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PubMed · 12444685

Daucane phytoestrogens: a structure-activity study.

Giovanni Appendino·Paola Spagliardi·Giancarlo Cravotto·Victoria Pocock·Stuart Milligan
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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 alpha. 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.

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BenzoatesBinding, CompetitiveBridged Bicyclo CompoundsCycloheptanesDose-Response Relationship, DrugEsterificationEstrogen Receptor alphaEstrogens, Non-SteroidalFemaleFerulaHumansIsoflavonesItalyPhytoestrogensPlant PreparationsPlants, MedicinalReceptors, EstrogenSaccharomyces cerevisiaeSesquiterpenesStructure-Activity RelationshipJournal ArticleResearch Support, Non-U.S. Gov't

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Giovanni Appendino, Paola Spagliardi, Giancarlo Cravotto, Victoria Pocock, Stuart Milligan. 2002. Daucane phytoestrogens: a structure-activity study.. https://doi.org/10.1021/np0201671

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