Daucane Phytoestrogens: A Structure−Activity Study
- 18 September 2002
- journal article
- review article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 65 (11), 1612-1615
- https://doi.org/10.1021/np0201671
Abstract
The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor α. Rather strict structure−activity relationships were observed. Thus, while the parent polyol (jaeschkeanadiol, 2a) was inactive, the presence of a p-hydroxybenzoyl moiety was necessary for activity in the yeast screen. Homologation and vinylation were both detrimental for activity, as were methylation of the p-hydroxyl substituent and the introduction of oxygen functions on the adjacent carbons.Keywords
This publication has 9 references indexed in Scilit:
- Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringeninReproduction, 2002
- Comparison of in-patient and out-patient penile prosthesis surgeryInternational Journal Of Impotence Research, 2001
- The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of LigandsToxicological Sciences, 2000
- Estrogenic Effects ofp-Hydroxybenzoic Acid in CD1 MiceEnvironmental Research, 1997
- Molecular basis of agonism and antagonism in the oestrogen receptorNature, 1997
- The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding siteSteroids, 1997
- Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screenEnvironmental Toxicology and Chemistry, 1996
- The daucane (carotane) class of sesquiterpenesPhytochemistry, 1994
- Oestrogenic rhythm induced by a single administration of the extract ofFerula jaeschkeana to immature ratsPhytotherapy Research, 1994