2016 |
Sepulveda, B; Quispe, C; Simirgiotis, M; Garcia-Beltran, O; Areche, C Bioorganic & Medicinal Chemistry Letters, 26 (14), pp. 3220-3222, 2016, ISSN: 0960-894x. Resumen | Enlaces | BibTeX | Etiquetas: azorella biotransformation, compacta, cuatrecasasii, gastric madreporica microbial mulinane, transformation, ulcer @article{RN288, title = {Gastroprotective Effects of New Diterpenoid Derivatives from Azorella Cuatrecasasii Mathias & Constance Obtained Using a Beta-Cyclodextrin Complex with Microbial and Chemical Transformations}, author = { B. Sepulveda and C. Quispe and M. Simirgiotis and O. Garcia-Beltran and C. Areche}, url = {/brokenurl#<Go to ISI>://WOS:000377471400003}, doi = {10.1016/j.bmcl.2016.05.081}, issn = {0960-894x}, year = {2016}, date = {2016-01-01}, journal = {Bioorganic & Medicinal Chemistry Letters}, volume = {26}, number = {14}, pages = {3220-3222}, publisher = {2016 Elsevier Ltd.}, abstract = {Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a beta-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13 alpha-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20 mg/kg. The highest gastroprotective activity was shown by 7 alpha,16-dihydroxymulin-11,13-dien- 20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13- dien-20-oic acid 4 was as active as lansoprazole.}, keywords = {azorella biotransformation, compacta, cuatrecasasii, gastric madreporica microbial mulinane, transformation, ulcer}, pubstate = {published}, tppubtype = {article} } Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a beta-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13 alpha-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20 mg/kg. The highest gastroprotective activity was shown by 7 alpha,16-dihydroxymulin-11,13-dien- 20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13- dien-20-oic acid 4 was as active as lansoprazole. |
2012 |
Diaz, C; Valenzuela, M L; Carrillo, D; Riquelme, J; Diaz, R The Inclusion of Organometallic Derivatives of Cyclotriphosphazenes inside Sio2 Matrix and Their Conversion to Nanostructured Metal-Oxides and Phosphates Artículo de revista Journal of Inorganic and Organometallic Polymers and Materials, 22 (5), pp. 1101-1112, 2012, ISSN: 1574-1443. Resumen | Enlaces | BibTeX | Etiquetas: bridged catalyst, copper cyclotriphospahzenes, mesoporous metallic nanoparticles, nanostructures, phosphoric-acid polysilsesquioxanes, precursors, silica, sol-gel sol-gel, synthesis, thermolytic thin-films, transformation, xerogel @article{RN88, title = {The Inclusion of Organometallic Derivatives of Cyclotriphosphazenes inside Sio2 Matrix and Their Conversion to Nanostructured Metal-Oxides and Phosphates}, author = { C. Diaz and M.L. Valenzuela and D. Carrillo and J. Riquelme and R. Diaz}, url = {/brokenurl#<Go to ISI>://WOS:000307754600022}, doi = {10.1007/s10904-012-9692-x}, issn = {1574-1443}, year = {2012}, date = {2012-01-01}, journal = {Journal of Inorganic and Organometallic Polymers and Materials}, volume = {22}, number = {5}, pages = {1101-1112}, abstract = {Organometallic derivatives of the cyclotriphosphazene N3P3[OC6H4CH2CN center dot TiClCp2](6) (1), N3P3(O6H5)(5)[OC6H4N center dot W(CO)(5)] (2), N3P3[OC6H4CH2CN center dot Mo(CO)(5)](6) (3), [N3P3(O6H5)(5)(OC5H4N center dot CpRu(PPh3)(2))][PF6] (4), [N3P3(O2C12H8)(2)OC5H4N center dot Ag(PPh3)][OSO2CF3] (5), N3P3[OC6H5](5) [OC5H4N center dot Cu][PF6] (6) and N3P3[OC6H4CH2CN center dot CuCl](6)[PF6](6) (7),were incorporated inside SiO2 through the sol-gel method. The metal-organic nanocomposites of the general formula N3P3[OC6H4CH2CN center dot TiClCp2](6)center dot nSiO(2) (G (1) ), N3P3[OC6H4N center dot W(CO)(5)]center dot nSiO(2) (G (2) ), N3P3[OC6H4CH2CN center dot Mo(CO)(5)](6)center dot nSiO(2) (G (3) ), N3P3(O6H5)(5)OC5H4N center dot CpRu(PPh3)(2)][PF6]center dot nSiO(2) (G (4) ), [N3P3(O2C12H8)(2)OC5H4N center dot Ag(PPh3)][OSO2CF3]center dot nSiO(2) (G (5) ), N3P3[OC6H5](5)[OC5H4N center dot Cu][PF6]center dot(SiO2) (n) (G (6) ), and N3P3[OC6H4CH2CN center dot CuCl](6)[PF6](6)center dot(SiO2) (n) (G (7) ), were characterized by IR spectroscopy; C-12, (31) P and Si-29 MAS NMR measurements as well as UV-Visible diffuse reflectance spectra, indicating the presence of the respective organometallic derivatives of the cyclotriphosphazene incorporated into SiO2. Pyrolysis of these nanocomposites under air at 800 A degrees C gives rise to nanostructured metal-oxides and metal phosphates incorporated into amorphous SiO2, with the presence in some cases of complexes phase mixtures. From some precursors, we obtained metal-oxides/phosphates nanoparticles separated from the SiO2 nanoparticles instead the oxides/phosphates nanoparticles inside the SiO2 matrix. Additionally and for comparison purposes, we used the compound N3P3[NH(CH2)(3)Si(OEt)(3)](6) as gelator. Nanocomposites (G' (1) ), (G' (2) ) and (G' (3) ) exhibited mainly morphological differences while in some cases composition differences when using TEOS as gelator., Some simple metal-containing compounds as (O3SCF3)Ag(PPh3)(HOC5H4N), [CuCl2 center dot NC5H4OH] and [CuCl2 center dot NCCH2C6H4OH]-which are useful models of the most complexes (G (5) ), (G (6) ) and (G (7) ) were also prepared and incorporated in amorphous silica. Their pyrolytic products were compared with those of more complex cyclotriphosphazene analogous. Interestingly, the pyrolysis of the nanocomposite [(O3SCF3)Ag(PPh3)(HOC5H4N)][SiO2] (n) affords the firstly-reported materials containing Ag2O along with SiO2 nanoparticles.}, keywords = {bridged catalyst, copper cyclotriphospahzenes, mesoporous metallic nanoparticles, nanostructures, phosphoric-acid polysilsesquioxanes, precursors, silica, sol-gel sol-gel, synthesis, thermolytic thin-films, transformation, xerogel}, pubstate = {published}, tppubtype = {article} } Organometallic derivatives of the cyclotriphosphazene N3P3[OC6H4CH2CN center dot TiClCp2](6) (1), N3P3(O6H5)(5)[OC6H4N center dot W(CO)(5)] (2), N3P3[OC6H4CH2CN center dot Mo(CO)(5)](6) (3), [N3P3(O6H5)(5)(OC5H4N center dot CpRu(PPh3)(2))][PF6] (4), [N3P3(O2C12H8)(2)OC5H4N center dot Ag(PPh3)][OSO2CF3] (5), N3P3[OC6H5](5) [OC5H4N center dot Cu][PF6] (6) and N3P3[OC6H4CH2CN center dot CuCl](6)[PF6](6) (7),were incorporated inside SiO2 through the sol-gel method. The metal-organic nanocomposites of the general formula N3P3[OC6H4CH2CN center dot TiClCp2](6)center dot nSiO(2) (G (1) ), N3P3[OC6H4N center dot W(CO)(5)]center dot nSiO(2) (G (2) ), N3P3[OC6H4CH2CN center dot Mo(CO)(5)](6)center dot nSiO(2) (G (3) ), N3P3(O6H5)(5)OC5H4N center dot CpRu(PPh3)(2)][PF6]center dot nSiO(2) (G (4) ), [N3P3(O2C12H8)(2)OC5H4N center dot Ag(PPh3)][OSO2CF3]center dot nSiO(2) (G (5) ), N3P3[OC6H5](5)[OC5H4N center dot Cu][PF6]center dot(SiO2) (n) (G (6) ), and N3P3[OC6H4CH2CN center dot CuCl](6)[PF6](6)center dot(SiO2) (n) (G (7) ), were characterized by IR spectroscopy; C-12, (31) P and Si-29 MAS NMR measurements as well as UV-Visible diffuse reflectance spectra, indicating the presence of the respective organometallic derivatives of the cyclotriphosphazene incorporated into SiO2. Pyrolysis of these nanocomposites under air at 800 A degrees C gives rise to nanostructured metal-oxides and metal phosphates incorporated into amorphous SiO2, with the presence in some cases of complexes phase mixtures. From some precursors, we obtained metal-oxides/phosphates nanoparticles separated from the SiO2 nanoparticles instead the oxides/phosphates nanoparticles inside the SiO2 matrix. Additionally and for comparison purposes, we used the compound N3P3[NH(CH2)(3)Si(OEt)(3)](6) as gelator. Nanocomposites (G' (1) ), (G' (2) ) and (G' (3) ) exhibited mainly morphological differences while in some cases composition differences when using TEOS as gelator., Some simple metal-containing compounds as (O3SCF3)Ag(PPh3)(HOC5H4N), [CuCl2 center dot NC5H4OH] and [CuCl2 center dot NCCH2C6H4OH]-which are useful models of the most complexes (G (5) ), (G (6) ) and (G (7) ) were also prepared and incorporated in amorphous silica. Their pyrolytic products were compared with those of more complex cyclotriphosphazene analogous. Interestingly, the pyrolysis of the nanocomposite [(O3SCF3)Ag(PPh3)(HOC5H4N)][SiO2] (n) affords the firstly-reported materials containing Ag2O along with SiO2 nanoparticles. |
2011 |
Espinosa, Y; Trebotich, J; Sepulveda, F; Cadena, J; Vargas-Straube, M J; Vaca, I; Bull, P; Levican, G; Chavez, R Production of a Heterologous Recombinant Protein Using Fragments of the Glyceraldehyde-3-Phosphate Dehydrogenase Promoter from Penicillium Camemberti Artículo de revista World Journal of Microbiology & Biotechnology, 27 (12), pp. 3019-3023, 2011, ISSN: 0959-3993. Resumen | Enlaces | BibTeX | Etiquetas: aspergillus-nidulans, beta-galactosidase, camemberti, cloning, dehydrogenase elements, expression, functional gene, glyceraldehyde-3-phosphate gpda heterologous nidulans penicillium promoter, protein region sequence-analysis, transformation, yeast @article{RN37c, title = {Production of a Heterologous Recombinant Protein Using Fragments of the Glyceraldehyde-3-Phosphate Dehydrogenase Promoter from Penicillium Camemberti}, author = { Y. Espinosa and J. Trebotich and F. Sepulveda and J. Cadena and M.J. Vargas-Straube and I. Vaca and P. Bull and G. Levican and R. Chavez}, url = {/brokenurl#<Go to ISI>://WOS:000297594400033}, doi = {10.1007/s11274-011-0782-7}, issn = {0959-3993}, year = {2011}, date = {2011-01-01}, journal = {World Journal of Microbiology & Biotechnology}, volume = {27}, number = {12}, pages = {3019-3023}, abstract = {The biotechnological applications of cheese-ripening fungi have been limited by a lack of genetics tools, in particular the identification and characterization of suitable promoters for protein expression. In this study, the suitability of the glyceraldehyde-3-phosphate dehydrogenase (gpdP) promoter from Penicillium camemberti to drive the production of a recombinant protein was evaluated. The gpdP gene and its promoter were isolated using PCR and Genome Walker. The promoter of gpdP has two regions with high identity to the regulatory elements gpd-box and ct-box previously described in Aspergillus nidulans. Two fragments of the promoter containing the gpd- and ct-box or the ct-box alone were used to drive the in vivo production of recombinant beta-galactosidase using A. nidulans as host. Our results indicate that larger fragment containing gpd-box enhances the production of beta-galactosidase activity levels respect to ct-box alone, and that both boxes are necessary to obtain maximal enzymatic activity production. The smaller fragment (187 nt) containing the ct-box alone was able to trigger up to 27% of beta-galactosidase activity, and to our knowledge this is the smallest fragment from a gpd gene used to produce a recombinant protein. Differences were not observed when glycerol, galactose or glucose were used as carbon sources, suggesting that the promoter activity is carbohydrate-independent. This is the first report in which a Penicillium gpd promoter is used for recombinant protein production. Our results open the way for the future development of a system for recombinant proteins expression in the biotechnologically important cheese-ripening fungus P. camemberti.}, keywords = {aspergillus-nidulans, beta-galactosidase, camemberti, cloning, dehydrogenase elements, expression, functional gene, glyceraldehyde-3-phosphate gpda heterologous nidulans penicillium promoter, protein region sequence-analysis, transformation, yeast}, pubstate = {published}, tppubtype = {article} } The biotechnological applications of cheese-ripening fungi have been limited by a lack of genetics tools, in particular the identification and characterization of suitable promoters for protein expression. In this study, the suitability of the glyceraldehyde-3-phosphate dehydrogenase (gpdP) promoter from Penicillium camemberti to drive the production of a recombinant protein was evaluated. The gpdP gene and its promoter were isolated using PCR and Genome Walker. The promoter of gpdP has two regions with high identity to the regulatory elements gpd-box and ct-box previously described in Aspergillus nidulans. Two fragments of the promoter containing the gpd- and ct-box or the ct-box alone were used to drive the in vivo production of recombinant beta-galactosidase using A. nidulans as host. Our results indicate that larger fragment containing gpd-box enhances the production of beta-galactosidase activity levels respect to ct-box alone, and that both boxes are necessary to obtain maximal enzymatic activity production. The smaller fragment (187 nt) containing the ct-box alone was able to trigger up to 27% of beta-galactosidase activity, and to our knowledge this is the smallest fragment from a gpd gene used to produce a recombinant protein. Differences were not observed when glycerol, galactose or glucose were used as carbon sources, suggesting that the promoter activity is carbohydrate-independent. This is the first report in which a Penicillium gpd promoter is used for recombinant protein production. Our results open the way for the future development of a system for recombinant proteins expression in the biotechnologically important cheese-ripening fungus P. camemberti. |
2016 |
Bioorganic & Medicinal Chemistry Letters, 26 (14), pp. 3220-3222, 2016, ISSN: 0960-894x. |
2012 |
The Inclusion of Organometallic Derivatives of Cyclotriphosphazenes inside Sio2 Matrix and Their Conversion to Nanostructured Metal-Oxides and Phosphates Artículo de revista Journal of Inorganic and Organometallic Polymers and Materials, 22 (5), pp. 1101-1112, 2012, ISSN: 1574-1443. |
2011 |
Production of a Heterologous Recombinant Protein Using Fragments of the Glyceraldehyde-3-Phosphate Dehydrogenase Promoter from Penicillium Camemberti Artículo de revista World Journal of Microbiology & Biotechnology, 27 (12), pp. 3019-3023, 2011, ISSN: 0959-3993. |