• Title/Summary/Keyword: 4-Hydroxybenzoic acid

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Phenolic Constituents and Their Anti-inflammatory Activity from Echinochloa utilis Grains

  • Nguyen, Duc Hung;Zhao, Bing Tian;Le, Duc Dat;Kim, Ki Yun;Kim, Young Ho;Yoon, Young Ho;Ko, Jee Youn;Woo, Koan Sik;Woo, Mi Hee
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.140-145
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    • 2016
  • Seven phenolic compounds including p-coumaric acid (1), 4-hydroxybenzoic acid (2), 4-hydroxybenzaldehyde (3), vanillic acid (4), luteolin (5), acacetin (6), and tricin (7), were isolated from the methylene chloride and ethyl acetate fractions of Echinochloa utilis grains. Compounds (1 - 4, 6) were isolated for the first time from this plant. These compounds were tested for inhibitory activities against LPS-induced NO production in RAW 264.7 cells. Compounds 5 and 6 displayed significant inhibitory effects, with $IC_{50}$ values of $27.9{\pm}2.6$ and $14.0{\pm}1.1{\mu}M$, respectively. The results suggested that E. utilis ethanolic extract may be used as a potential source of anti-inflammatory agents and functional foods for the treatment of allergic diseases.

Synthesis of New Aromatic Ester Plasticizers and Their Endocrine Disrupting Screening (새로운 방향족 에스테르계 가소제 합성 및 내분비계 장애성 시험)

  • Yoo, Kyung-Ho;Ryu, Jae-Chun
    • Journal of the Korean Applied Science and Technology
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    • v.24 no.3
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    • pp.211-218
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    • 2007
  • Based on the Benzoflex (Vesicol Chemical Co.) as PVC plasticizer substituents for Di-n-octyl phthalate (DOP), a series of new aromatic carboxylic acid ester compounds were designed as plasticizers, synthesized, and screened for the endocrine disrupting activity. 2-Hydroxybenzoic acid (1) and 2-methoxybenzoic acid (2) as the commercially available starting materials were reacted with diethylene glycol (3) in the presence of p-toluenesulfonic acid using Dean-Stark column to give diethylene glycol di-(2-hydroxy)benzoate (4, KH01) and diethylene glycol di-(2-methoxy)benzoate (5, KH02), respectively. And diethylene glycol di-(3-pyridinyl) ester (7, KH03) and dipropylene glycol di-(3-pyridinyl) ester (9, KH04) were obtained in high yields by treatment of nicotinoyl chloride (6) with diethylene glycol (3) and dipropylene glycol (8) in the presence of triethylamine as a base. To determine the estrogenic disrupting effect of new synthetic phthalate analogues, E-screen assay method was used. Of these compounds, 4 (KH01) was found to be compound without endocrine disrupting effect.

The Chemical Structures and Their Antioxidant Activity of the Components Isolated from the Heartwood of Hemiptelea davidii (시무나무(Hemiptelea davidii) 심재의 성분과 그 항산화 활성)

  • Chang, Bok-Sim;Kwon, Yong-Soo;Kim, Chang-Min
    • Korean Journal of Pharmacognosy
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    • v.35 no.1 s.136
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    • pp.80-87
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    • 2004
  • From the $CHCl_3$ and BuOH soluble fractions of the heartwood of Hemiptelea davidii, eleven compounds have been isolated. On the basis of spectral data, they were identified as ${\beta}-sitosterol$ (1), scopoletin (2), kaempferol (3), 4-hydroxybenzoic acid (4), 2-(4-hydroxyphenyl) ethanol (5), aromadendrin (6), scopolin (7), kaempferol 6-C-glucoside (8), aromadendrin 6-C-glucoside (9), taxifolin 6-C-glucoside (10) and quercetin 6-C-glucoside (11), respectively. Among these compounds, compounds 3, 8, 10, and 11 showed potent DPPH radical scavenging activity with $IC_{50}$ values of 11.9, 14.7, 10.3 and $6.2\;{\mu}g/ml$, respectively.

Uptake and Distribution of Bisphenol A and Its Metabolites in Lettuce Grown in Sandy Loam and Loam Soil

  • Cho, Il Kyu;Jeon, Yong-Bae;Oh, Young Goun;Rahman, Md. Musfiqur;Kim, Won-Il;Lee, Young-Deuk
    • Korean Journal of Environmental Agriculture
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    • v.39 no.4
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    • pp.375-383
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    • 2020
  • BACKGROUND: Bisphenol A (BPA) is a chemical widely used in polycarbonate plastics, epoxy resins. BPA is an endocrine disruptor. Residue of BPA in agricultural environments is a major concern. The objective of this study was to understand the characteristics of the uptake and distribution of BPA and its metabolites introduced into the agricultural environment to crops, and to use it as basic data for further research on reduction of BPA in agricultural products. METHODS AND RESULTS: This study established the analysis method of BPA and its metabolites in soil and crops, and estimated the intake of BPA and its metabolites from lettuce (Lactuca sativa) grown in sandy loam and loam soil, which are representative soils in Korea. The two major metabolites of BPA were 4-hydroxyacetophenone (4-HAP) and 4-hydroxybenzoic acid (4-HBA). BPA, 4-HAP and 4-HBA have been analyzed by using liquid chromatography tandem mass spectrometry (LC-MS/MS). These substances were detected in sandy loam and loam soil, indicating that certain portions of BPA were converted to 4-HAP and 4-HBA in the soil; however, it was observed that only 4-HBA migrated to lettuce through the roots into crops. CONCLUSION: The uptake residues showed the BPA and 4-HAP were not detected in lettuces grown on sandy loam (SL) and loam (L) soil treatments that were applied with of 10 ng/g, 50 ng/kg and 500 ng/g of BPA. However, the 4-HBA was detected at the level of 7 ng/g and 11 ng/g in the lettuce grown in sandy loam and loam soil that were treated with the 500 ng/g of BPA, respectively, while the 8 ng/g of 4-HBA was measured in the lettuce cultivated in the loam that was treated with 100 ng/g of BPA. This result presents that the BPA persisting in the soil of the pot was absorbed through the lettuce roots and then distributed in the lettuce leaves at the converted form of 4-HBA, what is the oxidative metabolite of BPA.

Resistance to Pine Gall-midge and Phenolic Acid Content in Pine Needles (소나무류의 솔잎혹파리에 대한 저항성과 침엽내(內) Phenolic Acid의 농도)

  • Eom, Tae-Jin;Son, Doo-Sik;Lee, Sang-Woo;Seo, Jae-Durk
    • Journal of the Korean Wood Science and Technology
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    • v.26 no.3
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    • pp.33-40
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    • 1998
  • The phenolic acids in needles of five pine species such as Pinus densiflora, P. thunbergii. P. virginiana. P. rigida. and P. koraiensis were analyzed seasionally (March, June, September and December) in order to investigate the resistant factors against pine gall-midge(Thecodiplosis japonensis Uchida et Inouye). The interrelation of resistance to pine gall-midge and the content of phenolic acids in pine needles was investigated in the artificial hybride pine species. The contents of salicylic acid in susceptible species (P. densiflora and P. thunbergii) to pine gall-midge which watered with salicylic acid solution in a pot was determined. The results can be concluded as follows, 1. There was a little change in total phenolic constituents of resistant and susceptible pines seasonally. The each content of benzoic acid, salicylic acid and p-hydroxybenzoic acid in June was the highest through four seasons. 2. In June, resistant species showed higher content of salicylic acid than susceptible species, while the content of gallic acid was the highest in December. 3. Among the 21 artificial hybrids(P. densiflora ${\times}$ P. virginiana. P. thunbergii ${\times}$ P. virginiana), the hybrides of the higher salicylic acid content showed the lower rate of pine gall formation. 4. Pine gall formation of the susceptible species which were watered with salicylic acid solution remarkably decreased.

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Inhibitory Effect of the Phenolic Compounds from Geranium thunbergii on Rat Lens Aldose Reductase and Galactitol Formation (현초에서 분리된 페놀성 화합물들의 흰쥐 수정체 유래 알도즈 환원효소 및 갈락티톨 생성 억제 효과)

  • Choi, Se-Jin;Kim, Jin-Kyu;Jang, Jai-Man;Lim, Soon-Sung
    • Korean Journal of Medicinal Crop Science
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    • v.20 no.4
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    • pp.222-230
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    • 2012
  • We evaluated the inhibitory effects of extracts and components of Geranium thunbergii on aldose reductase (AR) and galactitol formation in rat lenses with high levels of galactose as a part of our ongoing search of natural sources for therapeutic and preventive agents for diabetic complications. The inhibitory effects of water, methanol and ethanol extracts of G. thunbergii on rat lens AR (RLAR) were determined. Comparing inhibitory effects of various solvent extracts, ethanol extract showed RLAR inhibitory activity ($IC_{50}$ values, 5.24 and $6.39{\mu}g/m{\ell}$, respectively). The ethanol extract was fractionated to chloroform, ethyl acetate and water. Of these, the ethyl acetate fraction from ethanol extract of G. thunbergii exhibited RLAR inhibitory activity ($IC_{50}$ value, $2.64{\mu}g/m{\ell}$). In order to identify the bioactive components of ethyl acetate soluble fraction of ethanol extract from G. thunbergii, eight compounds, namely gallic acid (1), protocatechuic acid (2), p-hydroxybenzoic acid (3), brevifolin carboxylic acid (4), geraniin (5), ellagic acid (6), kaempferol-3-O-arabinofuranosyl-7-O-rhamnopyranoside (7), kaempferitrin (8) were isolated. The isolates were subjected to in vitro bioassays to evaluate their inhibitory activity on RLAR and galactitol formation in rat lenses. The ellagic tannins (5, 6) and flavonoid (7) exhibited strong inhibitory effects on RLAR. Also, these three compounds (5, 6 and 7) suppressed galactitol accumulation in rat lens under high galactose conditions, demonstrating the potential to prevent galactitol accumulation exo vivo. These results suggest that the extracts and components of G. thunbergii are a promising agent in the prevention or treatment of diabetic complications.

Thermal Decomposition Behavior and Durability Evaluation of Thermotropic Liquid Crystalline Polymers

  • Shin, Sang-Mi;Kim, Seong-Hun;Song, Jun-Kwang
    • Macromolecular Research
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    • v.17 no.3
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    • pp.149-155
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    • 2009
  • The thermal decomposition behavior and degradation characteristics off our different thermotropic liquid crystalline polymers (TLCPs) were studied. The thermal decomposition behavior was determined by means of thermogravimetric analysis (TGA) at different heating rates in nitrogen and air. The order of the thermal stability was as follows: multi-aromatic polyester > hydroxybenzoic acid (HBA)/hydroxynaphthoic acid (HNA) copolyester > HNA/hydroxyl acetaniline (HAA)/terephthalic acid (TA) copolyester > HBA/Poly(ethylene terephthalate) (PET) copolyester. The activation energies of the thermal degradation were calculated by four multiple heating rate methods: Flynn-Wall, Friedman, Kissinger, and Kim-Park. The Flynn-Wall and Kim-Park methods were the most suitable methods to calculate the activation energy. Samples were exposed to an accelerated degradation test (ADT), under fixed conditions of heat ($63{\pm}3^{\circ}C$), humidity ($30{\pm}4%$) and Xenon arc radiation ($1.10\;W/m^2$), and the changes in surface morphology and color difference with time were determined. The TLCPs decomposed, discolored and cracked upon exposure to ultraviolet radiation.

Phenolic Acid Composition and Antioxidative Activity of Red Ginseng Prepared by High Temperature and High Pressure Process (고온고압 처리 홍삼의 페놀산 조성과 항산화 활성)

  • Jung, Kyung Hee;Hong, Hee-Do;Cho, Chang-Won;Lee, Min-Young;Choi, Ung-Kyu;Kim, Young-Chan
    • The Korean Journal of Food And Nutrition
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    • v.25 no.4
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    • pp.827-832
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    • 2012
  • This study was conducted to develop HTHP ginseng (high temperature and high pressure ginseng) with improved antioxidative activity and phenolic acid composition by high temperature and high pressure process. The HTHP ginseng extract was analyzed for the total phenol content, DPPH radical scavenging activity and phenolic acid composition. The total phenol content was increased in HTHP ginseng (14.76 mg/g) compared to raw ginseng (3.59 mg/g) and red ginseng (3.93 mg/g). DPPH radical scavenging activities of HTHP ginseng, raw ginseng and red ginseng extracts were 4.8~78.4%, 1~47.4% and 1.8~56.5% at $1{\sim}100mg/m{\ell}$ concentration. Also ABTS radical scavenging activities of HTHP ginseng, raw ginseng and red ginseng extracts were 8.9~99.8%, 3.4~96% and 1.2~96.5% at $1{\sim}100mg/m{\ell}$ concentration. In HPLC analysis, amounts of measured phenolic acid of HTHP ginseng greatly increased than raw ginseng and red ginseng, but salicylic acid was not detected in HTHP ginseng. In addition, DPPH radical scavenging activity of phenolic acid from HTHP ginseng was increased. Consequently, we believe high temperature and high pressure process is better method than existing method to increase the bioactivity of ginseng.

Changes in physiologically active ingredients and anti-inflammatory properties of underutilized wild vegetables by complex fermentation using beneficial microorganisms (유용미생물에 의한 저이용 산채류의 복합발효 중 생리활성 성분 및 항염증 변화)

  • Sang-Hyeob Sim;Ha KyoungChoi;Da Eun Lee;Soo Chang Na;Dae Il Hwang;Hyo Bin Oh;Yi Teak Lim;Tae-Young Kim;Dae-Woon Kim
    • Food Science and Preservation
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    • v.31 no.2
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    • pp.287-297
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    • 2024
  • It was confirmed that complex fermentation (CF) was more efficient than single-strain fermentations in inducing changes in the contents of phenolic compounds of Maclura tricuspidate and Pyrus Montana Nakai. A mixture of Maclura tricuspidata, Pyrus montana Nakai, Platycodon grandiflorum and Codonopsis lanceolata were fermented in CF using Aspergillus shirousamii (koji), yeast, and lactic acid bacteria (LAB) for 24 days, and the pH, °Brix, total acidity, anti-oxidant activity, polyphenol content, nitric oxide (NO), and Western blotting of inducible nitric oxide synthase (iNOS), cyclo-oxygenase-2 (COX-2), and tumor necrosis factor-𝛼 (TNF-𝛼) of the sample were determined. There was no significant change in pH and total acidity. °Brix significantly decreased from day 6 onwards. HPLC confirmed that the concentrations of chlorogenic acid, 4-hydrobenzoic acid, vanillic acid, and caffeic acid significantly increased from day 18 during the fermentation. Additionally, DPPH, ABTS radical scavenging activity, total phenol, and total flavonoid were confirmed to be increased until 18 days. NO was significantly inhibited from day 6, along with significant inhibition of iNOS, COX-2, and TNF-a. In conclusion, this study confirmed that CF of low-use (or underutilized) wild vegetables enhances phenolic compounds. It effectively suppresses NO, iNOS, COX-2, and TNF-𝛼, markers of inflammation-related pathogenesis. Altogether, our results suggest that CF of the above plants has a potential anti-inflammatory effect.

Characterization of degradation products of the Balsalazide by Mass spectrometry: Optimization of stability-indicating HPLC method for separation and quantification of process related impurities of Balsalazide

  • Chilakabattina Naga Narasimha Babu;Ch. Srinivasa Reddy;Bhagya Kumar Tatavarti;M. Radha Madhavi;Venkateswara Rao Anna
    • Analytical Science and Technology
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    • v.37 no.1
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    • pp.25-38
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    • 2024
  • The study aimed to investigate a novel approach by utilizing liquid chromatography (LC) and liquid chromatography-mass spectrometry (LC-MS) to separate, identify and characterize very nominal quantities of degradation products (DPs) of balsalazide along with its process related impurities without isolation from their reaction mixtures. The impurities along with balsalazide were resolved on spherisorb ODS2 (250×4.6 mm, 5.0 ㎛) column at room temperature using 0.2 M sodium acetate solution at pH 4.5 and methanol in the ratio of 55:45 (v/v) as mobile phase pumped isocratically at 1.0 mL/min as mobile phase and UV detection at 255 nm. The method shows sensitive detection limit of 0.003 ㎍/mL, 0.015 ㎍/mL and 0.009 ㎍/mL respectively for impurity 1, 2 and 3 with calibration curve liner in the range of 50-300 ㎍/mL for balsalazide and 0.05-0.30 for its impurities. The balsalazide pure compound was subjected to stress studies and a total of four degradation products (DPs) were formed during the stress study and all the DPs were characterized with the help of their fragmentation pattern and the masses obtained upon LC-MS/MS. The DPs were identified as 3-({4-[(E)-(4-hydroxyphenyl) diazenyl]benzoyl}amino)propanoic acid (DP 1), 4-[(E)-(4-hydroxyphenyl)diazenyl] benzamide (DP 2), 5-[(E)-(4-carbamoylphenyl)diazenyl]-2-hydroxybenzoic acid (DP 3) and 3-({4-[(E)-phenyldiazenyl]benzoyl}amino)propanoic acid (DP 4). Based on findings, it was concluded that, the proposed method was successfully applicable for routine analysis of balsalazide and its process related impurities in pure drug and formulations and also applicable for identification of known and unknown impurities of balsalazide.