Philanthus triangulum

It is of particular interest that polyamines closely related to CNS 2103 have been found not only in other spider species (29) but also in the venom of the solitary digger wasp Philanthus triangulum (32). The similarity of these wasp and spider neurotoxins provides a notable example of convergence in the evolution of secondary metabolites aimed at a common target. 

Fig. 36 Structure of philanthotoxin (PhTX-433) from Philanthus triangulum...

Herzner, G., Schmitt, T., Peschke, K, Hilpert, A. and Strohm, E. (2007b). Food wrapping with the postpharyngeal gland secretion by females of the European beewolf Philanthus triangulum. J. Chem. Ecol., 33, 849-859. 

Schmidt, J.O., McDaniel, C. A., and Simon Thomas, R.T. (1990). Chemistry of male mandibular gland secretions of Philanthus triangulum. J. Chem. Ecol., 16, 2135-2143. 

Acylpolyamines have also been identified from the poison gland secretion of a solitary wasp, Philanthus triangulum As in the case of spiders, this wasp s venom represents a complex mixture which contains several acylpolyamines as major components. The philanthotoxins, for example, PhTX433 (163) inhibit glutamate as well as nicotinic acid receptors (Figure 42). 

Figure 42 PhTX433, an acylpolyamine from the wasp, Philanthus triangulum.

C23H41N5O3, Mr 435.61. The toxin of the solitary wasp Philanthus triangulum acts as a potent, non-competitive glutamate receptor antagonist (neurotoxic effect on prey insects, e. g., grasshoppers). The main component is the polyamine P., which closely resembles the polyamines occurring in spider venoms. 

Philanthotoxin-433 (16, PhTX-433 Fig. 17.1) is a structurally related, albeit somewhat simpler polyamine toxin, which was isolated from the Egyptian digger wasp Philanthus triangulum. It was isolated, characterized, and synthesized by a collaborative effort by Nakanishi, Usherwood, and coworkers (Eldefrawi et al. 1988). 

---