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.
Highlights
The isomers 8-prenylnaringenin (8PN) and 6-prenylnaringenin (6PN) are two representatives of prenylated flavonoids -secondary metabolites occurring in hops. 8PN, the most potent phytoestrogen known so far [1], shows a cytotoxic potential even in multi-resistant cancer cells [2]
Can be demethylated to Preliminary experiments experiments showed showed that that xanthohumol xanthohumol (XN)
The demethylation of XN to 8PN and 6PN could be optimized to an overall yield of 76% (HPLC)
Summary
The isomers 8-prenylnaringenin (8PN) and 6-prenylnaringenin (6PN) are two representatives of prenylated flavonoids -secondary metabolites occurring in hops. 8PN, the most potent phytoestrogen known so far [1], shows a cytotoxic potential even in multi-resistant cancer cells [2]. Both compounds slightly induce differentiation in neural precursor cells and can promote the development of neurons from stem cells [8]. These facts make it worthwhile to search for sources for these special flavonoids. In order to meet the needs, not the extraction but the synthetic production is recommended. The synthesis of both flavonoids is characterized by modest yields, several steps using expensive and other medicinal plants ofsynthesis.
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