• International Journal of Oral Biology
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• v.43 no.1
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• pp.29-35
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• 2018

It is noted that chalcone derivatives have characteristic diverse pharmacological properties, and that precise evidence has been growing that they could regulate a tumor necrosis $factor-{\alpha}$ ($TNF-{\alpha}$) induced insulin resistance. The purpose of the present investigation is to elucidate the effects of the identified chalcone derivatives on adipogenesis, and to find the underlying mechanism of action in that case. Consequently, we first investigated whether the chalcone derivatives could affect the identified $PPAR{\gamma}$-induced transcriptional activity on the proliferator-activated receptor response elements (PPRE) at target promoters, and find that trans-chalcone most significantly increased the $PPAR{\gamma}$-induced transcriptional activity. Additionally, we confirmed that there were up-regulatory effects of trans-chalcone during the adipogenesis and lipid accumulation, and on the mRNA of adipogenic factors in 3T3-L1 cells. Next, we examined the effect of trans-chalcone on the inhibition induced by $TNF-{\alpha}$ on adipogenesis. To that end, we noted that the treatment with trans-chalcone attenuated the effect of $TNF-{\alpha}$ mediated secretion of various adipokines that are involved in insulin sensitivity. For this reason, we noted that this study clearly demonstrates that trans-chalcone enhanced adipogenesis, in part, by its potent effect on $PPAR{\gamma}$ activation and by its reverse effect on $TNF-{\alpha}$.

• Bulletin of the Korean Chemical Society
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• v.23 no.3
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• pp.469-476
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• 2002

Photocrosslinkable soluble polyimide and polymethacrylate compound were synthesized for studying the optically induced anisotropy of the thin films. Chalcone group was introduced into the side chain unit of two polymers. We observed a photodimerization behavior between the double bonds in the chalcone group and an optical anisotropy of these materials by irradiation of a linearly polarized UV light (LPL). Optical anisotropy of the thin film was also investigated by using polarized UV absorption spectroscopy. The dynamic property of optical anisotropy in photoreactive polyimide was compared to that in polymethacrylate containing chalcone group in the side chain.

• Bulletin of the Korean Chemical Society
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• v.22 no.11
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• pp.1207-1212
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• 2001

A new photochemically bifunctional epoxy and dimethacrylate compounds were synthesized for investigating the photosensitivity under UV irradiation. Photosensitivity of the synthesized chalcone-based compounds was investigated by using UV-visible absorption and Fourier transformed infrared (FT-IR) spectroscopies. The result of spectroscopic analysis substantiated that the two chalcone-based compounds have functions of both photocrosslinking and photopolymerization by UV exposure in the presence of photoinitiator. Two kinds of photochemical reactions proceeded competitively during UV exposure. Particularly, we studied the effect of photopolymerization on the rate of photocrosslink due to cycloaddition in the two oligomeric compounds.

• YAKHAK HOEJI
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• v.54 no.1
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• pp.27-31
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• 2010

Xanthohumol, a prenylated chalcone of the Hop plant (Humulus lupulus L.), has been reported to suppress tumor growth. 4-hydroxychalcone and isobavachalcone are chalcone derivatives and they have similar structure with xanthohumol. In the present study, we investigated the cytotoxic activities of chalcone and its derivatives, 4-hydroxychalcone, xanthohumol, and isobavachalcone, in MCF-7 and adriamycin resistant MCF-7 (MCF-7/ADR) breast cancer cells and HT-1080 fibrosarcoma cells. In a cell viability assay using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reagent, chalcone and 4-hydroxychalcone decreased cell viability in HT-1080 cells, but not in MCF-7 and MCF-7/ADR cells. Isobavachalcone showed similar cytotoxicity in HT-1080 cells, and only limited cytotoxicity in MCF-7 and MCF-7/ADR cells at very high concentration (50 ${\mu}M$). In contrast, xanthohumol showed concentration-dependent cytotoxicity in MCF-7, MCF-7/ADR, and HT-1080 cancer cells. Taken together, the structure-activity relationship of chalcone and its derivatives indicate that chalcones may be valuable cytotoxic compounds against selective cancer types.

• Bulletin of the Korean Chemical Society
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• v.30 no.11
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• pp.2563-2566
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• 2009

The first total synthesis of naturally occurring prorepensin with a bis-geranylated chalcone has been achieved by a convergent sequence. The key strategy involved in the synthesis of prorepensin was chalcone formation by aldol condensation of the corresponding geranylated acetophenone with geranylated benzaldehyde.

• Bulletin of the Korean Chemical Society
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• v.24 no.4
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• pp.441-445
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• 2003

We synthesized three copolymers bearing photochromic spiropyran dye and chalcone moiety in the side chain for studying the dynamic properties of their photochromism. They contain methacrylate-spiropyran (MAspiropyran) and methacrylate-chalcone (MA-chalcone) with the different concentration. The photosensitivity of the newly synthesized copolymers was investigated by using UV-Vis absorption spectroscopy. We observed photodimerization and photochromic behavior under UV irradiation at the same time. The effect of photocrosslink on the rate and stability of photochromism in three copolymers was considered in this study. This study might be helpful to design photochromic materials for irreversible optical memory by virtue of photocrosslinking reaction.

• 한국정보디스플레이학회:학술대회논문집
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• 2002.08a
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• pp.479-482
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• 2002

Benzylideneacetophenones are known as chalcones[1]. The chalcone has been known to be a photo-isomerizable and photo-dimerizable chromophore. The chalcone derivatives were prepared by base-catalyzed condensation of aldehydes and acetophenones, which were substituted with various alkyl chains. The synthesized chalcone was introduced into the t-BOC protected diamine through William synthesis reaction. Photocrosslinkable polyimide was prepared via one-step imidization reaction of DOCDA (5-(2,5-dioxotetrahydro furyl}-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride) and the chalcone introduced diamine using isoquinoline (5 wt%) in m-cresol. The polyimide solutions were spin-coated onto the quartz, silicone wafer and glass substrates and the obtained thin films were irradiated obliquely with linearly polarized UV light.

• Bulletin of the Korean Chemical Society
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• v.23 no.4
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• pp.587-592
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• 2002

Photocrosslinkable chalcone-epoxy compound comprising 1,3-bis-(4-hydroxy-phenyl)-propenone was synthe-sized for fabricating the photo-alignment layer of liquid crystals. Chalcone group was introduced into the main chain unit of the epoxy oligomer. We observed a photodimerization behavior and an optical anisotropy of this material by irradiation of a linearly polarized UV(LP-UV) light. With a trace amount of cationic photoinitiator (TRS-HFA), polymerization of epoxy groups was also conducted at the similar wavelength range used for photodimerization. Linearly polarized UV irradiation on the chalcone-epoxy films with cationic photoinitiator induced optical anisotropy of the film and the resultant film can be used for alignment layers for low molecular weight nematic liquid crystals.

• Macromolecular Research
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• v.15 no.1
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• pp.74-81
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• 2007

A series of photoreactive mesogens based on chalcone were prepared and their morphological behavior and reactivity were studied according to a variable number of alkyloxy tail carbons. The linear ester compounds 3a-h comprised two chalcone units connected to a benzene ring through ester linkages. All linear ester compounds showed enantiotropic liquid crystalline phases. The X-ray diffractograms for the mesophases of compounds 3a-h showed a set of reflections in the small-angle region which consisted of more than three sharp diffraction peaks with d spacings in the ratio of 1:1/2:1/3, confirming the well defined smectic A structures of the compounds. Compounds 3a-h were considered to be bifunctional monomers due to the presence of two photoreactive chalcone groups. Upon UV irradiation, its polymerization proceeded through the [2+2] addition reaction between chalcone units in a stepwise manner. An image pattern was obtained by the photopolymerization of the liquid crystal of the compound (3h) with decyloxy tails through a photomask. The irradiated part became dark while the masked part remained birefringent under polarized optical microscopy, which was ascribed to the production via the UV irradiation of a polymer or a dimer having cyclobutane rings by [2+2] addition, which thereby disrupted the alignment of the molecules.

• Archives of Pharmacal Research
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• v.28 no.1
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• pp.81-86
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• 2005

The hepatoprotective effects of chalcone derivatives were evaluated in D-galactosamine/lipopolysaccharide (D-GaIN/LPS)-induced fulminant hepatic failure in mouse. Thirteen chalcone derivatives were synthesized for study and their hepatoprotective effects were evaluated by assessing aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels in serum. Chalcone preparations were injected into mice at 12 hand 1 h before intraperitoneal injection of D-GaIN/LPS. After abdominal administration, changes in AST and ALT between the control and treated groups were observed. Ten of the synthesized chalcone derivatives exhibited inhibitory effects on D-GaIN/LPS-induced levels of AST and ALT in mice. Compounds 2, 3, 8, 9, and 12 markedly reduced serum AST and ALT at 8 h, inhibited hepatocyte necrosis and showed significant hepatoprotective activities. The activity of compound 3 was compared with the bifendate (DDB) through oral administration. Compound 3 showed much higher inhibitory effects than bifendate for decreasing AST and ALT activity. The results indicate that compound 3 has strong hepatoprotective activity through suppression of tumor necrosis factor­alpha (TNF-alpha) preduction, reduction of the histological change in the liver, and attenuated of hepatocyte apoptosis confirmed by DNA fragmentation assay.