• Title/Summary/Keyword: Diphenyl ether

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Chemical Constituents Isolated from the Moss-derived Fungus Talaromyces sp.

  • Hwang, Hoseong;Kwon, Hak Cheol;Kwon, Jaeyoung
    • Journal of the Korean Magnetic Resonance Society
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    • v.24 no.4
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    • pp.123-128
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    • 2020
  • All plants in natural ecosystems are living in symbiosis with endophytes. Recently, there has been an increasing interest in endophytes since these organisms can interact with the hosts and produce various structurally or biologically interesting molecules. This study aimed to identify these molecules from endophytes. Chemical investigation of Climacium dendroides-derived fungus Talaromyces sp. resulted in the isolation of two diphenyl ether derivatives, purpactin A (1) and penicillide (2), and two steroids, dankasterone A (3) and calvasterol B (4). The structures of the compounds were identified via extensive spectroscopic and spectrometric methods. Four compounds did not show any antioxidative activities in the on-line antioxidant activity screening system.

Solution Phase Photolyses of Substituted Diphenyl Ether Herbicides under Simulated Environmental Conditions (모조(模造) 환경조건하(環境條件下)에서의 치환(置換) Diphenyl Ether 제초제(除草劑)의 광분해(光分解)에 관(關)한 연구(硏究))

  • Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.17 no.3
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    • pp.149-176
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    • 1974
  • Eight substituted diphenyl ether herbicides and some of their photoproducts were studied in terms of solution phase photolysis under simulated environmental conditions by using a Rayonet photochemical reactor. The test compounds absorbed sufficient light energy at the wavelength of 300 nm to undergo various photoreactions. All the photoproducts were confirmed by means of tlc, glc, ir, ms, and/or nmr spectrometry. The results obtained are summarized as follows: Solution phase photolysis of C-6989: An exceedingly large amount of p-nitrophenol formed strongly indicates the readiness of the ether linkage cleavage of this compound as the main reaction in all solvents used. Photoreduction of nitro to amino group(s) and photooxidation of trifluoromethyl to carboxyl group were recognized as minor reactions. Aqueous photolysis of p-nitrophenol: Quinone(0.28%), hydroquinone (0.66%), and p-aminophenol (0.42%) were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. The mechanisms of formation of these products were proposed to be the nitro-nitrite rearrangement via $n{\rightarrow}{\pi}^*$ excitation and the photoreduction through hydrogen abstractions by radicals, respectively. Solution phase photolysis of Nitrofen: Photochemical reduction leading to the p-amino derivative was the main reaction in n-hexane. In aqueous solution, the photoreduction of nitro to amino group and hydroxylation predominated over the ether linkage cleavage. Nucleophilic displacement of the nitro group by hydroxide ion and replacement of chlorine substituents by hydroxyl group or, to a lesser extent, hydrogen were also observed as minor reactoins. Solution phase photolysis of MO-338: Photoreduction of the nitro to amino group was marked in the n-hexane solution photolysis. In the aqueous solution, photoreduction of the nitro substituent and hydroxylation were the main reactions with replacement of chlorine substituents by the hydroxyl group and hydrogen, and cleavage of the ether linkage as minor reactions. Photolyses of MC-4379, MC-3761, MC-5127, MC-6063, and MC-7181 in n-hexane and cyclohexane: Photoreduction of the nitro group leading to the corresponding amino derivative and replacement of one of the halogen substituents by hydrogen from the solvent used were the key reactions in each compound. Aqueous photolysis of MC-4379: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, hydroxylation, and replacement of the nitro by hydroxy group were prominent with photoreduction and dechlorination as minor reactions. Aqueous photolysis of MC-3761: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, and photoreduction followed by hydroxylation were the main reactions. Aqueous photolysis of MC-5127: Replacement of carboxyethyl by hydrogen was predominant with ether linkage cleavage, photoreduction, and dechlorination as minor reactions. It was obvious that the decarboxyethylation proceeded more readily than decarboxymethylation occurring in the other compounds. Aqueous photolysis of MC-6063: Cleavage of the ether linkage and photodechlorination were the main reactions. Aqueous photolysis of MC-7181: Replacement of the carboxymethyl group by hydrogen and monodechlorination were the remarkable reactions. Cleavage of the ether linkage and hydroxylation were thought to be the minor reactions. Aqueous photolysis of 3-carboxymethyl-4-nitrophenol: The photo-induced Fries rearrangement common to aromatic esters did not appear to occur in the carboxymethyl group of this type of compound. Conversion of nitro to nitroso group was the main reaction.

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Degradation of the Herbicide, TOK(2,4-dichloro-4'-nitro diphenyl ether) in Soil (제초제(除草劑) TOK의 토양중(土壤中) 분해(分解))

  • Lee, Jae-Koo;Kim, Ki-Cheol;Kim, Chang-Han
    • Applied Biological Chemistry
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    • v.23 no.2
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    • pp.131-139
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    • 1980
  • TOK (2,4-Dichlolo-4'-nitrodiphenyl ether) was applied to two Korean soils possessing different physico-chemical properties at a certain concentration and incubated for a certain time under flooded conditions. The metabolites and the soil microorganisms involved in the degradation of TOK are studied. Chong Ju and Chung Ju soils treated with TOK at a concentration of 500 ppm and incubated for two, four, and six months at $30^{\circ}C$ yielded 4-chloro-4'-amino diphenyl ether, 2, 4-dichloro-4'-amino diphenyl ether(amino-TOK), N-[4'-(4-chloro-phenoxy)] phenyl acetamide, and N-[4'-(4-chloro-phenoxy)] phenyl formamide as the major metabolites. TOK underwent the reduction of nitrogroup to amino group, dechlorination, acetylation, and formylation. No cleavage at the ether linkage was recognized. TOK was more readily degraded in Chung Ju soil which is characterized by the higher pH (PH 6.43), clay loam in textural class, and the higher cation exchange capacity. The toxicity of TOK as a possible environmental contaminant is expected to be considerably reduced as a result of the above degradation Twelve strains of soil bacteria were isolated from the TOK-treated Chong Ju and Chung Ju soils. As a result of the incubation of TOK in pure cultures of the isolates, T-1-1 strain isolated from Chong Ju soil had almost no degradability, whereas T-2-3 strain turned out to be the most potent. The degradation of TOK by the isolates constituted mostly the reduction of the nitro group to amino group. The citrate buffer extract of Chung Ju soil reduced TOK more readily to amino-TOK than that of Chong Ju soil.

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Synthesis of Chiral Azophenolic Pyridino-18-Crown-6 Ether and Its Enantiomeric Recognition toward Chiral Primary Amines

  • Kim, Jae-kon;Song, Su-Hee;Kim, Jae-Hong;Kim, Tae-Hyun;Kim, Ha-suck;Suh, Hong-Suk
    • Bulletin of the Korean Chemical Society
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    • v.27 no.10
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    • pp.1577-1580
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    • 2006
  • The article reports the synthesis and enantiomeric recognition of a new chiral azophenolic pyridino-18-crown-6 ether, (S,S)-6, possessing diphenyl groups as chiral barriers. The association constants for the enantiomeric recognition of chiral primary amines (7-12) using chiral azophenolic pyridino-18-crown-6 ether, (S,S)-6, were determined by UV-visible titration method in acetonitrile at $25{^{\circ}C}$.

Antioxidant and Antimicrobial Activities of Korean Mistletoe (Viscum album var. coloratum) Extracts against Food Poisoning Bacteria (한국산 겨우살이 (Viscum album var. coloratum) 추출물의 식중독 세균 증식 억제 및 항산화 활성)

  • Kang, Seo-Jin;Chung, Shin-Kyo
    • Food Science and Preservation
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    • v.19 no.6
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    • pp.919-924
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    • 2012
  • This study was conducted to investigate the antimicrobial activities and antioxidant activities of the Korean mistletoe extract and its solvent fractions (e.g. n-hexane, ethyl ether, ethyl acetate, butanol). Ethyl ether fraction against Bacillus cereus showed stronger activities than benzoic acid (2.5 mg/mL). The MIC of korean mistletoe extract and slovent fractions were in the range of 6.25-25 mg/mL. The MIC (6.25 mg/mL) of ethyl acetate fraction onto Staphylocossus aureus was the lowest among them. Ethyl ether fraction which showed the strongest antioxidant activities by DPPH (1,1-diphenyl-2-picryl-hydrazyl) and FRAP (ferric ion reducing antioxidant power) methods had the highest total phenolic contents. It is suggested that Korean mistletoe could be utilized as natural preservative material through the study of the active compounds from ethyl ether fraction.

Antioxidant Properties of Flavone-6(4')-Carboxaldehyde Oxime Ether Derivatives

  • Gulgun, Ayhan-Kilcigil;Coban, Tulay;Tuncbilek, Meral;Benay, Can-Eke;Oya, Bozda-Dundar;Ertan, Rahmiye;Iscan, Mumtaz
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.610-614
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    • 2004
  • The in vitro antioxidant properties of some flavone-6(4)-carboxaldehyde oxime ether deriva-tives (Ia-f, lIa-f) were determined by their effects on the rat liver microsomal NADPH-dependent lipid peroxidation (LP) levels by measuring the formation of 2-thiobarbituric acid reactive substances. The free radical scavenging properties of the compounds were also examined in vitro by determining their capacity to scavenge superoxide anions and interact with the stable free radical 2, 2-diphenyl-1-picrylhydrazyl (DPPH). The most active compounds, lib (Flavone-4'-carboxaldehyde-O-ethyl oxime) and Id (Flavone-6-carboxaldehyde-O-[2-(1-pyrolidino) ethyl] oxime), caused 98 and 79% inhibition of superoxide anion production and DPPH stable free radical at $10^{-3}{\;}M$, respectively.

Convergence study of oxidative stress from fraction of Xanthium strumarium L. (도꼬마리 추출물의 산화적 스트레스에 대한 융합연구)

  • Min, Young-Sil
    • Journal of the Korea Convergence Society
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    • v.8 no.12
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    • pp.215-220
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    • 2017
  • Xanthium strumarium L. is an annual plant belongs to the family Asteraceae which is is called a 'Cocklebur' that is used for medicinal purposes. Convergent phyto-activity of various extracts of Xanthium strumarium L. (Asteraceae) was examined. We estimated antioxidant activity from ground part and fruit extract of X. strumarium using 1, 1-diphenyl-2-picrylhydrazyl radical (DPPH) and ABTS assay. The extract of X. strumarium was separated each fraction that of ethanol, petroleum ether, and ethyl acetate. It showed potent radical scavenging effect against the DPPH radical and ABTS. The study revealed that X. strumarium could be used as a potential source of natural antioxidant.

Antioxidant and Antimicrobial Activities of Seaweed, Ulva lactuca (갈파래 (Ulva lactuca) 추출물의 항균 및 항산화 효과)

  • Kim In-Hae;Lee Hee-Hyun;Jang Jeong-Su;Lee Sang-Hyun;Ha Jong-Myung;Ha Bae-Jin;Lee Jae-Hwa
    • Environmental Mutagens and Carcinogens
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    • v.26 no.2
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    • pp.48-52
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    • 2006
  • Our investigation of the seaweed extracts, Ulva lactuca. The biological activities antioxidant, antimicrobial activity, antifungal and haemolytic activity of ethy-ether and ethyl-acetate extracts from the seaweed, Ulva lactuca were investigated. They were separately extracted using ethyl-ether and ethyl-acetate from dried samples at room temperature and freeze dried. Seaweed extracts were found to cause significant free radical scavenging effects on DPPH (1,1-diphenyl-2-picrylhydrazyl). Seaweed extracts had not significant haemolytic activity against human erythrocyte. This extracts exhibited in vitro broad-spectrum antimicrobial activity of gram-negative, gram-positive bacteria and without antifungal activity.

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Polybrominated Diphenyl Ethers (PBDEs) in the Piglet Liver (축산물 중의 Polybrominated Diphenyl Ethers (PBDEs) 분석)

  • Ahn, Yun Gyong;Lee, Kyu Keon;Shin, Jeoung Hwa
    • The Korean Journal of Community Living Science
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    • v.25 no.4
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    • pp.629-636
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    • 2014
  • Polybrominated diphenyl ethers (PBDEs) as flame-retardant additives have been used in a wide array of products, including building materials, electronics, furnishings, motor vehicles, airplanes, plastics, polyurethane foams, and textiles. They are structurally similar to PCBs and other polyhalogenated compounds. PBDEs are found in a variety of foods, and 95% of all human exposure to POPs comes from food. The major food sources are fish/seafood and dairy products. A number of studies have reported high levels of PBDEs in animals, increasing the public's concern over PBDE levels in animals. This study evaluates the relationship between the level of PBDEs according to piglet diseases. Salmonella spp. and Streptococcus are bacterial diseases. Porcine respiratory reproductive syndrome (PRRS) is a viral disease. The concentration of PBDEs in the piglet liver from viral diseases was higher than that from bacterial diseases. BDE-47 and BDE-99 were detected in most samples. More PBDEs were detected in the piglet liver from PRRS of North American type than from that of European type.

Evaluation of proficiency and improvement of accuracy on the analysis of brominated flame retardants (PBDEs) in ABS polymer (ABS수지 중 polybrominated diphenyl ether(PBDE)류 분석 숙련도 평가 및 정확도 향상)

  • Ryu, Jehoon;Kim, Dalho
    • Analytical Science and Technology
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    • v.28 no.6
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    • pp.446-452
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    • 2015
  • In order to evaluate and improve the ability of Korean testing laboratories to measure Polybrominated diphenyl ethers in acrylonitrile-butadiene-styrene (ABS), a proficiency test was organised by Korea Research Institute of Standards and Science (KRISS) based on ISO/IEC 17043. The proficiency test material used was 10 g of a granular ABS fortified with a mixture of congeners of PBDE (BDE-154, 183, 206, 209). Homogeneity and stability were investigated to assess the adequacy of the test material. The certified value established by KRISS based on the national reference was used for assigned value of each PBDE. The test materials were distributed to the 16 participating laboratories. The participating laboratories were requested to analyse the samples employing the methods used in their routine analysis. Each laboratory was given it’s own code to secure the anonymity. Participants results were evaluated with z-scores according to ISO/IEC 17043. The standard deviation for proficiency assessment was set by standard deviation of the participants results except for outlier. The results, the laboratory's performance and improvement of accuracy were discussed.