• Title/Summary/Keyword: heterocyclic

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Inhibitory Effect of Korean Fermented Soybean (Chungkookjang) Extract and Genistein Against Trp-P-1 Induced Genotoxicity in HepG2 Cells

  • Song, Eun Jeong;Kim, Nam Yee;Heo, Moon Young
    • Journal of Food Hygiene and Safety
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    • v.32 no.3
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    • pp.171-178
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    • 2017
  • This study evaluated the protective effect of Chungkookjang (CKJ) extract, a Korean traditional fermented soybean product made from Bacillus species in rice straw and boiled soybean, and one of its main flavonoids, genistein, against Trp-P-1 induced cytotoxicity and DNA damage in HepG2 cells. CKJ and genistein exhibited protective effect against Trp-P-1 induced cytotoxicity and Trp-P-1 induced DNA single strand breaks. CKJ and genistein inhibited Trp-P-1 induced CYP1A1 and CYP1A2 transcription in HepG2 cells. Our results indicated that CKJ and genistein have the protective effect against Trp-P-1 induced cytotoxicity and DNA damage. Via inhibiting expression of CYP1A1 and CYP1A2. CKJ can be used as a promising functional food material that prevents the genotoxicity induced by carcinogens produced by the heat treatment of foods such as heterocyclic amines (HCAs) that cause genomic instability.

Synthesis and herbicidal activities of heterocyclic PPO inhibitor derivatives substituted with epoxy groups (Epoxy Group이 치환된 헤테로고리형 PPO 저해제의 합성과 제초활성)

  • Jeon, Dong-Ju;Park, Kwaun-Yong;Park, Chang-Min;So, Won-Young;Kim, Hyoung-Rae;Song, Jong-Hwan;Hwang, In-Taek
    • The Korean Journal of Pesticide Science
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    • v.9 no.2
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    • pp.181-184
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    • 2005
  • The heterocyclic PPO inhibitor compounds have been studied due to their potent herbicidal effects without toxic to human and animals. We have designed and synthesized 4,5,6,7-tetrahydroindazole, maleimide, and tetrahydrophthalimide compounds carrying diverse epoxide substituents at 5- position of the phenyl group. Their herbicidal activities were evaluated under submerged paddy conditions. These results showed that 4,5,6,7-tetrahydroindazole compounds gave potent herbicidal activities especially to ECHOR, MOOVA, and CYPSE at a relatively low rate of 16 g/ha and improved tolerance on rice compared to S-275 as a standard herbicide in this experiment.

Separation and Recovery of Indole from Model Coal Tar Fraction by Batch Cocurrent 5 Stages Equilibrium Extraction (회분 병류 5단 평형추출에 의한 모델 콜타르 유분 중에 함유된 Indole의 분리 및 회수)

  • Kim, Su Jin;Chun, Yong Jin;Jeong, Hwa Jin
    • Applied Chemistry for Engineering
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    • v.18 no.2
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    • pp.168-172
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    • 2007
  • The separation of indole from a model mixture comprising four kinds of nitrogen heterocyclic compounds [indole (In), quinoline (Q), iso-quinoline (iQ), quinaldine (Qu)], three kinds of bicyclic aromatic compounds [1-methylnaphthalene (1MN), 2-methylnaphthalene (2MN), dimethylnaphthalene (DMN)], biphenyl (Bp) and phenyl ether (Pe) was examined by batch cocurrent 4 stages equilibrium extraction. The model mixture used as a raw material in this work was prepared according to the components and compositions contained in coal tar fraction (the temperature ranges of fraction: $240{\sim}265^{\circ}C$). An aqueous solution of formamide was used as a solvent. Indole was recovered more than 99% through 4 stages of the equilibrium extraction. The range of selectivity of indole in reference to DMN obtained through the 5 stages equilibrium extraction was found to be 63~118. The process for separation and recovery of indole contained in coal tar was studied by using the experimental results obtained from this work and the previous work.

Flavour Chemistry of Chicken Meat: A Review

  • Jayasena, Dinesh D.;Ahn, Dong Uk;Nam, Ki Chang;Jo, Cheorun
    • Asian-Australasian Journal of Animal Sciences
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    • v.26 no.5
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    • pp.732-742
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    • 2013
  • Flavour comprises mainly of taste and aroma and is involved in consumers' meat-buying behavior and preferences. Chicken meat flavour is supposed to be affected by a number of ante- and post-mortem factors, including breed, diet, post-mortem ageing, method of cooking, etc. Additionally, chicken meat is more susceptible to quality deterioration mainly due to lipid oxidation with resulting off-flavours. Therefore, the intent of this paper is to highlight the mechanisms and chemical compounds responsible for chicken meat flavour and off-flavour development to help producers in producing the most flavourful and consistent product possible. Chicken meat flavour is thermally derived and the Maillard reaction, thermal degradation of lipids, and interaction between these 2 reactions are mainly responsible for the generation of flavour and aroma compounds. The reaction of cysteine and sugar can lead to characteristic meat flavour specially for chicken and pork. Volatile compounds including 2-methyl-3-furanthiol, 2-furfurylthiol, methionol, 2,4,5-trimethyl-thiazole, nonanol, 2-trans-nonenal, and other compounds have been identified as important for the flavour of chicken. However 2-methyl-3-furanthiol is considered as the most vital chemical compound for chicken flavour development. In addition, a large number of heterocyclic compounds are formed when higher temperature and low moisture conditions are used during certain cooking methods of chicken meat such as roasting, grilling, frying or pressure cooking compared to boiled chicken meat. Major volatile compounds responsible for fried chicken are 3,5-dimethyl-1,2,4-trithiolanes, 2,4,6-trimethylperhydro-1,3,5-dithiazines, 3,5-diisobutyl-1,2,4-trithiolane, 3-methyl-5-butyl-1,2,4-trithiolane, 3-methyl-5-pentyl-1,2,4-trithiolane, 2,4-decadienal and trans-4,5-epoxy-trans-2-decenal. Alkylpyrazines were reported in the flavours of fried chicken and roasted chicken but not in chicken broth. The main reason for flavour deterioration and formation of undesirable "warmed over flavour" in chicken meat products are supposed to be the lack of ${\alpha}$-tocopherol in chicken meat.

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis (이중고리 합성에 블록제로서 이용된 피란과 피리딘)

  • El-Hashash, Maher.A.;El-Sawy, Abdallah.A.;Eissa, Abdelmonem.M.F.
    • Journal of the Korean Chemical Society
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    • v.53 no.3
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    • pp.308-324
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    • 2009
  • The present work is devoted to study the interaction of $\beta$-aroylacrylic acid derivative (3) with malononitrile in (DMF) in the presence of piperidine and/or ammonium acetate, then using the formed compounds as starting materials for synthesizing fused and isolated heterocyclic systems. It has been established that the $\beta$-aroylacrylic acid (3) reacts with malononitrile in (DMF) in the presence of piperidine as a catalyst with the formation of 4H-pyran derivative (4). By changing the catalyst into ammonium acetate, pyridine derivative (5) has been obtained. Also the N-maleamic acid derivatives (19) and (27) have been synthesized via the interaction of (4) and (5) with maleic anhydride. The purpose of this step is to study the behavior of the formed maleamic acid derivatives – as analogies of $\beta$-aroylacrylic acids – towards different active methylene compounds under Michael addition reaction.

Evaluation of the in vitro biological activity of selected 35 chemicals (35종의 특정 화학성분들의 in vitro 활성 평가)

  • Shin, Han-Jae;Sohn, Hyung-Ok;Park, Chul-Hoon;Lee, Hyeong-Seok;Min, Young-Keun;Hyun, Hak-Chul
    • Journal of the Korean Society of Tobacco Science
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    • v.29 no.1
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    • pp.30-40
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    • 2007
  • The objective of this study was to investigate the contribution of various smoke constituents to the toxicological activity of total particulate matter(TPM) or the gas/vapor phase(GVP). These components included phenol compounds, aromatic amines, polycyclic aromatic hydrocarbons, heterocyclic amines, and carbonyl compounds. The mutagenic and cytotoxic potencies were assessed using the Salmonella mutagenicity assay with S. typimurium TA98 strain and the neutral red uptake cytotoxicity assay(NRU) with BALB/c 3T3 fibroblast cells, respectively. The Salmonella mutagenicity test showed that heterocyclic amines exhibited significantly higher levels of toxicity compared to other smoke constituents. Among them, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline(MeIQ) was shown the most mutagenic compound with a specific mutagenicity of $7.9{\times}10^5\;revertants/{\mu}g$. An analysis of the possible contribution revealed that MeIQ account for only 0.85% of the 2R4F-TPM mutagenicity in TA98. NRU data demonstrated that high cytotoxic activity was obtained for hydroquinone, formaldehyde, and acrolein. Based on the results of the present study, the contribution of acrolein to the cytotoxicity of the GVP fraction was calculated as 61%. Thus, a large proportion of the cytotoxic activity of this complex mixture, cigarette smoke gas phase, can be attributed to the acrolein.

Kinetic Study on the Oxidation Reaction of Substituted Benzyl Alcohols by Cr(VI)-Heterocyclic Complex (2,2'-Bipyridinium Dichromate) (크롬(VI)-헤테로고리 착물(2,2'-Bipyridinium Dichromate)에 의한 치환 벤질 알코올류의 산화반응에 대한 속도론적 연구)

  • Kim, Young Sik;Park, Young Cho
    • Applied Chemistry for Engineering
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    • v.23 no.2
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    • pp.241-246
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    • 2012
  • Cr(VI)-heterocyclic complex (2,2'-bipyridinium dichromate) was synthesized by the reaction between of 2,2'-bipyridine and chromium trioxide in $H_2O$, and characterized by IR and ICP. The oxidation of benzyl alcohol using 2,2'-bipyridinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant, in the order: cyclohexene < chloroform < acetone < N,N-dimethylformamide. In the presence of DMF solvent with acidic catalyst such as $H_2SO_4$ solution, 2,2'-bipyridinium dichromate oxidized the benzyl alcohol and its derivatives (p-$p-OCH_3$, $m-CH_3$, H, $m-OCH_3$, m-Cl, $m-NO_2$). Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant was -0.66 (303 K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.

Preparation and Characterization of Poly(Arylene Ether) Having Heterocyclic Quaternary Ammonium Functional Groups for Anion Exchange Membranes (음이온교환막용 헤테로고리형 4차 암모늄 작용기를 갖는 폴리(아릴렌 이써)의 제조 및 특성 분석)

  • LEE, SANG HYEOK;YOO, DONG JIN
    • Transactions of the Korean hydrogen and new energy society
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    • v.33 no.4
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    • pp.372-382
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    • 2022
  • In this study, anion exchange membranes were prepared by synthesizing the main chain into a poly(arylene ether) (PAE) structure, and the structures capable of improving the physical and chemical stability of the membrane by introducing a heterocyclic quaternary ammonium functional groups were studied. The chemical structure and thermal properties of the prepared polymer were confirmed by 1H-NMR, FT-IR, TGA, and DSC, and surface analysis was performed through AFM measurement. Additionally, dimensional stability and chemical properties was studied by measuring water uptake and swelling ratio, IEC and ionic conductivity. At 90℃, the quaternized poly(arylene ether) (QPAE)/1-methylpiperidine (MP) membrane exhibited the highest ionic conductivity of 27.2 mS cm-1, while the QPAE/1-methylimidazole (MI) membrane and QPAE/1-methylmorpholine (MM) membrane exhibited values of 14.5 mS cm-1 and 11.5 mS cm-1, respectively. In addition, the prepared anion exchange membrane exhibited high chemical stability in alkaline solution.

Antioxidant Activities of Volatile Aroma Components from Cudrania tricuspidata (Carr.) Bureau Extracts (꾸지 뽕나무 휘발성 향기성분의 항산화활성)

  • Ko, Keun Hee;Nam, Sanghae
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.41 no.11
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    • pp.1493-1501
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    • 2012
  • The antioxidant activities of volatile aroma extracts from Cudrania tricuspidata (Carr.) Bureau were examined using two antioxidant assays. Ten volatile aroma compounds identified in this plant were also tested for antioxidant activity. The volatile aroma extracts of stem and root from C. tricuspidata exhibited antioxidant activities with a clear dose response relationship in both aldehyde/carboxylic acid and lipid/malonaldehyde assays. Antioxidant activities of volatile aroma extracts from C. tricuspidata at $500{\mu}g/mL$ were $77.02{\pm}8.12%$ (stem) and $74.19{\pm}6.82%$ (root) in the aldehyde/carboxylic acid assay. Antioxidant activities of volatile aroma extracts from C. tricuspidata at $160{\mu}g/mL$ were $76.17{\pm}4.25%$ (stem) and $61.43{\pm}2.11%$ (root) in the lipid/malonaldehyde assay. Positively identified volatile aroma components in extracts of stem and root from C. tricuspidata were seven terpenes and terpenoides, 14 alkyl compounds, 11 nitrogen containing heterocyclic compounds, three oxygen containing heterocyclic compounds, 12 aromatic compounds, nine lactones, and seven miscellaneous compounds (possible contaminants). Among the positively identified compounds, eugenol, isoeugenol, and 2,4-bis (1,1-dimethylethyl)phenol exhibited antioxidant activities comparable to those of BHT and ${\alpha}$-tocopherol. Vanillin and 2-acetylpyrrole showed moderate activities in the lipid/malonaldehyde assay. These results suggest that consumption of antioxidant-rich beverages prepared from C. tricuspidata could have beneficial effects on human health by preventing diseases caused by oxidative damage.

Determination of Heterocyclic Amines in Roasted Fish and Shellfish by Liquid Chromatography-Electrospray Ionization/Mass Spectrometry (Liquid chromatography-mass spectrometry를 이용한 가열 조리된 어패류에서의 heterocyclic amines 함량 분석)

  • Lee, Jae-Hwan;Back, Yoo-Mi;Lee, Kwang-Geun;Shin, Han-Seung
    • Korean Journal of Food Science and Technology
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    • v.41 no.3
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    • pp.326-333
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    • 2009
  • Heterocyclic aromatic amines (HCAs) are mutagenic and carcinogenic substances that are formed during the heating of protein-rich foods. HCAs are generally found at low amounts in a complex matrix, which requires sophisticated analysis. In this study, HCAs were extracted from lyophilized fish and shellfish samples using solid-phase extraction (SPE) and determined by liquid chromatography-electrospray ionization/mass spectrometry (LC-ESI-MS). The HCA recoveries in the fish and shellfish ranged from 15.7 to 74.7% with standard deviations from 0.2 to 7.63%. And HCA concentrations ranged from 0.8 to 1,117.7 $ng/g^{-1}$ in cooked food samples. 1-methyl-9H-pyrido[3,4-b]indole (Harman), 9H-pyrido[3,4-b]indole (Norharman), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) were the most abundant HCAs formed in the muscle of fried mackerel, at levels of 1,117.7, 926.6, and 133.7 ng/g, respectively. 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2), 2-aminodipiryrido[1,2-a:3,2-d]imidazole(Glu-P-2), 2-amino-9H-pyrido[2,3-b]indole(A${\alpha}$C), 2-amino-3methyl-9H-pyrido [1,2-a:3,2-d]imidazole(MeA${\alpha}$C), 2-amino-3,4,7,8-tetramethylimidazo[4,5-f]quinoxaline (TriMeIQx), 2-amino-3,7,8-trimethylimidazo [4,5-f]quinoxaline(7,8-DiMeIQx), and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) were only detected by small quantities ranged from 1.5 to 98.6 ng/g. Overall, this study provides useful information on HCA levels in fish and shellfish products consumed in Korea.