Monoamine oxidase inhibitory activities of indolylalkaloid toxins from the venom of the colonial spider Parawixia bistriata: Functional characterization of PwTX-I
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Data
2009-11-01
Autores
Saidemberg, Daniel M. [UNESP]
Ferreira, Marco A. B.
Takahashi, Tatiane N. [UNESP]
Gomes, Paulo C. [UNESP]
Cesar-Tognoli, Lilian M. M. [UNESP]
da Silva-Filho, Luiz C. [UNESP]
Tormena, Claudio F.
da Silva, Gil V. J.
Palma, Mario Sergio [UNESP]
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Editor
Pergamon-Elsevier B.V. Ltd
Resumo
Colonial spiders evolved a differential prey-capture behaviour in concert with their venom chemistry, which may be a source of novel drugs. Some highly active tetrahydro-beta-carboline (TH beta C) toxins were recently isolated from the venom of the colonial spider Parawixia bistriata; the spiders use these toxins as part of their chemical arsenal to kill and/or paralyze preys. The major TH beta C compound isolated from this venom was identified as 6-hydroxytrypargine, also known as PwTX-I. Most natural compounds of animal origin occur in low abundance, and the natural abundance of PwTX-I is insufficient for complete functional characterization. Thus, PwTx-I was synthesized using a Pictet-Spengler condensation strategy, and the stereoisomers of the synthetic toxin were separated by chiral chromatography. The fraction of venom containing a mixture of three natural TH beta C toxins and enantiomers of PwTx-I were analyzed for inhibition of monoamine oxidase (MAO)-A and -B and for toxicity to insects. We reveal that the mixture of the natural TH beta C toxins, as well as the enantiomers of PwTx-I, were non-competitive inhibitors of MAO-A and MAO-B and caused potent paralysis of honeybees. The (-)-PwTX-I enantiomer is 2-fold more potent than the (+)-PwTX-I enantiomer in the assays performed. (C) 2009 Elsevier Ltd. All rights reserved.
Descrição
Palavras-chave
Spider venom, Parawixiatoxin, Indoylalkaloid, Chiral chromatography, Monoamine oxidase
Como citar
Toxicon. Oxford: Pergamon-Elsevier B.V. Ltd, v. 54, n. 6, p. 717-724, 2009.