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Planta Med 1978; 34(8): 381-389
DOI: 10.1055/s-0028-1097467
Research Articles

© Georg Thieme Verlag Stuttgart · New York

The Biosynthesis of the Ipecac Alkaloids and of Ipecoside and Alangiside

Naotaka Nagakura, Gerhard Höfle1 , Dianella Coggiola, Meinhart H. Zenk
  • Lehrstuhl für Pflanzenphysiologie, Ruhr–Universität Bochum, Federal Republic of Germany.
  • 1Organisch–Chemisches Institut, Technische Universität Berlin.
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Publication History

Publication Date:
13 January 2009 (online)

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Abstract

The synthesis of (1–3H, 3–14C)–(1α)–desacetylisoipecoside and –(1β)–desacetylipecoside is described. Feeding experiments with the pure epimers showed that in contrast to previous assumptions, desacetylisoipecoside is the true precursor for the ipecac alkaloids (cephaeline and emetine) in both Cephaelis and Alangium. The 1β epimer, desacetylipecoside, is the precursor only of the alkaloidal glucosides, ipecoside and alangiside, both of which posses the β–configuration. A biosynthetic scheme for the formation of these compounds is proposed and the difference between this pathway and monoterpenoid indole alkaloid biosynthesis is discussed.

Key Word Index

Cephaelis ipecacuanha - Rubiaceae - Alangium lamarckii - Alangiaceae - Alangiside - Cephaeline - Emetine - Ipecoside - Biosynthesis of Monoterpenoid Isoquinoline Alkaloids

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