Carlos Areche

University of Chile

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Beatriz Sepúlveda

Viña del Mar University

Mario J. Simirgiotis

Austral University of Chile

Olimpo García‐Beltrán

Universidad de Ibagué

Alberto Cornejo

Universidad Andrés Bello

Juana Rovirosa

Universidad de Magallanes

Jorge Bórquez

University of Antofagasta

Aurelio San-Martı́n

Universidad de Magallanes

Grover Castañeta

Higher University of San Andrés

Pedro Joseph‐Nathan

Instituto Politécnico Nacional

José Cheel

Czech Academy of Sciences, Institute of Microbiology

Cooperative Institutions

University of Chile

Universidad Andrés Bello

Pontificia Universidad Católica de Chile

University of Talca

Universidad de Santiago de Chile

University of Antofagasta

Austral University of Chile

Universidad Católica del Norte

Instituto Politécnico Nacional

Universidade Estadual de Campinas (UNICAMP)

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In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease

Frontiers in Chemistry (2021)

Osvaldo Yañéz Manuel I. Osorio Eugenio Uriarte Carlos Areche William Tiznado

The pandemic that started in Wuhan (China) in 2019 has caused a large number of deaths, and infected people around the world due to the absence of effective therapy against coronavirus 2 of the severe acute respiratory syndrome (SARS-CoV-2). Viral maturation requires the activity of the main viral protease (M

Docking (animal)

2019-20 coronavirus outbreak

10.3389/fchem.2020.595097

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Citations (38)

STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS

Journal of the Chilean Chemical Society (2012)

Olimpo García‐Beltrán Jorge Soto‐Delgado Patricio Iturriaga‐Vásquez Carlos Areche Bruce K. Cassels

The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of 1, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their 1 H and 13 C NMR spectra were completely assigned using 2D experiments (H-H COSY, HMQC, HMBC and H-H NOESY).Our assignments for 1-5 agree well with the literature, but the present work shows that the published interpretation of the spectra of 6 must be revised.A combined study based on NMR data and quantum-mechanical calculations using DFT/GIAO indicate that 6 is the correct structure of epierythratidine.

10.4067/s0717-97072012000300027

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Stereostructure Reassignment and Absolute Configuration of Isoepitaondiol, a Meroditerpenoid from Stypopodium flabelliforme

Journal of Natural Products (2009)

Carlos Areche Aurelio San-Martı́n Juana Rovirosa Marcelo A. Muñoz A. Hernandez-Barragan

Careful examination of the published NMR data for isoepitaondiol, a meroditerpenoid from Stypopodium flabelliforme, suggests that its published structure 1 must be revised. On the basis of extensive 1D and 2D NMR studies, we now propose that structure 2, with a trans-anti-trans-anti-cis arrangement fits isoepitaondiol diacetate. The relative configuration of 2 was confirmed by single-crystal X-ray diffraction, while the absolute configuration was evidenced by vibrational circular dichroism in combination with DFT B3LYP/DGDZVP calculations.

Absolute Configuration

Vibrational Circular Dichroism

10.1021/np900553p

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Citations (36)

ChemInform Abstract: An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella trifurcata (Gaertn) Pers.

ChemInform (2015)

Carlos Areche Beatriz Sepúlveda Aurelio San Martín Olimpo García‐Beltrán Mario J. Simirgiotis

Abstract Four new mulinane‐type diterpenoids are isolated from Azorella trifurcata.

Apiaceae

10.1002/chin.201504213

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Metabolomic Analysis of Two Parmotrema Lichens: P. robustum (Degel.) Hale and P. andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS

Molecules (2017)

Alfredo Torres-Benítez María Rivera-Montalvo Beatriz Sepúlveda Olivio N. Castro Édgar Nagles

Lichens are symbiotic associations of fungi with microalgae and/or cyanobacteria. Lichens belonging to the Parmeliaceae family comprise 2700 species of lichens, including the Parmotrema genus which is composed of 300 species. The metabolites of this genus include depsides, depsidones, phenolics, polysaccharides, lipids, diphenylethers and dibenzofurans, which are responsible for the biological activities reported including antidiabetic, antihelmintic, anticancer, antioxidant, antibacterial, anti-inflammatory, antimitotic, antitumoral, antifungal, and antioxidant enzyme inhibitory. Due to scarce knowledge of metabolomic profiles of Parmotrema species (P. andinum and P. robustum), a full metabolome study based on ultra-high performance liquid chromatography- diode array detector-electrospray ionization-quadrupole-orbitrap-mass-spectrometry (UHPLC-DAD-ESI-Q-orbitrap MS) was performed for a comprehensive characterization of their substances. From the methanolic extracts of these species, a total of 54 metabolites were identified for the first time using this hyphenated technique, including thirty compounds in P. andinum, and thirty-seven in P. robustum. Moreover, two compounds were not identified as known compounds, and could be new structures, according to our data. This report shows that this technique is effective and accurate for rapid chemical identification of lichen substances and the compounds identified could serve as chemotaxonomic markers to differentiate these ruffle lichens.

Parmeliaceae

Orbitrap

Metabolome

10.3390/molecules22111861

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Citations (33)

Variations in the chemical profile, free radical scavenging, antioxidant and gastroprotective activities of licorice (Glycyrrhiza glabra L.): as influenced by harvest times

José Cheel Carlos Areche Pierre Van Antwerpen Jean Nève Karim Zouaoui Boudjeltia

Glycyrrhiza

Scavenging

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Dictyostelium discoideum-assisted pharmacognosy of plant resources for discovering antivirulence molecules targetingKlebsiella pneumoniae

bioRxiv (Cold Spring Harbor Laboratory) (2023)

Marco Hernández Carlos Areche Grover Castañeta Diego Rojas Macarena A. Varas

ABSTRACT The rise of antibiotic-resistant bacterial strains poses a significant global health challenge, underscoring the critical need for innovative strategies to address this threat. Natural products and their derivatives have emerged as a promising reservoir for drug discovery. The social amoeba Dictyostelium discoideum is an advantageous model organism in this effort. Using this invertebrate model, we introduce a novel perspective to screen natural plant extracts for molecules with potential antivirulence activity. As a proof of concept, we established a simple high-throughput assay to screen for antivirulence molecules targeting Klebsiella pneumoniae among extracts of Helenium aromaticum . Thus, we aimed to identify compounds attenuating K. pneumoniae virulence without inducing cytotoxic effects on amoeba cells. Notably, the methanolic root extract of H. aromaticum but not other extracts fulfilled these prerequisites. Further analysis via UHPLC-ESI-MS/MS led to the identification of 24 chemical compounds boasting potential antivirulence attributes. This research underscores the potential of employing D. discoideum -assisted pharmacognosy for unearthing novel antivirulence agents against multidrug-resistant pathogens. Table of Content Graphic

10.1101/2023.10.27.564015

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Dammarane triterpenes targeting α-synuclein: biological activity and evaluation of binding sites by molecular docking

Journal of Enzyme Inhibition and Medicinal Chemistry (2020)

Alberto Cornejo Julio Caballero Mario J. Simirgiotis Vanessa Torres L.E Mallea Sanchez

Parkinson's disease (PD) is a neurodegenerative disorder that affects adult people whose treatment is palliative. Thus, we decided to test three dammarane triterpenes 1, 1a, 1b, and we determined that 1 and 1a inhibit β-aggregation through thioflavine T rather than 1b. Since compound 1 was most active, we determined the interaction between α-synuclein and 1 at 50 µM (Kd) through microscale thermophoresis. Also, we observed differences in height and diameter of aggregates, and α-synuclein remains unfolded in the presence of 1. Also, aggregates treated with 1 do not provoke neurites' retraction in N2a cells previously induced by retinoic acid. Finally, we studied the potential sites of interaction between 1 with α-synuclein fibrils using molecular modelling. Docking experiments suggest that 1 preferably interact with the site 2 of α-synuclein through hydrogen bonds with residues Y39 and T44.

Microscale Thermophoresis

Docking (animal)

Molecular model

Dammarane

10.1080/14756366.2020.1851216

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Citations (8)

HPLC-UV-MS Profiles of Phenolic Compounds and Antioxidant Activity of Fruits from Three Citrus Species Consumed in Northern Chile

Molecules (2014)

Anghel Brito Javier A. Ramírez Carlos Areche Beatriz Sepúlveda Mario J. Simirgiotis

Peels and edible pulp from three species of citrus including Citrus aurantifolia (varieties pica and sutil) and Citrus x lemon var. Genova widely cultivated and consumed in Northern Chile (I and II region) were analyzed for phenolic compounds and antioxidant activity for the first time. A high performance electrospray ionization mass spectrometry (HPLC-UV-ESI-MS) method was developed for the rapid identification of phenolics in extracts from peels and juices of all species. Several flavonoids including one kaempferol-O-hexoside (peak 16) and one hesperidin derivative (peak 22) three quercetin derivatives (peaks 4, 19 and 36), five isorhamnetin derivatives (peaks 5, 23, 24, 26 and 29) four luteolin derivatives (peaks 14, 25, 27 and 40), seven apigenin derivatives (peaks 2, 3, 12, 20, 34, 35 and 39), seven diosmetin derivatives (peaks 7–9, 17, 21, 31 and 37), three chrysoeriol derivatives (peaks 10, 18 and 30), and four eryodictiol derivatives (peaks 6, 13, 15 and 38) were identified in negative and positive mode using full scan mass measurements and MSn fragmentations. Ascorbic acid content was higher in the pulps of the varieties Genova and Sutil (60.13 ± 1.28 and 56.53 ± 1.06 mg ascorbic acid per g dry weight, respectively) while total phenolic content was higher in Pica peels followed by Sutil peels (34.59 ± 0.81 and 25.58 ± 1.02 mg/g GAE dry weight, respectively). The antioxidant capacity was also higher for Pica peels (10.34 ± 1.23 µg/mL in the DPPH assay and 120.63 ± 2.45 µM trolox equivalents/g dry weight in the FRAP assay). The antioxidant features together with the high polyphenolic contents can support at least in part, the usage of the peel extracts as nutraceutical supplements, especially to be used as anti-ageing products.

10.3390/molecules191117400

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Citations (324)

Triterpenoids from Azorella trifurcata (Gaertn.) Pers and their effect against the enzyme acetylcholinesterase

Química Nova (2009)

Carlos Areche Patricia Cejas Pablo Thomas Aurelio San-Martı́n Luís Astudillo

The inhibition of the enzyme acetylcholinesterase is considered as a strategy for the treatment of Alzheimer's disease, senile dementia, ataxia, and myasthenia gravis. Three lanostane- and two cycloartane-type triterpenes, together with two mulinane-type diterpenes were isolated from petroleum ether extract of the whole shrub of Azorella trifurcata (Gaertn.) Pers. Their effect on the enzyme acetylcholinesterase was assessed as well. In addition, this is the first report of these triterpenes in the genus Azorella.

Terpene

Lanostane

10.1590/s0100-40422009000800008

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Citations (17)