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Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities

The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC(50) 47.44 and 47.40 µg mL(−1), respectively). Gel filtration on Sephadex LH-20 and further RP-C(18) p...

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Autores principales: Pecio, Łukasz, Alilou, Mostafa, Kozachok, Solomiia, Erdogan Orhan, Ilkay, Eren, Gokcen, Senol Deniz, Fatma Sezer, Stuppner, Hermann, Oleszek, Wiesław
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891570/
https://www.ncbi.nlm.nih.gov/pubmed/31744162
http://dx.doi.org/10.3390/molecules24224162
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author Pecio, Łukasz
Alilou, Mostafa
Kozachok, Solomiia
Erdogan Orhan, Ilkay
Eren, Gokcen
Senol Deniz, Fatma Sezer
Stuppner, Hermann
Oleszek, Wiesław
author_facet Pecio, Łukasz
Alilou, Mostafa
Kozachok, Solomiia
Erdogan Orhan, Ilkay
Eren, Gokcen
Senol Deniz, Fatma Sezer
Stuppner, Hermann
Oleszek, Wiesław
author_sort Pecio, Łukasz
collection PubMed
description The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC(50) 47.44 and 47.40 µg mL(−1), respectively). Gel filtration on Sephadex LH-20 and further RP-C(18) preparative HPLC of EtOAc fraction afforded 15 known and 3 new compounds, stereoisomers of larixinol. The structures of the isolated spirobiflavonoids 15, 26, and 29 were elucidated using 1D and 2D NMR and MS spectroscopic techniques. The relative configuration of isolated compounds was assigned based on coupling constants and ROESY (rotating-frame Overhauser spectroscopy) correlations along with applying the DP4+ probability method in case of ambiguous chiral centers. Determination of absolute configuration was performed by comparing calculated electronic circular dichroism (ECD) spectra with experimental ones. Compounds 26 and 29, obtained in sufficient amounts, were evaluated for activities against AChE and BChE, and they showed a weak inhibition only towards AChE (IC(50) 294.18 µM for 26, and 655.18 µM for 29). Furthermore, molecular docking simulations were performed to investigate the possible binding modes of 26 and 29 with AChE.
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spelling pubmed-68915702019-12-18 Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities Pecio, Łukasz Alilou, Mostafa Kozachok, Solomiia Erdogan Orhan, Ilkay Eren, Gokcen Senol Deniz, Fatma Sezer Stuppner, Hermann Oleszek, Wiesław Molecules Article The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC(50) 47.44 and 47.40 µg mL(−1), respectively). Gel filtration on Sephadex LH-20 and further RP-C(18) preparative HPLC of EtOAc fraction afforded 15 known and 3 new compounds, stereoisomers of larixinol. The structures of the isolated spirobiflavonoids 15, 26, and 29 were elucidated using 1D and 2D NMR and MS spectroscopic techniques. The relative configuration of isolated compounds was assigned based on coupling constants and ROESY (rotating-frame Overhauser spectroscopy) correlations along with applying the DP4+ probability method in case of ambiguous chiral centers. Determination of absolute configuration was performed by comparing calculated electronic circular dichroism (ECD) spectra with experimental ones. Compounds 26 and 29, obtained in sufficient amounts, were evaluated for activities against AChE and BChE, and they showed a weak inhibition only towards AChE (IC(50) 294.18 µM for 26, and 655.18 µM for 29). Furthermore, molecular docking simulations were performed to investigate the possible binding modes of 26 and 29 with AChE. MDPI 2019-11-16 /pmc/articles/PMC6891570/ /pubmed/31744162 http://dx.doi.org/10.3390/molecules24224162 Text en © 2019 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pecio, Łukasz
Alilou, Mostafa
Kozachok, Solomiia
Erdogan Orhan, Ilkay
Eren, Gokcen
Senol Deniz, Fatma Sezer
Stuppner, Hermann
Oleszek, Wiesław
Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title_full Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title_fullStr Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title_full_unstemmed Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title_short Yuccalechins A–C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities
title_sort yuccalechins a–c from the yucca schidigera roezl ex ortgies bark: elucidation of the relative and absolute configurations of three new spirobiflavonoids and their cholinesterase inhibitory activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891570/
https://www.ncbi.nlm.nih.gov/pubmed/31744162
http://dx.doi.org/10.3390/molecules24224162
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