189299-03-4Relevant academic research and scientific papers
Fate of xanthohumol and related prenylflavonoids from hops to beer
Stevens, Jan F.,Taylor, Alan W.,Clawson, Jeff E.,Deinzer, Max L.
, p. 2421 - 2428 (1999)
The fate of three prenylated flavonoids of the chalcone type, xanthohumol, desmethylxanthohumol, and 3'-geranylchalconaringenin, was monitored with LC/MS-MS from hops (Humulus lupulus L.) to beer in two brewing trials. The three prenylchalcones were largely converted into their isomeric flavanones, isoxanthohumol, prenylnaringenins, and geranylnaringenins, respectively, in the boiling wort. Losses of prenylflavonoids were due to incomplete extraction from the hops into the wort (13-25%), adsorption to insoluble malt proteins (18-26%), and adsorption to yeast cells (11-32%) during fermentation. The overall yield of xanthohumol, after lagering of the beer and largely in the form of isoxanthohumol, amounted to 22-30% of the hops' xanthohumol. About 10% of the hops' desmethylxanthohumol, completely converted into prenylnaringenins, remained in the beers. 3'- Geranylchalconaringenin behaved similarly to desmethylxanthohumol. Solubility experiments indicated that (1) malt carbohydrates form soluble complexes with xanthohumol and isoxanthohumol and (2) solubility does not dictate the isoxanthohumol levels of finished beers.
Synthesis of natural 3′-Prenylchalconaringenin and biological evaluation of ameliorating non-alcoholic fatty liver disease and metabolic syndrome
Zhang, Mengdi,Wang, Zhaoxin,Hao, Siyu,Hao, Lei,Zhang, Xinying,Yu, Peng,Sun, Hua
, (2020/08/12)
Non-alcoholic fatty liver disease (NAFLD) is the most common cause of chronic liver disease and important risk factor for cardiac diseases, diabetes and extrahepatic cancers. Natural 3′-geranylchalconaringenin (GC) and desmethylxanthohumol (DX) from hop w
A facile synthetic approach to prenylated flavanones: First total syntheses of (±)-bonannione A and (±)-sophoraflavanone A
Wang,Tan,Li,Li
, p. 196 - 199 (2007/10/03)
A facile and efficient approach for the syntheses of both C-8 and C-6 prenylated flavonoids has been developed that features a highly regioselective prenylation of 2,4,6-trihydroxyacetophenone and regioselective cyclization of prenylated polyhydroxy chalcones. Thus, the first efficient total syntheses of (±)sophoraflavanone A (1) and (±)-bonannione A (2), two naturally occurring geranylated flavanones with antibacterial activities, have been achieved starting from the key intermediate 3 via regioselective cyclization of geranylated tetrahydroxychalcone 4.
