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 |
Figueroa, L; Jimenez, C; Rodriguez, J; Areche, C; Chavez, R; Henriquez, M; Cruz, De La M; Diaz, C; Segade, Y; Vaca, I 3-Nitroasterric Acid Derivatives from an Antarctic Sponge-Derived Pseudogymnoascus Sp Fungus Artículo de revista Journal of Natural Products, 78 (4), pp. 919-923, 2015, ISSN: 0163-3864. Resumen | Enlaces | BibTeX | Etiquetas: ascomycete asterric geomyces, metabolites, natural-products @article{RN239, title = {3-Nitroasterric Acid Derivatives from an Antarctic Sponge-Derived Pseudogymnoascus Sp Fungus}, author = { L. Figueroa and C. Jimenez and J. Rodriguez and C. Areche and R. Chavez and M. Henriquez and M. De La Cruz and C. Diaz and Y. Segade and I. Vaca}, url = {/brokenurl#<Go to ISI>://WOS:000353665100042}, doi = {10.1021/np500906k}, issn = {0163-3864}, year = {2015}, date = {2015-01-01}, journal = {Journal of Natural Products}, volume = {78}, number = {4}, pages = {919-923}, abstract = {Four new nitroasterric acid derivatives, pseudogymnoascins A-C (1-3) and 3-nitroasterric acid (4), along with the two known compounds, questin and pyriculamide, were obtained from the cultures of a Pseudogymnoascus sp. fungus isolated from an Antarctic marine sponge belonging to the genus Hymeniacidon. The structures of the new compounds were determined by extensive NMR and MS analyses. These compounds are the first nitro derivatives of the known fungal metabolite asterric acid. Several asterric acid derivatives isolated from other fungal strains have shown antibacterial and antifungal activities. However, the new compounds described in this work were inactive against a panel of bacteria and fungi (MIC > 64 mu g/mL).}, keywords = {ascomycete asterric geomyces, metabolites, natural-products}, pubstate = {published}, tppubtype = {article} } Four new nitroasterric acid derivatives, pseudogymnoascins A-C (1-3) and 3-nitroasterric acid (4), along with the two known compounds, questin and pyriculamide, were obtained from the cultures of a Pseudogymnoascus sp. fungus isolated from an Antarctic marine sponge belonging to the genus Hymeniacidon. The structures of the new compounds were determined by extensive NMR and MS analyses. These compounds are the first nitro derivatives of the known fungal metabolite asterric acid. Several asterric acid derivatives isolated from other fungal strains have shown antibacterial and antifungal activities. However, the new compounds described in this work were inactive against a panel of bacteria and fungi (MIC > 64 mu g/mL). |
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 |
Rovirosa, J; Soler, A; Blanc, V; Leon, R; San-Martin, A Bioactive Monoterpenes from Antarctic Plocamium Cartilagineum Artículo de revista Journal of the Chilean Chemical Society, 58 (4), pp. 2025-2026, 2013, ISSN: 0717-9707. Resumen | Enlaces | BibTeX | Etiquetas: antarctic, cartilagineum, halogenated marine monoterpenes monoterpenes, natural-products, plocamium plocamium, red @article{RN113, title = {Bioactive Monoterpenes from Antarctic Plocamium Cartilagineum}, author = { J. Rovirosa and A. Soler and V. Blanc and R. Leon and A. San-Martin}, url = {/brokenurl#<Go to ISI>://WOS:000331238800022}, doi = {10.4067/S0717-97072013000400026}, issn = {0717-9707}, year = {2013}, date = {2013-01-01}, journal = {Journal of the Chilean Chemical Society}, volume = {58}, number = {4}, pages = {2025-2026}, abstract = {In a chemical analysis of the red seaweed Plocamium cartilagineum collected in Antarctic Peninsula, four polyhalogenated monoterpenes were isolated. Their structures were established by spectroscopic techniques. Two of them are acyclic monoterpenes and the others are cyclic. We report the antimicrobial, insecticide and acaricide activities of compounds.}, keywords = {antarctic, cartilagineum, halogenated marine monoterpenes monoterpenes, natural-products, plocamium plocamium, red}, pubstate = {published}, tppubtype = {article} } In a chemical analysis of the red seaweed Plocamium cartilagineum collected in Antarctic Peninsula, four polyhalogenated monoterpenes were isolated. Their structures were established by spectroscopic techniques. Two of them are acyclic monoterpenes and the others are cyclic. We report the antimicrobial, insecticide and acaricide activities of compounds. |
Areche, C; Rojas-Alvarez, F; Campos-Briones, C; Lima, C; Perez, E G; Sepulveda, B Further Mulinane Diterpenoids from Azorella Compacta Artículo de revista Journal of Pharmacy and Pharmacology, 65 (8), pp. 1231-1238, 2013, ISSN: 0022-3573. Resumen | Enlaces | BibTeX | Etiquetas: acids activity, azorella carbon compacta, crassifolium, diterpenoid, gastric gastroprotective laretia-acaulis, lesions, llareta, mulinane, natural-products, rats, skeleton, ulcer @article{RN116, title = {Further Mulinane Diterpenoids from Azorella Compacta}, author = { C. Areche and F. Rojas-Alvarez and C. Campos-Briones and C. Lima and E.G. Perez and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000321504500014}, doi = {10.1111/jphp.12083}, issn = {0022-3573}, year = {2013}, date = {2013-01-01}, journal = {Journal of Pharmacy and Pharmacology}, volume = {65}, number = {8}, pages = {1231-1238}, abstract = {Objectives The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity., Methods Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity., keywords findings The new diterpenoids, 13-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13-methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A.compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13-hydroxyazorellane (5), 13-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20mg/kg reduced gastric lesions by 69%, 71% and 73%, respectively, being statistically similar to lansoprazole at the same dose., Conclusions The results corroborate the intraspecific chemical variations detected previously in specimens of A.compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay.}, keywords = {acids activity, azorella carbon compacta, crassifolium, diterpenoid, gastric gastroprotective laretia-acaulis, lesions, llareta, mulinane, natural-products, rats, skeleton, ulcer}, pubstate = {published}, tppubtype = {article} } Objectives The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity., Methods Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity., keywords findings The new diterpenoids, 13-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13-methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A.compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13-hydroxyazorellane (5), 13-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20mg/kg reduced gastric lesions by 69%, 71% and 73%, respectively, being statistically similar to lansoprazole at the same dose., Conclusions The results corroborate the intraspecific chemical variations detected previously in specimens of A.compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay. |
2011 |
Pereira, D M; Cheel, J; Areche, C; San-Martin, A; Rovirosa, J; Silva, L R; Valentao, P; Andrade, P B Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium Flabelliforme against Several Cancer Cell Lines Artículo de revista Marine Drugs, 9 (5), pp. 852-862, 2011, ISSN: 1660-3397. Resumen | Enlaces | BibTeX | Etiquetas: activity, anti-proliferative, antimicrobial antimicrobial, assay epitaondiol, extracts, flabelliforme, marine-algae, meroditerpenoids, natural-products, stypopodium @article{RN3_28, title = {Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium Flabelliforme against Several Cancer Cell Lines}, author = { D.M. Pereira and J. Cheel and C. Areche and A. San-Martin and J. Rovirosa and L.R. Silva and P. Valentao and P.B. Andrade}, url = {/brokenurl#<Go to ISI>://WOS:000292632500013}, doi = {10.3390/md9050852}, issn = {1660-3397}, year = {2011}, date = {2011-01-01}, journal = {Marine Drugs}, volume = {9}, number = {5}, pages = {852-862}, abstract = {The sea constitutes one of the most promising sources of novel compounds with potential application in human therapeutics. In particular, algae have proved to be an interesting source of new bioactive compounds. In this work, six meroditerpenoids (epitaondiol, epitaondiol diacetate, epitaondiol monoacetate, stypotriol triacetate, 14-ketostypodiol diacetate and stypodiol) isolated from the brown alga Stypopodium flabelliforme were tested for their cell proliferation inhibitory activity in five cell lines. Cell lines tested included human colon adenocarcinoma (Caco-2), human neuroblastoma (SH-SY5Y), rat basophilic leukemia (RBL-2H3), murine macrophages (RAW. 267) and Chinese hamster fibroblasts (V79). Antimicrobial activity of the compounds was also evaluated against Staphylococcus aureus, Salmonella typhimurium, Proteus mirabilis, Bacillus cereus, Enterococcus faecalis and Micrococcus luteus. Overall, the compounds showed good activity against all cell lines, with SH-SY5Y and RAW. 267 being the most susceptible. Antimicrobial capacity was observed for epitaondiol monoacetate, stypotriol triacetate and stypodiol, with the first being the most active. The results suggest that these molecules deserve further studies in order to evaluate their potential as therapeutic agents.}, keywords = {activity, anti-proliferative, antimicrobial antimicrobial, assay epitaondiol, extracts, flabelliforme, marine-algae, meroditerpenoids, natural-products, stypopodium}, pubstate = {published}, tppubtype = {article} } The sea constitutes one of the most promising sources of novel compounds with potential application in human therapeutics. In particular, algae have proved to be an interesting source of new bioactive compounds. In this work, six meroditerpenoids (epitaondiol, epitaondiol diacetate, epitaondiol monoacetate, stypotriol triacetate, 14-ketostypodiol diacetate and stypodiol) isolated from the brown alga Stypopodium flabelliforme were tested for their cell proliferation inhibitory activity in five cell lines. Cell lines tested included human colon adenocarcinoma (Caco-2), human neuroblastoma (SH-SY5Y), rat basophilic leukemia (RBL-2H3), murine macrophages (RAW. 267) and Chinese hamster fibroblasts (V79). Antimicrobial activity of the compounds was also evaluated against Staphylococcus aureus, Salmonella typhimurium, Proteus mirabilis, Bacillus cereus, Enterococcus faecalis and Micrococcus luteus. Overall, the compounds showed good activity against all cell lines, with SH-SY5Y and RAW. 267 being the most susceptible. Antimicrobial capacity was observed for epitaondiol monoacetate, stypotriol triacetate and stypodiol, with the first being the most active. The results suggest that these molecules deserve further studies in order to evaluate their potential as therapeutic agents. |
Vaca, I; Casqueiro, J; Ullan, R V; Rumbero, A; Chavez, R; Martin, J F Journal of Antibiotics, 64 (6), pp. 447-451, 2011, ISSN: 0021-8820. Resumen | Enlaces | BibTeX | Etiquetas: biosynthesis, cephalosporin-c, chrysogenum, conversion, hplc, isopenicillin liquid-chromatography n, natural-products, penicillium-chrysogenum, purification, stability, storage, system temperature @article{RN36h, title = {A Preparative Method for the Purification of Isopenicillin N from Genetically Blocked Acremonium Chrysogenum Strain Td189: Studies on the Degradation Kinetics and Storage Conditions}, author = { I. Vaca and J. Casqueiro and R.V. Ullan and A. Rumbero and R. Chavez and J.F. Martin}, url = {/brokenurl#<Go to ISI>://WOS:000292090800006}, doi = {10.1038/ja.2011.30}, issn = {0021-8820}, year = {2011}, date = {2011-01-01}, journal = {Journal of Antibiotics}, volume = {64}, number = {6}, pages = {447-451}, abstract = {A protocol for preparative isopenicillin N (IPN) purification, a highly interesting and hitherto unavailable intermediate of the penicillin and cephalosporin biosynthetic pathway due to its high unstability, is described. Culture broths of Acremonium chrysogenum TD189, a strain blocked in cephalosporin biosynthesis that accumulates this metabolite, were treated with acetone and filtered though charcoal and a hydrophobic resin in a single step as tandem columns. The cleared broth was then lyophilized and passed though a Sephadex G-25 column. The last step was the purification to homogeneity of IPN in a semipreparative HPLC equipment and, optionally, a desalting step by Sephadex G-10 column. Once purified, a complete analysis of the stability of the compound and the conditions for its long-term storage was carried out. Our results suggest a first-order model for IPN decomposition for all the pH and temperature analyzed. IPN is more stable at neutral pH, and once lyophilized, can be stored under vacuum and -75 degrees C with a half-life of 770 days. The Journal of Antibiotics (2011); published online 27 April 2011}, keywords = {biosynthesis, cephalosporin-c, chrysogenum, conversion, hplc, isopenicillin liquid-chromatography n, natural-products, penicillium-chrysogenum, purification, stability, storage, system temperature}, pubstate = {published}, tppubtype = {article} } A protocol for preparative isopenicillin N (IPN) purification, a highly interesting and hitherto unavailable intermediate of the penicillin and cephalosporin biosynthetic pathway due to its high unstability, is described. Culture broths of Acremonium chrysogenum TD189, a strain blocked in cephalosporin biosynthesis that accumulates this metabolite, were treated with acetone and filtered though charcoal and a hydrophobic resin in a single step as tandem columns. The cleared broth was then lyophilized and passed though a Sephadex G-25 column. The last step was the purification to homogeneity of IPN in a semipreparative HPLC equipment and, optionally, a desalting step by Sephadex G-10 column. Once purified, a complete analysis of the stability of the compound and the conditions for its long-term storage was carried out. Our results suggest a first-order model for IPN decomposition for all the pH and temperature analyzed. IPN is more stable at neutral pH, and once lyophilized, can be stored under vacuum and -75 degrees C with a half-life of 770 days. The Journal of Antibiotics (2011); published online 27 April 2011 |
2018 |
Gastroprotective Activity of Parastrephia Quadrangularis (Meyen), Cabrera from the Atacama Desert Artículo de revista Molecules, 23 (9), 2018, ISSN: 1420-3049. |
2015 |
3-Nitroasterric Acid Derivatives from an Antarctic Sponge-Derived Pseudogymnoascus Sp Fungus Artículo de revista Journal of Natural Products, 78 (4), pp. 919-923, 2015, ISSN: 0163-3864. |
2014 |
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. |
2013 |
Bioactive Monoterpenes from Antarctic Plocamium Cartilagineum Artículo de revista Journal of the Chilean Chemical Society, 58 (4), pp. 2025-2026, 2013, ISSN: 0717-9707. |
Further Mulinane Diterpenoids from Azorella Compacta Artículo de revista Journal of Pharmacy and Pharmacology, 65 (8), pp. 1231-1238, 2013, ISSN: 0022-3573. |
2011 |
Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium Flabelliforme against Several Cancer Cell Lines Artículo de revista Marine Drugs, 9 (5), pp. 852-862, 2011, ISSN: 1660-3397. |
Journal of Antibiotics, 64 (6), pp. 447-451, 2011, ISSN: 0021-8820. |