Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000058.xml
Planta Med 2001; 67(3): 292-294
DOI: 10.1055/s-2001-11998
DOI: 10.1055/s-2001-11998
Letter
© Georg Thieme Verlag Stuttgart · New York
On the Absolute Configuration of Matricin
Further Information
Publication History
April 7, 2000
July 16, 2000
Publication Date:
31 December 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
- 1 Appendino G, Calleri M, Chiari G, Viterbo D. Structure and conformation of a stoichiometric adduct of 4-epimatricin with 3β-hydroxydihydrocostunolide and of 4-epimatricin alone. J. Chem. Soc. Perkin Trans.. 1985; II 203-7
- 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
- 4 Barrero A F, Sánchez M J, Barron A, Del Mar Salas M. Guaianolides from Tanacetum annuum . Phytochemistry. 1990; 29 3575-80
- 5 Stahl E. Über das Cham-Azulen und dessen Vorstufen. Chem. Ber.. 1954; 87 202-5, 505 - 7, 1626 - 8
-
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