Small Molecules from Spiders Used as Chemical Probes

Abstract

Spiders are important species in ecological systems and as major predators of insects they are endowed with a plethora of low-molecular-weight natural products having intriguing biological activities. The isolation and biological characterization of these entities are well established, however, only very recently have these compounds been used as templates for the design, synthesis, and biological evaluation of synthetic analogues. In contrast, the investigation of compounds responsible for chemical communication between spiders is far less developed, but recently new light has been shed onto the area of pheromones and allomones from spiders. Herein, we recapitulate these recent results, put them into perspective with previous findings, and provide an outlook for future studies of these chemotypes.

Regioselective solid-phase synthesis of N-mono-hydroxylated and N-mono-methylated acylpolyamine spider toxins using an 2-(ortho-nitrophenyl)ethanal-modified resin

“…), 2975w, 2932w, 2873w, 1678s, 1606w, 1536w, 1499m, 1478m, 1418m, 1390w, 1365m, 1301m, 1248m, 1160s, 898w, 865w, 773w, 732m, 648w. 1 3 C and CH 2 ); 1.34 (s, (H 3 C) 3 C). 13 Resin 27 (142 µmol) was swelled in dry CH 2 Cl 2 (5 ml) and cooled to −20°C.…”

Research with Chemistry and Pharmacology of Natural Products in Brazil: A Comparison with 70 Selected Countries from 5 Continents

“…[7][8][9] Karlson and Butenendt s 3 and Law and Rengier s 4 article were limited to pheromones. However, today it is also well established that pheromones and other semiochemicals (or small molecules, as Meinwald 7 called them) are found in microorganisms [10][11][12][13][14][15][16] , amphibinas [17][18][19][20][21] , spiders [22][23][24][25][26][27][28] , birds [29][30][31][32][33] , marine organisms [34][35][36][37][38][39][40][41] , non-human mammals [42][43][44][45][46] , and humans. [47][48][49][50][51][52][53] According to Verpoorte 54 there are some 250,000 of such 'natural products' and some 4,000 new ones are reported ev...…”

Venoms-based discovery of novel modulators of human neuronal α7 and α3* nicotinic acetylcholine receptors

“…Acylpolyamines can selectively block ionotropic glutamate receptors from insects and vertebrates including mammals (for a review see (Olsen, 2011)). Because glutamate is the main neurotransmitter at the neuromuscular junctions in insects, block of glutamatergic receptors by acylpolyamines induces paralysis (Piek, 1971;Piek and Njio, 1975).…”

“…Venomous animals use their venom to hunt prey and/or protect themselves against predators (Billen, 2008;Olsen, 2011). Most animal venoms are a complex mixture of salts, small organic compounds, peptides and proteins (Escoubas, 2006b;Zhang, 2015b), with activity against a wide range of receptors (Inserra, 2013; and ion channels (Billen, 2008;DeBin, 1993;Nirthanan, 2002).…”

“…In addition to polyamines, other small molecules can be found in spider venoms, such as amino acids (GABA, glutamate, acetylcholine), adenosine triphosphate (ATP) and adenosine monophosphate (ADP) (for reviews, see (Estrada, 2007; King and Hardy, 2013; Olsen, 2006Olsen, , 2011. These molecules are endogenous modulators of ion channels and receptors both in invertebrates and vertebrates but their lack of selectivity makes these molecules unsuitable as drug leads (for a review, see (King and Hardy, 2013)).…”