2018 |
Ardiles, A; Barrientos, R; Simirgiotis, M J; Borquez, J; Sepulveda, B; Areche, C Gastroprotective Activity of Parastrephia Quadrangularis (Meyen), Cabrera from the Atacama Desert Artículo de revista Molecules, 23 (9), 2018, ISSN: 1420-3049. Resumen | Enlaces | BibTeX | Etiquetas: clerodanes, derivatives, diterpenoids, endemic extracts, gastric gastroprotective, lc-ms/ms, lesions, medicine, mode, natural-products, plants, prostaglandins, rats tremetones, ulcer @article{RN379, title = {Gastroprotective Activity of Parastrephia Quadrangularis (Meyen), Cabrera from the Atacama Desert}, author = { A. Ardiles and R. Barrientos and M.J. Simirgiotis and J. Borquez and B. Sepulveda and C. Areche}, url = {/brokenurl#<Go to ISI>://WOS:000447365100272}, doi = {10.3390/molecules23092361}, issn = {1420-3049}, year = {2018}, date = {2018-01-01}, journal = {Molecules}, volume = {23}, number = {9}, abstract = {Forty-three metabolites including several methoxylated flavonoids, tremetones, and ent-clerodane diterpenes were accurately identified for the first time in the ethanolic extract of P. quadrangularis by means of hyphenated UHPLC-quadrupole Orbitrap mass spectrometry, and seven isolated compounds were tested regarding gastroprotective activity using the HCl/EtOH-induced lesion model in mice. A new tremetone (compound 6) is reported based on spectroscopic evidence. The isolated clerodanes and tremetones showed gastroprotective activity in a mouse model, evidenced by compound 7 (p-coumaroyloxytremetone), which showed the highest gastroprotective activity (76%), which was higher than the control drug lansoprazole (72%). Our findings revealed that several constituents of this plant have gastroprotective activity, and particularly, p-coumaroyloxytremetone could be considered as a lead molecule to explore new gastroprotective agents. This plant is a rich source of biologically active tremetones and terpenoids which can support the ethnobotanical use of the plant.}, keywords = {clerodanes, derivatives, diterpenoids, endemic extracts, gastric gastroprotective, lc-ms/ms, lesions, medicine, mode, natural-products, plants, prostaglandins, rats tremetones, ulcer}, pubstate = {published}, tppubtype = {article} } Forty-three metabolites including several methoxylated flavonoids, tremetones, and ent-clerodane diterpenes were accurately identified for the first time in the ethanolic extract of P. quadrangularis by means of hyphenated UHPLC-quadrupole Orbitrap mass spectrometry, and seven isolated compounds were tested regarding gastroprotective activity using the HCl/EtOH-induced lesion model in mice. A new tremetone (compound 6) is reported based on spectroscopic evidence. The isolated clerodanes and tremetones showed gastroprotective activity in a mouse model, evidenced by compound 7 (p-coumaroyloxytremetone), which showed the highest gastroprotective activity (76%), which was higher than the control drug lansoprazole (72%). Our findings revealed that several constituents of this plant have gastroprotective activity, and particularly, p-coumaroyloxytremetone could be considered as a lead molecule to explore new gastroprotective agents. This plant is a rich source of biologically active tremetones and terpenoids which can support the ethnobotanical use of the plant. |
Fuentes-Barros, G; Castro-Saavedra, S; Liberona, L; Acevedo-Fuentes, W; Tirapegui, C; Mattar, C; Cassels, B K Variation of the Alkaloid Content of Peumus Boldus (Boldo) Artículo de revista Fitoterapia, 127 , pp. 179-185, 2018, ISSN: 0367-326x. Resumen | Enlaces | BibTeX | Etiquetas: activity, alkaloids, antioxidant boldine, boldus, herbal in-vitro, inhibition, leaves, medicine, peumus peumus-boldus, phenanthrene phytochemistry, plants, products, reticuline traditional uhplc-ms/ms @article{RN386, title = {Variation of the Alkaloid Content of Peumus Boldus (Boldo)}, author = { G. Fuentes-Barros and S. Castro-Saavedra and L. Liberona and W. Acevedo-Fuentes and C. Tirapegui and C. Mattar and B.K. Cassels}, url = {/brokenurl#<Go to ISI>://WOS:000437551000027}, doi = {10.1016/j.fitote.2018.02.020}, issn = {0367-326x}, year = {2018}, date = {2018-01-01}, journal = {Fitoterapia}, volume = {127}, pages = {179-185}, abstract = {Eighteen alkaloids were detected in the bark, leaves, wood and roots of Peumus boldus, including traces of secoboldine, N-methylsecoboldine (boldine methine), glaucine and norreticuline, not reported previously as constituents of this species. Using appropriate standards, we quantified thirteen of them by UHPLC-MS/MS. Boldine was dominant in the bark, and laurolitsine in wood and roots. The alkaloid composition of the leaves, determined for 130 individually identified trees, classified by age and sex, was highly variable, where N-methyllaurotetanine, laurotetanine, coclaurine and in some cases isocorydine predominated, but not boldine.}, keywords = {activity, alkaloids, antioxidant boldine, boldus, herbal in-vitro, inhibition, leaves, medicine, peumus peumus-boldus, phenanthrene phytochemistry, plants, products, reticuline traditional uhplc-ms/ms}, pubstate = {published}, tppubtype = {article} } Eighteen alkaloids were detected in the bark, leaves, wood and roots of Peumus boldus, including traces of secoboldine, N-methylsecoboldine (boldine methine), glaucine and norreticuline, not reported previously as constituents of this species. Using appropriate standards, we quantified thirteen of them by UHPLC-MS/MS. Boldine was dominant in the bark, and laurolitsine in wood and roots. The alkaloid composition of the leaves, determined for 130 individually identified trees, classified by age and sex, was highly variable, where N-methyllaurotetanine, laurotetanine, coclaurine and in some cases isocorydine predominated, but not boldine. |
2017 |
Simirgiotis, M J; Quispe, C; Mocan, A; Villatoro, J M; Areche, C; Borquez, J; Sepulveda, B; Echiburu-Chau, C Uhplc High Resolution Orbitrap Metabolomic Fingerprinting of the Unique Species Ophryosporus Triangularis Meyen from the Atacama Desert, Northern Chile Artículo de revista Revista Brasileira De Farmacognosia-Brazilian Journal of Pharmacognosy, 27 (2), pp. 179-187, 2017, ISSN: 0102-695x. Resumen | Enlaces | BibTeX | Etiquetas: analysis, antioxidant benzofurans capacities, chilean constituents, dad-ms, driven esi-tof-ms, essential flavonoids, high liquid-chromatography, mass mass-spectrometry, oils, ophryosporus, orbitrap paposo performance phenolic-compounds, plants, resolution spectrometry, uhplc, valley @article{RN336, title = {Uhplc High Resolution Orbitrap Metabolomic Fingerprinting of the Unique Species Ophryosporus Triangularis Meyen from the Atacama Desert, Northern Chile}, author = { M.J. Simirgiotis and C. Quispe and A. Mocan and J.M. Villatoro and C. Areche and J. Borquez and B. Sepulveda and C. Echiburu-Chau}, url = {/brokenurl#<Go to ISI>://WOS:000397844800008}, doi = {10.1016/j.bjp.2016.10.002}, issn = {0102-695x}, year = {2017}, date = {2017-01-01}, journal = {Revista Brasileira De Farmacognosia-Brazilian Journal of Pharmacognosy}, volume = {27}, number = {2}, pages = {179-187}, publisher = {2016 Sociedade Brasileira de Farmacognosia. Published by Elsevier Editora Ltda.}, abstract = {High-resolution mass spectrometry is currently used to determine the mass of biologically active compounds in plants and UHPLC-Orbitrap is a relatively new technology that allows fast fingerprinting and metabolomics analysis. In this work, several phenolic compounds including eleven phenolic acids, two fatty acids, two chromones and fourteen flavones were rapidly identified in the methanolic extracts of aerial parts and flowers of the unique Chilean species Ophryosporus triangularis Meyen, Asteraceae, growing in the Atacama Desert by means of ultrahigh resolution liquid chromatography orbitrap MS analysis (UHPLC-PDA-OT-MS) for the first time. The UHPLC-MS fingerprint generated can be used for the authentication of this endemic species. The methanolic extracts of the aerial parts and flowers showedalso antioxidant capacities (65.34 +/- 1.32 and 52.41 +/- 1.87 mu g/ml in the DPPH assay, 184.88 +/- 13.22 and 196.80 +/- 13.28 mu mol TE/g dry weight in the ferric reducing power assay and 56.17 +/- 3.03 and 65.41 +/- 1.96% in the superoxide anion scavenging assay, respectively).}, keywords = {analysis, antioxidant benzofurans capacities, chilean constituents, dad-ms, driven esi-tof-ms, essential flavonoids, high liquid-chromatography, mass mass-spectrometry, oils, ophryosporus, orbitrap paposo performance phenolic-compounds, plants, resolution spectrometry, uhplc, valley}, pubstate = {published}, tppubtype = {article} } High-resolution mass spectrometry is currently used to determine the mass of biologically active compounds in plants and UHPLC-Orbitrap is a relatively new technology that allows fast fingerprinting and metabolomics analysis. In this work, several phenolic compounds including eleven phenolic acids, two fatty acids, two chromones and fourteen flavones were rapidly identified in the methanolic extracts of aerial parts and flowers of the unique Chilean species Ophryosporus triangularis Meyen, Asteraceae, growing in the Atacama Desert by means of ultrahigh resolution liquid chromatography orbitrap MS analysis (UHPLC-PDA-OT-MS) for the first time. The UHPLC-MS fingerprint generated can be used for the authentication of this endemic species. The methanolic extracts of the aerial parts and flowers showedalso antioxidant capacities (65.34 +/- 1.32 and 52.41 +/- 1.87 mu g/ml in the DPPH assay, 184.88 +/- 13.22 and 196.80 +/- 13.28 mu mol TE/g dry weight in the ferric reducing power assay and 56.17 +/- 3.03 and 65.41 +/- 1.96% in the superoxide anion scavenging assay, respectively). |
Nett, R S; Montanares, M; Marcassa, A; Lul, X; Nagel, R; Charles, T C; Hedden, P; Rojas, M C; Peters, R J Elucidation of Gibberellin Biosynthesis in Bacteria Reveals Convergent Evolution Artículo de revista Nature Chemical Biology, 13 (1), pp. 69-74, 2017, ISSN: 1552-4450. Resumen | Enlaces | BibTeX | Etiquetas: artemisinin biosynthesis, bradyrhizobium-japonicum, cloning, cytochrome-p450 ent-kaurene, fungi, gene-cluster, green-revolution, identification, plants, rearrangement @article{RN347, title = {Elucidation of Gibberellin Biosynthesis in Bacteria Reveals Convergent Evolution}, author = { R.S. Nett and M. Montanares and A. Marcassa and X. Lul and R. Nagel and T.C. Charles and P. Hedden and M.C. Rojas and R.J. Peters}, url = {/brokenurl#<Go to ISI>://WOS:000393267200015}, doi = {10.1038/Nchembio.2232}, issn = {1552-4450}, year = {2017}, date = {2017-01-01}, journal = {Nature Chemical Biology}, volume = {13}, number = {1}, pages = {69-74}, abstract = {Gibberellins (GAs) are crucial phytohormones involved in many aspects of plant growth and development, including plant-microbe interactions, which has led to GA production by plant-associated fungi and bacteria as well. While the GA biosynthetic pathways in plants and fungi have been elucidated and found to have arisen independently through convergent evolution, little has been uncovered about GA biosynthesis in bacteria. Some nitrogen-fixing, symbiotic, legume-associated rhizobia, including Bradyrhizobium japonicum-the symbiont of soybean and Sinorhizobium fredii-a broad-host-nodulating species-contain a putative GA biosynthetic operon, or gene cluster. Through functional characterization of five unknown genes, we demonstrate that this operon encodes the enzymes necessary to produce GA(9), thereby elucidating bacterial GA biosynthesis. The distinct nature of these enzymes indicates that bacteria have independently evolved a third biosynthetic pathway for GA production. Furthermore, our results also reveal a central biochemical logic that is followed in all three convergently evolved GA biosynthetic pathways.}, keywords = {artemisinin biosynthesis, bradyrhizobium-japonicum, cloning, cytochrome-p450 ent-kaurene, fungi, gene-cluster, green-revolution, identification, plants, rearrangement}, pubstate = {published}, tppubtype = {article} } Gibberellins (GAs) are crucial phytohormones involved in many aspects of plant growth and development, including plant-microbe interactions, which has led to GA production by plant-associated fungi and bacteria as well. While the GA biosynthetic pathways in plants and fungi have been elucidated and found to have arisen independently through convergent evolution, little has been uncovered about GA biosynthesis in bacteria. Some nitrogen-fixing, symbiotic, legume-associated rhizobia, including Bradyrhizobium japonicum-the symbiont of soybean and Sinorhizobium fredii-a broad-host-nodulating species-contain a putative GA biosynthetic operon, or gene cluster. Through functional characterization of five unknown genes, we demonstrate that this operon encodes the enzymes necessary to produce GA(9), thereby elucidating bacterial GA biosynthesis. The distinct nature of these enzymes indicates that bacteria have independently evolved a third biosynthetic pathway for GA production. Furthermore, our results also reveal a central biochemical logic that is followed in all three convergently evolved GA biosynthetic pathways. |
2015 |
Simirgiotis, M J; Benites, J; Areche, C; Sepulveda, B Antioxidant Capacities and Analysis of Phenolic Compounds in Three Endemic Nolana Species by Hplc-Pda-Esi-Ms Artículo de revista Molecules, 20 (6), pp. 11490-11507, 2015, ISSN: 1420-3049. Resumen | Enlaces | BibTeX | Etiquetas: antioxidant atacama berries, capacity, chilean constituents, desert, diterpenoids, extracts fruits, hplc-ms, nolana, paposo phenolics, plants, quantification, valley @article{RN237, title = {Antioxidant Capacities and Analysis of Phenolic Compounds in Three Endemic Nolana Species by Hplc-Pda-Esi-Ms}, author = { M.J. Simirgiotis and J. Benites and C. Areche and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000357992700121}, doi = {10.3390/molecules200611490}, issn = {1420-3049}, year = {2015}, date = {2015-01-01}, journal = {Molecules}, volume = {20}, number = {6}, pages = {11490-11507}, abstract = {The antioxidant features, polyphenolic composition and chromatographic fingerprints of the aerial parts from three Chilean endemic plants from the Paposo Valley located on the cost of the Atacama Desert were investigated for the first time using high pressure liquid chromatography coupled with photodiode array detector and electrospray ionization mass analysis (HPLC-PDA-ESI-MS) and spectroscopic methods. The phenolic fingerprints obtained for the plants were compared and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP) and quantification of the total content of phenolics and flavonoids measured by spectroscopic methods. Thirty phenolics were identified for the first time for these species, mostly phenolic acids, flavanones, flavonols and some of their glycoside derivatives, together with three saturated fatty acids (stearic, palmitic and arachidic acids). Nolana ramosissima showed the highest antioxidant activity (26.35 +/- 1.02 g/mL, 116.07 +/- 3.42 M Trolox equivalents/g dry weight and 81.23% +/- 3.77% of inhibition in the DPPH, FRAP and scavenging activity (SA) assays, respectively), followed by N. aplocaryoides (85.19 +/- 1.64 g/mL, 65.87 +/- 2.33 M TE/g DW and 53.27% +/- 3.07%) and N. leptophylla (124.71 +/- 3.01, 44.23 +/- 5.18 M TE/g DW and 38.63% +/- 1.85%).}, keywords = {antioxidant atacama berries, capacity, chilean constituents, desert, diterpenoids, extracts fruits, hplc-ms, nolana, paposo phenolics, plants, quantification, valley}, pubstate = {published}, tppubtype = {article} } The antioxidant features, polyphenolic composition and chromatographic fingerprints of the aerial parts from three Chilean endemic plants from the Paposo Valley located on the cost of the Atacama Desert were investigated for the first time using high pressure liquid chromatography coupled with photodiode array detector and electrospray ionization mass analysis (HPLC-PDA-ESI-MS) and spectroscopic methods. The phenolic fingerprints obtained for the plants were compared and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP) and quantification of the total content of phenolics and flavonoids measured by spectroscopic methods. Thirty phenolics were identified for the first time for these species, mostly phenolic acids, flavanones, flavonols and some of their glycoside derivatives, together with three saturated fatty acids (stearic, palmitic and arachidic acids). Nolana ramosissima showed the highest antioxidant activity (26.35 +/- 1.02 g/mL, 116.07 +/- 3.42 M Trolox equivalents/g dry weight and 81.23% +/- 3.77% of inhibition in the DPPH, FRAP and scavenging activity (SA) assays, respectively), followed by N. aplocaryoides (85.19 +/- 1.64 g/mL, 65.87 +/- 2.33 M TE/g DW and 53.27% +/- 3.07%) and N. leptophylla (124.71 +/- 3.01, 44.23 +/- 5.18 M TE/g DW and 38.63% +/- 1.85%). |
2018 |
Gastroprotective Activity of Parastrephia Quadrangularis (Meyen), Cabrera from the Atacama Desert Artículo de revista Molecules, 23 (9), 2018, ISSN: 1420-3049. |
Variation of the Alkaloid Content of Peumus Boldus (Boldo) Artículo de revista Fitoterapia, 127 , pp. 179-185, 2018, ISSN: 0367-326x. |
2017 |
Uhplc High Resolution Orbitrap Metabolomic Fingerprinting of the Unique Species Ophryosporus Triangularis Meyen from the Atacama Desert, Northern Chile Artículo de revista Revista Brasileira De Farmacognosia-Brazilian Journal of Pharmacognosy, 27 (2), pp. 179-187, 2017, ISSN: 0102-695x. |
Elucidation of Gibberellin Biosynthesis in Bacteria Reveals Convergent Evolution Artículo de revista Nature Chemical Biology, 13 (1), pp. 69-74, 2017, ISSN: 1552-4450. |
2015 |
Antioxidant Capacities and Analysis of Phenolic Compounds in Three Endemic Nolana Species by Hplc-Pda-Esi-Ms Artículo de revista Molecules, 20 (6), pp. 11490-11507, 2015, ISSN: 1420-3049. |