• Title/Summary/Keyword: $^1$H-NMR spectra

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Whitening and Anti-inflammatory Constituents from the Extract of Citrullus lanatus Vines (수박 덩굴 추출물 유래 미백 및 항염 활성 성분)

  • Jeon, Ah Lim;Kim, Jung Eun;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.43 no.1
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    • pp.53-60
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    • 2017
  • In this study, we investigated whitening and anti-inflammatory constituents from a watermelon (Citrullus lanatus, C. lanatus) vines (leaves and stems). As anti-melanogenesis and anti-inflammatory activities were screened for the ethanol extract and solvent fractions, n-hexane (n-Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex and EtOAc fractions of C. lanatus; ${\alpha}-linolenic$ acid (1), sigmast-7-en-O-${\beta}$-D-glucopyranoside (2), 1-feruloyl-${\beta}$-D-glucopyrinoside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening and anti-inflammatory effects were studied for the isolated compounds. Upon the anti-melanogenesis tests using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. For the anti-inflammation tests using lipopolysaccharide (LPS)-induced RAW 264.7 cells, the isolates 1 and 3 were determined to decrease the production of nitric oxide (NO) and pro-inflammatory cytokines ($TNF-{\alpha}$, IL-6). Based on these results, C. lanatus vines extract could be potentially applicable as whitening and anti-inflammatory ingredients in cosmetic formulations.

Synthesis of Dodecyl Ether Sulfates Containing Various Ethylene Oxide and Isopropylene Oxide (EO, PO가 부가된 도데실 에테르 황산화물의 합성)

  • Yoo, Young-Chang;Rho, Sung-Ho;Ju, Myung-Jong;Nam, Ki-Dae
    • Applied Chemistry for Engineering
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    • v.7 no.2
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    • pp.289-298
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    • 1996
  • Eight kinds of poly(oxyethylene, oxyisopropylene) dodecyl ethers were synthesized by adding ethylene oxide and isopropylene oxide with each 5 and 10 moles alternatively on dodecanol. The addition of EO and PO for eight kinds of sodium poly(oxyethylene, oxyisopropylene) dodecyl ether sulfates was identified with HPLC, $^1H$ NMR, hydroxy value, and IR spectrum. In order to verify the sulfation the number of EO and PO molecules was obtained by spectra and Epton method. The yields of products sulfated by chlorosulfonic acid were 90~96%.

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Sonochemical Synthesis of Closed [5,6]-bridged Aziridino[70]fullerene Derivative and Self-assembled Multilayer Films

  • Yoon, Shin-Sook;Hwang, Sung-Ho;Hong, Sung-Kyu;Lee, Jeong-Ho;Ko, Weon-Bae
    • Carbon letters
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    • v.10 no.4
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    • pp.325-328
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    • 2009
  • This cycloaddition of [70]fullerene with methyl azidoacetate in benzene under ultrasonic irradiated condition afforded the closed [5,6]-bridged aziridino[70]fullerene derivative, which was unusual product of cycloaddition to the 5,6-junction of fullerene. Its structure was determined by FAB-MS, UV-vis, $^1H-$ and $^{13}C$-NMR spectral data. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films were self-assembled using the layer-by-layer method on the reactive of glass slides functionalized with 3-mercaptopropyl trimethoxysilane. The functionalized glass slides were alternately soaked in the solution containing closed the [5,6]-bridged aziridino[70]fullerene and 4-aminothiophenoxide/hexanethiolate-protected gold nanoparticles. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films have grown up to 5 layers depending on the immersion time. The self-assembled nanoparticle multilayer films were characterized using UV-vis spectroscopy showed that the surface plasmon band of gold at 527 nm gradually became more evident as successive layers were added to the films.

Biocompatibility of oxidized alginate/gelatin/BCP -based hydrogel composites

  • Phuong, Nguyen Thi;Min, Young-Ki;Yang, Hun-Mo;Song, Ho-Yeon;Lee, Byong-Teak
    • Proceedings of the Materials Research Society of Korea Conference
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    • 2010.05a
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    • pp.40.2-40.2
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    • 2010
  • In this study, oxidized alginate/gelatin/biphase calcium phosphate (BCP)- based hydrogel composites were fabricated. Alginate sodium was oxidized by periodate. The oxidized product was confirmed by using $^1H$ and $^{13}C$ NMR spectra. The number average molecular weight ($M_n$), the average molecular weight ($M_w$) of the oxidized alginate were determined by Gel Permeation Chromatography (GPC). The hydrogel was formed from the oxidized alginate and gelatin solution via Schift-base reaction. The hydrogel showed a highly porosity by a Scanning Electron Microscope (SEM) and Mercury Intrusion Porosimetry (MIP). Crosslinked density of the gel matrix were assessd by trinitrobenzene sulfonic acid (TNBS) assay that shows a high effect on swelling ratio. Increment of the crosslinked desity resulted in enhancing compressive strength of the hydrogel composite. The cytotoxity of hydrogel was assessed with osteoblast MG-63. The hydrogel composites show a high compatibility. The obtained results showed a potential application for bone regeneration in future.

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C-Ring Cleavage of Isoflavones Daidzein and Genistein by a Newly-Isolated Human Intestinal Bacterium Eubacterium ramulus Julong 601

  • Wang, Xiu-Ling;Kim, Ki-Tae;Lee, Je-Hyeon;Hur, Hor-Gil;Kim, Su-Il
    • Journal of Microbiology and Biotechnology
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    • v.14 no.4
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    • pp.766-771
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    • 2004
  • Julong 601, a Gram-positive anaerobic bacterium strain capable of cleaving the C-ring of isoflavones daidzein and genistein, was isolated from human feces. BLAST search revealed that its complete 16S rDNA gene sequence has 99% similarity to Eubacterium ramulus. Metabolites of daidzein and genistein were determined as O-desmethylangolensin (O-Dma) and 2-(4-hydroxyphenyl) propionic acid (2-HPPA), respectively, based on UV, EI-MS, and $^1H$ and ^{13}C$ NMR spectral analyses. Enantiomers of O-Dma and 2-HPPA were isolated by chiral stationary-phase HPLC (CSP HPLC). Cleavage of the C-ring of daidzein and genistein by strain Julong 601 was highly enantioselective. Specific rotation ([$\alpha]_D$) and circular dichroism (CD) spectra of the enantiomers are reported here for the first time. Biotransformation kinetics of daidzein and genistein indicated that the C-ring of genistein has a higher susceptibility to bacterial degradation than that of daidzein.

Bulk Coordination Polymerization of Dicyclopentadiene (DCPD) by Pd Complexes Containing β-Ketoiminate or β-Diketiminate Ligands

  • Lee, Eung Jun;Kim, Ho Sup;Lee, Byoung Ki;Hwang, Woon Sung;Sung, Ik Kyoung;Lee, Ik Mo
    • Bulletin of the Korean Chemical Society
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    • v.33 no.12
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    • pp.4131-4136
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    • 2012
  • Several palladium complexes containing ${\beta}$-ketoiminate and ${\beta}$-diketiminate ligands successfully produced poly(DCPD) possibly via vinyl addition. It was found that catalysts with ${\beta}$-diketiminate ligands containing bulkier aryl substituents showed the highest activity in the presence of MAO as a cocatalyst. Purity of DCPD is quite essential for the higher activity and small amount of organic solvent such as $CH_2Cl_2$ and toluene is required to reduce the viscosity of the reactant mixture for the higher activity. $^1H$ NMR spectra of produced polymers with N,N-dimethylanilinium tetra(pentafluorophenyl)borate (N,N-DAPFAr"$_4$) show that 5,6-double bond of DCPD is removed with 2,3-double bond remaining. Produced poly(DCPD) with MAO cocatalyst is quite rigid and insoluble in common organic solvents but rather brittle.

Synthesis of a Novel Phosphorus-containing Flame Retardant for Epoxy Resins

  • Xu, Hong-Jun;Jin, Fan-Long;Park, Soo-Jin
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2643-2646
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    • 2009
  • In this study, a novel phosphorus-containing flame retardant copolymer of spirocyclic pentaerythritol di(phosphate monochloride) and bisphenol S (SPD-BS) was successfully synthesized and used as a flame retardant in diglycidyl ether of bisphenol A (DGEBA) epoxy resins. The chemical structure of the SPD-BS was characterized using FT-IR and $^1H$ NMR spectra. The thermal properties were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The effects of SPD-BS and nano-$CaCO_3$ on the flame-retardant properties of DGEBA/SPD-BS systems were evaluated by measurement of the burning rate. As a result, the thermal stabilities of the DGEBA/SPD-BS systems were decreased with increasing SPD-BS content. The flame-retardant properties and char yields of the systems were significantly increased when SPD-BS content increased. The synergism of nano-$CaCO_3$ incorporation on flame retardancy was found for the DGEBA/SPD-BS systems.

Isolation and Identification of Anthocyanins from Purple Sweet Potatoes

  • Lee, Lan-Sook;Chang, Eun-Ju;Rhim, Jong-Whan;Ko, Byoung-Seob;Park, Sang-Won
    • Preventive Nutrition and Food Science
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    • v.2 no.2
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    • pp.83-88
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    • 1997
  • Anthocyanin pigments of purple sweet potato roots (Ipomoea batatas L.) were extracted with 0.5% TFA (Trifluoroacetic acid) in 95% EtOh, and further isolated an purified by Amberlite XAD-7 and ODS column chromatography, and final preparative HPLC. Among nine anthocyanins isolated, the structure of three major anthocyanins were identified as 3-O-(6-O-trans-caffeyl)-2-O-(6-O-trans-caffeylglucopyranosyl)-$\beta$-D-glucopyranosyl-5-O-($\beta$-D-glucopyranosyl)-peonidin, 3-O-(6-O-trans-caffeyl)-2-O-(6-O-trans-feruloyl-glucopyranosyl)-$\beta$-D-glucopyranosyl-5-O-($\beta$-D-glucopyranosyl)-peonidin, and 3-O-(6-O-trans-caffeyl)-2-O-(6-O-p-hydroxylbenzoylglucopyranosyl)-$\beta$-D-glucopyranosyl)-peonidin, by using UV-visible absorption spectra, $^1$H-NMR and FAB-MS analysis.

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Anti-inflammatory and Anti-bacterial Constituents from the Extracts of Daucus carota var. sativa Aerial Parts (당근 지상부 추출물 유래 항염 및 항균 활성 성분)

  • Kim, Jung Eun;Jo, Yeon Jeong;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.44 no.4
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    • pp.427-436
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    • 2018
  • In this study, we investigated anti-inflammatory and anti-bacterial constituents from Daucus carota var. sativa (carrot) areal parts. For the extract and solvent fractions, the anti-inflammatory activities were examined by measuring the nitric oxide (NO) production using LPS-stimulated RAW 264.7 cells. Among them, the ethyl acetate (EtOAc) fraction decreased the NO level in a dose-dependent manner. To elucidate further anti-inflammatory mechanisms, EtOAc fraction was evaluated by estimating their effects on the production of prostaglandin $E_2$ and pro-inflammatory cytokines as well as on the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). As a result, the EtOAc fraction was determined to inhibit the production of $PGE_2$, IL-$1{\beta}$, IL-6 and reduce the iNOS, COX-2 protein expression. Upon the anti-bacterial tests using Staphylococcus epidermidis and Propionibacterium acnes, n-hexane (Hex) and EtOAc fractions showed the most potent activities. Three phytochemicals were isolated form the EtOAc fraction; diosmetin (1), diosmin (2), cynaroside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literatures. Anti-inflammatory and anti-bacterial effects were studied for the isolates. All of the compounds (1 - 3) decreased the NO production, effectively. Also, compound 3 showed anti-bacterial activity on P. acnes. Based on these results, D. carota var. sativa extract could be potentially applicable as anti-inflammatory and anti-bacterial ingredients in cosmetic formulations.

Isolation of Bioactive Compounds from the Ethylacetate Fraction of Fermented Garlic Complex and their Tyrosinase Inhibition Activities (대산(大蒜)을 포함하는 복합발효물의 에틸아세테이트 분획으로부터 Tyrosinase 저해활성 성분의 분리 및 동정)

  • Song, Hyo-Nam;Baek, Nam-In
    • Korean Journal of Plant Resources
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    • v.33 no.2
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    • pp.63-72
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    • 2020
  • Fermented complex from garlic and nine medicinal plants were developed as a natural whitening material. Tyrosinase inhibition activity was determined and four active compounds were isolated. The nutritional components of fermented garlic complex (FGC) were analyzed to confirm the applicability as a functional food material. Tyrosinase inhibitory effect of FGC was 88.6%. Methanol extract was partitioned with EtOAc, n-BuOH and H2O. From the EtOAc fraction (47 g), which showed the highest yield, active fractions were separated by repeated TLC, silica gel and ODS column chromatography to isolate active compounds. The chemical structures of the isolated compounds were analyzed by NMR and MS spectra. Phenylpropanoid compounds of 2,4,5-trihydroxy-benzenepropanoic acid (1) (1.9 mg) and 2,3,5-trihydroxy-benzenepropanoic acid (2) were confirmed. In addition, 2,4-dihydroxy-hydrocinnamic acid (3) (3.3 mg) and (+)sesamin (4) (6.1 mg) were isolated. These compounds will be useful as index compounds or functional compounds in FGC.