68682-02-0Relevant articles and documents
Transformation of 8-prenylnaringenin by Absidia coerulea and Beauveria bassiana
Bartmanska, Agnieszka,Tronina, Tomasz,Huszcza, Ewa
, p. 6451 - 6453 (2012)
Beauveria bassiana AM278 and Absidia coerulea AM93 converted 8-prenylnaringenin (1) into two glycoside derivatives (7-O-β-d- glucopyranoside) (2) and 7-O-β-d-4?-O-methylglucopyranoside) (3) in high yields in processes conducted in Saboraud medium. 8-Prenylnaringenin 7-O-β-d-4?-O-methylglucopyranoside (3) is a new compound. 8-Prenylnaringenin-7-sulfate (4) was obtained in transformation of 1 by Absidia coerulea AM93 in a buffer. Formation of conjugated products in this study proceeds in a manner analogous to mammalian systems which indicates the potential use of microbes to mimic mammalian metabolism.
Prenylated flavonoids with potential antimicrobial activity: Synthesis, biological activity, and in silico study
Osorio, Mauricio,Carvajal, Marcela,Vergara, Alejandra,Butassi, Estefania,Zacchino, Susana,Mascayano, Carolina,Montoya, Margarita,Mejías, Sophia,Martín, Marcelo Cortez-San,Vásquez-Martínez, Yesseny
, (2021/05/28)
Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7–13, with an emphasis on antimicrobial ones. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4′ are key to the antibacterial activity. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy; however, more studies are needed to support this result.
Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study
Aigner, Ludwig,Bieler, Lara,Couillard-Despres, Sebastien,Priglinger, Eleni,Riepl, Herbert M.,Urmann, Corinna
supporting information, p. 2675 - 2682 (2021/10/12)
Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad
Semi-Synthetic Approach Leading to 8-Prenylnaringenin and 6-Prenylnaringenin: Optimization of the Microwave-Assisted Demethylation of Xanthohumol Using Design of Experiments
Riepl, Herbert,Urmann, Corinna
, (2020/09/17)
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.
Formation of (2 R)- And (2 S)-8-Prenylnaringenin Glucuronides by Human UDP-Glucuronosyltransferases
Fang, Jin-Bo,Nikoli?, Dejan,Lankin, David C.,Simmler, Charlotte,Chen, Shao-Nong,Ramos Alvarenga, Rene F.,Liu, Yang,Pauli, Guido F.,Van Breemen, Richard B.
, p. 11650 - 11656 (2019/10/21)
Occurring in hops (Humulus lupulus) and beer as a racemic mixture, (2R,2S)-8-prenylnaringenin (8-PN) is a potent phytoestrogen in hop dietary supplements used by women as alternatives to conventional hormone therapy. With a half-life exceeding 20 h, 8-PN is excreted primarily as 8-PN-7-O-glucuronide or 8-PN-4′-O-glucuronide. Human liver microsomes and 11 recombinant human UDP-glucuronosyltransferases (UGTs) were used to catalyze the formation of the two oxygen-linked glucuronides of purified (2R)-8-PN and (2S)-8-PN, which were subsequently identified using mass spectrometry and nuclear magnetic resonance spectroscopy. Formation of (2R)- and (2S)-8-PN-7-O-glucuronides predominated over the 8-PN-4′-O-glucuronides except for intestinal UGT1A10, which formed more (2S)-8-PN-4′-O-glucuronide. (2R)-8-PN was a better substrate for all 11 UGTs except for UGT1A1, which formed more of both (2S)-8-PN glucuronides than (2R)-8-PN glucuronides. Although several UGTs conjugated both enantiomers of 8-PN, some conjugated just one enantiomer, suggesting that human phenotypic variation might affect the routes of metabolism of this chiral estrogenic constituent of hops.
In vitro effect of 8-prenylnaringenin and naringenin on fibroblasts and glioblastoma cells-cellular accumulation and cytotoxicity
Stompor, Monika,Uram, ?ukasz,Podgórski, Rafa?
, (2017/08/29)
Gliomas are one of the most aggressive and treatment-resistant types of human brain cancer. Identification and evaluation of anticancer properties of compounds found in plants, such as naringenin (N) and 8-prenylnaringenin (8PN), are among the most promising applications in glioma therapy. The prenyl group seems to be crucial to the anticancer activity of flavones, since it may lead to enhanced cell membrane targeting and thus increased intracellular activity. It should be noted that 8PN content in hop cones is 10 to 100 times lower compared to other flavonoids, such as xanthohumol. In the study presented, we used a simple method for the synthesis of 8PN from isoxanthohumol - O-demethylation, with a high yield of 97%. Cellular accumulation and cytotoxicity of naringenin and 8-prenylnaringenin in normal (BJ) and cancer cells (U-118 MG) was also examined. Obtained data indicated that 8-prenylnaringenin exhibited higher cytotoxicity against used cell lines than naringenin, and the effect of both flavones was stronger in U-118 MG cells than in normal fibroblasts. The anticancer properties of 8PN correlated with its significantly greater (37%) accumulation in glioblastoma cells than in normal fibroblasts. Additionally, naringenin demonstrated higher selectivity for glioblastoma cells, as it was over six times more toxic for cancer than normal cells. Our results provide evidence that examined prenylated and non-prenylated flavanones have different biological activities against normal and cancer cell lines, and this property may be useful in designing new anticancer drugs for glioblastoma therapy.
Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells
Luescher, Sandro,Urmann, Corinna,Butterweck, Veronika
, p. 925 - 931 (2017/05/05)
For the prenylated hops phenols 6- and 8-prenylnaringenin (1 and 2), xanthohumol (3), and isoxanthohumol (4), a variety of biological activities has been described. In the current study, a transwell based in vitro model using the human intestinal epithelial cell line Caco-2 was developed to assess potential beneficial effects of compounds 1-4 on TNF-α-induced impairment of tight junction (TJ) permeability. Transepithelial electrical resistance (TEER) was measured using the latest cellZScope online monitoring device. TNF-α treatment (25 ng/mL) induced a significant decrease in TEER values (204.71 ± 4.57 at 72 h) compared to that in control values (245.94 ± 1.68 at 72 h). To determine preventive effects on TNF-α-induced impairment of TJ permeability, 1-4 were added to the apical compartment of Caco-2 monolayers 1 h before TNF-α treatment; afterward, TNF-α was added to the basolateral compartment to induce TJ dysfunction and incubated for a further 72 h. Using this setting, only 1 and 2 prevented epithelial disruption induced by TNF-α. To evaluate restorative effects of 1-4, TNF-α was added to the basolateral compartment of Caco-2 cell monolayers. After 48 h of incubation, 1-4 were added to the apical side, and TEER values were monitored online for a further 72 h. Under these experimental conditions, only 2 restored TNF-α induced barrier dysfunction.
Sensomics Analysis of Key Bitter Compounds in the Hard Resin of Hops (Humulus lupulus L.) and Their Contribution to the Bitter Profile of Pilsner-Type Beer
Dresel, Michael,Dunkel, Andreas,Hofmann, Thomas
, p. 3402 - 3418 (2015/04/14)
Recent brewing trials indicated the occurrence of valuable bitter compounds in the hard resin fraction of hop. Aiming at the discovery of these compounds, hop's ε-resin was separated by means of a sensory guided fractionation approach and the key taste mo
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
, 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.
A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation
Lemke, Marie-Kristin,Schwab, Pia,Fischer, Petra,Tischer, Sandra,Witt, Morris,Noehringer, Laurence,Rogachev, Victor,Jaeger, Anne,Kataeva, Olga,Froehlich, Roland,Metz, Peter
, p. 11651 - 11655 (2013/11/06)
A surprisingly selective, non-enzymatic kinetic resolution of readily available, racemic β-chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p-toluenesulfonyl). Copyright
