Structure--activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core

Journal of Natural Products
Giovanni AppendinoStuart Milligan

Abstract

Esterification 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 alpha-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.

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Citations

Oct 4, 2015·Chemical Biology & Drug Design·Rémi SafiEvelyne Delfourne
Feb 3, 2009·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·M ZavattiP Zanoli
Mar 2, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chun-Tao CheChristopher Wai Kei Lam
Sep 29, 2011·Phytotherapy Research : PTR·Zedan Zeid IbraheimMarcel Jaspars
May 30, 2014·Systems Biology in Reproductive Medicine·Nasra N AyuobSoad S Abdulhadi
Sep 15, 2006·Physiology & Behavior·Manuela ZavattiPaola Zanoli
Aug 9, 2017·Drug Development Research·Yueting ZhouXiaoqiang Han
Dec 1, 2007·Biopharmaceutics & Drug Disposition·H Greige-GergesN Ouaini
Jul 28, 2005·Natural Product Reports·Braulio M Fraga
Jan 3, 2019·Journal of Natural Products·José F Quílez Del MoralAlejandro F Barrero

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