3162-03-6Relevant articles and documents
Ability of prenylflavanones present in hops to induce apoptosis in a human burkitt lymphoma cell line
Diller, Reinhard A.,Riepl, Herbert M.,Rose, Oliver,Frias, Corazon,Henze, Guenter,Prokop, Aram
, p. 755 - 761 (2007)
The identification of effective cancer preventive compounds from hops has become an important issue in public health-related research. We compared the antiproliferative and apoptosis-inducing effects of side chain variants of prenylflavanones, e.g., 8-prenylnaringenin (7) and 8-geranylnaringenin (10), which have been identified in hops (Humulus lupulus), and their synthetic variations 8-furanmethylnaringenin (8) and 8-cinnamylnaringenin (9). These were accessible by a Mitsunobu reaction and Claisen rearrangement. Flavanones 9 and 10 showed cytotoxic and apoptotic activities. Apoptosis was induced in a mitochondrial dependent manner. 8-Cinnamylnaringenin (9) displayed noticeably improved apoptotic effects when compared to 8-prenylnaringenin. The potential of 8-prenylnaringenin (7) is shown in an ex vivo experiment on a multi-drug resistant leukaemia blast. Georg Thieme Verlag KG Stuttgart.
Synthesis of xanthohumol and xanthohumol-d3from naringenin
?cianowski, Jacek,Andrusiak, Joanna,Budny, Marcin,Mylkie, Kinga,Wolan, Andrzej,Wysocka, Ma?gorzata
, p. 28934 - 28939 (2021/09/22)
A six-step synthesis of xanthohumol (1a) and its d3-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound1bwas used as an internal standard in stable isotope dilution assays of1ain two Polish beers.
Molecular docking and panicolytic effect of 8-prenylnaringenin in the elevated T-maze
Bagatin, Mariane Cristovo,Tozatti, Camila Santos Suniga,Abiko, Layara Akemi,Dos Santos Yamazaki, Diego Alberto,Silva, Priscila Rebeca Alves,Perego, Leonardo Martins,Audi, Elisabeth Aparecida,Seixas, Flavio Augusto Vicente,Basso, Ernani Abicht,De Freitas Gauze, Gisele
supporting information, p. 1231 - 1237 (2015/02/18)
The purpose of this study was to investigate the effects of the chronic administration of a racemic mixture of 8-prenylnaringenin (8-PN) on rats submitted to the elevated T-maze (ETM) model of generalized anxiety and panic disorders. The selective serotonin (SERT) reuptake inhibitor fluoxetine was used as a positive control. Rat locomotion was assessed in a circular arena following each drug treatment. The administration of racemic 8-PN for 21 d in rats increased one-way escape latencies from the ETM open arm, indicating a panicolytic effect. To evaluate the interactions of 8-PN with monoamine transporters, a docking study was performed for both the R and S configurations of 8-PN towards SERT, norepinephrine (NET) and dopamine transporters (DAT). The application of the docking protocol showed that (R)-8-PN provides greater affinity to all transporters than does the S enantiomer. This result suggests that enantiomer (R)-8-PN is the active form in the in vivo test of the racemic mixture.
