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Biological profiling of semisynthetic C19-functionalized ferruginol and sugiol analogues


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Title: Biological profiling of semisynthetic C19-functionalized ferruginol and sugiol analogues
Authors : González Cardenete, Miguel Ángel
Rivas, Fatima
Bassett, Rachel
Stadler, Marco
Hering, Steffen
Padrón Carrillo, José Manuel
Zaragozá Cardells, Ramón José
Dea Ayuela, María Auxiliadora
Keywords: Paludismo - Farmacoterapia.Pharmacology.Farmacología.Malaria - Chemotherapy.
Publisher: MDPI
Citation: González-Cardenete, M.A., Rivas, F., Basset, R., Stadler, M., Hering, S., Padrón, J.M., Zaragozá, R.J. & Dea-Ayuela, M. A. (2021). Biological profiling of semisynthetic C19-functionalized Ferruginol and Sugiol analogues. Antibiotics, vol. 10, i. 2 (12 feb.), art. 184. DOI:
Abstract: The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure–activity relationship (SAR) elements. In particular, the ferruginol and sugiol analogs compounds 10–16 were characterized by the presence of a phenol moiety, higher oxidization states at C-7 (ketone), and the hydroxyl, methyl ester or free carboxylic acid at C19. The biological profiling of these compounds was investigated against a panel of six human solid tumor cell lines (HBL-100, A549, HeLa, T-47D, SW1573 and WiDr), four parasitic Leishmania species (L. donovani, L. infantum, L. guyanensis and L. amazonensis) and two malaria strains (3D7 and K1). Furthermore, the capacity of the compounds to modulate gamma-aminobutyric acid type A (GABAA) receptors ( 1 2 2s) is also described. A comparison of the biological results with those previously reported of the corresponding C18-functionalized analogs was conducted.
Description: Este artículo se encuentra disponible en la siguiente URL:
Este artículo pertenece al número especial "Search of New Natural Products with Antimicrobial Activity".
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ISSN: 2079-6382 (Electrónico)
Issue Date: 12-Feb-2021
Center : Universidad Cardenal Herrera-CEU
Appears in Collections:Dpto. Farmacia

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