Cell-Free Synthesis of the Alkaloids Ammodendrine and Smipine

The bipiperidyl alkaloid ammodendrine was detected in 28 plant species as a minor alkaloid besides quinolizidine alkaloids. Cadaverine serves as a precursor for both quinolizidine alkaloids and for ammodendrine, since labelled cadaverine is incorporated into both rings of amm oden­ drine. 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 ammoden­ drine other alkaloids such as smipine, tetrahydroanabasine and tripiperideine could be detected. Possible reaction schemes are discussed.