primitive hunting spider, Plectreuris tristis (Simon) Toxicon 31 1993 920 924
23. H.A. Robertson Harmaline-induced tremor: the benzodiazepine receptor as a site of action Eur. J. Pharmacol. 67 1980 129 132
24. M.C.A. Rodrigues, R. Guizzo, W.F. dos Santos, and N.G. Cairasco A comparative neuroethological study of limbic seizures induced by Parawixia bistriata venom and kainic acid injections in rats Brain Res. Bull. 55 2001 79 86
25. M.C.A. Rodrigues, A.M. Ribeiro, A.B. Pizzo, A.C.K. Fontana, R.O. Beleboni, J. Coutinho-Neto, A. Miranda, and W.F. Santos Anticovulsant and GABA uptake inhibition properties of P. bistriata and S.raptoria spider venom fractions Pharm. Bull. 55 2002 79 86
26. M.C.A. Rodrigues, R. Guizzo, L. Gobbo-Neto, R.J. Ward, N.P. Lopes, and W.F. dos Santos The biological activity in mammals and insects of the nucleosidic fraction from the spider Parawixia bistriata Toxicon 43 2004 375 383
27. M. Shimizu, M. Ishikawa, Y. Komoda, Y. Matsubara, and T. Nakajima A new synthesis of (±) Trypargine Chem. Pharm. Bull. 30 1982 4529 4533
28. M. Shimizu, M. Ishikawa, Y. Komoda, and T. Nakajima Total synthesis of (-) Trypargine Chem. Pharm. Bull. 30 1982 909 914
29. W.S. Skinner, P.A. Dennis, A.L. Robert, and G.B. Quistad Chemical characterization of acylpolyamine toxins from venom of a trap-door spider and tarantulas Toxicon 28 1990 541 546
30. C. Szantáy, G. Blaskó, K. Honty, and G. Dörnyei A. Brossi The Alkaloids vol. 27 1986 Academic Press New York 131
31. R.M.V. Wagoner, J. Jompa, and C.M. Ireland Trypargine alkaloid from previously undescribed Eudistoma sp Ascidian. J. Nat. Prod. 62 1999 794 797