• 약학회지
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• 제54권1호
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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.

• International Journal of Oral Biology
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• 제43권1호
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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 $TNF-{\alpha}$.

• Archives of Pharmacal Research
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• 제28권1호
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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.

• Applied Biological Chemistry
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• 제41권6호
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• pp.477-482
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• 1998

새로운 Leukotriene $D_4$ antagonists를 찾기 위해 구조-활성간 연구를 수행하였다. 이미 알려진 chalcone 유도체의 구조와 생물학적 활성 자료를 이용하여 구조-활성간 계산을 수행한 결과 새로운 화합물을 발견하였고, 이를 합성하여 효과를 측정한 결과를 보고하고자 한다.

• Journal of Photoscience
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• 제8권1호
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• pp.9-12
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• 2001

The photoisomerization behavior of benzylideneacetophenones, known as chalcones, was studied. We synthesized the chalcone derivatives that have ether groups at 4 and 4＇ positions. Due to the electron donating ability of the ether oxygen, the bond order of the single bond between two phenyl ring of the chalcone strengthened, which eventually increased the rotational barrier of the single bond. The rotational barrier of the single bond is about 20-22 kcal/mole. Thermal recovery of this process took about 1 min. The UV-visible spectra of these chromophores exhibit two characteristic absorption peaks at 276 nm and 340 nm. The relative intensity of the peaks varies depending on the alkyl chain length of the substituent. Photo-irradiation with the 365 nm light monotonously decreases the 340 nm peak. However, the photo-irradiation with 254 nm light induce two competing processes and produced rather complicated absorption profile.

• 한국응용과학기술학회지
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• 제10권1호
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• pp.75-81
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• 1993

The hydrolysis kinetics of 2-furyl chalcone derivatives $[I]{\sim}[V]$ was investigated by ultraviolet spectrophotometery in 30% dioxane-$H_{2}O$ at $25^{\circ}C$ and the structure of these compounds were ascertained by means of ultraviolet, infrared and NMR spectra. The rate equations which were applied over a wide pH range(pH $1.0{\sim}12.0$) were obtained. The substituent effects on 2-furyl chalcone derivatives $[I]{\sim}[V]$ were studied, and the hydrolysis were facilitated by the electron attrecting groups. On the basis of the rate equation, substituent effect, general base effect and final product. the plausible hydrolysis mechaism was proposed: Below pH 4.0, it was only proportional to concentration of hydronium ion, at pH $4.0{\sim}9.0$, neutral $H_{2}O$ molecule competitively attacked on the double bond. By contrast, above pH 9.0, it was proportional to concentration of hydroxide ion.

• 한국응용과학기술학회지
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• 제10권2호
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• pp.73-80
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• 1993

The hydrolysis reaction kinetics of 2-thienyl chalcone derivatives $[II]{\sim}[V]$ was investigated by ultraviolet spectrophotometery in 20% dioxane-$H_2O$ at $25^{\circ}C$ and the structure of these compounds were ascertained by means of ultraviolet, infrared and NMR spectra. The rate equations which were applied over a wide pH range(pH $1.0{\sim}13.0$) were obtained. The substituent effects on 2-thienyl chalcone derivatives$[II]{\sim}[V]$ were studied, and the hydrolysis were facilitated by electron attracting groups. On the basis of the rate equation, substitutent effect and final product, the plausible hydrolysis reaction mechanism was proposed : At pH $1.0{\sim}9.0$, not relevant to the hydrogen ion concentration, neutral $H_2O$ molecule competitvely attacked on the double bond. By contraries, above pH 9.0, it was proportional to concentration of hydroxide ion.

• 한국응용과학기술학회지
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• 제13권1호
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• pp.107-113
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• 1996

Fluorenylidene chalcone derivatives were synthesized by condensation. The structure of these compounds were ascertained by means of UV, melting point, IR and $^1H-NMR$ spectra. The nucleophilic addition reaction kinetics of Thioglycolic acid to fluorenylidene chalcone was investigate by UV in 20% $dioxane-H_2O$ at $25^{\circ}C$. The rate equation which were applied over a wide $pH1.0{\sim}13.0$ range. On the basis of general base catalysis and confirmation of addition reaction product, the nucleophilic addtion reaction kinetics of thioglycolic acid to fluorenylidene chalcone were measured by the pH change. From the result of the above caption, a plausible nucleophilic addition reaction mechanism of thioglycolic acid to fluorenylidene chalcone was proposed. These compounds may be used as the starting materials for the preparation of the engineering plastics or the germicide.

• Biomolecules & Therapeutics
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• 제29권4호
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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.

• Archives of Pharmacal Research
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• 제29권6호
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• pp.497-502
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• 2006

A new natural C-benzylated chalcone, $2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6{\c}-methoxychalcone$ (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCl-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with $IC_{50}$ values of 1.40, 5.31 and $13.92\;{\mu}g/mL$, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an $IC_{50}$ value of $7.1\;{\mu}g/mL$ as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.