25515-46-2

Usage

Compound class

Chalcones, which are natural phenolic compounds.

Antioxidant properties

Capable of inhibiting oxidation in other molecules, thus preventing cell damage and potential health issues.

Biological activities

Has shown promise in various biological activities, including anti-inflammatory, anti-cancer, and anti-diabetic properties.

Cancer cell growth inhibition

Demonstrated potential in inhibiting cancer cell growth and inducing apoptosis (cell death) in cancer cells.

Inflammation reduction

Has the ability to reduce inflammation, which can contribute to various health issues.

Upstream product

• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 524-14-1 malonyl-CoA 
• 30802-00-7 hydroxycinnamoyl-S-CoA 
• 30802-00-7 4-coumaroyl-coenzyme A 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 61777-22-8 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 55260-28-1 1-[2,4,6-Tris-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 28090-12-2 4-(3-methyl-but-2-enyloxy)-benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 

Downstream Products

• 60-82-2 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 158196-35-1 naringenin-4'-O-β-D-glucuronide 
• 1174375-93-9 naringenin chalcone-2'-O-β-D-glucuronide 
• 158196-34-0 Naringenin 7-O-glucuronide 
• 480-41-1 naringenin 
• 480-41-1 (+)-Naringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 724434-08-6 dihydrokaempferol 
• 20565-42-8 chalconaringenin 2'-glucoside 

Relevant academic research and scientific papers

Enzymatic formation of a resorcylic acid by creating a structure-guided single-point mutation in stilbene synthase

A novel C17 resorcylic acid was synthesized by a structure-guided Vitis vinifera stilbene synthase (STS) mutant, in which threonine 197 was replaced with glycine (T197G). Altering the architecture of the coumaroyl binding and cyclization pocket of the enzyme led to the attachment of an extra acetyl unit, derived from malonyl-CoA, to p-coumaroyl-CoA. The resulting novel pentaketide can be produced strictly by STS-like enzymes and not by Chalcone synthase-like type III polyketide synthases; due to the unique thioesterase like activity of STS-like enzymes. We utilized a liquid chromatography mass spectrometry-based data analysis approach to directly compare the reaction products of the mutant and wild type STS. The findings suggest an easy to employ platform for precursor-directed biosynthesis and identification of unnatural polyketides by structure-guided mutation of STS-like enzymes.

Enzymatic formation of long-chain polyketide pyrones by plant type III polyketide synthases

Recombinant chalcone synthase from Scutellaria baicalensis and stilbene synthase from Arachis hypogaea accepted CoA esters of long-chain fatty acid as a starter substrate, and carried out sequential condensations with malonyl-CoA, leading to formation of triketide and tetraketide α-pyrones. Recombinant chalcone synthase (CHS) from Scutellaria baicalensis and stilbene synthase (STS) from Arachis hypogaea accepted CoA esters of long-chain fatty acid (CHS up to the C12 ester, while STS up to the C14 ester) as a starter substrate, and carried out sequential condensations with malonyl-CoA, leading to formation of triketide and tetraketide α-pyrones. Interestingly, the C6, C8, and C10 esters were kinetically favored by the enzymes over the physiological starter substrate; the k cat/KM values were 1.2- to 1.9-fold higher than that of p-coumaroyl-CoA. The catalytic diversities of the enzymes provided further mechanistic insights into the type III PKS reactions, and suggested involvement of the CHS-superfamily enzymes in the biosynthesis of long-chain alkyl polyphenols such as urushiol and ginkgolic acid in plants.

Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro

Prenylated flavonoids found in hops and beer, i.e., prenylchalcones and prenylflavanones, were examined for their ability to inhibit in vitro oxidation of human low-density lipoprotein (LDL). The oxidation of LDL was assessed by the formation of conjugate

Isoliquiritigenin Derivatives Inhibit RANKL-Induced Osteoclastogenesis by Regulating p38 and NF-κB Activation in RAW 264.7 Cells

Bone diseases may not be imminently life-threatening or a leading cause of death such as heart diseases or cancers. However, as aging population grows in almost every part of the world, they surely impose significant socioeconomic burden on the society, not to mention the patients and their families. Osteoporosis is the most common type of bone disease, which frequently develops in seniors, especially in postmenopausal women. Although currently several anti-osteoclastic drugs designed to suppress excessive osteoclast activation, a major cause of osteoporosis, are commercially available, accompanying adverse effects ranging from mild to severe have been reported as well. Natural products have become increasingly popular because of their effectiveness with fewer side effects. Isoliquiritigenin (ILG), a natural flavonoid from licorice, has been reported to suppress osteoclast differentiation and activation. In the present study, newly synthesized ILG derivatives were screened for their anti-osteoporotic activity as more potent substitute candidates to ILG. Out of the 12 ILG derivatives tested, two compounds demonstrated significantly improved bone loss in vitro by inhibiting both osteoclastogenesis and osteoclast activity. The results of the present study indicate that these compounds may serve as a potential drug for osteoporosis and warrant further studies to evaluate their in vivo efficacy.

A kind of A ring with methyl of [...] compound, preparation method and anti-inflammatory activity

The invention discloses a quinoid chalcone compound with a methyl group at an A ring, and a preparation method and anti-inflammatory activity thereof. The compound has a structure as shown in a general formula (I) which is described in the specification. The preparation method comprises the following steps: (1) synthesizing 2-hydroxy-4,6-dimethoxyacetophenone; (2) synthesizing 2'-hydroxy-4',6'-dimethoxychalcone derivative; (3) synthesizing 2',4',6'-trihydroxy chalcone derivative; and (4) synthesizing the quinoid chalcone compound with a methyl group at the A ring. The compound is simple to prepare and has obvious anti-inflammatory action.

Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives

Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.

In Vitro Osteogenic Differentiation and Antibacterial Potentials of Chalcone Derivatives

Chalcone derivatives have been investigated as therapeutic agents for the anticancer, antioxidant, and anti-inflammatory fields. In this study, we have synthesized four different types of chalcone derivatives and demonstrated in vitro bioactivities. We divided these derivatives into two groups of chalcones on the basis of similar substituents on the aromatic rings, and we tested cell viability and proliferation potentials, which indicated that the methoxy substituent on the A ring could enhance cytotoxicity and antiproliferation potential depending on the chalcone concentration. We also investigated osteogenic differentiation of C2C12 cells by ALP staining, the early marker for osteogenesis, which demonstrated that the chalcones could not only induce activity of BMP-2 but also inhibit the activity of noggin, a BMP antagonist. In addition, chalcone bearing hydroxyl groups at the 2-, 4-, and 6-position on the A ring inhibited treptococcus mutans growth, a major causative agent of dental caries. Therefore, we concluded that the chalcone derivatives synthesized in this research can be good candidates for therapeutic agents promoting bone differentiation, with an expectation of inhibiting S. mutans, in dentistry.

Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line).

Antimicrobial activity of xanthohumol and its selected structural analogues

The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group - all of them have it at the C-4 position - demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4′-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4′-methoxychalcones or its replacement by a halogen atom (-Cl, -Br), nitro group (-NO2), ethoxy group (-OCH2CH3), or aliphatic substituent (-CH3, -CH2CH3) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4′-methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis

(Methyl)malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl)malonate from (methyl)Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl)malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone.