2017 |
Martinez-Cifuentes, M; Weiss-Lopez, B; Araya-Maturana, R Theoretical Study About the Effect of Halogen Substitution on the Reactivity of Antitumor 3-Formylchromones and Their Free Radicals Artículo de revista Journal of Chemistry, 10.1155/2017/9254831 , 2017, ISSN: 2090-9063. Resumen | Enlaces | BibTeX | Etiquetas: activity, antidiabetic antioxidants, chromone, chromonyl-2, derivatives, flavonoids, in-vitro, inhibitors polyphenolic respiration, tumor-cell @article{RN373, title = {Theoretical Study About the Effect of Halogen Substitution on the Reactivity of Antitumor 3-Formylchromones and Their Free Radicals}, author = { M. Martinez-Cifuentes and B. Weiss-Lopez and R. Araya-Maturana}, url = {/brokenurl#<Go to ISI>://WOS:000396251800001}, doi = {10.1155/2017/9254831}, issn = {2090-9063}, year = {2017}, date = {2017-01-01}, journal = {Journal of Chemistry}, volume = {10.1155/2017/9254831}, abstract = {The mandatory presence of a chlorine atom on the aromatic ring of 6-hydroxy-3-formyl angular chromones, on the respiration inhibition of mammary carcinoma mouse, is explained through a computational study of these compounds. This study analyzes the reactivity of the neutral molecules and their free radicals, in gas phase and with water solvation, incorporated by the polarizable continuum medium (PCM) approach. Electrophilic reactivities were evaluated using Fukui (f(+)) and Parr (P+) functions. The stabilities of radical species formed by the abstraction of a hydrogen atom from the O-H bond were evaluated by bond dissociation enthalpy (BDE) and spin density (SD) calculations. This study has potential implications for the design of chromone analogues as anticancer compounds.}, keywords = {activity, antidiabetic antioxidants, chromone, chromonyl-2, derivatives, flavonoids, in-vitro, inhibitors polyphenolic respiration, tumor-cell}, pubstate = {published}, tppubtype = {article} } The mandatory presence of a chlorine atom on the aromatic ring of 6-hydroxy-3-formyl angular chromones, on the respiration inhibition of mammary carcinoma mouse, is explained through a computational study of these compounds. This study analyzes the reactivity of the neutral molecules and their free radicals, in gas phase and with water solvation, incorporated by the polarizable continuum medium (PCM) approach. Electrophilic reactivities were evaluated using Fukui (f(+)) and Parr (P+) functions. The stabilities of radical species formed by the abstraction of a hydrogen atom from the O-H bond were evaluated by bond dissociation enthalpy (BDE) and spin density (SD) calculations. This study has potential implications for the design of chromone analogues as anticancer compounds. |
2016 |
Simirgiotis, M J; Quispe, C; Borquez, J; Areche, C; Sepulveda, B Molecules, 21 (1), 2016, ISSN: 1420-3049. Resumen | Enlaces | BibTeX | Etiquetas: activity, antioxidant capacity, chile, chilean de esi-ms, flavonoids, fruits, hplc-dad, ms/ms, northern orbitrap parts pascua, pda, pears, pera phenolics, proanthocyanidins, products, uhplc-ms @article{RN289, title = {Fast Detection of Phenolic Compounds in Extracts of Easter Pears (Pyrus Communis) from the Atacama Desert by Ultrahigh-Performance Liquid Chromatography and Mass Spectrometry (Uhplc-Q/Orbitrap/Ms/Ms)}, author = { M.J. Simirgiotis and C. Quispe and J. Borquez and C. Areche and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000369486800014}, doi = {10.3390/molecules21010092}, issn = {1420-3049}, year = {2016}, date = {2016-01-01}, journal = {Molecules}, volume = {21}, number = {1}, abstract = {A small Chilean variety of pears growing in the town of Toconao, an oasis located at the northeastern edge of the Salar de Atacama, northern Chile, was studied by means of modern PDA and high resolution mass spectral data (UHPLC-PDA-HESI-orbitrap-MS/MS). In addition, the antioxidant features of the fruits were compared with the varieties Packhman's Triumph and Abate Fetel and correlated with the presence of phenolic compounds. The non-pigmented phenolics were fingerprinted and related to the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics and flavonoids measured by spectroscopic methods. The machine allowed a fast separation of 15 min employing a flow rate of 1 mL per minute and could accurately identify 25 compounds, including several isorhamnetin derivatives and phenolic acids, present in the peel and pulps of this Chilean variety for the first time. The compounds were monitored using a wavelength range of 210-800 nm. The native small Chilean pear showed the highest antioxidant activity measured as the bleaching of the DPPH radical, the ferric reducing antioxidant power and superoxide anion scavenging activity (8.61 +/- 0.65 g/mL, 712.63 +/- 12.12 micromols trolox equivalents (mol/TE)/100 g FW, and 82.89% +/- 2.52% at 100 g/mL, respectively).}, keywords = {activity, antioxidant capacity, chile, chilean de esi-ms, flavonoids, fruits, hplc-dad, ms/ms, northern orbitrap parts pascua, pda, pears, pera phenolics, proanthocyanidins, products, uhplc-ms}, pubstate = {published}, tppubtype = {article} } A small Chilean variety of pears growing in the town of Toconao, an oasis located at the northeastern edge of the Salar de Atacama, northern Chile, was studied by means of modern PDA and high resolution mass spectral data (UHPLC-PDA-HESI-orbitrap-MS/MS). In addition, the antioxidant features of the fruits were compared with the varieties Packhman's Triumph and Abate Fetel and correlated with the presence of phenolic compounds. The non-pigmented phenolics were fingerprinted and related to the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics and flavonoids measured by spectroscopic methods. The machine allowed a fast separation of 15 min employing a flow rate of 1 mL per minute and could accurately identify 25 compounds, including several isorhamnetin derivatives and phenolic acids, present in the peel and pulps of this Chilean variety for the first time. The compounds were monitored using a wavelength range of 210-800 nm. The native small Chilean pear showed the highest antioxidant activity measured as the bleaching of the DPPH radical, the ferric reducing antioxidant power and superoxide anion scavenging activity (8.61 +/- 0.65 g/mL, 712.63 +/- 12.12 micromols trolox equivalents (mol/TE)/100 g FW, and 82.89% +/- 2.52% at 100 g/mL, respectively). |
2015 |
San-Martin, A; Donoso, V; Leiva, S; Bacho, M; Nunez, S; Gutierrez, M; Rovirosa, J; Bailon-Moscoso, N; Camacho, S C; Aviles, O M; Cazar, M E Molecular Docking Studies of the Antitumoral Activity and Characterization of New Chalcone Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1743-1749, 2015, ISSN: 1568-0266. Resumen | Enlaces | BibTeX | Etiquetas: antibacterial, antimicrobial antitumoral, azorella azorella-madreporica, biological chalcone, compacta diterpenes, diterpenoids, docking, evaluation, flavonoids, madreporica, mulinane, potential yareta @article{RN234, title = {Molecular Docking Studies of the Antitumoral Activity and Characterization of New Chalcone}, author = { A. San-Martin and V. Donoso and S. Leiva and M. Bacho and S. Nunez and M. Gutierrez and J. Rovirosa and N. Bailon-Moscoso and S.C. Camacho and O.M. Aviles and M.E. Cazar}, url = {/brokenurl#<Go to ISI>://WOS:000355570800010}, doi = {10.2174/1568026615666150427125033}, issn = {1568-0266}, year = {2015}, date = {2015-01-01}, journal = {Current Topics in Medicinal Chemistry}, volume = {15}, number = {17}, pages = {1743-1749}, abstract = {Phytochemical investigation of Azorella madreporica led to the isolation of four known compounds and an unknown chalcone. The structure of the new compound was identified by spectroscopy, including two-dimensional NMR techniques and comparison with published spectral data. The antioxidant activity of chalcone (compound 1) was measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay, and the bioactivity was evaluated against five bacteria (Mycobacterium smegmatis ATCC 14468, clinical isolates of Staphylococcus aureus, Klebsiella granulomatis, Morganella morganii and Escherichia coli) and four cancer cell lines. Docking studies with the tested cancer related proteins revealed nearby values of energy between doxorubicin and compound 1. Besides, protein-ligand interactions correlate with these energy values.}, keywords = {antibacterial, antimicrobial antitumoral, azorella azorella-madreporica, biological chalcone, compacta diterpenes, diterpenoids, docking, evaluation, flavonoids, madreporica, mulinane, potential yareta}, pubstate = {published}, tppubtype = {article} } Phytochemical investigation of Azorella madreporica led to the isolation of four known compounds and an unknown chalcone. The structure of the new compound was identified by spectroscopy, including two-dimensional NMR techniques and comparison with published spectral data. The antioxidant activity of chalcone (compound 1) was measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay, and the bioactivity was evaluated against five bacteria (Mycobacterium smegmatis ATCC 14468, clinical isolates of Staphylococcus aureus, Klebsiella granulomatis, Morganella morganii and Escherichia coli) and four cancer cell lines. Docking studies with the tested cancer related proteins revealed nearby values of energy between doxorubicin and compound 1. Besides, protein-ligand interactions correlate with these energy values. |
2013 |
Cheel, J; Tumova, L; Areche, C; Antwerpen, Van P; Neve, J; Zouaoui-Boudjeltia, K; Martin, A S; Vokral, I; Wsol, V; Neugebauerova, J Variations in the Chemical Profile and Biological Activities of Licorice (Glycyrrhiza Glabra L.), as Influenced by Harvest Times Artículo de revista Acta Physiologiae Plantarum, 35 (4), pp. 1337-1349, 2013, ISSN: 0137-5881. Resumen | Enlaces | BibTeX | Etiquetas: activity, antioxidant constituents, extracts, flavonoids, fruits harvest hplc, ldl licorice, liquid-chromatography, myeloperoxidase, oxidation, performance roots, seasonal-variations, times @article{RN115, title = {Variations in the Chemical Profile and Biological Activities of Licorice (Glycyrrhiza Glabra L.), as Influenced by Harvest Times}, author = { J. Cheel and L. Tumova and C. Areche and P. Van Antwerpen and J. Neve and K. Zouaoui-Boudjeltia and A.S. Martin and I. Vokral and V. Wsol and J. Neugebauerova}, url = {/brokenurl#<Go to ISI>://WOS:000316339400032}, doi = {10.1007/s11738-012-1174-9}, issn = {0137-5881}, year = {2013}, date = {2013-01-01}, journal = {Acta Physiologiae Plantarum}, volume = {35}, number = {4}, pages = {1337-1349}, abstract = {This study investigates the variations in the chemical profile, free radical scavenging, antioxidant and gastroprotective activities of licorice extracts (LE) from plants harvested during the months of February to November. Correlations between biological properties and the chemical composition of LE were also investigated. The results showed that the total contents of phenols, flavonoids and tannins in LE varied at different harvest times. Liquiritin and glycyrrhizin, the major components of LE, varied in the range of 28.65-62.80 and 41.84-114.33 mg g(-1), respectively. The relative proportion of glycyrrhizin derivative (3), glabridin (4), glabrene (5) and liquiritigenin derivative (6), varied in the range of 0.88-11.38 %, 1.86-10.03 %, 1.80-18.40 % and 5.53-16.31 %, respectively. These fluctuations correlated positively with changes in the antioxidant and free radical scavenging activities of licorice. In general, the samples from May and November showed the most favorable free radical scavenging and antioxidant effects, whereas the best gastroprotective effect was in May. Liquiritin and glycyrrhizin, the major constituents in the February and May LE, appeared to contribute to the superoxide radical scavenging and gastroprotective effects. Glabridin and glabrene, the compounds with the highest relative proportion in the November LE, accounted for the antioxidant and DPPH scavenging activities of licorice. It is concluded that the chemical profile of licorice quantitatively varied at different harvest times and these fluctuations determined changes in its bioactivities. These data could pave the way to optimize harvesting protocols for licorice in relation with its health-promoting properties.}, keywords = {activity, antioxidant constituents, extracts, flavonoids, fruits harvest hplc, ldl licorice, liquid-chromatography, myeloperoxidase, oxidation, performance roots, seasonal-variations, times}, pubstate = {published}, tppubtype = {article} } This study investigates the variations in the chemical profile, free radical scavenging, antioxidant and gastroprotective activities of licorice extracts (LE) from plants harvested during the months of February to November. Correlations between biological properties and the chemical composition of LE were also investigated. The results showed that the total contents of phenols, flavonoids and tannins in LE varied at different harvest times. Liquiritin and glycyrrhizin, the major components of LE, varied in the range of 28.65-62.80 and 41.84-114.33 mg g(-1), respectively. The relative proportion of glycyrrhizin derivative (3), glabridin (4), glabrene (5) and liquiritigenin derivative (6), varied in the range of 0.88-11.38 %, 1.86-10.03 %, 1.80-18.40 % and 5.53-16.31 %, respectively. These fluctuations correlated positively with changes in the antioxidant and free radical scavenging activities of licorice. In general, the samples from May and November showed the most favorable free radical scavenging and antioxidant effects, whereas the best gastroprotective effect was in May. Liquiritin and glycyrrhizin, the major constituents in the February and May LE, appeared to contribute to the superoxide radical scavenging and gastroprotective effects. Glabridin and glabrene, the compounds with the highest relative proportion in the November LE, accounted for the antioxidant and DPPH scavenging activities of licorice. It is concluded that the chemical profile of licorice quantitatively varied at different harvest times and these fluctuations determined changes in its bioactivities. These data could pave the way to optimize harvesting protocols for licorice in relation with its health-promoting properties. |
2011 |
Faini, F; Torres, R; Rodilla, J M; Labbe, C; Delporte, C; Jana, F Chemistry and Bioactivity of Haplopappus Remyanus ("Bailahuen"), a Chilean Medicinal Plant Artículo de revista Journal of the Brazilian Chemical Society, 22 (12), pp. 2344-U2134, 2011, ISSN: 0103-5053. Resumen | Enlaces | BibTeX | Etiquetas: anti-inflammatory antioxidant, arachidonic-acid, constituents, cytotoxic esters, exudate, flavonoids, haplopappus inflammation remyanus, resinous @article{RN10b, title = {Chemistry and Bioactivity of Haplopappus Remyanus ("Bailahuen"), a Chilean Medicinal Plant}, author = { F. Faini and R. Torres and J.M. Rodilla and C. Labbe and C. Delporte and F. Jana}, url = {/brokenurl#<Go to ISI>://WOS:000299000600014}, doi = {10.1590/S0103-50532011001200015}, issn = {0103-5053}, year = {2011}, date = {2011-01-01}, journal = {Journal of the Brazilian Chemical Society}, volume = {22}, number = {12}, pages = {2344-U2134}, abstract = {Chromatography on the resinous extract of aerial parts of Haplopappus remyanus led to the isolation of 18-acetoxy-labda-7,13E-dien-15-oic acid along with the monoterpene derivatives 9-hydroxy-alpha-terpineol, 9-benzoyloxy-alpha-terpineol, 7-hydroxy-9-benzoyloxy-alpha-terpineol and 9-benzoyloxy-(1-formyl)-alpha-terpineol. Structures for the new compounds are proposed on spectroscopic evidence. The presence of quercetin and five other known flavonoids identified in this study could account for the reported high antioxidant activity and the moderate topic anti-inflammatory effect on induced ear oedema. MTT assay with CCRF-CEM tumor cells showed 50% of the cytotoxic activity displayed by doxorubicin under the same conditions. Quantitative differences in chemical composition were detected in comparison with previous studies of the species that could be attributed to environmental factors.}, keywords = {anti-inflammatory antioxidant, arachidonic-acid, constituents, cytotoxic esters, exudate, flavonoids, haplopappus inflammation remyanus, resinous}, pubstate = {published}, tppubtype = {article} } Chromatography on the resinous extract of aerial parts of Haplopappus remyanus led to the isolation of 18-acetoxy-labda-7,13E-dien-15-oic acid along with the monoterpene derivatives 9-hydroxy-alpha-terpineol, 9-benzoyloxy-alpha-terpineol, 7-hydroxy-9-benzoyloxy-alpha-terpineol and 9-benzoyloxy-(1-formyl)-alpha-terpineol. Structures for the new compounds are proposed on spectroscopic evidence. The presence of quercetin and five other known flavonoids identified in this study could account for the reported high antioxidant activity and the moderate topic anti-inflammatory effect on induced ear oedema. MTT assay with CCRF-CEM tumor cells showed 50% of the cytotoxic activity displayed by doxorubicin under the same conditions. Quantitative differences in chemical composition were detected in comparison with previous studies of the species that could be attributed to environmental factors. |
2017 |
Theoretical Study About the Effect of Halogen Substitution on the Reactivity of Antitumor 3-Formylchromones and Their Free Radicals Artículo de revista Journal of Chemistry, 10.1155/2017/9254831 , 2017, ISSN: 2090-9063. |
2016 |
Molecules, 21 (1), 2016, ISSN: 1420-3049. |
2015 |
Molecular Docking Studies of the Antitumoral Activity and Characterization of New Chalcone Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1743-1749, 2015, ISSN: 1568-0266. |
2013 |
Variations in the Chemical Profile and Biological Activities of Licorice (Glycyrrhiza Glabra L.), as Influenced by Harvest Times Artículo de revista Acta Physiologiae Plantarum, 35 (4), pp. 1337-1349, 2013, ISSN: 0137-5881. |
2011 |
Chemistry and Bioactivity of Haplopappus Remyanus ("Bailahuen"), a Chilean Medicinal Plant Artículo de revista Journal of the Brazilian Chemical Society, 22 (12), pp. 2344-U2134, 2011, ISSN: 0103-5053. |