Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Pecio, Łukasz, Pecio, Solomiia, Mroczek, Tomasz, Oleszek, Wiesław
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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
_version_ 1785081504838189056
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
work_keys_str_mv AT peciołukasz spiroflavonoidsinnatureacriticalreviewofstructuraldiversityandbioactivity
AT peciosolomiia spiroflavonoidsinnatureacriticalreviewofstructuraldiversityandbioactivity
AT mroczektomasz spiroflavonoidsinnatureacriticalreviewofstructuraldiversityandbioactivity
AT oleszekwiesław spiroflavonoidsinnatureacriticalreviewofstructuraldiversityandbioactivity