STRUCTURE-TOXICITY RELATIONSHIPS OF THE EREMOPHILANE PHOMENONE AND PR-TOXIN

Article abstract of DOI:10.1016/0031-9422(84)83015-0

The structure-toxicity relationships of phomenone were studied on cuttings and seedlings of tomato, and on larvae of brine shrimp.Four derivatives prepared by chemical modification of phomenone were tested in comparison with PR-toxin.The toxicity to tomato cuttings (wilting and necroses of leaflets) appeared to be dependent on the integrity of the phomenone molecule, as any structural modification markedly reduced or completely abolished its phytotoxicity.By contrast, the toxicity to tomato seedlings (growth inhibition of shoots and rootlets) and to brine shrimp (larvae mortality) suggested a role for the epoxy rings in eremophilane molecules, which was enhanced by acetylation, as demonstrated by the progressive loss of activity for the sequence PR-toxin, phomenone and 9-methoxy-6,7-de-epoxyphomenone.Key Word Index - Lycopersicon esculentum; Solanaceae; phomenone; phomenone derivatives; PR-toxin; eremophilane sesquiterpenes; phytotoxins; mycotoxins.