title: Structures of compounds with antigonadotropic activity obtained by in vitro oxidation of caffeic acid.
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-1-(3', 4'-dihydroxy)-phenyl-1, 2-dihydronaphthalene (1) and 3-carboxy-6,7-dihydroxy-1-(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.
authors.affiliation: Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Münster, Federal Republic of Germany.
authors.forename: A
authors.initials: A
authors.lastname: Nahrstedt
authors.forename: M
authors.initials: M
authors.lastname: Albrecht
authors.forename: V
authors.initials: V
authors.lastname: Wray
authors.forename: H G
authors.initials: HG
authors.lastname: Gumbinger
authors.forename: M
authors.initials: M
authors.lastname: John
authors.forename: H
authors.initials: H
authors.lastname: Winterhoff
authors.forename: F H
authors.initials: FH
authors.lastname: Kemper
mesh_terms: D000818:Animals; D002109:Caffeic Acids / Q000378:metabolism* / Q000494:pharmacology; D002396:Catechols / Q000302:isolation & purification / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D006062:Gonadotropins / Q000037:antagonists & inhibitors*; D007985:Leydig Cells / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009284:Naphthols / Q000302:isolation & purification / Q000494:pharmacology*; D010084:Oxidation-Reduction
chemical_list: D002109:Caffeic Acids; D002396:Catechols; D006062:Gonadotropins; D009284:Naphthols; C066187:KS IV; C066186:KS I; C040048:caffeic acid