Cristina Theoduloz

University of Talca

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Guillermo Schmeda‐Hirschmann

University of Talca

102

Jaime Rodrı́guez

Universidade da Coruña

Felipe Jiménez‐Aspee

University of Hohenheim

Alberto Burgos-Edwards

University of Talca

Mariano Pertino

University of Talca

Jaime A. Valderrama

Arturo Prat University

Tania Yáñez

University of Talca

Nélida Nina

University of Talca

Gabriela E. Feresin

National University of San Juan

Cristina Quispe

Arturo Prat University

Cooperative Institutions

University of Talca

University of Chile

Pontificia Universidad Católica de Chile

Consejo Nacional de Investigaciones Científicas y Técnicas

Universidad de Santiago de Chile

Centro de Estudios Científicos

Rede de Química e Tecnologia

University of Concepción

Arturo Prat University

Universidad Nacional de Asunción

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Phenolics and enzyme inhibitors from the Patagonian Empetrum rubrum berries

LWT (2024)

Alberto Burgos-Edwards Cristina Theoduloz Crister Ramírez Ricardo Rozzi Debasish Ghosh

The small fruits from Empetrum rubrum were consumed by Native Americans in southern Patagonia. Two samples collected close to the Magellan Street and the Beagle channel in Tierra del Fuego were investigated. Three different extracts from the berries were analyzed, namely: methanol, phenolic-enriched (PEE) and ethyl acetate (EtOAc). The total phenolic, flavonoid, procyanidin and anthocyanin content of the extracts was determined. The effect of the extracts towards the metabolic syndrome-associated enzymes α-glucosidase, α-amylase and pancreatic lipase was assessed. In addition, the antioxidant capacity was measured using DPPH, FRAP, TEAC and ORAC assays. The composition of the extracts was determined by HPLC-MS/MS. Seventy-one compounds were identified for the first time in the berries, including 10 anthocyanins, 35 flavonoids, 11 phenylpropanoids and 13 procyanidins. The main compounds were quantified by HPLC-DAD. The extracts displayed strong activity as α-glucosidase inhibitors, with IC50 values ranging from 0.10 to 0.19 μg/mL for the PEE and 0.82–1.95 μg/mL for the EtOAc extracts, respectively. The results show high chemical diversity and differences with the boreal species E. nigrum.

10.1016/j.lwt.2024.116655

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Synthesis and antiproliferative evaluation of new isomeric ellipticine quinones

Boletin Latinoamericano y del Caribe de plantas Medicinales y Aromaticas (2014)

Jaime A. Valderrama Juana Andrea Ibacache Cristina Theoduloz

Se describe la sintesis de las nuevas quinonas 3a-c, isomericas de elipticina, y sus actividades antiproliferativas in vitro en lineas de celulas de cancer. Las quinonas N-heterociclicas 3a-c se sintetizaron a traves de una secuencia que involucra: a) preparacion de 4- metoxicarbonil-3,4-dimetlisoquinolin-5,8-quinone 1 a partir de 2,5-dihidroxiacetofenona, aminocrotonato de metilo y oxido de plata (I); b) aminacion regioselectiva de 1 con arilaminas para producir las aminoquinonas 2a-c y c) acoplamiento oxidante intramolecular de 7- aminoisoquinolin-5,8-quinonas 2a-c catalizado con paladio. La actividad antiproliferative in vitro de los nuevos compuestos fue evaluada en una linea celular normal (fibroblastos de pulmon) y lineas de celulas de cancer gastrico, pulmon y vejiga en ensayos de exposicion de 72 horas a la droga. Las quinonas 3a-c exhiben interesantes propiedades antiproliferativas destacando la elipticinquinona isomerica 2b en celulas de cancer de vejiga (IC50: 2.4 µM) comparado con etoposido usada como droga anticancer de referencia. Los nuevos compuestos mostraron actividades antiproliferativa similar o mayor respecto de las correspondientes quinonas precursoras 2a-c. La elipticin quinona isomerica 2b corresponde al miembro mas activo en celulas de câncer de vejiga (IC50: 2.4 µM), comparable a la del etoposido, usada como droga anticancer de referencia

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Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations

Natural Products and Bioprospecting (2022)

Natividad Herrera Cano Sebastián A. Andújar Cristina Theoduloz Daniel A. Wunderlin Ana N. Santiago

Abstract Triadimefon (TDM) and cyproconazole (CPZ) are two triazoles widely used as fungicides. Several azoles were synthesised starting from commercial TDM and CPZ. The compounds were evaluated against phytopathogenic filamentous fungi, including Aspergillus fumigatus (AF), A. niger (AN), A. ustus (AU), A. japonicus (AJ), A. terreus (AT), Fusarium oxysporum and Botrytis cinerea isolated from grapevine in the province of San Juan, Argentina. Three of the synthesised compounds (1-(Biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one, 1 ; 2-(Biphenyl-4-yl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 3 ; 3-Cyclopropyl-2-(4’-fluorobiphenyl-4-yl)-1-(1H-1,2,4-triazol1-yl)butan-2-ol, 4 ) presented remarkable in vitro fungicidal properties , with better effects than TDM and CPZ on some of the target fungi. Cytotoxicity was assessed using human lung fibroblasts MRC5. Derivative 1 , with IC 50 values of 389.4 µM, was less toxic towards MRC-5 human lung fibroblasts than commercial TDM (248.5 µM) and CPZ (267.4 µM). Docking analysis and molecular dynamics simulations suggest that the compounds present the same interaction in the binding pocket of the CYP51B enzyme and with the same amino acids as CPZ. The derivatives investigated could be considered broad-spectrum but with some selectivity towards imperfect fungi. Graphical abstract

Plant biochemistry

Bioorganic chemistry

Docking (animal)

10.1007/s13659-022-00329-0

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Citations (1)

Gastroprotective effect of the Mapuche crude drug Araucaria araucana resin and its main constituents

Journal of Ethnopharmacology (2005)

Guillermo Schmeda‐Hirschmann Luís Astudillo Jaime Rodrı́guez Cristina Theoduloz Tania Yáñez

Lansoprazole

Araucaria

IC50

10.1016/j.jep.2005.04.027

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Citations (44)

Hypotensive and diuretic effect of Equisetum bogotense and Fuchsia magellanica and micropropagation of E. bogotense

Phytotherapy Research (1994)

J. A. Rodríguez Patrícia Pacheco Iván Razmilic J. I. Loyola Guillermo Schmeda‐Hirschmann

Abstract Equisetum bogotense (Equisetaceae) and Fuchsia magellanica (Onagraceae) were used by the Mapuche Amerindians as diuretics. Intravenous administration of hydroalcoholic extracts to rats elicited a hypotensive response of −29.0% ±4.5% and −24.2% ±0.5% respectively in the mean blood pressure of normotensive animals at a dose of 5 mg crude extract/kg body weight. The activity was found to be related with polar compounds. For Fuchsia , the active principles are related to tannins. A single oral dose of 500 mg/kg body weight Equisetum extract produced a significant increase ( p < 0.05) in the urine output in rats, while in Fuchsia a reduction in diuresis was observed. The diuretic effect of the Equisetum extract was weak compared with hydrochlorothiazide at 25 mg/kg body weight. The data presented support the use of E. bogotense in Chilean traditional medicine. A micropropagation method for E. bogotense was established by culturing shoot tips in Murashige‐Skoog medium with macro and micronutrients diluted 4‐fold and containing 0.1 mg/L thiamine, 100 mg/L myoinositol, 1.0 mg/L NAA and 0.1 mg/L BAP.

Onagraceae

10.1002/ptr.2650080308

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Gastroprotective Effect of Carnosic Acid γ-Lactone Derivatives

Journal of Natural Products (2010)

Mariano Pertino Cristina Theoduloz Jaime Rodrı́guez Tania Yáñez Viviana Lazo

Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid γ-lactone (3). To determine structure−activity relationships, a series of 17 esters of 3 were prepared including aliphatic, aromatic, and heterocyclic derivatives. Also, two units of 3 were coupled with succinic and phthalic acid as linkers. The compounds were assessed for their gastroprotective effect in the HCl/EtOH-induced gastric lesions model in mice and for cytotoxicity in human lung fibroblasts, human adenocarcinoma AGS cells, and Hep G2 hepatocellular carcinoma cells. At a single oral dose of 40 mg/kg, the gastroprotective effect increased moderately with the length of the alkyl chain. The best effects were observed for the butyrate (9) and chloroacetate (6) derivatives. Activity of fatty acid esters increased with chain length but decreased with unsaturation. The best gastroprotective effect, with lowest cytotoxicity, was found for the palmitate (11) and oleate (12) derivatives.

Carnosic acid

Succinic acid

Phthalic acid

10.1021/np900822x

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Synthesis of tricyclic analogs of stephaoxocanidine and their evaluation as acetylcholinesterase inhibitors

Bioorganic & Medicinal Chemistry Letters (2005)

Darı́o A. Bianchi Guillermo Schmeda‐Hirschmann Cristina Theoduloz Andrea B. J. Bracca Teodoro S. Kaufman

Isoquinoline

Galantamine

Natural product

Tricyclic

Cholinesterase

10.1016/j.bmcl.2005.04.005

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Citations (18)

Effect of simulated gastrointestinal digestion on polyphenols and bioactivity of the native Chilean red strawberry (Fragaria chiloensis ssp. chiloensis f. patagonica)

Food Research International (2019)

Samanta Thomas‐Valdés Cristina Theoduloz Felipe Jiménez‐Aspee Guillermo Schmeda‐Hirschmann

Fragaria

Digestion

10.1016/j.foodres.2019.04.039

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Citations (28)

1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity

Molecules (2013)

Mariano Pertino Cecilia López Cristina Theoduloz Guillermo Schmeda‐Hirschmann

Hybrid compounds are relevant products when searching for structure-activity relationships of natural products. Starting from the naturally occurring triterpene oleanolic acid, alkyl esters were prepared and treated with different aromatic azides using click chemistry to produce hybrid compounds. Some 18 new oleanolic acid derivatives were synthesized and the structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new derivatives was evaluated towards normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), promyelocytic leukemia (HL-60), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. The alkyne esters 1 and 3 showed activity on all cell lines but without selectivity (19.6-23.1 μM and 14.1-56.2 μM, respectively), their respective methyl esters were inactive. Compounds with a benzene and p-anisole attached to the triazole ring, showed no antiproliferative effect. Introduction of a chlorine atom into the benzene ring (compound 9) elicited a selective effect against AGS cells (IC50 value: 8.9 μM). The activity was lost when the COOH function at C-28 was methylated. Better antiproliferative effect was found for compounds 11 and 15 bearing a p-toluenesulphonyl group, with values in the range of 10.8-47.1 μM and 11.5-22.2 μM, respectively. The effect, however, was not associated with selectivity.

Triazole

10.3390/molecules18077661

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Citations (42)

Gastroprotective and ulcer-healing activity of oleanolic acid derivatives: In vitro–in vivo relationships

Life Sciences (2006)

Marianela Sánchez Cristina Theoduloz Guillermo Schmeda‐Hirschmann Iván Razmilic Tania Yáñez

10.1016/j.lfs.2006.03.044

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Citations (67)