ArticleJournal of agricultural and food chemistry2013
Dynamic residual complexity of the isoliquiritigenin-liquiritigenin interconversion during bioassay.
Article in Journal of agricultural and food chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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Who cites it
40 citing papers in PubMed.
- Isoliquiritigenin as a Neuronal Radiation Mitigant: Mitigating Radiation-Induced Anhedonia Tendency Targeting Grik3/Grm8/Grin3a via Integrated Proteomics and AI-Driven Discovery.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Harnessing Liquiritigenin: A Flavonoid-Based Approach for the Prevention and Treatment of Cancer.Cancers · 2025Review
- Elucidating the metabolic roles of isoflavone synthase-mediated protein-protein interactions in yeast.bioRxiv : the preprint server for biology · 2024Article
- A Review of Recent Curcumin Analogues and Their Antioxidant, Anti-Inflammatory, and Anticancer Activities.Antioxidants (Basel, Switzerland) · 2024Review
- Chemical Composition of Methanol Extracts from Leaves and Flowers ofInternational journal of molecular sciences · 2024Article
- Auto-hydrolysis of red clover as "green" approach to (iso)flavonoid enriched products.Fitoterapia · 2021Article
- Do Certain Flavonoid IMPS Have a Vital Function?Frontiers in nutrition · 2021Review
- Development of an Improved Menopausal Symptom-Alleviating Licorice (Journal of microbiology and biotechnology · 2020Article
- Dynamics of the isoflavone metabolome of traditional preparations of Trifolium pratense L.Journal of ethnopharmacology · 2019Article
- High-Resolution Structure of ClpC1-Rufomycin and Ligand Binding Studies Provide a Framework to Design and Optimize Anti-Tuberculosis Leads.ACS infectious diseases · 2019Article
- Liquiritigenin Reduces Blood Glucose Level and Bone Adverse Effects in Hyperglycemic Adult Zebrafish.Nutrients · 2019Article
- Evidence for Chemopreventive and Resilience Activity of Licorice:Cancer prevention research (Philadelphia, Pa.) · 2018Article
- Licorice root components mimic estrogens in an object location task but not an object recognition task.Hormones and behavior · 2018Article
- Synthesis and Antiproliferative Activity of Minor Hops Prenylflavonoids and New Insights on Prenyl Group Cyclization.Molecules (Basel, Switzerland) · 2018Article
- Phytochemical and Pharmacological Role of Liquiritigenin and Isoliquiritigenin From Radix Glycyrrhizae in Human Health and Disease Models.Frontiers in aging neuroscience · 2018Review
- Cytochrome P450 inhibition by three licorice species and fourteen licorice constituents.European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences · 2017Article
- Isolation and structural characterization of dihydrobenzofuran congeners of licochalcone A.Fitoterapia · 2017Article
- DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women's Health.Journal of natural products · 2017Article
- Medicago truncatula ABCG10 is a transporter of 4-coumarate and liquiritigenin in the medicarpin biosynthetic pathway.Journal of experimental botany · 2017Article
- Curcumin May (Not) Defy Science.ACS medicinal chemistry letters · 2017Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Bioactive components in food plants can undergo dynamic processes that involve multiple chemical species. For example, 2'-hydroxychalcones can readily isomerize into flavanones. Although chemically well documented, this reaction has barely been explored in the context of cell-based assays. The present time-resolved study fills this gap by investigating the isomerization of isoliquiritigenin (a 2'-hydroxychalcone) and liquiritigenin (a flavanone) in two culture media (Dulbecco's modified eagle medium and Roswell Park Memorial Institute medium) with and without MCF-7 cells, using high-performance liquid chromatography-diode array detector-electrospray ionization/atmospheric pressure chemical ionization-mass spectrometry for analysis. Both compounds were isomerized and epimerized under all investigated biological conditions, leading to mixtures of isoliquiritigenin and R/S-liquiritigenin, with 19.6% R enantiomeric excess. Consequently, all three species can potentially modulate the biological responses. This exemplifies dynamic residual complexity and demonstrates how both nonchiral reactions and enantiomeric discrimination can occur in bioassay media, with or without cells. The findings highlight the importance of controlling in situ chemical reactivity, influenced by biological systems when evaluating the mode of action of bioactives.
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