• Title/Summary/Keyword: benzoic acid derivatives

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A Pyridyl Alkaloid and Benzoic Acid Derivatives from the Rhizomes of Anemarrhena asphodeloides

  • Youn, Ui-Joung;Lee, Yoo-Jin;Jeon, Ha-Rim;Shin, Hyun-Ji;Son, Young-Min;Nam, Joo-Won;Han, Ah-Reum;Seo, Eun-Kyoung
    • Natural Product Sciences
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    • v.16 no.4
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    • pp.203-206
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    • 2010
  • A pyridyl alkaloid, 3-pyridylcarbinol (1) and benzoic acid derivatives, 4-hydroxy benzoic acid (2), 4-hydroxyactophenone (3), vanilic acid (4), and benzoic acid (5) were isolated from the rhizomes of Anemarrhena asphodeloides on the basis of spectroscopic and physicochemical analyses including 1D- and 2D- NMR techniques as well as by comparison of their data with the published values. Compounds 1 - 5 were isolated for the first time from this plant source.

The New Substituent Constants in the Excited States (II)

  • Sang-Chul Shim;Joon-Won Park;Heui-Suk Ham;Jin-Soon Chung
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.45-47
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    • 1983
  • In order to standardize the ${\sigma}^*,\;{\rho}^*$ is taken as unity for the benzoic acids by analogy with the fact that ${\rho}$ of benzoic acids in the ground state is taken as unity. The $pK_{\alpha}^*$ of many benzoic acid derivatives are determined by UV spectroscopy and fluorescence spectral analysis whenever possible. The ${\sigma}^*$ constants are derived from the Hammett equation utilizing these $pK_{\alpha}^*$ values and the $pK_{\alpha}^*$ of the benozic acid derivatives showed better correlationship with ${\sigma}^*$ than ${\sigma},\;{\sigma}^+\;and\;{\sigma}^-$ as expected. From these ${\sigma}^*$ values, ${\rho}^*$ of the phenol derivatives was calculated to be 1.28. The new standardized ${\sigma}^*$ values are calculated from the $pK_{\alpha}^*$ values of phenols since more accurate and abundant data are available for phenols than the benzoic acid derivatives.

Synthesis, Characterization and Antimicrobial Activity of Bifunctional Sulfonamide-Amide Derivatives

  • Abbavaram, Babul Reddy A.;Reddyvari, Hymavathi R.V.
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.731-737
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    • 2013
  • A convenient synthesis of bifunctional sulfonamide-amide derivatives was reported. Amide coupling of 4-methyl benzoic acid 1 followed by reaction with chlorosulfonic acid produce ethyl-4-(3-(chlorosulfonyl)-4-methylbenzoyl)piperazine-1-carboxylate 4. The resulted compound on further treatment with various anilines produces the title sulfonamide-amide derivatives 5a-n. The configurations of these compounds were established by elemental analysis, IR, $^1H$ NMR, mass spectra, and by their preparation from the corresponding 4-methyl benzoic acid 1 and chlorosulfonic acid. All these new compounds demonstrate significant in vitro antibacterial and antifungal activities against all bacterial and fungal strains.

Metabolic Fate of Phenylalanine in the Corn Smut Fungus Ustilago maydis (옥수수 깜부기균에 의한 페닐알라닌의 대사적 분해)

  • Hyun, Min-Woo;Kim, Seong-Hwan
    • The Korean Journal of Mycology
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    • v.39 no.3
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    • pp.249-253
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    • 2011
  • Cetecol has been known as a component of melanin in teliospores of the corn smut fungus Ustilago maydis. Its metabolic precursor has been assumed to be benzoic acid but it has not been proven yet. This study was carried out to verify the synthesis of benzoic acid and to chase its metabolic origin in U. maydis. For this aim, the catabolic process of phenylalanine was investigated by culturing the fungus in the complete medium containing L-$^{14}C$-phenylalanine and $^{14}C$-trans-cinnamic acid. We detected trans-cinnamic acid, benzoic acid, 4-hydroxybenzoic acid and hydroxybenzoic acid derivatives from the extracts of the fungus cells and cultural filtrates by thin layered chromatography analysis. We also observed that the fungus could completely catabolize L-$^{14}C$-phenylalanine and produce $^{14}CO_2$ in the air. Conclusively, this study provided an evidence that U. maydis could produce benzoic acid through catabolic process of phenylalanine.

Induction of Kanamycin Resistance Gene of Plasmid pUCD615 by Benzoic Acid and Phenols

  • Mitchell Robert J.;Hong Han-Na;Gu Man-Bock
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1125-1131
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    • 2006
  • A kan'::luxCDABE fusion strain that was both highly bioluminescent and responsive to benzoic acid was constructed by transforming E. coli strain W3110 with the plasmid pUCDK, which was constructed by digesting and removing the 7-kb KpnI fragment from the promoterless luxCDABE plasmid pUCD615. Experiments using buffered media showed that this induction was dependent on the pH of the media, which influences the degree of benzoic acid protonation, and the expression levels seen are likely due to acidification of the cytoplasm by uncoupling of benzoic acid. Consequently, the sensitivity of this strain for benzoic acid was increased by nearly 20-fold when the pH was shifted from 8.0 to 6.5. Benzoic acid derivatives and several phenolics also resulted in significantly increased bioluminescent signals. Although these compounds are known to damage membranes and induce the heat-shock response within E. coli, bacterial strains harboring mutations in the fadR and rpoH genes, which are responsible for fatty acid biosynthesis during membrane stress and induction of the heat-shock response, respectively, showed that these mutations had no effect on the responses observed.

The Cell Regenerative Effect of Benzoic Acid Derivatives Against Chomium Trioxide-Induced Cytotoxicity (벤조산 유도체의 Chromium Trioxide 독성에 대한 세포 재생효과)

  • Han, Du-Seok;Choi, Byung-Nam;Lee, Jae-Sug;Choi, Hwa-Jung;Baek, Seung-Hwa
    • YAKHAK HOEJI
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    • v.52 no.5
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    • pp.361-369
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    • 2008
  • In order to evaluate the cytotoxicity of chromium trioxide, and the cell regenerative effect of phenolic acid against chromium trioxide-induced cytotoxicity, cell viability, cell adhesion activity, lactate dehydrogenase (LDH) activity, and morphological changes of cells were performed in these cultures. The toxicity of chromium trioxide (${IC}_{50}$, 44.0 ${\mu}M$) was high according to the toxic criteria. Cell regeneration of benzoic acid derivatives against ${IC}_{50}$ value of chromium trioxide in cell morphology was increased in concentration-dependent manner. These results suggest that benzoic acid derivatives may be used as a cell regenerative agent against chromium-mediated cytotoxicity.

Simultaneous Determination of Preservatives in Food by GC/MS (Gas Chromatography/Mass Spectrometry를 이용한 식품보존료의 동시분석방법 연구)

  • 김승기;노동석
    • Journal of Food Hygiene and Safety
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    • v.14 no.2
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    • pp.140-145
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    • 1999
  • Analytical method for preservatives in food was developed using gas chromatography/mass spectrometry (GC/MS). Propionic acid, sorbic acid, benzoic acid, ethyl salicylate, ethyl p-hydroxy benzoate, iso-propyl p-hydroxy benzoate, n-propyl p-hydroxy benzoate, iso-butyl p-hydroxy benzoate, n-butyl p-hydroxy benzoate, p-hydroxy benzoic acid and dehydro acetic acid were extracted from cooling beverage with diethyl ether. The polar hydroxyl and carboxyl groups of food preservatives were derivatized with N-methyl-N-tert-butyldimethylisilyl-trifluoroscetamide (MTBSTFA) to form the corresponding tert-bytyldimethyl-silylated derivatives, and submitted to GC/MS analysis. The mass spectra of the derivatives were investigated for the selection of monitoring ions for multi-residue analysis of 11 preservatives by GC/MS. The macro program was also developed for the qualitative analysis of these preservatives in food.

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A Study on Separation of Benzoic Acid and Its Derivatives by Anion Exchange Chromatography (음이온 교환크로마토그래피에 의한 벤조산 및 그 유도체들의 분리에 관한 연구)

  • Kang Sam Woo
    • Journal of the Korean Chemical Society
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    • v.18 no.5
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    • pp.358-362
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    • 1974
  • The anion exchange separation of a number of benzoic acid and its derivatives has been studied in various concentrations of $NiCl_2-methanol$ solvent medium. The volume distribution coefficients with Amberlite CG-400, $Cl^-$form have been measured in these medium. Several synthetic mixtures of organic acids were separated quantitatively by elution with a suitable concentration of $NiCl_2-MeOH$ solution suggested by the distribution data. The concentration of organic acids were determined by UV spectrophotometry.

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Screening of Phenolic Compounds with Inhibitory Activities against HMG-CoA Reductase (페놀 화합물로부터 HMG-CoA reductase 저해 활성 물질 탐색)

  • Son, Kun Ho;Lee, Ju Yeon;Lee, Jeong Soon;Kang, Sam Sik;Sohn, Ho Yong;Kwon, Chong Suk
    • Journal of Life Science
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    • v.27 no.3
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    • pp.325-333
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    • 2017
  • High level of plasma cholesterol is strongly associated with the development of atherosclerosis and coronary heart disease. Clinical trials designed to reduce plasma cholesterol level by diet or pharmacological intervention have resulted in marked reduction of disease incidence. The enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase which reduces cholesterol biosynthesis in the liver is the key enzyme of the mevalonate pathway that produces cholesterol. In this study, 71 naturally occurring phenolic compounds were tested for inhibitory activities against HMG-CoA reductase. Eleven compounds out of 71 showed inhibitory activities: three hydrolyzable tannin (geraniin, acetonyl geraniin and pentagalloyl ${\beta}-D-glucose$), four benzoic acid derivatives (benzoic acid, trans-cinnamic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid), and four naphthoquinone derivatives (1,2-naphthoquinone, 1,4-naphthoquinone, plumbagin and shikonin). At the concentration of $10{\mu}g/ml$, 1,4-naphthoquinone inhibited HMG-CoA reductase by 99.4%, and then plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonyl geraniin 30.2%, benzoic acid 28.5%, geraniin 28.3% and 2,5-dihydroxybenzoic acid 22.3%, respectively. $IC_{50}$ values of 1,4-naphthoquinone and plumbagin was $2.1{\mu}g/ml$ and $5.8{\mu}g/ml$, respectively.