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Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.

Gypothamnium pinifolium Phil. (Asteraceae) is a small shrub that grows in the Paposo Valley of the II Antofagasta Region of Chile. This initial study is of the high-resolution phenolic fingerprinting, antioxidant activity, the relaxation effects in rat aorta, the inhibitory enzyme potential, plus th...

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Autores principales: Barrientos, Ruth E., Ibáñez, Elena, Puerta, Adrián, Padrón, José M., Paredes, Adrián, Cifuentes, Fredi, Romero-Parra, Javier, Palacios, Javier, Bórquez, Jorge, Simirgiotis, Mario J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9774750/
https://www.ncbi.nlm.nih.gov/pubmed/36552522
http://dx.doi.org/10.3390/antiox11122313
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author Barrientos, Ruth E.
Ibáñez, Elena
Puerta, Adrián
Padrón, José M.
Paredes, Adrián
Cifuentes, Fredi
Romero-Parra, Javier
Palacios, Javier
Bórquez, Jorge
Simirgiotis, Mario J.
author_facet Barrientos, Ruth E.
Ibáñez, Elena
Puerta, Adrián
Padrón, José M.
Paredes, Adrián
Cifuentes, Fredi
Romero-Parra, Javier
Palacios, Javier
Bórquez, Jorge
Simirgiotis, Mario J.
author_sort Barrientos, Ruth E.
collection PubMed
description Gypothamnium pinifolium Phil. (Asteraceae) is a small shrub that grows in the Paposo Valley of the II Antofagasta Region of Chile. This initial study is of the high-resolution phenolic fingerprinting, antioxidant activity, the relaxation effects in rat aorta, the inhibitory enzyme potential, plus the antiproliferative activity of the ethyl acetate and n-hexane extract from G. pinifolium and its two major isolated secondary metabolites (one coumarin: 2-nor-1,2-secolycoserone, and one diterpene: ent-labda-8,13-E-diene-15-ol). The study involves using ultra-high-performance liquid chromatography todiode array detection coupled with Q-Orbitrap mass spectrometry analysis (UHPLC-PDA-Orbi-trap-MS), in which various compounds were identified, including specific coumarins. The n-hexane extract showed total phenolic and flavonoid contents of 517.4 ± 12.5 mg GAE/100 g extract and 72.3 ± 3.7 mg QE/100 g extract, respectively. In addition, the antioxidant activity of the n-hexane extract was assessed using in-vitro assays such as bleaching of DPPH and ABTS (IC(50): 14.3 ± 0.52 and 2.51 ± 0.43 µg extract/mL, respectively), FRAP (347.12 ± 1.15 μmol Trolox equivalent/g extract), and ORAC (287.3 ± 1.54 μmol Trolox equivalents/g extract). Furthermore, the inhibition against cholinesterases (acetylcholinesterase (AChE) 4.58 ± 0.04 µg/mL, butyrylcholinesterase (BChE) IC(50): 23.44 ± 0.03 µg/mL) and tyrosinase (IC(50): 9.25 ± 0.15 µg/mL) enzymes of the n-hexane extract, and main compounds (IC(50): 1.21 ± 0.03 µg/mL, 11.23 ± 0.02 µg/mL, 3.23 ± 0.12 µg/mL, and 103.43 ± 16.86 µg/mL, correspondingly for the most active coumarin 1) were measured. The antiproliferative potential of the extracts and the two principal compounds against several solid human cancer cells was investigated. All of them showed good activity against cancer cells. Label-free live-cell imaging studies on HeLa cells exposed to the isolated coumarin and the diterpene enabled the observation of cell death and several apoptotic hallmarks. Our results indicate that G. pinifolium Phil. is a valuable source of secondary metabolites with potential activity against noncommunicable diseases.
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spelling pubmed-97747502022-12-23 Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil. Barrientos, Ruth E. Ibáñez, Elena Puerta, Adrián Padrón, José M. Paredes, Adrián Cifuentes, Fredi Romero-Parra, Javier Palacios, Javier Bórquez, Jorge Simirgiotis, Mario J. Antioxidants (Basel) Article Gypothamnium pinifolium Phil. (Asteraceae) is a small shrub that grows in the Paposo Valley of the II Antofagasta Region of Chile. This initial study is of the high-resolution phenolic fingerprinting, antioxidant activity, the relaxation effects in rat aorta, the inhibitory enzyme potential, plus the antiproliferative activity of the ethyl acetate and n-hexane extract from G. pinifolium and its two major isolated secondary metabolites (one coumarin: 2-nor-1,2-secolycoserone, and one diterpene: ent-labda-8,13-E-diene-15-ol). The study involves using ultra-high-performance liquid chromatography todiode array detection coupled with Q-Orbitrap mass spectrometry analysis (UHPLC-PDA-Orbi-trap-MS), in which various compounds were identified, including specific coumarins. The n-hexane extract showed total phenolic and flavonoid contents of 517.4 ± 12.5 mg GAE/100 g extract and 72.3 ± 3.7 mg QE/100 g extract, respectively. In addition, the antioxidant activity of the n-hexane extract was assessed using in-vitro assays such as bleaching of DPPH and ABTS (IC(50): 14.3 ± 0.52 and 2.51 ± 0.43 µg extract/mL, respectively), FRAP (347.12 ± 1.15 μmol Trolox equivalent/g extract), and ORAC (287.3 ± 1.54 μmol Trolox equivalents/g extract). Furthermore, the inhibition against cholinesterases (acetylcholinesterase (AChE) 4.58 ± 0.04 µg/mL, butyrylcholinesterase (BChE) IC(50): 23.44 ± 0.03 µg/mL) and tyrosinase (IC(50): 9.25 ± 0.15 µg/mL) enzymes of the n-hexane extract, and main compounds (IC(50): 1.21 ± 0.03 µg/mL, 11.23 ± 0.02 µg/mL, 3.23 ± 0.12 µg/mL, and 103.43 ± 16.86 µg/mL, correspondingly for the most active coumarin 1) were measured. The antiproliferative potential of the extracts and the two principal compounds against several solid human cancer cells was investigated. All of them showed good activity against cancer cells. Label-free live-cell imaging studies on HeLa cells exposed to the isolated coumarin and the diterpene enabled the observation of cell death and several apoptotic hallmarks. Our results indicate that G. pinifolium Phil. is a valuable source of secondary metabolites with potential activity against noncommunicable diseases. MDPI 2022-11-22 /pmc/articles/PMC9774750/ /pubmed/36552522 http://dx.doi.org/10.3390/antiox11122313 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Barrientos, Ruth E.
Ibáñez, Elena
Puerta, Adrián
Padrón, José M.
Paredes, Adrián
Cifuentes, Fredi
Romero-Parra, Javier
Palacios, Javier
Bórquez, Jorge
Simirgiotis, Mario J.
Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title_full Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title_fullStr Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title_full_unstemmed Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title_short Phenolic Fingerprinting and Bioactivity Profiling of Extracts and Isolated Compounds from Gypothamnium pinifolium Phil.
title_sort phenolic fingerprinting and bioactivity profiling of extracts and isolated compounds from gypothamnium pinifolium phil.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9774750/
https://www.ncbi.nlm.nih.gov/pubmed/36552522
http://dx.doi.org/10.3390/antiox11122313
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