• Title/Summary/Keyword: 1,4-diphenyl-l

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Kinetic Studies of the Solvolyses of 4-Nitrophenyl Phenyl Thiophosphorochloridate

  • Koh, Han-Joong;Kang, Suk-Jin
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2413-2418
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    • 2009
  • Rates of solvolyses of 4-nitrophenyl phenyl thiophosphorochloridate (4-N$O_2$PhOP(S)(Cl)OPh, $\underline{1}$) in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, and 2,2,2-trifluroethanol (TFE) are reported. Thermodynamic parameters were determined at several temperatures in three representative solvents. The extended Grunwald-Winstein equation was applied to 29 solvents and the correlation coefficient (R) showed 0.959. The sensitivities (l = 1.37 and m = 0.62) are similar to those obtained for diphenyl thiophosphorochloridate (($PhO)_2$PSCl, $\underline{2}$), diphenyl phosphorochloridate (($PhO)_2$POCl, $\underline{3}$), diphenyl phosphinic chloride ($Ph_2$POCl, $\underline{4}$), and diphenyl thiophosphinic chloride ($Ph_2$PSCl, $\underline{5}$). The solvolytic reaction mechanism of 4-nitrophenyl phenyl thiophosphorochloridate ($\underline{1}$) is suggested to be proceeded a $S_N$2 process as previously reported result. The activation enthalpies are shown as slightly low as ${\Delta}H^{\neq}\;=\;9.62\;to\;11.9\;kcal{\cdot}mol^{-1}$ and the activation entropies are shown as slightly high negative value as ${\Delta}S^{\neq}\;=\;-34.1\;to\;-44.9\;cal{\cdot}mol^{-1}{\cdot}K^{-1}$ compared to the expected $S_N$2 reaction mechanism. Kinetic solvent isotope effects are accord with a typical $S_N$2 mechanism as shown in the range of 2.41 in MeOH/ MeOD and 2.57 in $H_2O/D_2O$ solvent mixtures.

Anti-Inflammatory and Anti-Oxidative Effects of Danggwisusan on Macrophages

  • Jo, Na Young
    • Journal of Acupuncture Research
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    • v.35 no.1
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    • pp.41-45
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    • 2018
  • Background: Danggwisusan is a herbal medicine which is used to treat bruises, static blood, external injuries, and somatalgia in Korean medicine. The objectives of this study were to investigate whether Danggwisusan hot aqueous extract had an inhibitory effect upon inflammatory cytokine production and oxidation. Methods: Cytotoxic activity of Danggwisusan extract was examined by 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide assay. The amount of nitric oxide produced was measured using Griess reagent. Prostaglandin E2 production was measured using an enzyme immunoassay. Inflammatory cytokines ($IL-1{\beta}$, IL-6 and $TNF-{\alpha}$) were measured by an enzyme linked immunosorbent assay. The anti-oxidative effect of Danggwisusan was measured by the 1,1-Diphenyl-2-picryl hydrazyl method. The amount of polyphenol and flavonoid contents were measured by Folin and Ciocalteauea phenol reagent and aluminum nitrate. Results: Danggwisusan hot aqueous extracts did not show significant toxicity at 10, 20, 50, and $100{\mu}g/mL$. At a dose of $100{\mu}g/mL$, Danggwisusan hot aqueous extract significantly inhibited nitric oxide and $PGE_2$ production, and significantly reduced $IL-1{\beta}$, IL-6 and $TNF-{\alpha}$ production. At a dose of $100{\mu}g/mL$, 1,1-Diphenyl-2-picryl hydrazyl free radical scavenging capability was over 50%. Conclusion: This study showed that Danggwisusan hot aqueous extract may have anti-inflammatory and anti-oxidative effects on macrophages.

Effects of Salviae Miltiorrhizae Radix Hot Aqueous Extract on Nitric Oxide and Prostaglandin E2 Production and on 1,1-diphenyl-2-picryl hydrazyl Radical Scavenging in Macrophages

  • Yeo, In Ho;Lee, Cham Kyul;Lee, Eun Yong
    • Journal of Pharmacopuncture
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    • v.17 no.1
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    • pp.7-12
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    • 2014
  • Objectives: The objective of this study is to investigate the effects of Salviae Miltiorrhizae Radix hot aqueous extract on nitric oxide (NO) and prostaglandin $E_2$ ($PGE_2$) production and on 1,1-diphenyl-2-picryl hydrazyl (DPPH) free-radical scavenging in macrophages. Methods: Salviae Miltiorrhizae Radix (300 g) was heated at $100^{\circ}C$ with distilled water (2 L) for 4 hours. The extract was filtered and concentrated to 100 mL by using a rotary evaporator, was frozen at $-80^{\circ}C$, and was then freeze-dried by using a freezing-drying system. The RAW 264.7 macrophage was subcultured by using $10-{\mu}g/mL$ lipopolysaccharide (LPS). In order to evaluate cytotoxicity, we performed 3-(4,5-dimrthylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays and measured the cell viability. The NO production was measured by using Griess assays, and the $PGE_2$ production was measured by using enzyme immunoassays. The antioxidant activity, the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free-radical scavenging capability, was measured by using the DPPH method. Results: Cell viability with the 1-, 5-, 25-, 125- and $625-{\mu}g/mL$ Salviae Miltiorrhizae Radix hot aqueous extract was not significantly decreased compared to the cell viability without the extract. When 125 and $625{\mu}g/mL$ of Salviae Miltiorrhizae Radix hot aqueous extract were used, nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages was significantly inhibited compared to that in the control group. When 25, 125, and $625{\mu}g/mL$ of Salviae Miltiorrhizae Radix hot aqueous extract were used, $PGE_2$ production in LPS-stimulated RAW 264.7 macrophages was significantly inhibited compared to that in the control group. The 125- and $625-{\mu}g/mL$ Salviae Miltiorrhizae Radix hot aqueous extracts had high DPPH free-radical scavenging capabilities in RAW 264.7 macrophages. Conclusion: This study indicates that Salviae Miltiorrhizae Radix hot aqueous extract suppresses NO and $PGE_2$ production and improves DPPH free-radical scavenging capability. Thus, it seems that Salviae Miltiorrhizae Radix hot aqueous extract may have an anti-inflammation effect and antioxidant activity.

Inhibitory Effects of Methanol Extract, Phenolic Acids and Flavonoids from the Leaves of Eucalyptus darylmpleana against 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Park, Jong-Cheol;Park, Ju-Gwon;Hur, Jae-Seoun;Choi, Myeong-Rak;Yoo, Eun-Jeong;Kim, Sung-Hwan;Son, Jin-Chang;Kim, Moon-Sung
    • Natural Product Sciences
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    • v.10 no.5
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    • pp.244-247
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    • 2004
  • The inhibitory effects of the leaves of Eucalyptus darylmpleana (Myrtaceae) on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was examined. The scavenging effect of the ethyl acetate fraction of Eucalyptus darylmpleana leaves on DPPH radical was stronger than the other fractions, and further purified by silica gel and Sephadex LH-20 column chromatography. 3,4-Dihydroxybenzoic acid, gallic acid, quercetin, quercetin $3-O-{\alpha}-_L-rhamnoside$, quercetin $3-O-{\beta}-_D-glucoside$ and quercetin 3-O-rutinoside were isolated and elucidated by spectroscopic data. Among these components, gallic acid and quercetin $3-O-{\alpha}-_L-rhamnoside$ exhibited potent scavenging activities on DPPH radical with $IC_{50}$ values of 6.02 and $5.54\;{\mu}M$, respectively.

Further Isolation of Antioxidative $(+)-1-Hydroxypinoresinol-1-O-{\beta}-D-glucoside$ from the Rhizome of Salvia miltiorrhiza that Acts on Peroxynitrite, Total ROS and 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Kang, Hye-Sook;Chung, Hae-Young;Byun, Dae-Seok;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.26 no.1
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    • pp.24-27
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    • 2003
  • A furanofuranoid lignan glycoside, with radical scavenging on peroxynitrite, total reactive oxygen species (ROS) and 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical, was isolated from the rhizome of Salvia miltiorrhiza and characterized as (+)-1-hydroxypinoresinol-1-Ο-$\beta$-D-glucoside based on spectroscopic evidence. The compound exhibited peroxynitrite, total ROS and DPPH radical scavenging activities with $IC_{50}$ values of 3.23$\pm$0.04, 2.26$\pm$0.07 and 32.3$\pm$0.13 $\mu$M, respectively. Penicillamine, Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and L-ascorbic acid, acting as positive controls, showed radical scavenging activities with $IC_{50}$ values of 6.72$\pm$0.25, 1.43$\pm$0.04 and 11.4$\pm$0.07 $\mu$M, respectively.

Antioxidative Activities of Triterpenoids and Lignans from Acanthopanax divaricatus var. albeofructus (백모오가피로부터 분리된 트리터페노이드 및 리그난의 항산화작용)

  • 김지연;양기숙
    • YAKHAK HOEJI
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    • v.48 no.4
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    • pp.236-240
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    • 2004
  • Acanthopanax species (Araliaceae) traditionally has been used as analgesics, stimulant of immune system, and replenishment of body functions. Acanthopanax divaricatus var. albeofructus is indigenous plant to Korea. The antioxidant activities of compounds from A divaricatus var. albeofructus were determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method and thiobarbituric acid reactive substance (TBARS) assay on human plasma low-density lipoprotein (LDL). The triterpenoid and lignan constituents from this plant showed antioxidant activities and the lignan, l-sesamin exhibited the most potent antioxidant activity in Cu$^{2+}$ -induced LDL oxidation.n.

Antioxidative Properties of Different Solvent Extracts from Persimmon (Diospyros kaki cv. Fuyu) Flower-Buds

  • You, Dong-Hyun;Lee, Seung-Cheol
    • Preventive Nutrition and Food Science
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    • v.16 no.4
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    • pp.328-332
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    • 2011
  • After preparation of acetone, ethanol, methanol, and water extracts (10 g/300 mL) of dried persimmon (Diospyros kaki cv. Fuyu) flower-buds, total phenolic contents (TPC), 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (RSA), 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) RSA, reducing power (RP), and tyrosinase inhibitory activity of the extracts were evaluated. The methanol extracts produced the highest TPC (113.39 mg gallic acid equivalents/g), DPPH RSA ($IC_{50}=40.25\;{\mu}g/mL$), ABTS RSA ($IC_{50}=58.17\;{\mu}g/mL$) and RP ($IC_{50}=69.43\;{\mu}g/mL$) activities while the water extracts generated the lowest values. The ethanol extract showed the highest tyrosinase inhibitor activity (88.90%) at a concentration of 1 mg/mL. These results indicated that persimmon flower-buds may be a useful source of natural antioxidants.

Biological Activities of Rosaceae Plants Extracts (장미과 식물 추출물의 생물학적 활성)

  • Seo Jeong Min;Ahn Jeung-Youb
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.4 s.48
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    • pp.499-502
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    • 2004
  • DPPH radical-generating system was used to evaluate the antioxidant properties of the Rosaceae. The inhibitory effects of ethanolic extracts from Rosaceae plants were investigated on melanin biosynthesis which is closely related to hyperpigmentation. Of the Rosaceae extracts, Prunus sargentii, Rubus coreanus, Chaenomeles sinensis, Photinia glabra and Pyrus pyrifolia showed a potent inhibition of tyrosinase, the enzyme which converts 3-(3,4-dihydroxyphenyl) alanine (dopa) to dopachrome in the melanin biosynthetic process. Furthermore, MMT assay was used to check the cytotoxicity of extracts on the human foreskin fibroblast cell line, Hs68. Among the Rosaceae, bark of Prunus sargentii, bark wood of Photinia glabra and all parts or Chaenomeles sinensis showed more than $50\%$ inhibition of mushroom tyrosinase activity at 100 ug/mL and more than $80\%$ of strong DPPH radical-scavenging activity at 10 ug/mL. In audition to, they had no cytotoxic activity on Hs68. These results suggest that these extracts might be except a controler in pigmentation.

Enhancement of the efficiency stabilization and the color coordinates in blue organic light-emitting devices with double emitting layers

  • Bang, H.S.;Han, S.M.;Lee, D.U.;Kim, T.W.;Kim, J.H.;Seo, J.H.;Kim, Y.K.
    • 한국정보디스플레이학회:학술대회논문집
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    • 2006.08a
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    • pp.1030-1033
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    • 2006
  • The efficiency stabilization and the color coordinates in blue organic light-emitting devices (OLEDs) with a double emitting layer (DEL) consisting of 4,4'-Bis(carbazol-9-yl)biphenyl (CBP) and 4,4'-Bis(2,2-diphenyl-ethen-1-yl)diphenyl were investigated. The efficiency of the OLEDs with a DEL did not significantly change with an increase in current density. The Commission Internationale de l'Eclairage coordinates of the OLEDs with a DEL 11 V were (0.150, 0.137), indicative of a deep blue color.

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(+)-Catechin, an Antioxidant Principle from the Leaves of Pinus densiflora that Acts on 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Choi, Jin-Ho;Kim, Hyun-Sook;Jung, Mee-Jung;Choi, Jae-Sue
    • Natural Product Sciences
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    • v.7 no.1
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    • pp.1-4
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    • 2001
  • The antioxidant activity of Pinus densiflora was determined by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. The methanol extract of P. densiflora showed strong antioxidant activity, and thus fractionated with several solvents. The antioxidant activity potential of the individual fraction was in the order of ethyl acetate>n-butanol>water>dichloromethane> n-hexane fraction. The ethyl acetate soluble fraction exhibiting strong antioxidant activity was further purified by repeated silica gel column chromatography. Antioxidant (+)-catechin was isolated as one of the active principles from the ethyl acetate fraction, together with the inactive components, dihydrokaempferol and 1-O-benzoylglucose. The radical scavenging effect of (+)-catechin on DPPH radical exceeded to that of L-ascorbic acid which is a well known antioxidant.

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