Cell-free synthesis of the alkaloids ammodendrine and smipine

Abstract

The bipiperidyl alkaloid amm odendrine was detected in 28 plant species as a minor alkaloid besides quinolizidine alkaloids. Cadaverine serves as a precursor for both quinolizidine alkaloids and for am m odendrine, since labelled cadaverine is incorporated intoboth rings of ammodendrine.Cell-free extracts of Lupinus arboreus and of Pisum sativum, which contain an active diamine oxidase form ammodendrine from cadaverine and pyruvate. In addition to ammodendrine other alkaloids such as smipine, tetrahydroanabasine and tripiperideine could be detected. Possible reaction schemes are discussed. © 1987, Walter de Gruyter. All rights reserved.