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Preparation and bactericidal activity of oxidation derivatives of austroeupatol, an ent-nor-furano diterpenoid of the labdane series from Austroeupatorium inulifolium

Author:
Chacón-Morales, Pablo A., Amaro-Luis, Juan M., Beltrán Rojas Fermín, Luis, Peixoto, Philippe A., Deffieux, Denis, Pouységu, Laurent, Quideau, Stéphane
Source:
Phytochemistry letters 2019 v.29 pp. 47-52
ISSN:
1874-3900
Subject:
Austroeupatorium inulifolium, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, aerial parts, alcohols, antibacterial properties, labdane, oxidation, reaction mechanisms
Abstract:
From aerial parts of Austroeupatorium inulifolium was obtained austroeupatol (1). The treatment of 1 with IBX generated the ketone 2 and keto-aldehyde 3. Due to the structural features of 1, the hydroxy group corresponding to the primary alcohol (at C-19) is less reactive than the oxymethine hydroxy groups of the structure. The oxidative cleavage of 1 produced the hemiacetal 4, since this reaction is quantitative and only this compound was detected, was proposed a reaction mechanism that involves the formation of a transition state that explain the generation of 4. The bactericidal activity of these oxidation derivatives was evaluated against four (4) bacterial strains [two Gram-positive (+) and two Gram-negative (-)]: Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa.
Agid:
6234958