Germination and Growth Inhibition of Acylnornicotines from Section Repandae of the Genus Nicotiana and Synthetic Acylnornicotines

Abstract

Ten acylnornicotines (mainly N′-hydroxyisotetradecanoyl)nornicotine) and acylanata-bine(N′-(3-hydroxyisotetradecanoyl)anatabine) were identified from the surface lipids of Nicotiana species in the section Repandae. Synthetic acylnornicotines (formyl to linolenyl nornicotine, and acylnornicotines containing hydroxylated fatty acids) were tested in a tobacco seed germination assay to study the structure-activity relationships of acylnornicotines. Among acylnornicotines without hydroxy groups, N′-hexanoyl, N′-octanoyl, and N′-decanoylnornicotine had high inhibiting activity. Among hydroxy acyl nornicotines, N′-(4-hydroxyundecanoyl), N′-(4-hydro-xydodecanoyl) and N′-hydroxydodecanoyl)nornicotine had high inhibiting activity.