Structure determination of a tetrahydro-beta-carboline of arthropod origin: A novel alkaloid-toxin subclass from the web of spider Nephila clavipes

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dc.contributor.authorMarques, M. R.
dc.contributor.authorMendes, M. A.
dc.contributor.authorTormena, C. F.
dc.contributor.authorSouza, B. M.
dc.contributor.authorCesar, LMM
dc.contributor.authorRittner, R.
dc.contributor.authorPalma, Mario Sergio [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.date.accessioned2014-05-20T13:54:21Z
dc.date.available2014-05-20T13:54:21Z
dc.date.issued2005-01-01
dc.description.abstractThe orb-web spiders are polyphagous animals in which the web plays a very important role in the capture of preys; oily droplets usually cover the capture-web of the spider Nephila clavipes and seem to be of great importance for prey capture. The knowledge of the chemical composition of these droplets is necessary to understand the function of this adhesive material in web mechanics and prey capture. A novel subclass of spider toxins, tetrahydro-beta-carboline, was identified among the weaponry of compounds present inside of oily droplets. This type of alkaloid is not common among the natural compounds of spider toxins. Apparently, when the prey arthropods get caught by the spider web, their bodies are covered with many adhesive oily droplets, which disrupt delivering the tetrahydro-beta-carboline to the direct contact with the prey integument. Toxicity assays demonstrated a potent lethal effect of the alkaloid toxin to the spider preys; topical applications of the teirahydro-beta-carboline at first caused clear signs of neurotoxicity, followed by the death of preys. The structure of the major component, a tetrahydro-beta-carboline, among the alkaloid toxins was elucidated by means of UV spectrophotometry, ESI mass spectrometry, H-1-NMR spectroscopy, and high-resolution mass spectrometry. The structure of the natural toxin was determined as 1-(2-guanidinoethyl)-1,2,3,4-tetrahydro-6-hydroxymethyl)-beta-carboline; the investigation of the pharmacological properties and neurotoxic actions of this compound may be used in the future as reference for the development of new drugs to be applied at level of pest control in agriculture.en
dc.description.affiliationUNESP, Inst Biosci, Dept Biol, CEIS,Lab Struct Biol & Zoochem, BR-13506900 Rio Claro, SP, Brazil
dc.description.affiliationUniv São Paulo, FFCLRP, Dept Chem, BR-14040901 Ribeirao Preto, SP, Brazil
dc.description.affiliationUNICAMP, Inst Chem, Phys Organ Chem Lab, BR-13084971 Campinas, SP, Brazil
dc.description.affiliationUnespUNESP, Inst Biosci, Dept Biol, CEIS,Lab Struct Biol & Zoochem, BR-13506900 Rio Claro, SP, Brazil
dc.format.extent525-534
dc.identifierhttp://dx.doi.org/10.1002/cbdv.200590034
dc.identifier.citationChemistry & Biodiversity. Zurich: Verlag Helvetica Chimica Acta Ag, v. 2, n. 4, p. 525-534, 2005.
dc.identifier.doi10.1002/cbdv.200590034
dc.identifier.issn1612-1872
dc.identifier.lattes2901888624506535
dc.identifier.urihttp://hdl.handle.net/11449/19421
dc.identifier.wosWOS:000228770000012
dc.language.isoeng
dc.publisherVerlag Helvetica Chimica Acta Ag
dc.relation.ispartofChemistry & Biodiversity
dc.relation.ispartofjcr1.617
dc.relation.ispartofsjr0,531
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleStructure determination of a tetrahydro-beta-carboline of arthropod origin: A novel alkaloid-toxin subclass from the web of spider Nephila clavipesen
dc.typeArtigo
dcterms.licensehttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dcterms.rightsHolderVerlag Helvetica Chimica Acta Ag
unesp.author.lattes2901888624506535
unesp.author.orcid0000-0002-2078-9286[2]
unesp.author.orcid0000-0002-4715-6139[6]
unesp.author.orcid0000-0002-7363-8211[7]
unesp.author.orcid0000-0002-1508-0694[3]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Biociências, Rio Claropt

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Artigos - Biologia - IBRC