Planta Med 2001; 67(3): 292-294
DOI: 10.1055/s-2001-11998
Letter

© Georg Thieme Verlag Stuttgart · New York

On the Absolute Configuration of Matricin

Susanne Goeters1 , Peter Imming1,*, Gregor Pawlitzki2 , Bernd Hempel3
  • 1 Institut für Pharmazeutische Chemie der Philipps-Universität Marburg, Marburg, Germany
  • 2 Kekulé-Institut für Organische Chemie und Biochemie, Bonn, Germany
  • 3 Robugen GmbH, Esslingen, Germany
Weitere Informationen

Publikationsverlauf

April 7, 2000

July 16, 2000

Publikationsdatum:
31. Dezember 2001 (online)

Abstract

The assignment of the absolute configuration of matricin rests on indirect evidence. On the basis of synthetic, NMR and CD studies with its decomposition product, chamazulene carboxylic acid, we were able to firmly establish the accepted 3S,3aR,4S,9R,9aS,9bS configuration of matricin.

References

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  • 2 See e.g., (a) Cox P J, Sim G A, Herz W. X-Ray crystallographic determination of the molecular structure of berlandin. J. Chem. Soc. Perkin Trans 1975; II: 459 - 63; (b) Barrero AF, Sánchez JF, Zafra MJ, Barrón A, San Feliciano A. Fulvene lactones from Tanacetum annuum. Phytochemistry 1987; 26: 1531 - 3; (c) Calderón JS, Quijano L, Gómez F, Ríos T. Prochamazulene sesquiterpene lactones from Stevia serrata .  Phytochemistry. 1989;  28 3526-7
  • 3 Flaskamp E, Zimmermann G, Nonnenmacher G, Isaac O. Untersuchungen zur Charakterisierung des Prochamazulens Matrizin aus Matricaria chamomilla L.  Z. Naturforsch.. 1982;  37b 508-11
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  • 6 Hempel B, Imming P, Goeters S, Hirschelmann R. Chamazulencarbonsäure-Verbindungen und deren Verwendung. German patent application (Robugen GmbH), filed December 30, 1999, file reference 199 63 900.0 
  • 7 Ghislandi V, La Manna A, Azzolina O, Gazzaniga A, Vercesi D. Configurational relationships in antiphlogistic hydratropic acids.  Farmaco, Ed. Sci.. 1982;  37 81-93
  • 8 Schmidt P C, Ness A. Isolation and characterization of a matricin standard.  Pharmazie. 1993;  48 146-7

Peter Imming

Institut für Pharmazeutische Chemie

Philipps-Universität Marburg

Marbacher Weg 6

35032 Marburg

Germany

eMail: imming@mailer.uni-marburg.de

Fax: +49-6421-2825893

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