Cytisine-like alkaloids from Ormosia hosiei Hemsl. & E.H. Wilson

I. Pouny (1) , M. Batut (1) , Laure Vendier (2) , B. David (3) , Sukyoung Yi (4) , F. Sautel (1) , P.B. Arimondo (1) , G. Massiot (1)

1 ETaC - Pharmacochimie de la Régulation Epigénétique du Cancer
2 LCC - Laboratoire de chimie de coordination
3 INSTITUT DE RECHERCHE PIERRE FABRE - Institut de Recherche Pierre FABRE
4 Chongqing Institute of Medicinal Plant Cultivation

Four alkaloids named hosieines A–D were isolated from the root and stem of Ormosia hosiei. Their flat structures were established by mass spectrometry and by a combination of NMR experiments. These molecules probably share a common biosynthetic origin with the lupin alkaloids but they differ in the formation of the last ring, being here part of a rare 2-azabicyclo[3.2.1]octane system. Their absolute configuration was determined by X-ray crystallography using CuKα radiation. As has been described for cytisine, they display a remarkable affinity towards neuronal nicotinic acetylcholine α4β2 receptor.

Domaines: Chimie de coordination

I. Pouny, M. Batut, Laure Vendier, B. David, Sukyoung Yi, et al.. Cytisine-like alkaloids from Ormosia hosiei Hemsl. & E.H. Wilson. Phytochemistry, 2014, 107, pp.97-101. ⟨10.1016/j.phytochem.2014.07.022⟩. ⟨hal-02023163⟩