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Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties

Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1–3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1...

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Detalles Bibliográficos
Autores principales: Songoen, Weerasak, Phanchai, Witthawat, Brecker, Lothar, Wenisch, Dominik, Jakupec, Michael A., Pluempanupat, Wanchai, Schinnerl, Johann
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7922997/
https://www.ncbi.nlm.nih.gov/pubmed/33670764
http://dx.doi.org/10.3390/molecules26041078
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author Songoen, Weerasak
Phanchai, Witthawat
Brecker, Lothar
Wenisch, Dominik
Jakupec, Michael A.
Pluempanupat, Wanchai
Schinnerl, Johann
author_facet Songoen, Weerasak
Phanchai, Witthawat
Brecker, Lothar
Wenisch, Dominik
Jakupec, Michael A.
Pluempanupat, Wanchai
Schinnerl, Johann
author_sort Songoen, Weerasak
collection PubMed
description Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1–3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1 to 3 feature 6/6/5/6/5/6 core structures. All structures were deduced by NMR and MS, while density functional theory (DFT) calculations on B3LYP theory level were performed of compounds 1 to 3 to support the stereochemistry in positions 2 and 3 in the C-ring. Possible biosynthetic pathways leading to 4 are discussed. The DPPH assay revealed high radical scavenging activities for 1 (EC(50) = 9.4 ± 1.0 µmol mL(−1)), 2 (12.2 ± 1.1), 3 (10.0 ± 1.5) and 4 (19.0 ± 2.6), remarkably lower than ascorbic acid (EC(50) = 34.9) and α-tocopherol (EC(50) = 48.6). A cytotoxicity assay revealed moderate but consistent antiproliferative properties of 1 in CH1/PA-1 (ovarian teratocarcinoma) and SW480 (colon carcinoma) cells, with IC(50) values of 25 ± 6 and 34 ± 4 µM, respectively, whereas effects in A549 (non-small cell lung cancer) cells were rather negligible. The performed DCFH-DA assay of 1 in the former cell lines confirmed potent antioxidative effects even in the cellular environment.
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spelling pubmed-79229972021-03-03 Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties Songoen, Weerasak Phanchai, Witthawat Brecker, Lothar Wenisch, Dominik Jakupec, Michael A. Pluempanupat, Wanchai Schinnerl, Johann Molecules Article Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1–3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1 to 3 feature 6/6/5/6/5/6 core structures. All structures were deduced by NMR and MS, while density functional theory (DFT) calculations on B3LYP theory level were performed of compounds 1 to 3 to support the stereochemistry in positions 2 and 3 in the C-ring. Possible biosynthetic pathways leading to 4 are discussed. The DPPH assay revealed high radical scavenging activities for 1 (EC(50) = 9.4 ± 1.0 µmol mL(−1)), 2 (12.2 ± 1.1), 3 (10.0 ± 1.5) and 4 (19.0 ± 2.6), remarkably lower than ascorbic acid (EC(50) = 34.9) and α-tocopherol (EC(50) = 48.6). A cytotoxicity assay revealed moderate but consistent antiproliferative properties of 1 in CH1/PA-1 (ovarian teratocarcinoma) and SW480 (colon carcinoma) cells, with IC(50) values of 25 ± 6 and 34 ± 4 µM, respectively, whereas effects in A549 (non-small cell lung cancer) cells were rather negligible. The performed DCFH-DA assay of 1 in the former cell lines confirmed potent antioxidative effects even in the cellular environment. MDPI 2021-02-18 /pmc/articles/PMC7922997/ /pubmed/33670764 http://dx.doi.org/10.3390/molecules26041078 Text en © 2021 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
Songoen, Weerasak
Phanchai, Witthawat
Brecker, Lothar
Wenisch, Dominik
Jakupec, Michael A.
Pluempanupat, Wanchai
Schinnerl, Johann
Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title_full Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title_fullStr Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title_full_unstemmed Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title_short Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties
title_sort highly aromatic flavan-3-ol derivatives from palaeotropical artocarpus lacucha buch.-ham possess radical scavenging and antiproliferative properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7922997/
https://www.ncbi.nlm.nih.gov/pubmed/33670764
http://dx.doi.org/10.3390/molecules26041078
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