480-43-3

Usage

Uses

Used in Pharmaceutical Industry:
ISOSAKURANETIN is used as a bioactive compound for its potential therapeutic properties. It has been found to possess various pharmacological activities, such as antioxidant, anti-inflammatory, and anticancer effects. Its presence in Citrus bergamia fruit makes it a promising candidate for the development of novel drugs and supplements targeting these health issues.
Used in Cosmetic Industry:
ISOSAKURANETIN is used as an active ingredient in cosmetics for its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to help protect the skin from environmental stressors, reduce inflammation, and promote a healthy, youthful appearance.
Used in Functional Foods and Nutraceuticals:
ISOSAKURANETIN is used as a functional ingredient in the development of foods and nutraceuticals that aim to promote health and well-being. Its antioxidant and anti-inflammatory properties can contribute to the overall health benefits of these products, making them more appealing to consumers seeking natural and healthy options.
Used in Agricultural Industry:
ISOSAKURANETIN can be used as a natural pesticide or growth promoter in the agricultural industry. Its bioactive properties may help protect crops from pests and diseases, while also promoting healthy growth and development.

InChI:InChI=1/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

Upstream product

• 491-69-0 (2S)-poncirenin 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 77-78-1 dimethyl sulfate 
• 108-73-6 3,5-dihydroxyphenol 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 327096-49-1 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 42996-84-9 p-methoxycinnamoyl chloride 
• 10236-47-2 naringin 
• 186581-53-3 diazomethane 
• 137225-57-1 (E)-3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 

Downstream Products

• 1181215-24-6 8-geranylisosakuranetin 
• 76172-68-4 3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 117894-08-3 5,7-diacetoxy-2-(4-methoxy-phenyl)-chroman-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 100-09-4 4-methoxybenzoic acid 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham

Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.

Iterative polyketide synthesis via a consecutive carbonyl-protecting strategy

To address the difficulty in protecting a β-polycarbonyl compound, a method for the sequential protection of elongating carbonyl groups was demonstrated. The iterative chain elongation of a carboxylic acid with malonic acid half thioester followed by the protection of the resulting β-ketothioester was performed via the stepwise formation of an isoxazole ring using an O-protected oxime functionality. Yangonin and isosakuranetin were synthesized according to this procedure.

Synthesis and biological evaluation of novel flavanone derivatives as potential antipsychotic agents

In this study, a series of novel flavanone derivatives were designed and synthesized, and the antipsychotic activities of the target compounds were evaluated in vitro and in vivo. The results showed that synthesized compounds 7a–7g decreased the activity of dopamine D2 receptors in HEK293 cells co-transfected with D2 receptor/G protein α16a, with IC50 values of 0.051–0.35?μm. Compounds 7a–7g inhibited the over-production of nitric oxide stimulated by lipopolysaccharide/interferon-γ in BV-2 microglial cells. In mice, intragastric administration of 7d, 7e, and 7g reversed the increase in locomotor activity induced by MK-801 (an antagonist of NMDA receptors) and decreased the hyperactivity of climbing behavior induced by apomorphine (a dopamine receptor agonist). These results suggest that some of the novel flavanone derivatives have potential antipsychotic effects and may be useful in the treatment of schizophrenia.

Flavanone derivative, preparation method and uses thereof

The present invention relates to a flavanone derivative, a preparation method and uses thereof, particularly to a compound represented by a formula I or a pharmaceutically acceptable salt thereof, a pharmaceutical composition, and a preparation method thereof, and uses of the pharmaceutical composition in prevention or treatment of mental disorders and nervous system diseases. According to the present invention, the compound has excellent microglia activation inhibition activity and excellent neuroinflammation reaction inhibition activity, can antagonize a dopamine type 2 receptor, can improve the behavioral changes of a variety of mental disorder animal models, can effectively inhibit neuroinflammation and myelinoclasis, and can be used for the prevention or the treatment of mental disorders and nervous system diseases. The formula I is defined in the specification.

Synthesis and biological evaluation of 5,7-dihydroxyflavanone derivatives as antimicrobial agents

A series of 5,7-dihydroxyflavanone derivatives were efficiently synthesized. Their antimicrobial efficacy on Gram-negative, Gram-positive bacteria and yeast were evaluated. Among these compounds, most of the halogenated derivatives exhibited the best antimicrobial activity against Gram-positive bacteria, the yeast Saccharomyces cerevisiae, and the Gram-negative bacterium Vibrio cholerae. The cytotoxicities of these compounds were low as evaluated on HepG2 cells using a cell viability assay. This study suggests that halogenated flavanones might represent promising pharmacological candidates for further drug development.

Synthesis and studies on antidepressant effect of 5,7-Dihydroxyflavanone derivatives

A series of 5,7-dihydroxyflavanone derivatives were synthesized and evaluated their antidepressant activities. The results showed that of nine compounds significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 4o (4'-methoxy-5,7,3'-trihydroxyflavanone) was found to be the most potent and it was observed that the compound 4o at dose of 10, 20 and 40 mg/kg significantly reduced the duration of immobility times in the Forced swimming test in mice 0.5 h after treatment.