Hamulic, DamirDea Ayuela, María AuxiliadoraStadler, MarcoHering, SteffenPadrón Carrillo, José ManuelBassett, RachelRivas, FatimaLoza Mejía, Marco AntonioGonzález Cardenete, Miguel ÁngelUCH. Departamento de FarmaciaProducción Científica UCH 20192020-09-162020-09-162019-03-06Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues : SAR studies. Journal of Natural Products, vol. 82, n. 4 (6 mar.), pp. 823-831. DOI: https://doi.org/10.1021/acs.jnatprod.8b008840163-38641520-6025 (Electrónico)http://hdl.handle.net/10637/11658Este artículo se encuentra disponible en la página web de la revista en la siguiente URL: https://pubs.acs.org/doi/10.1021/acs.jnatprod.8b00884Este es el pre-print del siguiente artículo: Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues: SAR studies. Journal of Natural Products, vol. 82, i. 4, pp. 823-831, que se ha publicado de forma definitiva en https://doi.org/10.1021/acs.jnatprod.8b00884This is the pre-peer reviewed version of the following article: Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues: SAR studies. Journal of Natural Products, vol. 82, i. 4, pp. 823-831, which has been published in final form at https://doi.org/10.1021/acs.jnatprod.8b00884The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoid acid (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (−)-abietic acid (1). Biological comparison was conducted according to the different functional groups leading to some basic structure-activity relationship (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16, were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s), is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.application/pdfenopen accessNuclear receptors (Biochemistry)Receptores nucleares (Bioquímica)Alkalies - Synthesis.Cells.Alcalis - Síntesis.Células.Artículohttps://doi.org/10.1021/acs.jnatprod.8b00884https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es