ArticleMolecules (Basel, Switzerland)2020
Semi-Synthetic Approach Leading to 8-Prenylnaringenin and 6-Prenylnaringenin: Optimization of the Microwave-Assisted Demethylation of Xanthohumol Using Design of Experiments.
Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 12 citations in OpenAlex.
- Extraction Behavior and Quantitative Profiling of Prenylated Flavonoids from Hops (Molecules (Basel, Switzerland) · 2025Article
- 6-Prenylnaringenin-Its Beneficial Biological Effects and Possible Applications.International journal of molecular sciences · 2025Review
- Mechanism of Action and Therapeutic Potential of Xanthohumol in Prevention of Selected Neurodegenerative Diseases.Molecules (Basel, Switzerland) · 2025Review
- Semi-Synthesis of Different Pyranoflavonoid Backbones and the Neurogenic Potential.Molecules (Basel, Switzerland) · 2023Article
- Naringenin and Phytoestrogen 8-Prenylnaringenin Protect against Islet Dysfunction and Inhibit Apoptotic Signaling in Insulin-Deficient Diabetic Mice.Molecules (Basel, Switzerland) · 2022Article
- Preparation of Hop Estrogen-Active Material for Production of Food Supplements.Molecules (Basel, Switzerland) · 2021Article
- Stable Isotope Dilution Analysis of the Major Prenylated Flavonoids Found in Beer, Hop Tea, and Hops.Frontiers in nutrition · 2020Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The isomers 8-prenylnaringenin and 6-prenylnaringenin, both secondary metabolites occurring in hops, show interesting biological effects, like estrogen-like, cytotoxic, or neuro regenerative activities. Accordingly, abundant sources for this special flavonoids are needed. Extraction is not recommended due to the very low amounts present in plants and different synthesis approaches are characterized by modest yields, multiple steps, the use of expensive chemicals, or an elaborate synthesis. An easy synthesis strategy is the demethylation of xanthohumol, which is available due to hop extraction industry, using lithium chloride and dimethylformamide, but byproducts and low yield did not make this feasible until now. In this study, the demethylation of xanthohumol to 8-prenylnaringenin and 6-prenylnaringenin is described the first time and this reaction was optimized using Design of Experiment and microwave irradiation. With the optimized conditions-temperature 198 °C, 55 eq. lithium chloride, and a reaction time of 9 min, a final yield of 76% of both prenylated flavonoids is reached.
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