Structure and insecticidal activity of picrotoxinin analogs

Natural products for pest control: an analysis of their role, value and future

“…photostability, spectrum). Other examples include efforts to build synthetic insecticides based on methyllycaconitine and picrotoxinin …”

Actions of picrodendrin antagonists on dieldrin‐sensitive and ‐resistant Drosophila GABA receptors

“…Decreases in C4-substituent hydrophobicity, which in the present study was represented by isohyenanchin, had similar effects on the potency of picrotoxinin analogues. Picrotin (which bears a C4 hydroxyisopropyl group) and x-picrotoxinone (C4 acetyl group) are weaker antagonists of RDLac homo-oligomers (Shirai et al, 1995) and of native vertebrate and insect GABA receptors than is picrotoxinin (Jarboe et al, 1968;Miller et al, 1979;Kudo et al, 1984;Olsen et al, 1989;Deng et al, 1991; 1992). Of all the terpenoids, picrodendrin-Q had the highest potency on both RDLaC homo-oligomers and rat GABAA retstitution on the potency of ceptors (Ozoe et al, 1994) this electronegative centre differentiates the optimal picrotoxIs Q, B and A (IC50s 17 nM, ane antagonist pharmacophore of RDLac homo-oligomers and more potent or equipotent rat GABAA receptors.…”

“…a picrotoxane skeleton. Analogues of picrotoxinin, which differ in the nature of their substituents at various carbon atoms on the common picrotoxane skeleton, have been the subject of a number of electrophysiological and radioligand binding studies which yield insights into the structural requirements for potent convulsant antagonism (Jarboe et al, 1968;Miller et al, 1979;Klunk et al, 1983;Kudo et al, 1984;Anthony et al, 1993;1994). Such data led Ozoe & Matsumura Figure 1, demonstrates the presence of all these features in the picrodendrin and tutin terpenoids studied here, although the positions of the electronegative centres of the terpenoids tested here differ slightly from those of picrotoxinin.…”

γ-BHC: Its history and mystery – why is only γ-BHC insecticidal?

“…However, dieldrin poisoning did not alter the nicotine sensitivity of the ganglion. In addition to γ-BHC and dieldrin, picrotoxinin was also shown to interact with the presynaptic area of the American cockroach CNS and to stimulate the excitatory neurotransmitter release [44,45]. The increase in ACh levels in the nerve cord of cockroaches treated with γ-BHC was also documented by other researchers [46].…”