• Journal of the Korean Wood Science and Technology
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• 제34권2호
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• pp.88-94
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• 2006

The purpose of this study is to examine the relationship between antioxidant activities and chemical structures of various chalcones. Twenty-two chalcones were assessed for their radical scavenging activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Of 22 compounds tested, the most active on DPPH radical was 2',4-dihydroxy-3,3'5-trimethoxy-5'-propylchacone (4) (72.6% at 100 ppm). It was followed by 3',4'-dihydroxy-3,4,5-trimethoxy-6'-methylchalcone (6), 2',4,4'-trihydroxy-3-methoxy-5-propenylchalcone (7) and 2',4,4'-trihydroxy-3,5-dimethoxychalcone (13). Based on the results, we concluded that the scavenging activity is controlled by the number and the position of the substitution in the compound.

• 약학회지
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• 제55권5호
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• pp.367-373
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• 2011

It was reported that the potency of TMMC derivatives was related to the presence of the 2'-hydroxy group on the A ring. Also, 4-dimethylamino group on the B ring lowered the anti-inflammatory potency of the chalcones. We synthesized various derivatives of 2'-hydroxy chalcones having other substituents on B ring. The synthetic derivatives showed the more potent anti-inflammatory effect, comparable to that of the TMMC derivatives reported previously.

• 한국미생물·생명공학회지
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• 제49권2호
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• pp.174-180
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• 2021

Chalcones exhibit multiple biological activities. Various studies have attempted to modify the structure of chalcones with a special focus on the addition of substituents to the benzene rings. However, these chemical modifications did not improve the water solubility and bioavailability of chalcones. Glycosylation can markedly affect the physical and chemical properties of hydrophobic compounds. Here, we evaluated the ability of a highly promiscuous glycosyltransferase (GT) BsGT1 from Bacillus subtilis ATCC 6633 to biosynthesize chalcone glucosides. Purified BsGT1 catalyzed the conversion of 4'-hydroxychalcone (compound 1), 4'-hydroxy-4-methylchalcone (compound 2), and 4-hydroxy-4'-methoxychalcone (compound 3), into chalcone 4'-O-β-D-glucoside (compound 1a), 4-methylchalcone 4'-O-β-D-glucoside (compound 2a), and 4'-methoxychalcone 4-O-β-D-glucoside (compound 3a), respectively. To avoid the addition of expensive uridine diphosphate glucose (UDP-Glc), a whole-cell biotransformation system was employed to provide a natural intracellular environment for in situ co-factor regeneration. The yields of compounds 1a, 2a, and 3a were as high as 90.38%, 100% and 74.79%, respectively. The successful co-expression of BsGT1 with phosphoglucomutase (PGM) and UDP-Glc pyrophosphorylase (GalU), which are involved in the biosynthetic pathway of UDP-Glc, further improved the conversion rates of chalcones (the yields of compounds 1a and 3a increased by approximately 10%). In conclusion, we demonstrated an effective whole-cell biocatalytic system for the enzymatic biosynthesis of chalcone β-D-glucoside derivatives.

• Bulletin of the Korean Chemical Society
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• 제33권8호
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• pp.2585-2591
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• 2012

A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring-containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalones was distinctly demonstrated in our work.

• Archives of Pharmacal Research
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• 제27권9호
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• pp.885-892
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• 2004

Due to the rapidly growing number of resistant strains of bacteria, the search for antibacterial agents with new modes of action will always remain an important and challenging task. Thus, the reaction of 2-substituted or. unsubstituted-4-(4-acetylanilino)-5,6,7,8-terahydrobenzo［b］ thieno［2,3-d］pyrimidine derivatives 1-3 with the hydrazine derivatives, semi and / or thiosemi-carbazides, provided the corresponding hydrazones 4-6 and semi and/or thiosemicarbazones 7-9. Claisen-Schmidt condensation of compounds 1 or 2 with the appropriate aldehyde yielded the chalcones 10, 11 which, when treated with hydroxylamine hydrochloride gave rise to the isoxazoline-containing compounds 12, 13. Furthermore, reacting the respective chalcones 10, 11 with different hydrazines, urea and/or thiourea, furnished compounds 14, 15, 16, and 17 respectively. Representative compounds were tested for their antimicrobial activity against Candida Albicans and certain gram-positive and gram-negative bacteria. Their MICs were then determined. Compound 15e, showed a broad spectrum of activity while most of the other com-pounds showed varying antimicrobial activity.

• 대한화학회지
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• 제58권1호
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• pp.49-56
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• 2014

Different pyrazoline derivatives (6a-h and 7a-h) were synthesized by cyclization of substituted chalcones with hydrazine hydrate in acidic as well as basic conditions. Both the reactions were performed under conventional heating and microwave irradiation and percentage yields were compared. All the reactions were accelerated in acidic and basic conditions under microwave irradiation, with higher yields. All the synthesized compounds were characterized by their spectral study (IR, MS, $^1H$ and $^{13}C$ NMR) and were tested for their antibacterial and antifungal activity. The compounds 6g and 7g exhibited significant activity against S. aureu, 7g against E. faecalis, 6b and 7b against E. coli and 6b, 6c, 7b, 7c against S. typhi. The compounds 6d and 7d exhibited significant activity against C. albicans and 6c against M. luteus. Rest of the synthesized compounds showed moderate to poor activity against tested species with compared to standard.

• Bulletin of the Korean Chemical Society
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• 제34권4호
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• pp.1263-1265
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• 2013

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.233.1-233.1
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• 2003

Interleukin (IL)-5 appears to be one of the main proinflammatory mediators among a growing number of cytokines and chemokines that induce eosinophilic inflammation. Sophoricoside and their analogs isolated from Sophora japonica show relatively potent inhibitory activity of interleukin (IL)-5 as a small molecule. Initial attempt to identify the structural requirement of this isoflavonone led to find new chalcones to exhibit the inhibitory activity of IL -5. (omitted)

• Natural Product Sciences
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• 제28권3호
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• pp.115-120
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• 2022

Ten compounds, consisting of neoflavonoids (1-5), isoflavonoids (6 and 7), flavanone (8), and chalcones (9 and 10) were isolated from the ethyl acetate and n-butanol-soluble fractions of the heartwood of Dalbergia melanoxylon. The chemical structures were identified on the basis of spectroscopic evidence and compared to previously reported spectra. Compounds 1-10 were evaluated for cytotoxicity against HCT116 human colorectal cancer, MDA-MB-231 human metastatic breast cancer, and A2058 human melanoma cell lines. Among them, compounds 3 and 10 showed the strongest cytotoxic activity with IC₅₀ values of 11.92±1.07 μM, 10.83±1.02 μM, and 14.37±1.02 μM, 13.62±1.09 μM against HCT116 and MDA-MB-231 cell lines, respectively. Compounds 9 and 10 also had cytotoxic activity with IC₅₀ values of 13.49±1.18 μM and 9.82±0.91 μM against A2058 cell lines, respectively. To the best our knowledge, compounds 2 and 5-10 were isolated from this source for the first time.

• Biomolecules & Therapeutics
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• 제22권5호
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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.