Isolation and Structure of an N-isoButyldienediynamide from Pellitory (Anacyclus pyrethrum DC.)

Abstract

THE roots of the North African plant Anacyclus pyrethrum DC. (pellitory) have been used in medicine since the time of Dioscorides, and mention of the drug is made in the B.P.C. 1934 (Pyrethri radix). It induces copious salivation when chewed and gives rise to an intense burning taste. In a recent investigation it has been found¹ that the crystalline sialogogue isolated by Gulland and Hopton² from this material, and named pellitorine (melting point 72°), is in fact a mixture of isobutylamides^3,4 of the general type Hydrogenation and acidic hydrolysis yield a mixture of decanoic, dodecanoic and tetradecanoic acids which can be separated by reversed-phase partition chromatography. Its nature will be discussed more fully elsewhere. During the isolation of pellitorine, a new crystalline substance of melting point 121° has been obtained, which crystallizes from chloroform–petrol in white needles. Unlike pellitorine, it is but sparingly soluble in petrol, has no sialogogue effect and only low insecticidal activity towards the grain insect Tenebrio molitor L.