Metabolomic Analysis, Fast Isolation of Phenolic Compounds, and Evaluation of Biological Activities of the Bark From Weinmannia trichosperma Cav. (Cunoniaceae)

Abstract

Weinmannia trichosperma Cav. (Cunoniaceae) (local name, tineo; Mapuche names, madeń, mëdehue) is an endemic species of Chile and Argentina used in Mapuche traditional medicine in the treatment of chronic diarrhea, inflammation, and wound healing. This study focused on the isolation, analysis, and characterization of the biological activity of compounds and bark extracts from this plant for the first time. The infusion and tincture of the bark were characterized regarding antioxidant and important enzyme inhibitory activities, phenolics, and flavonoids content and UHPLC-ESI-OT-MS metabolite profiling. Twenty-five metabolites were detected in the medicinal infusion of W. trichosperma, three flavonols were isolated: isoastilbin, neoisoastilbin, and neoastilbin ((2R,3S)-, (2S,3R)-, and (2S,3S)-dihydroquercetin 3-O-alpha-L-rhamnoside) by countercurrent chromatography, and the isomers were quantified in the bark using a validated analytical HPLC methodology. The antioxidant properties were measured by ABTS, DPPH, FRAP, ORAC, and TEAC methods. The infusion displayed a strong DPPH and ABTS scavenging activity (IC 50 = 20.58 and 3.070 µg ml −1 , respectively) while a moderated effect was observed in the FRAP, ORAC, and ABTS assays. The infusion showed a content of phenolic and flavonoid compounds of 442.1 mg GAE g −1 and 15.54 mg QE g −1 , respectively. Furthermore, the infusion showed a good and promissory inhibitory activity (33.80%, 33.12%, and 82.86% for AChE, BuChE, and 5-hLOX, respectively) and isoastilbin (51.70%, 50.10%, and 34.29-80.71% for AChE, BuChE, and 5-hLOX, respectively). The biomolecules identified in this study support the traditional uses of this bark and the potential industrial interest from this Valdivian plant species.

Multiple Biological Activities of Rhododendron przewalskii Maxim. Extracts and UPLC-ESI-Q-TOF/MS Characterization of Their Phytochemical Composition

“…Five milligrams of six standards were weighed and dissolved in 10 ml of methanol, respectively, from which 1 ml was taken and made up to 5 ml with solvent as this stock solution to inject. The equation of the curve and the coefficient of determination were calculated ( Barrientos et al, 2020 ). Three replicates were performed.…”

Chemical Fingerprinting and Biological Evaluation of the Endemic Chilean Fruit Greigia sphacelata (Ruiz and Pav.) Regel (Bromeliaceae) by UHPLC-PDA-Orbitrap-Mass Spectrometry

“…Supplementary Materials: The following are available online. Figure S1 (a-v): Full MS spectra and structures of compounds 1,3,7,9,12,13,15,25,27,28,29,35,37,42,43,44,46,48,51,53, and 55; Table S1: Binding energies obtained from docking experiments of most abundant compounds in G. sphacelata's fruit and the known cholinesterase inhibitor galantamine over acetylcholinesterase (TcAChE) and butyrylcholinesterase (hBuChE); Figure S2: Components of G. sphacelata fruits used in docking studies Figure S3: Predicted binding mode and predicted intermolecular interactions of all most abundant compounds in G. sphacelata pulp and seeds extracts and the residues of Torpedo californica acetylcholinesterase (TcAChE) catalytic site; Figure S4: Predicted binding mode and predicted intermolecular interactions of all most abundant compounds in G. sphacelata pulp and seeds extracts and the residues of human butyrylcholinesterase (hBuChE) catalytic site.…”

“…This is a dual high resolution with accurate mass (HRAM) spectrometer with an orbital trap (Orbitrap), a quadrupole (Q), and a high-performance collision cell (HCD), capable of producing high-resolution parent ions and diagnostic MS daughter fragments. The hyphenated ultrahigh performance liquid chromatography-photodiode array detection coupled with a Orbitrap mass spectrometry (UHPLC-PDA-Orbitrap-MS) approach is a key tool for the identification of secondary metabolites in plants and edible fruits [15][16][17].…”

Chemical Profiling, Antioxidant, Anticholinesterase, and Antiprotozoal Potentials of Artemisia copa Phil. (Asteraceae)

“…Some phenolic compounds were quantified using the UHPLC Dionex 3000 RS with photodiode array detector at flavonoid (255 and 265 nm) and phenolic acid (330 nm) wavelength as reported previously carried out according to ICH Guideline Q2 (R1) (Barrientos et al, 2020b). Some curves for representative compounds, each one covering six points from 0.01 to 0.5 mg/ml solutions, in triplicate, and injecting 10 ml.…”

“…Since herbal native infusions are receiving increasing attention for the number of physiological benefits they can bring to human health (Coelho et al, 2016) and as part of our continuing research of medicinal plants from Atacama Desert (Echiburu-Chau et al, 2017;Ardiles et al, 2018;Areche et al, 2020;Rodriguez et al, 2020) and native plants with potentiality as cholinesterase inhibitors (Barrientos et al, 2020a;Barrientos et al, 2020b), we investigated the infusions of the medicinal plant A. copa using screening tests to evaluate their antioxidant, antiprotozoal and enzyme inhibitory properties against cholinesterase and high-resolution UHPLC-MS/MS for the chemical profiling for the first time. Additionally, molecular docking of the major compounds was investigated.…”