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Planta Med 1990; 56(4): 395-398
DOI: 10.1055/s-2006-960992
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© Georg Thieme Verlag Stuttgart · New York

Structures of Compounds with Antigonadotropic Activity Obtained by in vitro Oxidation of Caffeic Acid

A. Nahrstedt1 , M. Albrecht1 , V. Wray2 , H. G. Gumbinger3 , M. John3 , H. Winterhoff3 , F. H. Kemper3
  • 1Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Hittorfstr. 56, D-4400 Münster, Federal Republic of Germany
  • 2Gesellschaft fär Biotechnologische Forschung mbH, Mascheroder Weg 1, D-3300 Braunschweig, Federal Republic of Germany
  • 3Institut für Pharmakologie und Toxikologie der Westfälischen Wilhelms-Universität, Domagkstr. 12, D-4400 Münster, Federal Republic of Germany
Further Information

Publication History

1989

Publication Date:
05 January 2007 (online)

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Abstract

Two new cyclolignan derivatives were isolated by HPLC from the mixture of substances obtained after oxidation of caffeic acid with KMnO4. Their structures were elucidated by spectroscopic methods as 2,3-dicarboxy-6,7-dihydroxy-l-(3′,4′-dihydroxy)-phenyl-1,2-dihydronaphthalene (1) and 3-carboxy-6,7-dihydroxy-l-(3′,4′-dihydroxy)-phenylnaphthalene (2). Compounds 1 and 2 exhibit antigonadotropic activity as do the extracts of crude drugs of Lycopus europaeus and Lithospermum officinale after oxidation by plant enzymes.

Key words

Lithospermum officinale - Lycopus europaeus - caffeic acid - cyclolignan derivatives - antigonadotropic activity - potassium permanganate oxidation

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