A new gluco indole alkaloid, 3,4-dehydro-5-carboxystrictosidine, from Peruvian Una de Gato (Uncaria tomentosa)

A new gluco indole alkaloid, 3,4-dehydro-5-carboxystrictosidine, was obtain ed from Peruvian Una de Gate (Cat's Claw original plant: Uncaria tomentosa) together with two known gluco indole alkaloids, This compound was the firs t example of isolation of a gluco monoterpenoid indole alkaloid having a 3, 4-dihydro-beta-carboline ring system from nature. A characteristic feature of the compound was the quick replacement of the methylene hydrogens on C-1 4 with deuterium that was observed when it was dissolved in CD,OD, We demon strated a similar proton-deuterium exchange on a model compound, 1-methyl-3 ,4-dihydro-beta-carboline, in CD3OD solution.