A New Gluco Indole Alkaloid, 3, 4-Dehydro-5-carboxystrictosidine, from Peruvian Una de Gato (Uncaria tomentosa).

Abstract

A new gluco indole alkaloid, 3, 4-dehydro-5-carboxystrictosidine, was obtained from Peruvian Una de Gato(Cat's Claw, original plant : Uncaria tomentosa) together with two known gluco indole alkaloids. This compound was the first example of isolation of a gluco monoterpenoid indole alkaloid having a 3, 4-dihydro-β-carboline ring system from nature. A characteristc feature of the compound was the quick replacement of the methylene hydrogens on C-14 with deuterium that was observed when it was dissolved in CD₃OD. We demonstrated a similar proton-deuterium exchange on a model compound, 1-methyl-3, 4-dihydro-β-carboline, in CD₃OD solution.