Examinando por Autor "Espinoza, L."

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    Ítem
    Eugenol and its Synthetic Analogues Inhibit Cell Growth of Human Cancer Cells (Part I)
    (Sociedad Brasilera de Química, 2008) Carrasco, H.; Espinoza, L.; Cardile, V.; Gallardo, C.; Cardona, W.; Lombardo, L.; Catálan, K.; Cuellar, M.; Russo, A.
    Eugenol (4-allyl-2-methoxyphenol) (1) has been reported to possess antioxidant and anticancer properties. In an attempt to enhance intrinsic activity of this natural compound, some derivatives were synthesized. Eugenol was extracted from cloves oil and further, the eugenol analogues (2-6) were obtained through acetylation and nitration reactions. Eugenol (1) and its analogues (2-6) were examined by in vitro model of cancer using two human cancer cell lines: DU-145 (androgen-insensitive prostate cancer cells) and KB (oral squamous carcinoma cells). Cell viability, by tetrazolium salts assay, was measured. Lactic dehydrogenase (LDH) release was also investigated to evaluate the presence of cell toxicity as a result of cell disruption, subsequent to membrane rupture. In the examined cancer cells, all compounds showed cell-growth inhibition activity. The obtained results demonstrate that the compounds 5-allyl-3-nitrobenzene-1,2-diol (3) and 4-allyl-2-methoxy-5-nitrophenyl acetate (5) were significantly (p < 0,001) more active than eugenol, with IC50 values in DU-145 cells of 19.02 x 10-6 and 21.5 × 10-6 mol L-1, respectively, and in KB cells of 18.11 × 10-6 and 21.26 × 10-6 mol L-1, respectively, suggesting that the presence of nitro and hydroxyl groups could be important in the activity of these compounds. In addition, our results seem to indicate that apoptotic cell demise appears to be induced in KB and DU-145 cells. In fact, in our experimental conditions, no statistically significant increase in LDH release was observed in cancer cells treated with eugenol and its analogues.
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    Ítem
    Phenolics, depsides and triterpenes from the chilean lichen pseudocyphellaria nudata (zahlbr.) D.J. Galloway
    (Sociedad Chilena de Química, 2008) Cuellar, M.; Quilhot, W.; Rubio, C.; Soto, C.; Espinoza, L.
    The lichen Pseudocyphellaria nudata is a species endemic to southern South América. From the lichen tallus, methyl orsellinate, 2-methoxy-3,6-dimethyl-4-hydroxybenzaldehyde, methyl-evernate, tenuiorin, hopan-6ß,22-diol and hopan-6α,76,22-triol were isolated and identified as the main lichen constituents. This is the first report of the occurrence of 2-methoxy-3,6-dimethyl-4-hydroxybenzaldehyde in lichens.
  • Miniatura
    Ítem
    Synthesis of five known brassinosteroid analogs from hyodeoxycholic acid and their activities as plant-growth regulators
    (MDPI, 2017-03) Durán, M.I.; González, C.; Acosta, A.; Olea, A.F.; Díaz, K.; Espinoza, L.
    Brassinosteroids (BRs) are plant hormones that promote growth in different plant organs and tissues. The structural requirements that these compounds should possess to exhibit this biological activity have been studied. In this work, a series of known BR analogs 5-15, were synthesized starting from hyodeoxycholic acid 4, and maintaining the alkyl side chain as cholic acid or its methyl ester. The growth-promoting effects of brassinolide (1) and synthesized analogs were evaluated by using the rice lamina inclination assay at concentrations ranging from 1 x 10(-8)-1 x 10(-6) M. Our results indicate that in this concentration range the induced bending angle of rice seedlings increases with increasing concentration of BRs. Analysis of the activities, determined at the lowest tested concentration, in terms of BR structures shows that the 2 alpha,3 alpha-dihydroxy-7-oxa-6-ketone moiety existing in brassinolide is required for the plant growing activity of these compounds, as it has been proposed by some structure-activity relationship studies. The effect of compound 8 on cell elongation was assessed by microscopy analysis, and the results indicate that the growth-promoting effect of analog 8 is mainly due to cell elongation of the adaxial sides, instead of an increase on cell number.