ArticleMolecules (Basel, Switzerland)2018
Synthesis and Antiproliferative Activity of Minor Hops Prenylflavonoids and New Insights on Prenyl Group Cyclization.
Article in Molecules (Basel, Switzerland), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers, 1 of them a synthesis that pooled it.
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Who cites it
13 citing papers in PubMed, 1 synthesis or guideline pooled it, 34 citations in OpenAlex.
- Disparities in Cisplatin-Induced Cytotoxicity-A Meta-Analysis of Selected Cancer Cell Lines.Molecules (Basel, Switzerland) · 2023Pooled it
- The Influence of Hop Prenylated Chalcones on Mitochondrial Membrane Potential Depolarization and a Response to Oxidative Stress in MCC13 Merkel Cells.Pharmaceuticals (Basel, Switzerland) · 2026Article
- The Role of Natural Chalcones and Their Derivatives in Targeting Prostate Cancer: Recent Updates.International journal of molecular sciences · 2025Review
- Recent Advances in the Synthesis and Biological Applications of Prenylated Chalcones.International journal of molecular sciences · 2025Review
- Review
- Excavating medicinal virtues of chalcones to illuminate a new scope in cancer chemotherapy.RSC advances · 2025Review
- The Effect of Xanthohumol Derivatives on Apoptosis Induction in Canine Lymphoma and Leukemia Cell Lines.International journal of molecular sciences · 2023Article
- Prenylated Flavonoids with Selective Toxicity against Human Cancers.International journal of molecular sciences · 2023Article
- Antioxidants in Hops: Bioavailability, Health Effects and Perspectives for New Products.Antioxidants (Basel, Switzerland) · 2022Review
- Anticancer Activity of Natural and Synthetic Chalcones.International journal of molecular sciences · 2021Review
- Bioactive Compounds Obtained from Polish "Marynka" Hop Variety Using Efficient Two-Step Supercritical Fluid Extraction and Comparison of Their Antibacterial, Cytotoxic, and Anti-Proliferative Activities In Vitro.Molecules (Basel, Switzerland) · 2021Article
- Analyzing bioactive effects of the minor hop compound xanthohumol C on human breast cancer cells using quantitative proteomics.PloS one · 2019Article
- Antimicrobial Properties of Spent Hops Extracts, Flavonoids Isolated Therefrom, and Their Derivatives.Molecules (Basel, Switzerland) · 2018Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops as a lead compound, a series of minor hop prenylflavonoids and synthetic derivatives were obtained by isomerization, cyclisation, oxidative-cyclisation, oxidation, reduction and demethylation reactions. Three human cancer cell lines-breast (MCF-7), prostate (PC-3) and colon (HT-29)-were used in antiproliferative assays, with cisplatin as a control compound. Five minor hop prenyl flavonoids and nine non-natural derivatives of xanthohumol have been synthetized. Syntheses of xanthohumol K, its dihydro- and tetrahydro-derivatives and 1″,2″,α,β-tetrahydroxanthohumol C were described for the first time. All of the minor hops prenyl flavonoids exhibited strong to moderate antiproliferative activity in vitro. The minor hops flavonoids xanthohumol C and 1″,2″-dihydroxanthohumol K and non-natural 2,3-dehydroisoxanthohumol exhibited the activity comparable to cisplatin. Results described in the article suggest that flavonoids containing chromane- and chromene-like moieties, especially chalcones, are potent antiproliferative agents. The developed new efficient, regioselective cyclisation reaction of the xanthohumol prenyl group to 1″,2″-dihydroxantohumol K may be used in the synthesis of other compounds with the chromane moiety.
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