NMR-spectroscopic screening of spider venom reveals sulfated nucleosides as major components for the brown recluse and related species

Abstract

Extensive chemical analyses of spider venoms from many species have revealed complex mixtures of biologically active compounds, of which several have provided important leads for drug development. We have recently shown that NMR spectroscopy can be used advantageously for a direct structural characterization of the small-molecule content of such complex mixtures. Here, we report the application of this strategy to a larger-scale analysis of a collection of spider venoms representing >70 species, which, in combination with mass spectrometric analyses, allowed the identification of a wide range of known, and several previously undescribed, small molecules. These include polyamines, common neurotransmitters, and amino acid derivatives as well as two additional members of a recently discovered family of natural products, the sulfated nucleosides. In the case of the well studied brown recluse spider, Loxosceles reclusa, sulfated guanosine derivatives were found to comprise the major small-molecule components of the venom. chemical prospecting ͉ Loxosceles ͉ metabolomics ͉ natural products ͉ neurotoxins

Defensive and chemical characterization of the froth produced by the cercopid Aphrophora cribrata

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Structure of Membrane-active Toxin from Crab Spider Heriaeus melloteei Suggests Parallel Evolution of Sodium Channel Gating Modifiers in Araneomorphae and Mygalomorphae

“…These venoms usually contain low molecular weight compounds (3,4), proteins (5,6), and peptides (7,8) with the latter group most often prevailing over the other two in terms of content and/or functional importance. Based on the target and structural features, most venom peptides can be classified into two large groups: linear cytolytic peptides (2,9) and disulfide-containing neurotoxins (1,2,7,8).…”

2D NMR-spectroscopic screening reveals polyketides in ladybugs

“…The method can thus be regarded as a useful alternative to chromatography-based approaches to NCE discovery, such as HPLC-NMR (24). Eliminating or reducing the need for chromatography as the first step in the analysis of biological samples of unknown composition is often desirable, as chromatographic fractionation necessarily risks loss or degradation of components with unexpected chemical properties (25). Use of higher field strength NMR spectrometers than employed in this study (600 MHz) could reduce signal overlap and may further improve detection of minor components.…”