• Title/Summary/Keyword: 4-hydroxyphenyl acetic acid

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Radical Scavenging Hydroxyphenyl Ethanoic Acid Derivatives from a Marine-Derived Fungus

  • Li Xifeng;Kim Se-Kwon;Kang Jung-Sook;Choi Hong-Dae;Son Byeng-Wha
    • Journal of Microbiology and Biotechnology
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    • v.16 no.4
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    • pp.637-638
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    • 2006
  • Bioassay-guided fractionation of an organic extract of the culture broth from an unidentified marine-derived fungus led to the isolation of a new metabolite, N-[2-(4-hydroxyphenyl) acetyl]formamide (1), along with four known polyketides, 4-hydroxyphenyl acetamide (2), 4-hydroxyphenyl acetic acid (3), 3,4-dihydroxyphenyl acetic acid (4), and N-[2-(4-hydroxyphenyl)ethenyl]formamide (5). The structures of 1-5 were elucidated by spectral data analyses. Among them, compounds 1, 4, and 5 exhibited significant radical scavenging activity against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) with $IC_{50}$ values of 8.4, 11.9, and $0.2{\mu}M$, respectively.

Production of Auxins and Auxin-like Compounds by Ginseng Growth-promoting Bacterium Pseudomonas fluorescens KGPP 207

  • Ten, Leonid N.;Lee, Mi Ja;Lee, Mee-Kyoung;Park, Hoon;Yoon, Jong Hyuk
    • Journal of Applied Biological Chemistry
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    • v.43 no.4
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    • pp.264-268
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    • 2000
  • High activity of acidic ethylacetate extract from the culture supernatant of ginseng growth-promoting bacterium Pseudomonas fluorescens KGPP 207 and its fractions were demonstrated through wheat coleoptile bioassay. The following auxins and auxin-like compounds were identified in these fractions by combined gas chromatography-mass spectrometry: indole-3-acetic acid, indole-3-acetic acid methyl and ethyl ester, indole-3-butyric acid, indole-3-lactic acid and its methyl ester, indole-3-propionic acid, indole-3-pyruvic acid, p-hydroxyphenyl acetic acid, p-hydroxyphenyl acetic acid methyl and ethyl ester, phenyl acetic acid and its methyl ester. The bacterium KGPP 207 belongs to the strain of P. fluorescens which produces plant growth regulators and its beneficial effect on the ginseng growth may be due to the formation of the identified compounds.

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Examining the performance of PAI/ZnO synthesized with diamine and nano particles

  • Jianwei Shi;Xiaoxu Teng
    • Advances in nano research
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    • v.14 no.2
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    • pp.201-210
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    • 2023
  • A ZnO/poly (amide-imide) hybrid nanocomposite film with different weight percentages of Zinc oxide (ZnO) nanoparticles is synthesized and characterized in this paper. A two-step reaction successfully synthesized a new kind of heteroaromatic diamine with bulky pendant groups. In order to produce 3, 5-dinitro-3, 3-bis (4-(4-Nitrophenoxy) phenyl) -2- benzofuran-1-one, 3, 3'-bis (4-hydroxyphenyl) benzofuran-1-one and 3'-bis (4-hydroxyphenyl) benzofuran-1-one were combined with 3'-bis (3-hydroxyphenyl) benzofuran-1-one. The obtained dinitro was then reduced by zinc dust and hydrochloric acid. The reaction of 4, 4* carbonyl diphthalic anhydride with amino acid L-alanine in acetic acid leads to the production of very high yields of chiral diacid monomer. As a result of the direct polymerization of these monomers, new optically active polymers were formed (amide-imide). In order to synthesize poly (amide-imide)/ZnO nanocomposites with different weight percentages (2, 4, 6, 8, and 10%), PAI and ZnO nanoparticles were combined using ultrasonication SEM, Fourier transform infrared spectroscopy, X-ray diffraction and thermal gravimetry were used to characterize the PAI films.

Anti-oxidant and Anti-inflammatory Effects of Rutin and Its Metabolites

  • Kim, Ji Hye;Park, Sang Hee;Beak, Eun Ji;Han, Chang Hee;Kang, Nam Joo
    • Current Research on Agriculture and Life Sciences
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    • v.31 no.3
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    • pp.165-169
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    • 2013
  • Rutin is one of the major flavonoids found in buckwheat (Fagopyrum esculentum Moench). While rutin is already known to exhibit anti-oxidative, anti-inflammatory, and anti-carcinogenic activities. However, the health beneficial function of rutin metabolites is not well understood. In DPPH radical scavenging assays, the present study found that 3,4-dihydroxyphenyl acetic acid had the highest total anti-oxidant activity, followed by 3,4-dihydroxyphenylacetic acid, rutin, homovanillic acid, and 3-hydroxyphenyl acetic acid. Further, 3,4-dihydroxyphenylacetic acid strongly reduced LPS-induced IL-6 production in RAW 264.7 cells, compared with other metabolites. Therefore, these results suggest that rutin metabolites have potential to be utilized as food ingredients with anti-oxidant and anti-inflammatory activities.

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Synthesis, Structure Investigation and Dyeing Assessment of Novel Bisazo Disperse Dyes Derived from 3-(2'-Hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones

  • Metwally, M.A.;Bondock, S.;El-Desouky, S.I.;Abdou, M.M.
    • Journal of the Korean Chemical Society
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    • v.56 no.3
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    • pp.348-356
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    • 2012
  • In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{3a-f}$ were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{2a-f}$. Compounds $\mathbf{3a-f}$ were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives $\mathbf{4a-f}$. The latter products as well as spectral data indicated that compounds $\mathbf{3a-f}$ exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes $\mathbf{3a-f}$ and $\mathbf{4a-f}$ were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates ($L^*$, $a^*$, $b^*$, $H^*$, $C^*$*) was assessed.

Biocompatible Individual Dispersion of Single-walled Carbon Nanotubes

  • Najeeb, C.K.;Kim, Duck-Jong
    • Proceedings of the Korean Vacuum Society Conference
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    • 2012.02a
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    • pp.529-529
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    • 2012
  • Dispersion of carbon nanotubes in biocompatible media are of particular interest for diverse biomedical and nanomedicine applications. Various biomolecules and biopolymers such as DNA, proteins, poly L-lysine, starch, gelatin, steroid biosurfactants, and chitosan have shown capability for the effective dispersion of carbon nanotubes in water. Chitosan has demonstrated capacity for effective dispersion of single-walled carbon nanotubes (SWCNTs) in acidic medium and it also showed tendency to preferentially disperse smaller diameter nanotubes. Chemical functionalizations of chitosan enable its solubility in neutral pH water by reducing the intra and inter molecular hydrogen bonding. Herein, we present a neutral pH water soluble chitosan derivative, chitosan-hydroxyphenyl acetamide (CHPA), obtained by functionalizing the amino groups of chitosan with 4-hydroxyphenyl acetic acid, as an efficient biocompatible dispersant for debundling and solubilization of SWNTs in neutral aqueous solutions. Various process conditions for individual dispersion of SWCNTs are analyzed based on optical absorption and Raman spectroscopy.

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Characterization of ent-Kaurenoic Acid 13-Hydroxylase in Steviol Biosynthesis of Stevia rebaudiana Bertoni (Stevia rebaudiana Bertoni의 Steviol 생합성 효소 ent-Kaurenoic Acid 13-Hydroxylase의 특성)

  • Shibata, Hitoshi;Kim, Keun-Ki
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.501-507
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    • 1997
  • Chloroplasts isolated from Stevia rebaudiana Bertoni leaves contained an enzyme activity which catalyzed hydroxylation of ent-kaurenoic acid (ent-kaur-16-en-19-oic acid; ent-KA) to steviol (ent-13-hydroxy kaur-16-en-19-oic acid), the diterpenoid carboxylic alcohol which is the aglycone of sweet stevioside-related glycosides. $[^(14)C]-methylated$ ent-KA was used to localize ent-KA hydroxylase. $[^(14)C]-methyl-KA$ was most actively was transformed into methyl-steviol in chloroplast. The enzymatic activity was found in stroma fraction but not in thylakoid membrane in Stevia rebaudiana Bertoni. However, ent-KA 13-hydroxylase activity was not detected in stroma fraction of either Spinacia oleracea and Solidago altissima. The reaction products using $[^(14)C]-methyl-KA$ were purified and identified on TLC autoradiogram. The hydroxylation of ent-KA from stromal protein to form steviol required NADPH and oxygen. FAD and riboflavin stimulated the enzyme activity 1.5-and 1.7-fold, respectively. It also turned out that the activity of this enzyme using methyl-KA as a substrate was 16.7% that of ent-KA. The purified ent-KA 13-hydroxylase did not act on t-cinnamic acid, 4-hydroxyphenyl acetic acid, choline and resorcinol, known as monooxygenase and hydroxylase substrates.

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Potent whitening effects of rutin metabolites (루틴 대사체의 미백 효능)

  • Kim, Ji Hye;Kang, Nam Joo
    • Food Science and Preservation
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    • v.22 no.4
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    • pp.607-612
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    • 2015
  • The aim of this research was to investigate the whitening effects of rutin and rutin metabolites including 3,4-dihydroxyphenyl acetic acid (DHPAA), 3-hydroxyphenyl acetic acid (HPAA), 3,4-dihydroxytolene (DHT) and homovanillic acid (HVA). The potent whitening effect of rutin and rutin metabolites were determined by mushroom tyrosinase inhibition assay and expressed as the half maximal inhibitory concentration ($IC_{50}$) against tyrosinase activity in vitro. The HVA showed the highest inhibitory effect ($IC_{50}=37.10{\mu}M$) of tyrosinase activity, followed by DHPAA ($IC_{50}=45.87{\mu}M$), HPAA ($IC_{50}=50.96{\mu}M$), rutin ($IC_{50}=57.98{\mu}M$), and DHT ($IC_{50}=66.09{\mu}M$), respectively. To evaluate cell cytotoxicity, MTT assay was performed with JB6 P+ mouse epidermal cells and expressed as a relative percentage of untreated control. The results showed that rutin and rutin metabolites had no cytotoxic effects on JB6 P+ cells up to $100{\mu}M$ except for DHT (up to $50{\mu}M$). These results suggests that rutin metabolites may be utilized as a potential tyrosinase inhibitors and the whitening agents for the future.

Preparation of Molecularly Imprinted Polymers Using Photocross-linkable Polyphosphazene and Selective Rebinding of Amino Acids

  • Lee, Seung-Cheol;Chang, Ji-Young
    • Macromolecular Research
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    • v.17 no.7
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    • pp.522-527
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    • 2009
  • A photocrosslinkable polyphosphazene was used for molecular imprinting. We synthesized polyphosphazene (3) having urea groups for complexation with N-carbobenzyloxyglycin (Z-Gly-OH, template) and chalcone groups for cross-linking reaction. As substituents, 4-hydroxycha1cone (1) and N-(4-hydroxyphenyl)-N'-ethylurea (2) were prepared. Choloro groups of poly(dichlorophosphazene) were replaced by the sequential treatment with sodium salts of compounds 1 and 2, and trifluoroethanol. The template molecule was complexed with the urea groups on the polymer chains via hydrogen bonding. A thin polymer film was prepared by casting a solution of the complex of polymer 3 and the template in dimethylformamide on a quartz cell and irradiated with 365 nm UV light to yield a cross-linked film with a thickness of about $16{\mu}m$. The template molecules in the film were removed by Soxhlet extraction with methanol/acetic acid. The control polymer film was prepared in the same manner for the preparation of the imprinted polymer film, except that the template and triethylamine were omitted. In the rebinding test, the imprinted film exhibited much higher recognition ability for the template than the control polymer. We also investigated the specific recognition ability of the imprinted polymer for the template and its structural analogues. The rebinding tests were conducted using Z-Glu-OH, Z-Asp($O^tBu$)-OH, and Z-Glu-OMe. The imprinted film showed higher specific recognition ability for the template and the lowest response for Z-Asp($O^tBu$)-OH.

Cognitive-Enhancing Effect of Dianthus superbus var. Longicalycinus on Scopolamine-Induced Memory Impairment in Mice

  • Weon, Jin Bae;Jung, Youn Sik;Ma, Choong Je
    • Biomolecules & Therapeutics
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    • v.24 no.3
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    • pp.298-304
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    • 2016
  • Dianthus superbus (D. superbus) is a traditional crude drug used for the treatment of urethritis, carbuncles and carcinomas. The objective of this study was to confirm the cognitive enhancing effect of D. superbus in memory impairment induced mice and to elucidate the possible potential mechanism. Effect of D. superbus on scopolamine induced memory impairment on mice was evaluated using the Morris water maze and passive avoidance tests. We also investigated acetylcholinesterase (AChE) activity and brain-derived neurotropic factor (BDNF) expression in scopolamine-induced mice. HPLC-DAD analysis was performed to identify active compounds in D. superbus. The results revealed that D. superbus attenuated the learning and memory impairment induced by scopolamine. D. superbus also inhibited AChE levels in the hippocampi of the scopolamine-injected mice. Moreover, D. superbus increased BDNF expression in the hippocampus. Eight compounds were identified using HPLC-DAD analysis. The content of 4-hydroxyphenyl acetic acid was higher than contents of other compounds. These results indicated that D. superbus improved memory functioning accompanied by inhibition of AChE and upregulation of BDNF, suggesting that D. superbus may be a useful therapeutic agent for the prevention or treatment of Alzheimer's disease.