68682-01-9

Usage

Uses

Used in Pharmaceutical Industry:
5,7,4'-trihydroxy-6-prenylflavanone is used as a bioactive compound for its antimicrobial properties. It demonstrates growth inhibition against various bacterial strains, such as Escherichia coli, Staphylococcus aureus, and Klebsiella pneumoniae, making it a promising candidate for the development of new antimicrobial agents to combat drug-resistant infections.
Used in Cosmetic Industry:
5,7,4'-trihydroxy-6-prenylflavanone can be used as an active ingredient in the cosmetic industry due to its potential antioxidant and anti-inflammatory properties. These characteristics may contribute to the development of skincare products aimed at promoting skin health and addressing various skin conditions.
Used in Food Industry:
As a natural product with antimicrobial properties, 5,7,4'-trihydroxy-6-prenylflavanone can be utilized in the food industry as a preservative to extend the shelf life of perishable products and maintain their quality. Its potential antioxidant activity may also be beneficial in the development of functional foods with added health benefits.
Used in Agricultural Industry:
The antimicrobial properties of 5,7,4'-trihydroxy-6-prenylflavanone can be harnessed in the agricultural industry for the development of natural pesticides or fungicides. These could be used to protect crops from various pathogens, reducing the reliance on synthetic chemicals and promoting sustainable agricultural practices.

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 480-41-1 naringenin 
• 1186-30-7 3,3-dimethylallyl diphosphate triammonium salt 
• 569-83-5 xanthohumol 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 870-63-3 prenyl bromide 
• 115063-39-3 desmethylxanthohumol 
• 1026476-67-4 7,4’-O,O-diacetoxy-6-prenylnaringenin 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 358-72-5 dimethylallyl diphosphate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 199393-58-3 2′,4,4′-trimethoxymethoxy-6′-hydroxy-3′-prenylchalcone 
• 160624-22-6 1-{2,4-bis(methoxymethoxy)-6-[(3-methylbut-2-en-1-yl)oxy]phenyl}ethanone 
• 90632-20-5 1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone 

Downstream Products

• 70872-26-3 5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H,8H-benzo-<1,2-b;5,4-b'>dipyran-4-one 
• 68634-19-5 (+/-)-3,4,8,9-Tetrahydro-5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-on 
• 68634-18-4 (+/-)-2,3,7,8-Tetrahydro-5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,6H-benzo<1,2-b:5,4-b'>dipyran-4-on 
• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 115063-39-3 desmethylxanthohumol 

Relevant academic research and scientific papers

Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC

Prenylflavonoids are an unique class of phytochemicals found in the inflorescences of the hop plant (Humulus lupulus). These flavonoids have demonstrated a wide range of biological activities, which may be influenced by their stereochemical configuration.

Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells

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.

Prenylated flavonoids with potential antimicrobial activity: Synthesis, biological activity, and in silico study

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

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

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Semi-Synthetic Approach Leading to 8-Prenylnaringenin and 6-Prenylnaringenin: Optimization of the Microwave-Assisted Demethylation of Xanthohumol Using Design of Experiments

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.

Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers

Since 6-prenylnaringenin (6-PNG) was recently identified as a novel T-type calcium channel blocker with the IC50 value around 1 μM, a series of flavanone derivatives were designed, synthesized and subsequently evaluated for T-channel-blocking a

Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.

Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities

NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3(2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism.

Selective C-6 prenylation of flavonoids via europium(III)-catalyzed claisen rearrangement and cross-metathesis

Starting from the readily available parent flavonoids, the flavanone 6-prenylnaringenin, the isoflavone 6-prenylgenistein (wighteone, erythrinin B) and a protected derivative of the flavonol 6-prenylquercetin (gancaonin P) have been synthesized in short reaction sequences featuring the title processes as key steps.