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. |
2015 |
Parra, T; Benites, J; Ruiz, L M; Sepulveda, B; Simirgiotis, M; Areche, C Gastroprotective Activity of Ent-Beyerene Derivatives in Mice: Effects on Gastric Secretion, Endogenous Prostaglandins and Non-Protein Sulfhydryls Artículo de revista Bioorganic & Medicinal Chemistry Letters, 25 (14), pp. 2813-2817, 2015, ISSN: 0960-894x. Resumen | Enlaces | BibTeX | Etiquetas: baccharis defense, derivatives, diterpenoids, ent-beyerene, gastric injury mucosal natural-products, semisynthetic tola, ulcer @article{RN236, title = {Gastroprotective Activity of Ent-Beyerene Derivatives in Mice: Effects on Gastric Secretion, Endogenous Prostaglandins and Non-Protein Sulfhydryls}, author = { T. Parra and J. Benites and L.M. Ruiz and B. Sepulveda and M. Simirgiotis and C. Areche}, url = {/brokenurl#<Go to ISI>://WOS:000355663100017}, doi = {10.1016/j.bmcl.2015.04.095}, issn = {0960-894x}, year = {2015}, date = {2015-01-01}, journal = {Bioorganic & Medicinal Chemistry Letters}, volume = {25}, number = {14}, pages = {2813-2817}, publisher = {2015 Elsevier Ltd.}, abstract = {Seventeen compounds (2-18) synthetized from the diterpenoid ent-beyer-15-en-18-ol (1) isolated from aerial part of Baccharis tola were tested for their gastroprotective activity on the model of HCl/EtOH-induced gastric lesions in mice. Furthermore cytotoxicity test toward fibroblasts and AGS cells were performed. The results showed that compound 1 (ED50 = 50 mg/kg), 2, 6 and 13 were the most active regarding gastroprotective activity. Compounds 8-10 and 17-18 showed the lowest cytotoxicity toward fibroblasts and AGS cells. Regarding to mode of gastroprotective action, the effect elicited by 6 (50 mg/kg) was reversed by Indomethacin but not by N-ethylmaleimide, NG-nitro-L-arginine methyl ester or ruthenium red, which suggests that prostaglandins are involved in the mode of gastroprotective action of 6.}, keywords = {baccharis defense, derivatives, diterpenoids, ent-beyerene, gastric injury mucosal natural-products, semisynthetic tola, ulcer}, pubstate = {published}, tppubtype = {article} } Seventeen compounds (2-18) synthetized from the diterpenoid ent-beyer-15-en-18-ol (1) isolated from aerial part of Baccharis tola were tested for their gastroprotective activity on the model of HCl/EtOH-induced gastric lesions in mice. Furthermore cytotoxicity test toward fibroblasts and AGS cells were performed. The results showed that compound 1 (ED50 = 50 mg/kg), 2, 6 and 13 were the most active regarding gastroprotective activity. Compounds 8-10 and 17-18 showed the lowest cytotoxicity toward fibroblasts and AGS cells. Regarding to mode of gastroprotective action, the effect elicited by 6 (50 mg/kg) was reversed by Indomethacin but not by N-ethylmaleimide, NG-nitro-L-arginine methyl ester or ruthenium red, which suggests that prostaglandins are involved in the mode of gastroprotective action of 6. |
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. |
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%). |
2014 |
Salgado, F; Areche, C; Sepulveda, B; Simirgiotis, M J; Caceres, F; Quispe, C; Quispe, L; Cano, T A New Mulinane Diterpenoid from the Cushion Shrub Azorella Compacta Growing in Peru Artículo de revista Pharmacognosy Magazine, 10 (39), pp. 543-548, 2014, ISSN: 0973-1296. Resumen | Enlaces | BibTeX | Etiquetas: acids activity, apiaceae, azorella carbon compacta, crassifolium, diterpenoids, gastroprotective madreporica, mulinanes, natural-products, skeleton, umbelliferae @article{RN185, title = {A New Mulinane Diterpenoid from the Cushion Shrub Azorella Compacta Growing in Peru}, author = { F. Salgado and C. Areche and B. Sepulveda and M.J. Simirgiotis and F. Caceres and C. Quispe and L. Quispe and T. Cano}, url = {/brokenurl#<Go to ISI>://WOS:000341875000014}, doi = {10.4103/0973-1296.139807}, issn = {0973-1296}, year = {2014}, date = {2014-01-01}, journal = {Pharmacognosy Magazine}, volume = {10}, number = {39}, pages = {543-548}, abstract = {Background: Azorella compacta is a rare yellow-green compact resinous cushion shrub growing from the high Andes of southern Per to northwestern Argentina, and which is a producer of biologically active and unique diterpenoids. Objective: This study investigated the secondary metabolites present in a Peruvian sample of Azorella compacta and the evaluation of gastroprotective activity of the isolated compounds in a gastric-induced ulcer model in mice. Material and Methods: Six secondary metabolites (diterpenoids 1-6) present in the dichloromethane (DCM) extract of A. compacta growing in Per were isolated by a combination of Sephadex LH-20 permeation and silica gel chromatography and their chemical structures were elucidated by spectroscopic methods (NMR) and molecular modeling. The gastroprotective activity of the new compound 1 was evaluated on the HCl/EtOH-induced gastric lesion model in mice and compared to the activity showed by the known compounds. Results: A new mulinane diterpene along with five known diterpenoids have been isolated from a Peruvian sample of A. compacta and the gastroprotective results show that compound 1 is less active than the other known mulinane diterpenoids isolated. Conclusions: A. compacta growing in Per showed the presence of the new mulinane 1, which was poorly active in the HCl/EtOH-induced gastric lesion model in mice. Indeed, the activity was lower than other diterpenoids (2-6) showing an oxygenated function at C-16 or/and C-20, which confirm the role of an oxygenated group (OH or carboxylic acid) for the gastroprotective activity of mulinane compounds.}, keywords = {acids activity, apiaceae, azorella carbon compacta, crassifolium, diterpenoids, gastroprotective madreporica, mulinanes, natural-products, skeleton, umbelliferae}, pubstate = {published}, tppubtype = {article} } Background: Azorella compacta is a rare yellow-green compact resinous cushion shrub growing from the high Andes of southern Per to northwestern Argentina, and which is a producer of biologically active and unique diterpenoids. Objective: This study investigated the secondary metabolites present in a Peruvian sample of Azorella compacta and the evaluation of gastroprotective activity of the isolated compounds in a gastric-induced ulcer model in mice. Material and Methods: Six secondary metabolites (diterpenoids 1-6) present in the dichloromethane (DCM) extract of A. compacta growing in Per were isolated by a combination of Sephadex LH-20 permeation and silica gel chromatography and their chemical structures were elucidated by spectroscopic methods (NMR) and molecular modeling. The gastroprotective activity of the new compound 1 was evaluated on the HCl/EtOH-induced gastric lesion model in mice and compared to the activity showed by the known compounds. Results: A new mulinane diterpene along with five known diterpenoids have been isolated from a Peruvian sample of A. compacta and the gastroprotective results show that compound 1 is less active than the other known mulinane diterpenoids isolated. Conclusions: A. compacta growing in Per showed the presence of the new mulinane 1, which was poorly active in the HCl/EtOH-induced gastric lesion model in mice. Indeed, the activity was lower than other diterpenoids (2-6) showing an oxygenated function at C-16 or/and C-20, which confirm the role of an oxygenated group (OH or carboxylic acid) for the gastroprotective activity of mulinane compounds. |
2013 |
Quesada, L; Gutierrez, M; studillo-Saavedra, L; San-Martin, A; Fuentes, E; Palomo, I; Penailillo, P Determination of Antibacterial, Antioxidant, Antiplatelet and Inhibition of Cholinesterase Activities from the Methanolic Extracts of Azorella Species (Apiaceae) Artículo de revista Boletin Latinoamericano Y Del Caribe De Plantas Medicinales Y Aromaticas, 12 (1), pp. 99-107, 2013, ISSN: 0717-7917. Resumen | Enlaces | BibTeX | Etiquetas: alzheimers-disease, antibacterial, antioxidant, antiplatelet, azorella, cholinesterase, compacta, diterpenoids, phenolics, products, total yareta @article{RN114, title = {Determination of Antibacterial, Antioxidant, Antiplatelet and Inhibition of Cholinesterase Activities from the Methanolic Extracts of Azorella Species (Apiaceae)}, author = { L. Quesada and M. Gutierrez and L. studillo-Saavedra and A. San-Martin and E. Fuentes and I. Palomo and P. Penailillo}, url = {/brokenurl#<Go to ISI>://WOS:000314060700011}, issn = {0717-7917}, year = {2013}, date = {2013-01-01}, journal = {Boletin Latinoamericano Y Del Caribe De Plantas Medicinales Y Aromaticas}, volume = {12}, number = {1}, pages = {99-107}, abstract = {In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only moderate inhibitory activity on acetylcholinesterase (AChE), the most active extract with IC50 = 27 mu g/mL was A. spinosa. Inhibition of platelet aggregation induced by ADP presented maximal aggregation to 70 and 57% on extracts of A. spinosa and A. monantha (Paso Vergara), respectively. The most active extract with antioxidant effect was A. spinosa with IC50 of 28.72 mu g/mL. Antibacterial activity of the extract on Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii was not present. The extracts of A. spinosa and A. monantha (Paso Vergara) presented the best results on the activities that were evaluated.}, keywords = {alzheimers-disease, antibacterial, antioxidant, antiplatelet, azorella, cholinesterase, compacta, diterpenoids, phenolics, products, total yareta}, pubstate = {published}, tppubtype = {article} } In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only moderate inhibitory activity on acetylcholinesterase (AChE), the most active extract with IC50 = 27 mu g/mL was A. spinosa. Inhibition of platelet aggregation induced by ADP presented maximal aggregation to 70 and 57% on extracts of A. spinosa and A. monantha (Paso Vergara), respectively. The most active extract with antioxidant effect was A. spinosa with IC50 of 28.72 mu g/mL. Antibacterial activity of the extract on Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii was not present. The extracts of A. spinosa and A. monantha (Paso Vergara) presented the best results on the activities that were evaluated. |