Structures of 4-aryl-coumarin (neoflavone) dimers isolated from Pistacia chinensis BUNGE and their estrogen-like activity.
Activity-guided fractionation of twigs of Pistacia chinensis resulted in the isolation and characterization of two novel ingredients as potent estrogen agonists. On the basis of spectral analysis and comparison with a related compound their structures were elucidated as 3,3''-dimers of 4-aryldihydrocoumarins (3,4-dihydro-4-(4'-hydroxyphenyl)-7-hydroxycoumarin) differing only in the stereochemical disposition of the linkage between the two 4-arylcoumarin moieties. These compounds are the first examples of bis-flavonoids which have been proven to possess estrogen-like activity.
Nishimura
S
S
Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Taki
M
M
Takaishi
S
S
Iijima
Y
Y
Akiyama
T
T
D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D003374:Coumarins / Q000737:chemistry* / Q000494:pharmacology*; D019281:Dimerization; D004958:Estradiol / Q000031:analogs & derivatives / Q000494:pharmacology; D004965:Estrogen Antagonists / Q000494:pharmacology; D004968:Estrogens, Non-Steroidal / Q000302:isolation & purification*; D007529:Isoflavones; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D048789:Phytoestrogens; D028321:Plant Preparations; D010946:Plants, Medicinal / Q000737:chemistry*; D053284:Polyunsaturated Alkamides; D011959:Receptors, Estradiol / Q000378:metabolism; D013237:Stereoisomerism
D003374:Coumarins; D004965:Estrogen Antagonists; D004968:Estrogens, Non-Steroidal; D007529:Isoflavones; D048789:Phytoestrogens; D028321:Plant Preparations; D053284:Polyunsaturated Alkamides; D011959:Receptors, Estradiol; D004958:Estradiol; C051781:ICI 164384