• Macromolecular Research
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• v.9 no.6
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• pp.339-344
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• 2001

In order to investigate the photoalignment mechanism of nematic liquid crystals on a polymer film, a new photoreactive polymer having chalcone groups as side chains was synthesized. Linearly polarized UV light causes preferential photoreactions of the chalcone unit along the polarization direction and thus induces the anisotrpy in the polymer alignment layer resulting in homogeneous LC alignment perpendicular to the polarization direction. The sequential investigations of photoalignment generated by the preferential E/Z isomerization and (2+2) cycloaddition reactions show that either photoreaction can solely induce the LC alignment in the direction perpendicular to UV polarization.

• Journal of Applied Biological Chemistry
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• v.55 no.3
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• pp.191-194
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• 2012

Novel pyrazolinecarbothioamide (5) was synthesized from chalcone (3) which was prepared from 2'-hydroxy-1'-acetonaphthone (1) and 2-methoxy benzaldehyde (2). Treatment of pyrazolinecarbothioamide (5) on HCT116 cancer cell showed upregulation of p21 and downregulation of cyclin D1 protein. Flowcytometer analysis revealed that pyrazolinecarbothioamide (5) controls the expression of cell cycle regulatory proteins, which blocks cell cycle progression of HCT116 cancer cell at the G1 phase.

• Journal of Applied Biological Chemistry
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• v.54 no.2
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• pp.143-146
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• 2011

Novel pyrazoline (4) was synthesized from chalcone (3) which was prepared from 2'-hydroxy-l'acetonaphthone (1) and 4-methoxy benzaldehyde (2). Pyrazoline (4) forms resonance assisted hydrogen bond between naphthol hydroxyl group and imine nitrogen in a pyrazoline ring. Pyrazoline (4) shows Poly ADP-ribose Polymerase (PARP) cleavage ability as a proof of apoptosis in cancer cell, which reveals its anti-cancer property.

• Bulletin of the Korean Chemical Society
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• v.34 no.3
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• pp.875-883
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• 2013

Ten new derivatives of 1,3-diazabicyclo[3.1.0]hex-3-enes linked via ether linkage to chalcones were synthesized and characterized by UV, FT-IR, $^1H$ NMR and $^{13}C$ NMR spectral techniques. The spectra of all synthesized compounds, confirmed structure-photochromic behavior relationships (SPBR) both in solution or in solid state by irradiation under UV light at 254 nm. In other efforts for first time photochromic behavior of ketoaziridines has been investigated.

• Bulletin of the Korean Chemical Society
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• v.29 no.6
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• pp.1125-1130
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• 2008

A series of dihydroxylated chalcone derivatives with diverse substitution patterns on a phenyl ring B and the para-substituents on a phenyl ring A were prepared, and their radical scavenging activities were evaluated by simple DPPH test to determine quantitative structure-activity relationship in these series of compounds. The chalcone compounds with the ortho- (i.e. 2',3'- and 3',4'-) and para- (i.e. 2,5'-) substitution patterns show an excellent antioxidant activities (80-90% of control at the concentration of 50 $\mu$M) which are comparable to those of ascorbic acid and $\alpha$ -tocopherol as positive reference materials. On the contrary, the compounds with meta- (i.e. 2',4'-, 3',5'-) substitution pattern demonstrate very dramatic decrease in activities which are around 25% of the control even at the concentration of 200 $\mu$ M (IC50 > 200 $\mu$ M). These dramatic differences could be interpreted in terms of the ease formation of fairly stable semiquinone radicals from the ortho- and parasubstituted chalcone molecules through facilitating electron delocalization. Our results indicate that the substitution patterns of two hydroxyl groups on ring B are very important structural factors for their radical scavenging activity enhancement. Meanwhile, the substituents at para-position of the phenyl ring A of chalcones have no influence on the activity.

• Biomolecules & Therapeutics
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• v.22 no.5
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• pp.390-399
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• 2014

Chalcones (1,3-diaryl-2-propen-1-ones), a flavonoid subfamily, are widely known for their anti-inflammatory properties. Propenone moiety in chalcones is known to play an important role in generating biological responses by chalcones. In the present study, we synthesized chalcone derivatives structurally modified in propenone moiety and examined inhibitory effect on nitric oxide (NO) production and its potential mechanisms. Among the chalcone derivatives used for this study, TI-I-174 (3-(2-Hydroxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one) most potently inhibited lipopolysaccharide (LPS)-stimulated nitrite production in RAW 264.7 macrophages. TI-I-174 treatment also markedly inhibited inducible nitric oxide synthase (iNOS) expression. However, TI-I-174 did not significantly affect production of IL-6, cyclooxygenase-2 (COX-2) and tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$), implying that TI-I-174 inhibits production of inflammatory mediators in a selective manner. Treatment of macrophages with TI-I-174 significantly inhibited transcriptional activity of activator protein-1 (AP-1) as determined by luciferase reporter gene assay, whereas nuclear factor-${\kappa}B$ (NF-${\kappa}B$) activity was not affected by TI-I-1744. In addition, TI-I-174 significantly inhibited activation of c-Jun-N-Terminal kinase (JNK) without affecting ERK1/2 and p38MAPK, indicating that down-regulation of iNOS gene expression by TI-I-174 is mainly attributed by blockade of JNK/AP-1 activation. We also demonstrated that TI-I-174 treatment led to an increase in heme oxygenase-1 (HO-1) expression both at mRNA and protein level. Transfection of siRNA targeting HO-1 reversed TI-I-174-mediated inhibition of nitrite production. Taken together, these results indicate that TI-I-174 suppresses NO production in LPS-stimulated RAW 264.7 macrophages via induction of HO-1 and blockade of AP-1 activation.

• Journal of Plant Biotechnology
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• v.46 no.4
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• pp.247-254
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• 2019

Flavonoids are widely distributed secondary metabolites in plants that have a variety biological functions, as well as beneficial biological and pharmacological activities. In barley (Hordeum vulgare L.), for example, high levels of saponarin accumulate during primary leaf development. However, the effect of saponarin biosynthetic pathway genes on the accumulation of saponarin in barley is poorly understood. Accordingly, the aim of the present study was to examine the saponarin contents and expression levels of saponarin biosynthetic pathway genes [chalcone synthase (CHS), chalcone isomerase (CHI), and UDP-Glc:isovitexin 7-O-glucosyltransferase (OGT)] during early seedling developmental and under several abiotic stress conditions. Interestingly, the upregulation of HvCHS, HvCHI, and HvOGT during early development was associated with saponarin accumulation during later stages. In addition, exposure to abiotic stress conditions (e.g., light/dark transition, drought, and low or high temperature) significantly affected the expression of HvCHS and HvCHI but failed to affect either HvOGT expression or saponarin accumulation. These findings suggested that the expression of HvOGT, which encodes an enzyme that catalyzes the final step of saponarin biosynthesis, is required for saponarin accumulation. Taken together, the results of the present study provide a basis for metabolic engineering in barley plants, especially in regards to enhancing the contents of useful secondary metabolites, such as saponarin.

• Biomolecules & Therapeutics
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• v.26 no.2
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• pp.191-200
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• 2018

Chalcone, (2E)-1,3-Diphenylprop-2-en-1-one, and its synthetic derivatives are known to possess anti-oxidative and anti-inflammatory properties. In the present study, we prepared a novel synthetic chalcone compound, (E)-1-(4-hydroxyphenyl)-3-(2-(trifluoromethoxy)phenyl)prop-2-en-1-one name (YJI-7), and investigated its inhibitory effects on endotoxin-stimulated production of reactive oxygen species (ROS) and expression of inflammatory mediators in macrophages. We demonstrated that treatment of RAW 264.7 macrophages with YJI-7 significantly suppressed lipopolysaccharide (LPS)-stimulated ROS production. We also found that YJI-7 substantially decreased NADPH oxidase activity stimulated by LPS, indicating that YJI-7 regulates ROS production via modulation of NADPH oxidase in macrophages. Furthermore, YJI-7 strongly inhibited the expression of a number of inflammatory mediators in a gene-selective manner, suggesting that YJI-7 possesses potent anti-inflammatory properties, as well as anti-oxidative activity. In continuing experiments to investigate the mechanisms that could underlie such biological effects, we revealed that YJI-7 suppressed phosphorylation of p38MAPK and JNK stimulated by LPS, whereas no significant effect on ERK was observed. Furthermore, LPS-stimulated production of ROS, activation of NADPH oxidase and expression of inflammatory mediators were markedly suppressed by treatment with selective inhibitor of p38MAPK (SB203580) and JNK (SP600125). Taken together, these results demonstrated that YJI-7, a novel synthetic chalcone derivative, suppressed LPS-stimulated ROS production via modulation of NADPH oxidase and diminished expression of inflammatory mediators, at least in part, via down-regulation of p38MAPK and JNK signaling in macrophages.

• Journal of Pharmacopuncture
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• v.20 no.3
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• pp.207-212
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• 2017

Objectives: Study of the mechanisms involved in cancer progression suggests that cyclooxygenase enzymes play an important role in the induction of inflammation, tumor formation, and metastasis of cancer cells. Thus, cyclooxygenase enzymes could be considered for cancer chemotherapy. Among these enzymes, cyclooxygenase 2 (COX-2) is associated with liver carcinogenesis. Various COX-2 inhibitors cause growth inhibition of human hepatocellular carcinoma cells, but many of them act in the COX-2 independent mechanism. Thus, the introduction of selective COX-2 inhibitors is necessary to achieve a clear result. The present study was aimed to determine the growth-inhibitory effects of new analogues of chalcone epoxide as selective COX-2 inhibitors on the human hepatocellular carcinoma (HepG2) cell line. Methods: Estimation of both cell growth and the amount of prostaglandin E2 (PGE2) production were used to study the effect of selective COX-2 inhibitors on the hepatocellular carcinoma cell. Cell growth determination has done by MTT assay in 24 h, 48 h and 72 h, and PGE2 production has estimated by using ELYSA kit in 48 h and 72 h. Results: The results showed growth inhibition of the HepG2 cell line in a concentration and time-dependent manner, as well as a reduction in the formation of PGE2 as a product of COX-2 activity. Among the compounds those analogues with methoxy and hydrogen group showed more inhibitory effect than others. Conclusion: The current in-vitro study indicates that the observed significant growth-inhibitory effect of chalcone-epoxide analogues on the HepG2 cell line may involve COX-dependent mechanisms and the PGE2 pathway parallel to the effect of celecoxib. It can be said that these analogues might be efficient compounds in chemotherapy of COX-2 dependent carcinoma specially preventing and treatment of hepatocellular carcinomas.

• Biomolecules & Therapeutics
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• v.29 no.4
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• pp.410-418
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• 2021

Helicobacter pylori causes chronic gastritis through cag pathogenicity island (cagPAI), vacuolating cytotoxin A (VacA), lipopolysaccharides (LPS), and flagellin as pathogen-related molecular patterns (PAMPs), which, in combination with the pattern recognition receptors (PRRs) of host cells promotes the expression and secretion of inflammation-causing cytokines and activates innate immune responses such as inflammasomes. To identify useful compounds against H. pylori-associated gastric disorders, the effect of chalcone derivatives to activate the nucleotide-binding oligomerization domain (NOD)-like receptor family, pyrin domain-containing 3 (NLRP3) inflammasome was examined in an H. pylori-infected human monocytic THP-1 cell line in this study. Among the five synthetic structurally-related chalcone derivatives examined, 2'-hydroxy-4',6'-dimethoxychalcone (8) and 2'-hydroxy-3,4,5-trimethoxychalcone (12) strongly blocked the NLRP3 inflammasome in H. pylori-infected THP-1 cells. At 10 μM, these compounds inhibited the production of active IL-1β, IL-18, and caspase-1, and apoptosis-associated speck-like protein containing a caspase recruitment domain (ASC) oligomerization, but did not affect the expression levels of NLRP3, ASC, and pro-caspase-1. The interruption of NLRP3 inflammasome activation by these compounds was found to be mediated via the inhibition of the interleukin-1 receptor-associated kinase 4 (IRAK4)/IκBα/NF-κB signaling pathway. These compounds also inhibited caspase-4 production associated with non-canonical NLRP3 inflammasome activation. These results show for the first time that certain chalcones could interrupt the activation of the NLRP3 inflammasome in H. pylori-infected THP-1 cells. Therefore, these chalcones may be helpful in alleviating H. pylori-related inflammatory disorders including chronic gastritis.