1,721,025 research outputs found
Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core
No full textEsterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity
Stearoyldelicone, an unstable protoilludane sesquiterpenoid from intact fruitbodies of Russula delica
No full textStructure and absolute configuration of protoilludane sesquiterpenes from Russula delica
No full textOxygenated sesquiterpenoids from a nonpoisonous Sardinian chemotypes of giant fennel (Ferula communis)
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OXYGENATED SESQUITERPENOIDS FROM A NONPOISONOUS SARDINIAN CHEMOTYPE OF GIANT FENNEL (FERULA COMMUNIS)
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