Antiandrogenic natural Diels--Alder-type adducts from Brosimum rubescens.
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.
Shirota
O
O
Division of Pharmacognosy and Phytochemistry, National Institute of Health Sciences, Tokyo, Japan.
Takizawa
K
K
Sekita
S
S
Satake
M
M
Hirayama
Y
Y
Hakamata
Y
Y
Hayashi
T
T
Yanagawa
T
T
D058891:5-alpha Reductase Inhibitors; D000726:Androgen Antagonists / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D059002:Androgen Receptor Antagonists; D000818:Animals; D002599:Chalcone / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010568:Peru; D019441:Plant Epidermis / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D017208:Rats, Wistar; D016339:Spectrometry, Mass, Fast Atom Bombardment
D058891:5-alpha Reductase Inhibitors; D000726:Androgen Antagonists; D059002:Androgen Receptor Antagonists; D003374:Coumarins; D002599:Chalcone