@article{PazPeterSchmidtetal.2012, author = {Paz, Cristian and Peter, Martin G. and Schmidt, Bernd and Becerra, Jose and Gutierrez, Margarita and Astudillo, Luis and Silva, Mario}, title = {Synthesis and AChE inhibiting activity of 2, 4 substituted 6-Phenyl Pyrimidines}, series = {Journal of the Chilean Chemical Society}, volume = {57}, journal = {Journal of the Chilean Chemical Society}, number = {3}, publisher = {Sociedad Chilena De Quimica}, address = {Concepcion}, issn = {0717-9324}, pages = {1292 -- 1294}, year = {2012}, abstract = {Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE.}, language = {en} } @article{PazBecerraSilvaetal.2015, author = {Paz, Cristian and Becerra, Jose and Silva, Mario and Burgos, Viviana and Heydenreich, Matthias and Schmidt, Bernd and Thu Tran, and Vetter, Irina}, title = {(-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia tupa with Agonist Activity at Nicotinic Acetylcholine Receptor}, series = {Natural product communications : an international journal for communications and reviews}, volume = {10}, journal = {Natural product communications : an international journal for communications and reviews}, number = {8}, publisher = {NPC}, address = {Westerville}, issn = {1934-578X}, pages = {1355 -- 1357}, year = {2015}, abstract = {Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at alpha 3 beta 2/alpha 3 beta 4 nAChR and alpha 7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR}, language = {en} } @article{PazBecerraSilvaetal.2016, author = {Paz, Cristian and Becerra, Jose and Silva, Mario and Cabrera-Pardo, Jaime and Burgos, Viviana and Heydenreich, Matthias and Schmidt, Bernd}, title = {(-)-8-Oxohobartine a New Indole Alkaloid from Aristotelia chilensis (Mol.) Stuntz}, series = {Records of Natural Products}, volume = {10}, journal = {Records of Natural Products}, publisher = {ACG Publications}, address = {Gebze-Kocaeli}, issn = {1307-6167}, pages = {68 -- 73}, year = {2016}, abstract = {The fruit of Aristotelia chilensis is considered a "super fruit" due to its high concentration of polyphenols displaying exceptional antioxidant capacities ORAC. From maqui berries have been reported several anthocyanins and glycosylated flavonoids, those benefits increase the attention to restudy the plant. From the leaves of A. chilensis several indole alkaloids have been reported, we in addition to aristoteline, aristone, aristoquinoline and 3-fromylindole report the spectroscopic elucidation of 8-oxo-9-dehydromakomakine (1), hobartine (2) and a new alkaloid named 8-oxohobartine (3). Compound 1 to 3 did not show bactericidal activity against E. coli and S. aureus till 200 mu g.}, language = {en} } @article{GonzalezChavarriaDupratRoaetal.2020, author = {Gonzalez-Chavarria, Ivan and Duprat, Felix and Roa, Francisco J. and Jara, Nery and Toledo, Jorge R. and Miranda, Felipe and Becerra, Jose and Inostroza, Alejandro and Kelling, Alexandra and Schilde, Uwe and Heydenreich, Matthias and Paz, Cristian}, title = {Maytenus disticha extract and an isolated β-Dihydroagarofuran induce mitochondrial depolarization and apoptosis in human cancer cells by increasing mitochondrial reactive oxygen species}, series = {Biomolecules}, volume = {10}, journal = {Biomolecules}, number = {3}, publisher = {MDPI}, address = {Basel}, issn = {2218-273X}, doi = {10.3390/biom10030377}, pages = {15}, year = {2020}, abstract = {Maytenus disticha (Hook F.), belonging to the Celastraceae family, is an evergreen shrub, native of the central southern mountains of Chile. Previous studies demonstrated that the total extract of M. disticha (MD) has an acetylcholinesterase inhibitory activity along with growth regulatory and insecticidal activities. beta-Dihydroagarofurans sesquiterpenes are the most active components in the plant. However, its activity in cancer has not been analyzed yet. Here, we demonstrate that MD has a cytotoxic activity on breast (MCF-7), lung (PC9), and prostate (C4-2B) human cancer cells with an IC50 (mu g/mL) of 40, 4.7, and 5 mu g/mL, respectively, an increasing Bax/Bcl2 ratio, and inducing a mitochondrial membrane depolarization. The beta-dihydroagarofuran-type sesquiterpene (MD-6), dihydromyricetin (MD-9), and dihydromyricetin-3-O-beta-glucoside (MD-10) were isolated as the major compounds from MD extracts. From these compounds, only MD-6 showed cytotoxic activity on MCF-7, PC9, and C4-2B with an IC50 of 31.02, 17.58, and 42.19 mu M, respectively. Furthermore, the MD-6 increases cell ROS generation, and MD and MD-6 induce a mitochondrial superoxide generation and apoptosis on MCF-7, PC9, and C4-2B, which suggests that the cytotoxic effect of MD is mediated in part by the beta-dihydroagarofuran-type that induces apoptosis by a mitochondrial dysfunction.}, language = {en} }