Novel quaternary ammonium salt-containing polyamines from the Agelenopsis aperta funnel-web spider

Two novel hydroxylamine-containing acylpolyamines, Agel 489a and Agel 505a, each bearing a terminal quaternary ammonium salt, were isolated from the venom of Agelenopsis aperta, a funnel-web spider found throughout the western United States. Published structures for these compounds were not consistent with our spectral data. On the basis of fast-atom bombardment (FAB) mass spectrometry and 1 H and 13 C NMR spectra, novel structures for Agel 489a and 505a are proposed. These structural assignments are confirmed by the total synthesis of Agel 489a