New constituents of derris root I

Abstract

A survey of the substances isolated from Derris root is given. The isolation and the properties of a substance, first discovered by Buckley, are described. A new optically active substance, termed derride, isomeric with Buckley's compound is recorded. Its formula is given and a few of its properties are described. Some derivatives of this substance have been prepared. A tabular comparison of Buckley's compound and derride is given. A new, optically active substance has been isolated from a sample of derris root of the Sumatra type. Its formula is suggested and a few of its properties are given. Sumatrol and l‐toxicarol have been isolated.

The Constituents of Derris and Other Rotenone-bearing Plants.

“…The purified compound, called at first Buckley's compound and subsequently elliptone6 (37), was optically inactive, and the suggestion was therefore made that the compound probably did not occur in the resin as such. This surmise proved correct, for a short time later (36,37,60) an optically active isomer that could be racemized to dZ-elliptone was obtained. Both compounds yielded the same dehydro compound, thus confirming further their relationship.…”

“…From the concentrated ether extract of a sample of Sumatra-type derris containing no rotenone and 23.7 per cent of total extractives, Meyer and Koolhaas (60) obtained a small amount of a yellowish solid material. On purification this material yielded greenish yellow needle-shaped crystals, which were optically active.…”

“…(60) proposed the structural formula XXVI for malaccol.i v i d u a l n o t d i r e c t l y a s s o c i a t e d w i t h s c i t e i s p r o h i b i t e d .…”

A Method for Determining Deguelin in Derris and Cube

“…The small amount of deguelin obtained by racemization as compared with the amount indicated by the Goodhue redcolor test suggests the presence of other unidentified compounds. Derride (11), called "elliptone" by Harper (6), is probably responsible for some of the additional red color, but not all, since little or no crystalline material was obtained by racemization. Some of these resins are being fractionated by molecular distillation, and the results of this investigation will be reported later.…”

The search for new insecticides

“…Its structure has been shown to be represented by (XX). Malaccol, C2oH160; (44,45), may be regarded as a hydroxyelliptone (XXI). Malaccol bears the same structural relation to elliptone as sumatrol to rotenone and toxicarol to deguelin.…”