• Title/Summary/Keyword: Phenol derivatives

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Isolation of Antimicrobial Substances from Hericium erinaceum

  • Kim, Dong-Myong;Pyun, Chul-Woo;Ko, Han-Gyu;Park, Won-Mok
    • Mycobiology
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    • v.28 no.1
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    • pp.33-38
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    • 2000
  • Mycelium of Hericium erinaceum isolate KU-1 was cultured in liquid medium (HL medium) and solid medium (Ko medium) at pH 4.0 in $28^{\circ}C$. 1.0% glucose or fructose was the most favorable carbon source, and 0.2% amonium acetate or $NaNO_3$ was an exellent nitrogen source for mycelial growth as well as production of antimicrobial substances. The mixture of saw dust 70% with rice bran 30% (SR medium) was the substrate for formation of sporophores. The active substrates in extracts from mycelium, culture filtrate and fruiting body were separated by TLC. The solvent for TLC was EtOAc: Chloroform: MeOH (10 : 5 : 10). Phenol-like substances appeared at Rf $0.5{\sim}0.9$, and fatty acid-like substances appeared at Rf $0.1{\sim}0.2$. The purified materials from the extracts showed antimicrobial effects to Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Aspergillus niger, Candida albicans and Microsporum gypseum. The S. aureus was the most inhibited. Minimal inhibitory concentration (MIC) of purified white powder and the Hercenone derivatives against S. aureus were $5.65\;{\mu}g/ml$ and $1.85\;{\mu}g/ml$, respectively.

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Inhibitory Effect of Cirsium japonicum Root or Flower Extract on Hepatic Stellate Cells Activation (엉겅퀴 뿌리 및 꽃 추출물의 간 성상세포 활성 억제 효과)

  • Kim, Sang-Jun;Kim, Seon-Young;Kim, Ji-Ae;Park, In-Sun;Yu, Kang-Yeol;Chung, Chang-Ho;Shim, Jae-Suk;Jang, Seon-Il;Jeong, Seung-Il
    • Korean Journal of Pharmacognosy
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    • v.43 no.1
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    • pp.27-31
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    • 2012
  • This study was designed to elucidate the effects of Cirsium japonicum (CJ) extracts on hepatic stellate cells (HSCs, LX-2 cells) proliferation, which is induced by platelet-derived growth factor (PDGF) or transforming growth factor-${\beta}$ (TGF-${\beta}$). The content of total phenol, flavonoid, and silymarin derivatives was more higher in CJ-flower than in CJ-root. Consistent with these results, the LX-2 cells growth inhibition was more effective in CJ-flower extract than in CJ-root extract, the complete growth inhibition concentration was $1{\mu}g/mL$ and $50{\mu}g/mL$, respectively. These results suggest that extracts from CJ-flower can be potentially used as therapeutic substances for the regulatioin of HSCs activation.

Composition and Contents of Free Amino Acids and Phenolic Acid and Flavonoids of Imperata cylindrica Beauvois var. koenigii Root extracts (백모근 추출물의 유리아미노산 및 Phenolic acid와 Flavonoids 조성 및 함량)

  • Lee, Soon-suk;Lee, Keun-Kwang
    • Journal of Digital Convergence
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    • v.18 no.7
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    • pp.397-403
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    • 2020
  • This study was carried out to investigate the free amino acid and derivatives and phenolic acid and flavonoid compositions and contents of hot water and 95% ethanol extracts of Imperata cylindrica Beauvois var. koenigii root. The purpose of this study is to obtain basic data and to confirm their applicability as functional cosmetic and functional food ingredients on extracts. 15 kinds and 9 kinds of free amino acids were detected in both extracts, respectively. 5 kinds and 4 kinds of protein free-amino acid derivatives were detected in both extracts, respectively. Total phenol contents were 116.50 ± 0.06 and 140.10 ± 0.04 mg% in both extracts, respectively. The total flavonoid contents were 31.80 ± 0.03 and 43.90 ± 0.05 mg% in both extracts, respectively. 5 kinds and 6 kinds of phenolic acids were detected in both extracts, respectively. In the case of flavonoid analysis, no flavonoid compound was detected in the hot water extract while taxifolin was identified in the 95% ethanol extract. Based on the above results, the hot water and 95% ethanol extracts of I. cylindrica Beauvois var. koenigii root are rich in free amino acids, amino acid derivatives, phenolic acids and flavonoids which confirm their potential for applications in cosmeceuticals, nutricosmetics formulations and functional foods.

Changes of Off-Odor Constituent and Parishin Derivatives of Fermentation of Gastrodia elata Rhizome by Lactic Acid Bacteria Strains (천마의 젖산발효에 따른 이취성분 및 Parishin 유도체의 변화)

  • Song, Young Eun;Lee, In Sok;Song, Eun Ju;Choi, Min Kyung;Han, Hyun Ah;Shin, So Hee;Choi, So Ra;Lee, Ki Kwon;Kim, Myung Kon;Park, Shin Young
    • The Korean Journal of Food And Nutrition
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    • v.30 no.5
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    • pp.973-982
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    • 2017
  • Gastrodia elata Blume often has been used for the treatment of headaches, convulsions, hypertension, and neurodegenerative diseases. The main active constituents are gastrodin, 4-hydroxybenzyl alcohol, vanillyl alcohol, 4-hydroxybenzylaldehyde and parishin A, B, C and E. Because Gastrodia elata has also unacceptable off-odor (swine barnyard-like) for food, there is a need to reduce it as well as allow for greater utilization as a functional food materials. In this study, a major off-odor producing substance of Gastrodia elata was fractionated by steam distillation and silica gel column chromatography. The substance was identified as p-cresol(4-methyl phenol) by GC-MS analysis and comparison of the retention time with that of an authentic compound in GC. The content of p-cresol in fermented Gastrodia elata was decreased. A fermented sample of Latobacillus sakei for 2 days was reduced to 54.7%, when compared with a unfermented sample. The five parishin derivatives in Gastrodia elata were identified by HPLC-MS analyses, and a comparison of HPLC retention times with those of authentic compounds. When compared with parishin derivatives of an unfermented Gastrodia elata, those of Gastrodia elata fermented by L. sakei, increased to 18.3% for 2 days. Increases of about 14.0~38.4% of the total phenolic compounds and 57.4~77.3% total flavonoids were found in fermented extracts, by 3 lactic acid bacteria strains. They were compared with $97.1{\pm}2.9{\mu}g/g$ and $40.9{\pm}2.0{\mu}g/g$ in the unfermented control, respectively. The extracts of Gastrodia elata Blume that were fermented by lactic acid bacteria had higher DPPH free radical scavenging activity and FRAP reducing power than the unfermented control.

Photochemistry of o-Nitrobenzyl System Coupled with a Benzylsulfonyl Chromophore (벤질술포닐 흡광단에 결합된 2-니트로벤질계의 광화학에 관한 연구)

  • Kim, Hee Jong;Chang, Sun Ki;Choo, Dong Joon
    • Applied Chemistry for Engineering
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    • v.10 no.1
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    • pp.124-128
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    • 1999
  • The photochemistry of the derivatives of o-nitrobenzylcarboxyl esters or benzylsulfonyl derivatives has been well studied separately. But little attempt has been made to combine the fruits these two studies. Being photochemically active, benzylsulphonyl and intro groups should influence the reactivity of each other's, especially when the excited states are fully mixed due to the proximity of their location. The questions which should be clearly answered are; what kind of effect will be excerted to the other group, and whether these two functional groups are coupled in the course of the reaction. To answer the questions raised above, wer have synthesized two sulfonyl esters and four amides from the newly available starting material, 2-nitro-${\alpha}$-toluenesulfonyl chloride. The products identified from the exploratory solution photochemistry were cyclohexanol, phenol, cyclohexylamine, and sulfur dioxide. The results are not much different from the products originally anticipated. It has been temporarily concluded that there is little interaction between the benzyl sulfonyl group and ortho-nitro chromophore. The fact that a base (an amine) has been photochemically generated in solution photochemistry was further confirmed by and utilized in the solid phase quantitative photochemistry done on the film, so as to carry out the photochemical epoxide cure.

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Palladium(II) Aryloxides of Pd(2,6-(CH2NMe2)2C6H3)(OC6H4-X-p) (X = Me, NO2): Synthesis, Property and Reactivity towards Diphenyliodium Chloride

  • Jung, Hyun-Sang;Park, Yun-Sik;Seul, Jung-Min;Kim, Jong-Sook;Lee, Ho-Jin;Park, Soon-Heum
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2711-2716
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    • 2011
  • para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4$-p-Me affords the hydrogen-bonding adduct complex 3 ($2{\cdot}HOC_6H_4$-p-Me). Complex 3 can also be obtained from benzene solution of 2 in the presence of free $HOC_6H_4$-p-Me. Complex 1 does not undergo adduct formation with $HOC_6H_4-p-NO_2$ neither from metathesis reaction of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4-p-NO_2$ nor from treatment of 1 with free $HOC_6H_4-p-NO_2$. Complex 3 undergoes fast exchange of the coordinated p-cresolate with the hydrogen-bonding p-cresol. Complex 2 undergoes ${\sigma}$-ligand exchange reaction with $HOC_6H_4-p-NO_2$ to give 1. The exchange reaction, however, is irreversible as readily anticipated from their respective $pK_a$ values of the phenol derivatives. Reaction of 2 with diphenyliodium chloride quantitatively produced Pd(NCN)Cl and PhI along with liberation of O-phenylated product $PhOC_6H_4$-p-Me which was identified by GC/MS spectroscopy.

Chemical Constituents from the Stems of Lagerstroemia indica and Their Anti-oxidant Effect (배롱나무의 항산화 활성 성분)

  • Woo, Kyeong Wan;Sim, Mi Ok;Park, Eel Jong;Kim, Min Suk;Suh, Won Se;Cho, Hyun Woo;Kwon, Hak Cheol;Park, Jong Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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    • pp.204-210
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    • 2016
  • Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl ${\beta}$-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6"-galloyl)-${\beta}$-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-${\beta}$-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-${\beta}$-D-glucopyranoside (13), 6R,9R-3-oxo-${\alpha}$-ionol-9-O-${\beta}$-D-glucopyranoside (14), dihydrophaseic acid 4'-O-${\beta}$-D-glucopyranoside (15), ${\beta}$-hydroxypropiovanillone 3-O-${\beta}$-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, $Fe^{2+}$ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.

Design, Synthesis, Antitumor Activity and Mode of Action of Novel Oxiranyl and Thiiranyl Phenol Derivatives

  • Yang, Zunhua;Kang, Jin-Ah;Kim, Won-Hee;Park, Ah-Young;Kim, Hyung-Sik;Kim, Jung-Su;Kim, Jin-Ah;Gong, Ping;Jeong, Lak-Shin;Moon, Hyung-Ryong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.7
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    • pp.1463-1469
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    • 2009
  • Eleven novel oxiranyl and thiiranyl phenolic compounds were synthesized as potential antitumor agents using epichlorohydrin and epithiohydrin in the presence of $K_2CO_3$. Cytotoxicities were found in range of I$C_{50}$ values of 2.5-14.8 $\mu$M, which was partially attributed to topoisomerase II inhibition. Bis-thiiranyl anthraquinone analog, 19 showed more cytotoxicity against MDA-MB-231 (breast cancer cell) and PC3 (prostate cancer cell) after 24 and/or 48 h and more potent topoisomerase II inhibitory activity than etoposide.

Studies on the Characteristics of Mineral Diluents Affecting the Decomposition of Sumithion in the Dust formulations (Sumithion 분제의 성분 변화에 영향을 미치는 증량제의 특성에 관한 연구)

  • Wuh K. D.;Han S. S.;Keum S. S.;Ahn S. H.;Lee C. N.
    • Korean journal of applied entomology
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    • v.10 no.2
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    • pp.77-83
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    • 1971
  • In order to find out the decomposing factors of Sumithion in mineral diluents, the physical and chemical properties of the diluents such as talcs, bentonites, diatomaceous earth and other clay minerals was studied in relation to the decomposition rate of Sumithion in dust formulations. The total base, moisture adsorption capacity, pH, specific surface, water contents, active $Fe^{++}$, ignition loss and cation exchange capacity were analysed as the properties of mineral diluents, and these properties were correlated with the stability of Sumithion in dust formulations. And in hope of finding out the main factors among those properties of diluents, the decomposed products of Sumithion in dust formulations prepared with standard Sumithion were separated by the methods of column chromatography and investigated by thin layer chromatography. The following results were otbained; 1. The total base, moisture adsorption capacity, specific surface, water contents, active $Fe^{++}$ and cation exchange capacity of mineral diluents were found to be highly effective on the rate of decomposition of Sumithion in dust formulations. 2. Decomposed products of Sumithion in dust formulations were found to be dimethylphosphorothionate, 3-methyl-4-nitro phenol and its derivatives. And one fraction was not dissolved in n-hexane and ethylether, but was soluble in methylalcohol and ethylalcohol. 3. The moat highly correlated properties of diluents with the decomposition rate of Sumithion in dust were found to be the total base and water contents. 4. In regard to the kind of diluents, it was found that the rate of decomposition of Sumithion in dust formulations was higher in order of bentonite, diatomaceous earth, kaolin and talc.

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Characterization of the Quinoline-Degrading Bacterium Pseudomonas sp. NFQ-1 Isolated from Dead Coal Pit Areas (폐광지역에서 분리한 quinoline 분해 세균인 Pseudomonas sp. NFQ-1의 특성연구)

  • 윤경하;황선영;권오성;오계헌
    • KSBB Journal
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    • v.18 no.3
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    • pp.174-179
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    • 2003
  • The bacterium NFQ-1 capable of utilizing quinoline (2,3-benzopyridine) as the sole source of carbon, nitrogen and energy was enriched and isolated from soil samples of dead coal pit areas. Strain NFQ-1 was identified as Pseudomonas nitroreducens NFQ-1 by BIOLOG system, and assigned to Pseudomonas sp. NFO-1. Pseudomonas sp. NFQ-1 was used with the concentration range of 1 to 10 mM quinoline. Strain NFQ-1 could degrade 2.5 mM quinoline within 9 hours of incubation. Initial pH 8.0 in the culture was reduced to 6.8, and eventually 7.0 as the incubation was proceeding. 2-Hydroxyquinoline, the first intermediate of the degradative pathway, accumulated transiently in the growth medium. The highest concentration of quinoline (15 mM) in this work inhibited cell growth and quinoline degradation. Pseudomonas sp. NFQ-1 was able to utilize various quinoline derivatives and aromatic compounds including 2-hydroxyquinoline, p-comaric acid, benzoic acid, p-cresol, p-hydroxybenzoate, protocatechuic acid, and catechol. The specific activity of catechol oxygenases was determined to approximately 184.7 unit/㎎ for catechol 1.2-dioxygenase and 33.19 unit/㎎ for catechol 2,3-dioxygenase, respectively. As the result, it showed that strain NFQ-1 degraded quinoline via mainly orthp-cleavage pathway, and in partial meta-cleavage pathway.