Structures of compounds with antigonadotropic activity obtained by in vitro oxidation of caffeic acid.
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.
Nahrstedt
A
A
Institut für Pharmazeutische Biologie und Phytochemie der Westfälischen Wilhelms-Universität, Münster, Federal Republic of Germany.
Albrecht
M
M
Wray
V
V
Gumbinger
H G
HG
John
M
M
Winterhoff
H
H
Kemper
F H
FH
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
D002109:Caffeic Acids; D002396:Catechols; D006062:Gonadotropins; D009284:Naphthols; C066187:KS IV; C066186:KS I; C040048:caffeic acid