Biological activity of cyclopaldic acid, a major toxin of Seiridium cupressi, its six derivatives, and iso-cyclopaldic acid.

Abstract

Cyclopaldic acid (CA), its six derivatives, and iso-cyclopaldic acid (IsoCA) were assayed for toxicity to cuttings of three species of cypress, as well as to mung bean, oat, and tomato explants. Toxicity to host and non-host plants of CA derivatives having one or both of the aldehyde groups transformed was less than that of CA. Shoot tissues of Cupressus macrocarpa artificially infected by Seiridium cupressi leached electrolytes more than those of C. sempervirens and C. arizonica. CA, IsoCA, and to a lesser extent the monoacetylated, phenylhydrazone and hydrogenated derivatives of CA caused loss of electrolytes from cypress tissues. CA, IsoCA, and monoacetyl CA caused limited callus development of cypress tissues. Diacetylhydrazone CA enhanced the yield of cypress callus tissue. CA derivatives having both aldehyde groups modified induced root formation on cypress cuttings. The antifungal activity showed by CA toward species of Botrytis, Fusarium, and Geotrichum markedly decreased in its derivatives. The inhibitory effect of CA on esterases was exhibited also by IsoCA and the monoacetylated derivative.