Unusual Tropane Alkaloid Pattern in Two African Convolvulaceous Species. Phytochemistry and Chemotaxonomy of the Convolvulaceae, Part 20 [1]

Sonja C. Ott 1 , Britta Tofern-Reblin 2 , Kristina Jenett-Siems 2 , Karsten Siems 3 , Frank Müller 4 , Monika Hilker 4 , Bernardina Onegi 5 , Ludger Witte 6 ,  and Eckart Eicha 2
  • 1 Institut für Pharmazie (Pharmazeutische Biologie), Freie Universität Berlin, Königin-Luise-Str. 2 – 4, 14195 Berlin, Germany
  • 2 Institut für Pharmazie (Pharmazeutische Biologie), Freie Universität Berlin, Königin-Luise-Str. 2 - 4, 14195 Berlin, Germany
  • 3 AnalytiCon Discovery, Hermannswerder Haus 17, 14473 Potsdam, Germany
  • 4 Institut für Biologie (Angewandte Zoologie / Ökologie der Tiere), Freie Universität Berlin, Haderslebener Str. 9, 12163 Berlin, Germany
  • 5 Department of Pharmacy (Pharmacognosy Unit), Makerere University, Kampala, Uganda
  • 6 Institut für Pharmazeutische Biologie, Technische Universität Braunschweig, Mendelssohnstraße 1, 38106 Braunschweig, Germany

An unusual and complex tropane alkaloid pattern has been detected in the root bark of Astripomoea malvacea and in the whole plant of Falkia repens (Convolvulaceae) by GC-MS analysis. The specific profile of both species is characterized by the presence of aliphatic 3- acyloxytropanes/-nortropanes (exclusively in A. malvacea; predominantly in F. repens in cooccurrence with a few aromatic as well as arylalkyl acyl congeners). The principal alkaloid of A. malvacea, astrimalvine A N-oxide [3β -(3-tigloyloxy-2-methylbutyryloxy)tropane N-oxide], isolated and structurally elucidated by detailed spectroscopic analysis, represents the first N-oxide of a 3β -tropanol derivative in the Convolvulaceae. Its minor tertiary congener astrimalvine B [3β -(3-hydroxy-2-methylbutyryloxy)tropane] turned out to be a metabolite of both convolvulaceaous species. This is the first phytochemical report on the African genera Astripomoea and Falkia.

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Zeitschrift für Naturforschung B is an international scientific journal which publishes original papers, microreviews, and letters from all areas of inorganic chemistry, solid state chemistry, coordination chemistry, molecular chemistry, and organic chemistry.

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