• Title/Summary/Keyword: 4-hydroxyacetophenone

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Phytochemical Study of Adenophora stricta Roots (당잔대(Adenophora stricta) 뿌리의 성분연구)

  • Rho, Taewoong;Yoon, Kee Dong
    • Korean Journal of Pharmacognosy
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    • v.50 no.2
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    • pp.73-80
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    • 2019
  • Adenophora stricta Miq. (Campanulaceae) is an annual herb, which has been used as a traditional medicine in Korea, Japan and China to treat bronchial asthma, tonsillitis, and hypertension. In this study, 12 compounds were isolated from the roots of A. stricta and isolates were identified to be methyl adenophorate (1), decursidin (2), L-tryptophan (3), D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid (4), vanillic acid 4-O-${\beta}$-D-glucopyranoside (5), syringic acid 4-O-${\beta}$-D-glucopyranoside (6), vanillin (7), vanillic acid (8), p-hydroxybenzaldehyde (9), p-hydroxybenzoic acid (10), p-hydroxyacetophenone (11) and linoleic acid (12). Decursidin (2) and D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid (4) is firstly reported from A. stricta in current study.

The first synthesis of 4' ${\alpha}$-C aryl branched carbocyclic nucleosides

  • Xu, Xiang-Shu;Ko, Ok-Hyun;Hong, Joon-Hee
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.346.2-346.2
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    • 2002
  • Recently, several branched-nucleosides have been synthesized and evaluated as potent antitumor or antiviral agents. Among them, 4'${\alpha}$--C-ethenyl and 4'${\alpha}$-C-ethynyl nucleosides which having an additional double or triple bond at 4'-position were reported to be as potent antiviral and anlitumor activities. Encouraged by these interesting structures and antiviral activities, it was determined to synthesize novel classes of nucleosides comprising branched carbocyclic nucleosides with an additional aryl group at 4'${\alpha}$-position using versatile reiterative three-step sequences from simple acyclic precursor '2-hydroxyacetophenone. Our efforts toward the synthesis of novel nucleosides analogues are reported herein.

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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.

Copolymers of p-acryloyloxyacetophenone (AcAP) with MMA: Synthesis, Characterization and their Antifouling (AF) Efficiency

  • Elango, S.;Sidharthan, M.;Viswanadh, G.S.;Cho, Ji-Young;Park, N.S.;Shin, H.W.
    • Proceedings of the Polymer Society of Korea Conference
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    • 2006.10a
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    • pp.381-381
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    • 2006
  • AcDP and AcAP were prepared by the reaction of acryloyl chloride (Ac) with 2,4,4' -trichloro-2' -hydroxydiphenyl ether (DP) and p-hydroxyacetophenone respectively in presence of triethylamine (TEA) in MEK at $0^{\circ}C$. The reaction was monitored by TLC and the prepared monomer was characterized by UV, IR, $1^H-NMR$ and GC-MS. Further, copolymers poly (AcDP-MMA-AcAP) were prepared in different feed ratio of monomers by free radical polymerization at $70^{\circ}C$, in which BPO as initiator and their molecular weight was determined by GPC. The AF activity of prepared polymers was investigated against representatives of marine microfoulers, shipfouling bacteria (B. macroides & P. aeruginosa) and microalgae (A.coffeaeformis & N. incerta). The antibacterial activity and diatom attachment assays showed significant AF potential of these polymers.

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Study on the Formation of Byproducts and the Decomposition of o-Chlorophenol by Addition of NaOH in Supercritical Water (초임계수 중에서 NaOH 첨가에 의한 o-chlorophenol의 분해 및 부산물 생성에 관한 연구)

  • Song, Byung-Joo;Kim, Jong-Guk;Lee, Geun-Hee
    • Journal of Korean Society of Environmental Engineers
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    • v.27 no.3
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    • pp.273-279
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    • 2005
  • The degradation of o-chlorophenol(o-CP) in the presence of NaOH and the byproducts formed were investigated in a supercritical water(SCW) destruction process. The conversion of o-CP in the absence of NaOH was less than 20%, however it showed 100% conversion in the presence of NaOH(mole ratio[NaOH]/[o-CP] over than 2) with a residence time of less than 1 second. The formation of PAHs and the phenolic compounds formed were decreased in the presence of NaOH. The results revealed that the formation of byproducts during the destruction of o-CP in SCW was effected by the addition of NaOH. Phenol, cresols, chlorinated phenols, PAHs, p,p'-dihydroxybiphenyl and oxygenated polyaromatic compounds such as 1-indanone, dibenzofuran and dibenzo-p-dioxin were detected in both conditions(presence and absence of NaOH). At the same time, in the presence of NaOH, 2-ethylphenol, o-hydroxyacetophenone, hydroquinone, 4-allylphenol, 3-phenoxyphenol and 4,4'-oxybisphenol were also detected. The observed results suggest that the destruction of o-CP in SCW with NaOH occurs through a number of complicated reaction pathways. Dibenzofuran and dibenzo-p-dioxin were also detected during destruction of o-CP by SCW. The above observation suggests that there may be a common relationship between the thermal incineration process and SCW decomposition process.

Determination of Peripheral Catechol O-methyltransferase (COMT) Activity in vivo using $[2-^{14}C]-3',4'-Dihydroxyacetophenone$

  • Kim, Eun-Joo;Ahn, Jong-Woong;Lee, Hye-Suk;Christ, Wolfram
    • Archives of Pharmacal Research
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    • v.14 no.4
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    • pp.290-294
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    • 1991
  • For the determination of peripheral COMT activity, we synthesized $[2-^{14}C]-3',4'-dihydroxyacetophenone([^{14}C]-DHAP)$, a model substrate closely related to catecholamines, which cannot be attacked by monoamine oxidase. After i.v.-injection of $[^{14}C]-DHAP$ in living animals, only 3',4'-dihydroxy-acetophenone (3',4'-DHAP) and 3'-methoxy-4'-hydroxyacetophenone (3'-MHAP) were detected in blood by thin layer radio chromatography. It could be speculated that 3',4'-DHAP was primarily O-methylated by COMT, followed by subsequent conjugations. The concentration of 3',4'-DHAP, a substrate for COMT, in blood at 5 min after injection of $[^{14}C]-DHAP$, were similar in all animals. The rate of 3'-MHAP formation can be therefore used as an indicator for peripheral COMT activity. The velocity of methylation in 15 min after i.v.-administration of $[^{14}C]-DHAP$ was $0.28\;{\mu}g/ml{\cdot}min$. From these results, 3',4'-DHAP was shown to be used as an appropriate substrate to determine the COMT activity in vivo.

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Constituents of Cynanchum auriculatum and their Inhibitory Effect on Melanogenesis in B16 Mouse Melanoma Cell Lines (이엽우피소의 성분 및 멜라닌 생성 억제활성)

  • Choi, Hyun-Gyu;Jiang, Yanfu;Roh, Eun-Mi-Ri;Kim, Young-Soo;Xu, Guang-Hua;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.41 no.4
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    • pp.238-244
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    • 2010
  • Fourteen compounds were isolated from the roots of Cynanchum auriculatum and their chemical structures were identified as ${\beta}$-sitosterol (1), acetovanillone (2), p-hydroxyacetophenone (3), 2,4-dihydroxyacetophenone (4), 2,5-dihydroxyacetophenone (5), cynandione A (6), methyleugenol (7), daucosterol (8), Succinic acid (9), cynauriculoside A (10), wilfoside C3N (11), wilfoside C1N (12), wilfoside K1N (13) and wilfoside C1G (14). Among them, compounds 2-5 were isolated from this plant for the first time. And 2, 5-dihydroxyacetophenone (5) showed the most potent inhibitory effect on melanogenesis in B-16 mouse melanoma cell lines with $IC_{50}$ value of $20\;{\mu}M$.

Bioassay-Guided Isolation and Identification of Compounds from Arecae Pericarpium with Anti-inflammatory, Anti-oxidative, and Melanogenesis Inhibition Activities

  • Indriana, Amelia;Lee, Kyoung Jin;Kim, Yeong Shik
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.193-200
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    • 2016
  • This study describes the anti-inflammatory, anti-oxidant, and melanogenesis inhibition activities of methanol extract and various organic solvent fractions of Arecae Pericarpium. We examined the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells, 1,1-diphenyl-2-picrylhydrazine (DPPH) scavenging activity, mushroom tyrosinase inhibition activity and melanin contents. The study showed that, among all tested fractions, methylene chloride fraction showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells ($IC_{50}$ value $8.89{\mu}g/mL$) and DPPH radical scavenging activity ($EC_{50}$ value $21.39{\mu}g/mL$). Methylene chloride and ethyl acetate fractions similarly inhibited mushroom tyrosinase activity. Methanol extract exhibited strongest reduction of melanin content in B16F10 melanoma cells. Based on the bioactivity assay results, methylene chloride and ethyl acetate fractions were further separated. Eight phenolic compounds were isolated, which are dimeric syringol (1), catechol (2), 4-hydroxybenzaldehyde (3), vanillin (4), 4-hydroxyacetophenone (5), apocynin (6), protocatechuic acid (7) and 4-hydroxybenzoic acid (8). Among the isolated compounds tested, catechol showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells. Catechol also showed the concentration-dependent NF-${\kappa}B$ inhibition activity. Arecae Pericarpium might have potentials to be developed as anti-inflammatory agent or dermatological product for skin-whitening agent.

Isolation of Acinetobacter calcoaceticus BP-2 Capable of Degradation of Bisphenol A (Bisphenol A 분해균주 Acinetobacter calcoaceticus BP-2의 분리 및 bisphenol A 분해 특성)

  • Kwon, Gi-Seok;Kim, Dong-Geol;Lee, Jung-Bok;Shin, Kee-Sun;Kum, Eun-Joo;Sohn, Ho-Yong
    • Journal of Life Science
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    • v.16 no.7 s.80
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    • pp.1158-1163
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    • 2006
  • Bisphenol A (BPA), 2,2-bis(4-hydroxyphenyl) propane, has been widely used as a monomer for production of epoxy resins and polycarbonate plastics, and final products of BPA include adhesives, protective coatings, paints, optical lens, building materials, compact disks and other electrical parts. Since BPA is a toxic chemical to elicit acute cell cytotoxicity and chronic endocrine disrupting activity, the degradation of BPA has been focused during last decades. To overcome the problem of photo-, and chemical-degradation of BPA, in this study, a bacterium that is able to biodegrade BPA, was isolated. The bacterium, isolated froln the soil of plastic factory, was identified as Acinetobacter calcoaceticus (strain BP-2) based on physiological and 16S rDNA sequencing analysis. A. calcoaceticus BP-2 was able to grow in the presence of $1140{\mu}g\;ml^{-1}$ BPA. Biodegradation experiments showed that BP-2 mineralized BPA via 4-hydroxybenzoic acid and 4-hydroxyacetophenone, and average degradation rate was $53.3{\mu}g\;ml^{-1}\;day^{-1}$ under optimal conditions (pH 7 and $30^{\circ}C$). In high density resting cell $(3.5g-dcw.1^{-1})$ experiments, the maximal degradation rate was increased to $89.7{\mu}g\;ml^{-1}\;h^{-1}$. Our results suggest that BP-2 has high potential as a catalyst for practical BPA bioremediation.

Improvement of Antifungal Activity of for Water-Dispersed Cosmetic Formulations (수분산 제형의 화장품에 대한 항진균력 향상)

  • Lee, Ye Ji;Seo, Jae Yong;Yang, Hyeon Gap;Lee, Ju kyeong;Baek, Sol Bee;Cho, Hyun Dae;Jeong, Noh Hee
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.48 no.2
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    • pp.135-146
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    • 2022
  • In order to prevent microbial contamination and safely use cosmetics, it is essential to possess preservative power. In this study, the antifungal effect was confirmed by improving the preservative system of the aqueous dispersion formulation, which has a weak preservative power against fungi, and various preservative systems were established to strengthen the preservative power against fungi. Five kinds of raw materials (sodium anisate, p-anisic acid, caprylhydroxamic acid, o-cymen-5-ol, hydroxyacetophenone) that have a benzene ring structure having a hydroxyl group and exist as protonated form in cosmetic formulations expected to improve antifungal activity in cosmetics were selected, and the minimum growth inhibitory concentration of the raw materials was determined through MIC assay. It was confirmed that the preservative power against mold was improved through the preservative efficacy test of 4 types of water dispersion formulations (cream, lotion, toner, and sun cream) in which 4 types of raw materials showing antimicrobial activity against mold were added to the preservative system. When p-anisic acid was used, it was confirmed that the preservative activity against mold was strengthened without the effect of inhibiting the preservative power against bacteria and yeast in all four formulations.