1. Antiandrogenic natural Diels--Alder-type adducts from Brosimum rubescens.
- Author
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Shirota O, Takizawa K, Sekita S, Satake M, Hirayama Y, Hakamata Y, Hayashi T, and Yanagawa T
- Subjects
- 5-alpha Reductase Inhibitors, Androgen Antagonists chemistry, Androgen Antagonists pharmacology, Androgen Receptor Antagonists, Animals, Chalcone analogs & derivatives, Chalcone chemistry, Chalcone pharmacology, Chromatography, High Pressure Liquid, Coumarins chemistry, Coumarins pharmacology, In Vitro Techniques, Magnetic Resonance Spectroscopy, Male, Peru, Plant Epidermis chemistry, Rats, Rats, Wistar, Spectrometry, Mass, Fast Atom Bombardment, Androgen Antagonists isolation & purification, Chalcone isolation & purification, Coumarins isolation & purification, Plants, Medicinal chemistry
- Abstract
The isolation and structure elucidation of five novel natural Diels--Alder-type adducts, named palodesangrens A-E (1-5), from the Peruvian folk medicine known as "palo de sangre" (Brosimum rubescens) is described. The structures of the Diels--Alder adducts, consisting of chalcone derivatives and a prenylcoumarin, were elucidated by analysis of spectroscopic data including 2D NMR. Some of these compounds showed potent inhibitory activity towards 5 alpha-dihydrotestosterone (DHT) binding with an androgen receptor to form a DHT-receptor complex that causes androgen-dependent diseases.
- Published
- 1997
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