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Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity
Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity. The review collects 65 unique structures, including spiro-bifl...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10385819/ https://www.ncbi.nlm.nih.gov/pubmed/37513292 http://dx.doi.org/10.3390/molecules28145420 |
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author | Pecio, Łukasz Pecio, Solomiia Mroczek, Tomasz Oleszek, Wiesław |
author_facet | Pecio, Łukasz Pecio, Solomiia Mroczek, Tomasz Oleszek, Wiesław |
author_sort | Pecio, Łukasz |
collection | PubMed |
description | Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity. The review collects 65 unique structures, including spiro-biflavonoids, spiro-triflavonoids, spiro-tetraflavonoids, spiro-flavostilbenoids, and scillascillin-type homoisoflavonoids. Scillascillin-type homoisoflavonoids comprise spiro[bicyclo[4.2.0]octane-7,3′-chromane]-1(6),2,4-trien-4′-one, while the other spiro-flavonoids contain either 2H,2′H-3,3′-spirobi[benzofuran]-2-one or 2′H,3H-2,3′-spirobi[benzofuran]-3-one in the core of their structures. Spiro-flavonoids have been described in more than 40 species of eight families, including Asparagaceae, Cistaceae, Cupressaceae, Fabaceae, Pentaphylacaceae, Pinaceae, Thymelaeaceae, and Vitaceae. The possible biosynthetic pathways for each group of spiro-flavonoids are summarized in detail. Anti-inflammatory and anticancer activities are the most important biological activities of spiro-flavonoids, both in vitro and in vivo. Our work identifies the most promising natural sources, the existing challenges in assigning the stereochemistry of these compounds, and future research perspectives. |
format | Online Article Text |
id | pubmed-10385819 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-103858192023-07-30 Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity Pecio, Łukasz Pecio, Solomiia Mroczek, Tomasz Oleszek, Wiesław Molecules Review Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity. The review collects 65 unique structures, including spiro-biflavonoids, spiro-triflavonoids, spiro-tetraflavonoids, spiro-flavostilbenoids, and scillascillin-type homoisoflavonoids. Scillascillin-type homoisoflavonoids comprise spiro[bicyclo[4.2.0]octane-7,3′-chromane]-1(6),2,4-trien-4′-one, while the other spiro-flavonoids contain either 2H,2′H-3,3′-spirobi[benzofuran]-2-one or 2′H,3H-2,3′-spirobi[benzofuran]-3-one in the core of their structures. Spiro-flavonoids have been described in more than 40 species of eight families, including Asparagaceae, Cistaceae, Cupressaceae, Fabaceae, Pentaphylacaceae, Pinaceae, Thymelaeaceae, and Vitaceae. The possible biosynthetic pathways for each group of spiro-flavonoids are summarized in detail. Anti-inflammatory and anticancer activities are the most important biological activities of spiro-flavonoids, both in vitro and in vivo. Our work identifies the most promising natural sources, the existing challenges in assigning the stereochemistry of these compounds, and future research perspectives. MDPI 2023-07-14 /pmc/articles/PMC10385819/ /pubmed/37513292 http://dx.doi.org/10.3390/molecules28145420 Text en © 2023 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 | Review Pecio, Łukasz Pecio, Solomiia Mroczek, Tomasz Oleszek, Wiesław Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title | Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title_full | Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title_fullStr | Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title_full_unstemmed | Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title_short | Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity |
title_sort | spiro-flavonoids in nature: a critical review of structural diversity and bioactivity |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10385819/ https://www.ncbi.nlm.nih.gov/pubmed/37513292 http://dx.doi.org/10.3390/molecules28145420 |
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